Electronic Supplementary MAterial for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _audit_creation_date 2007-08-31 _audit_creation_method 'by CrystalStructure 3.8.1' #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Dr. Peddy Vishweshwar' _publ_contact_author_email vishweshwarp@drreddys.com _publ_contact_author_fax '91 040 23045440' _publ_contact_author_phone '91 040 23045439' #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Crystalline forms and aqueous solubilities of an IBS drug, Tegaserod ; _publ_section_title_footnote ; DRL-Publication No. 662 ; loop_ _publ_author_name _publ_author_address R.Srivijaya ; Department of Analytical Research Discovery Research Dr.Reddy's Laboratories Ltd. Miyapur Hyderabad 500049 Andhrapradesh INDIA ; P.Vishweshwar ; Department of Analytical Research Discovery Research Dr.Reddy's Laboratories Ltd. Miyapur Hyderabad 500049 Andhrapradesh INDIA ; B.R.Sreekanth ; Department of Analytical Research Discovery Research Dr.Reddy's Laboratories Ltd. Miyapur Hyderabad 500049 Andhrapradesh INDIA ; K.Vyas ; Department of Analytical Research Discovery Research Dr.Reddy's Laboratories Ltd. Miyapur Hyderabad 500049 Andhrapradesh INDIA ; # End of CIF #============================================================================== # Attachment 'Tegaserod_Nicotinate_MeOH.cif' #============================================================================== data_Tegaserod_nicotinate_MeOH _database_code_depnum_ccdc_archive 'CCDC 653782' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C23 H32 N6 O4 ' _chemical_formula_moiety 'C16 H24 N5 O, C6 H4 N O2, C H4 O' _chemical_formula_weight 456.54 _chemical_melting_point 466.9 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 9.7496(9) _cell_length_b 19.3384(12) _cell_length_c 13.2982(10) _cell_angle_alpha 90.0000 _cell_angle_beta 103.445(3) _cell_angle_gamma 90.0000 _cell_volume 2438.5(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9896 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976.00 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.951 _exptl_absorpt_correction_T_max 0.981 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 27589 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.963 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5398 _reflns_number_gt 3175 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.0734 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 5398 _refine_ls_number_parameters 331 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 4218.2300 5765.9500 1573.5200 ; _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.40 _refine_diff_density_min -0.37 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 634(25) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.16161(15) -0.04085(8) 0.49740(12) 1.000 0.0710(5) . . N1 N Uani 0.51900(16) -0.21842(8) 0.36123(12) 1.000 0.0528(5) . . N2 N Uani 0.55810(16) 0.01349(8) 0.29482(12) 1.000 0.0511(5) . . N3 N Uani 0.63118(16) 0.06698(7) 0.26014(12) 1.000 0.0536(5) . . N4 N Uani 0.65608(17) 0.18422(8) 0.24657(13) 1.000 0.0570(6) . . N5 N Uani 0.46879(17) 0.14008(8) 0.30587(13) 1.000 0.0585(5) . . C1 C Uani 0.5956(2) -0.17361(9) 0.31789(14) 1.000 0.0516(6) . . C2 C Uani 0.54906(19) -0.10697(9) 0.32524(14) 1.000 0.0481(6) . . C3 C Uani 0.43659(18) -0.11097(9) 0.37768(14) 1.000 0.0465(5) . . C4 C Uani 0.35073(18) -0.06169(10) 0.40971(14) 1.000 0.0493(6) . . C5 C Uani 0.2519(2) -0.08388(10) 0.46145(15) 1.000 0.0538(6) . . C6 C Uani 0.2377(2) -0.15382(11) 0.48291(16) 1.000 0.0592(7) . . C7 C Uani 0.3199(2) -0.20366(10) 0.45121(15) 1.000 0.0554(7) . . C8 C Uani 0.42022(19) -0.18136(9) 0.39923(15) 1.000 0.0485(6) . . C9 C Uani 0.1610(2) 0.03012(11) 0.46965(19) 1.000 0.0714(8) . . C10 C Uani 0.60968(19) -0.04693(9) 0.28794(15) 1.000 0.0495(6) . . C11 C Uani 0.5849(2) 0.13160(9) 0.27204(15) 1.000 0.0491(6) . . C12 C Uani 0.4029(2) 0.20636(10) 0.31819(17) 1.000 0.0576(7) . . C13 C Uani 0.2787(2) 0.19595(10) 0.36685(17) 1.000 0.0584(7) . . C14 C Uani 0.2146(2) 0.26354(10) 0.39129(16) 1.000 0.0563(6) . . C15 C Uani 0.0907(2) 0.25347(13) 0.43968(19) 1.000 0.0762(9) . . C16 C Uani 0.0289(2) 0.32056(14) 0.4692(2) 1.000 0.0919(10) . . O2 O Uani -0.11553(15) 0.14895(7) 0.15467(12) 1.000 0.0681(5) . . O3 O Uani -0.11033(16) 0.04254(7) 0.21839(12) 1.000 0.0716(6) . . N6 N Uani 0.17591(19) 0.09552(9) -0.01464(14) 1.000 0.0652(6) . . C17 C Uani 0.0749(2) 0.10831(10) 0.03567(16) 1.000 0.0564(7) . . C18 C Uani 0.05060(18) 0.07029(9) 0.11700(14) 1.000 0.0452(5) . . C19 C Uani 0.1398(2) 0.01440(10) 0.14933(16) 1.000 0.0578(7) . . C20 C Uani 0.2463(2) 0.00075(12) 0.10121(18) 1.000 0.0684(8) . . C21 C Uani 0.2607(2) 0.04172(12) 0.01973(18) 1.000 0.0699(9) . . C22 C Uani -0.0675(2) 0.08861(9) 0.16735(15) 1.000 0.0508(6) . . O4 O Uani 0.64455(15) 0.32962(7) 0.30161(11) 1.000 0.0634(5) . . C23 C Uani 0.5391(2) 0.36566(12) 0.23007(19) 1.000 0.0804(9) . . H1 H Uiso 0.67050 -0.18650 0.28710 1.000 0.0630 calc R H3 H Uiso 0.71000 0.06070 0.24630 1.000 0.0680 calc R H4 H Uiso 0.36050 -0.01400 0.39610 1.000 0.0610 calc R H5 H Uiso 0.43180 0.10420 0.32130 1.000 0.0730 calc R H6 H Uiso 0.16960 -0.16760 0.51970 1.000 0.0730 calc R H7 H Uiso 0.30840 -0.25130 0.46440 1.000 0.0670 calc R H10 H Uiso 0.68830 -0.05210 0.25780 1.000 0.0620 calc R H11 H Uiso 0.53430 -0.26590 0.35860 1.000 0.0650 calc R H41 H Uiso 0.64010 0.22620 0.27160 1.000 0.0730 calc R H42 H Uiso 0.73450 0.17370 0.22160 1.000 0.0730 calc R H91 H Uiso 0.06990 0.04900 0.46560 1.000 0.0900 calc R H92 H Uiso 0.18420 0.03430 0.40440 1.000 0.0900 calc R H93 H Uiso 0.22840 0.05450 0.52040 1.000 0.0900 calc R H121 H Uiso 0.37090 0.22740 0.25230 1.000 0.0720 calc R H122 H Uiso 0.47020 0.23560 0.36120 1.000 0.0710 calc R H131 H Uiso 0.20840 0.17020 0.32040 1.000 0.0720 calc R H132 H Uiso 0.30990 0.17070 0.42920 1.000 0.0720 calc R H141 H Uiso 0.18380 0.28890 0.32890 1.000 0.0680 calc R H142 H Uiso 0.28490 0.28920 0.43790 1.000 0.0680 calc R H151 H Uiso 0.01900 0.22950 0.39170 1.000 0.0960 calc R H152 H Uiso 0.12070 0.22630 0.50030 1.000 0.0960 calc R H161 H Uiso -0.06910 0.31450 0.46450 1.000 0.1130 calc R H162 H Uiso 0.04230 0.35640 0.42350 1.000 0.1130 calc R H163 H Uiso 0.07470 0.33270 0.53810 1.000 0.1130 calc R H17 H Uiso 0.01430 0.14650 0.01290 1.000 0.0700 calc R H19 H Uiso 0.12660 -0.01420 0.20440 1.000 0.0700 calc R H20 H Uiso 0.30910 -0.03660 0.12370 1.000 0.0840 calc R H21 H Uiso 0.33460 0.03150 -0.01350 1.000 0.0880 calc R H231 H Uiso 0.53730 0.41250 0.25110 1.000 0.0960 calc R H232 H Uiso 0.45000 0.34500 0.22740 1.000 0.0960 calc R H233 H Uiso 0.55920 0.36380 0.16360 1.000 0.0960 calc R H411 H Uiso 0.65600 0.34840 0.36570 1.000 0.0780 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0627(8) 0.0668(9) 0.0972(11) 0.0013(8) 0.0465(8) 0.0049(7) N1 0.0594(9) 0.0369(8) 0.0667(10) 0.0036(7) 0.0241(8) 0.0027(7) N2 0.0507(8) 0.0415(8) 0.0671(10) 0.0009(7) 0.0261(7) -0.0019(6) N3 0.0561(9) 0.0374(7) 0.0775(11) 0.0028(7) 0.0364(8) 0.0006(6) N4 0.0685(10) 0.0399(8) 0.0732(11) 0.0007(7) 0.0380(8) -0.0007(7) N5 0.0582(9) 0.0410(8) 0.0841(11) 0.0016(8) 0.0327(8) 0.0029(7) C1 0.0563(11) 0.0413(10) 0.0612(12) -0.0005(8) 0.0220(9) 0.0035(8) C2 0.0487(10) 0.0410(9) 0.0582(11) 0.0001(8) 0.0195(8) 0.0008(7) C3 0.0450(9) 0.0447(9) 0.0512(10) 0.0010(8) 0.0138(8) -0.0015(7) C4 0.0458(9) 0.0450(9) 0.0614(11) -0.0007(8) 0.0210(8) 0.0007(7) C5 0.0461(10) 0.0564(11) 0.0624(12) 0.0016(9) 0.0200(9) 0.0010(8) C6 0.0513(11) 0.0630(12) 0.0689(13) 0.0077(10) 0.0252(9) -0.0072(9) C7 0.0571(11) 0.0482(11) 0.0633(12) 0.0085(9) 0.0187(9) -0.0066(8) C8 0.0491(10) 0.0432(9) 0.0536(10) 0.0020(8) 0.0128(8) -0.0013(8) C9 0.0664(13) 0.0612(13) 0.0966(17) -0.0065(12) 0.0394(12) 0.0080(11) C10 0.0487(10) 0.0428(9) 0.0633(12) -0.0013(8) 0.0257(9) 0.0008(7) C11 0.0502(10) 0.0446(10) 0.0560(11) 0.0012(8) 0.0195(8) 0.0022(8) C12 0.0549(11) 0.0461(10) 0.0772(14) 0.0021(9) 0.0265(10) 0.0084(8) C13 0.0492(10) 0.0561(11) 0.0744(14) -0.0016(10) 0.0238(10) 0.0015(9) C14 0.0489(10) 0.0585(11) 0.0634(12) 0.0014(9) 0.0170(9) 0.0033(9) C15 0.0652(14) 0.0866(17) 0.0872(17) 0.0031(13) 0.0387(13) 0.0116(12) C16 0.0802(17) 0.123(2) 0.0801(17) 0.0033(15) 0.0341(13) 0.0399(16) O2 0.0759(9) 0.0408(7) 0.1020(11) 0.0060(7) 0.0501(8) 0.0065(6) O3 0.0812(10) 0.0527(8) 0.0978(11) 0.0181(7) 0.0553(9) 0.0097(7) N6 0.0697(11) 0.0624(10) 0.0733(12) 0.0038(9) 0.0363(9) -0.0027(9) C17 0.0609(12) 0.0467(10) 0.0668(12) 0.0028(9) 0.0257(10) 0.0010(9) C18 0.0469(9) 0.0400(9) 0.0515(10) -0.0014(7) 0.0169(8) -0.0014(7) C19 0.0604(12) 0.0534(11) 0.0623(12) 0.0053(9) 0.0200(9) 0.0027(9) C20 0.0541(12) 0.0666(14) 0.0891(16) 0.0073(12) 0.0258(11) 0.0140(10) C21 0.0575(12) 0.0730(15) 0.0885(17) -0.0057(12) 0.0359(12) 0.0013(11) C22 0.0580(11) 0.0394(9) 0.0607(11) -0.0011(8) 0.0252(9) -0.0020(8) O4 0.0698(9) 0.0549(8) 0.0696(9) -0.0085(7) 0.0246(7) 0.0061(7) C23 0.0831(16) 0.0568(13) 0.0998(19) 0.0031(13) 0.0183(14) 0.0058(12) #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR2004 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8.1' _computing_molecular_graphics 'X-Seed 2.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.375(2) . . yes O1 C9 1.421(3) . . yes O2 C22 1.254(2) . . yes O3 C22 1.249(2) . . yes O4 C23 1.412(3) . . yes O4 H411 0.9100 . . no N1 C8 1.387(2) . . yes N1 C1 1.357(2) . . yes N2 C10 1.284(2) . . yes N2 N3 1.394(2) . . yes N3 C11 1.350(2) . . yes N4 C11 1.320(2) . . yes N5 C11 1.322(3) . . yes N5 C12 1.460(3) . . yes N1 H11 0.9300 . . no N3 H3 0.8400 . . no N4 H41 0.9000 . . no N4 H42 0.9200 . . no N5 H5 0.8300 . . no N6 C21 1.341(3) . . yes N6 C17 1.336(3) . . yes C1 C2 1.377(3) . . no C2 C10 1.442(3) . . no C2 C3 1.432(3) . . no C3 C8 1.408(2) . . no C3 C4 1.399(3) . . no C4 C5 1.376(3) . . no C5 C6 1.396(3) . . no C6 C7 1.381(3) . . no C7 C8 1.391(3) . . no C12 C13 1.513(3) . . no C13 C14 1.516(3) . . no C14 C15 1.508(3) . . no C15 C16 1.520(4) . . no C1 H1 0.9500 . . no C4 H4 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C9 H91 0.9500 . . no C9 H93 0.9500 . . no C9 H92 0.9500 . . no C10 H10 0.9500 . . no C12 H122 0.9500 . . no C12 H121 0.9500 . . no C13 H131 0.9500 . . no C13 H132 0.9500 . . no C14 H141 0.9500 . . no C14 H142 0.9500 . . no C15 H152 0.9500 . . no C15 H151 0.9500 . . no C16 H161 0.9500 . . no C16 H163 0.9500 . . no C16 H162 0.9500 . . no C17 C18 1.373(3) . . no C18 C19 1.391(3) . . no C18 C22 1.503(3) . . no C19 C20 1.366(3) . . no C20 C21 1.376(3) . . no C17 H17 0.9500 . . no C19 H19 0.9500 . . no C20 H20 0.9500 . . no C21 H21 0.9500 . . no C23 H231 0.9500 . . no C23 H232 0.9500 . . no C23 H233 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O1 C9 117.29(16) . . . yes C23 O4 H411 110.00 . . . no C1 N1 C8 108.80(15) . . . yes N3 N2 C10 114.39(16) . . . yes N2 N3 C11 115.95(15) . . . yes C11 N5 C12 125.53(16) . . . yes C1 N1 H11 120.00 . . . no C8 N1 H11 131.00 . . . no N2 N3 H3 122.00 . . . no C11 N3 H3 120.00 . . . no H41 N4 H42 124.00 . . . no C11 N4 H41 117.00 . . . no C11 N4 H42 117.00 . . . no C12 N5 H5 119.00 . . . no C11 N5 H5 116.00 . . . no C17 N6 C21 116.14(18) . . . yes N1 C1 C2 110.15(17) . . . yes C1 C2 C3 106.63(16) . . . no C1 C2 C10 124.11(17) . . . no C3 C2 C10 129.24(16) . . . no C2 C3 C8 106.70(15) . . . no C2 C3 C4 133.78(17) . . . no C4 C3 C8 119.52(17) . . . no C3 C4 C5 118.55(17) . . . no O1 C5 C4 124.35(18) . . . yes C4 C5 C6 121.24(18) . . . no O1 C5 C6 114.41(17) . . . yes C5 C6 C7 121.46(19) . . . no C6 C7 C8 117.42(18) . . . no C3 C8 C7 121.81(17) . . . no N1 C8 C7 130.47(17) . . . yes N1 C8 C3 107.72(16) . . . yes N2 C10 C2 120.64(17) . . . yes N4 C11 N5 122.33(17) . . . yes N3 C11 N4 118.27(18) . . . yes N3 C11 N5 119.38(17) . . . yes N5 C12 C13 110.36(16) . . . yes C12 C13 C14 112.81(16) . . . no C13 C14 C15 113.03(17) . . . no C14 C15 C16 113.90(19) . . . no N1 C1 H1 125.00 . . . no C2 C1 H1 125.00 . . . no C5 C4 H4 121.00 . . . no C3 C4 H4 121.00 . . . no C7 C6 H6 119.00 . . . no C5 C6 H6 119.00 . . . no C6 C7 H7 121.00 . . . no C8 C7 H7 121.00 . . . no O1 C9 H92 109.00 . . . no O1 C9 H93 110.00 . . . no H91 C9 H93 109.00 . . . no H92 C9 H93 110.00 . . . no H91 C9 H92 109.00 . . . no O1 C9 H91 109.00 . . . no C2 C10 H10 120.00 . . . no N2 C10 H10 120.00 . . . no C13 C12 H121 109.00 . . . no C13 C12 H122 109.00 . . . no N5 C12 H122 109.00 . . . no H121 C12 H122 109.00 . . . no N5 C12 H121 109.00 . . . no C12 C13 H132 108.00 . . . no C12 C13 H131 109.00 . . . no H131 C13 H132 110.00 . . . no C14 C13 H132 109.00 . . . no C14 C13 H131 109.00 . . . no C13 C14 H141 109.00 . . . no C15 C14 H141 109.00 . . . no C15 C14 H142 108.00 . . . no H141 C14 H142 109.00 . . . no C13 C14 H142 109.00 . . . no C16 C15 H151 108.00 . . . no C16 C15 H152 108.00 . . . no C14 C15 H152 108.00 . . . no C14 C15 H151 108.00 . . . no H151 C15 H152 109.00 . . . no C15 C16 H162 110.00 . . . no C15 C16 H163 110.00 . . . no H161 C16 H163 109.00 . . . no H162 C16 H163 109.00 . . . no C15 C16 H161 109.00 . . . no H161 C16 H162 109.00 . . . no N6 C17 C18 125.28(18) . . . yes C17 C18 C19 116.71(17) . . . no C17 C18 C22 121.00(16) . . . no C19 C18 C22 122.29(17) . . . no C18 C19 C20 119.60(19) . . . no C19 C20 C21 119.1(2) . . . no N6 C21 C20 123.2(2) . . . yes O2 C22 O3 125.11(19) . . . yes O3 C22 C18 117.48(16) . . . yes O2 C22 C18 117.41(17) . . . yes N6 C17 H17 117.00 . . . no C18 C17 H17 117.00 . . . no C20 C19 H19 120.00 . . . no C18 C19 H19 120.00 . . . no C19 C20 H20 120.00 . . . no C21 C20 H20 121.00 . . . no N6 C21 H21 118.00 . . . no C20 C21 H21 118.00 . . . no O4 C23 H231 109.00 . . . no O4 C23 H232 110.00 . . . no O4 C23 H233 109.00 . . . no H231 C23 H232 109.00 . . . no H231 C23 H233 109.00 . . . no H232 C23 H233 110.00 . . . no 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 C9 O1 C5 C4 6.8(3) . . . . no C9 O1 C5 C6 -174.10(18) . . . . no C8 N1 C1 C2 -0.6(2) . . . . no C1 N1 C8 C3 0.4(2) . . . . no C1 N1 C8 C7 -178.9(2) . . . . no C10 N2 N3 C11 -176.15(17) . . . . no N3 N2 C10 C2 177.16(16) . . . . no N2 N3 C11 N4 175.72(16) . . . . no N2 N3 C11 N5 -6.1(3) . . . . no C12 N5 C11 N3 -177.16(18) . . . . no C12 N5 C11 N4 1.0(3) . . . . no C11 N5 C12 C13 -175.39(19) . . . . no C17 N6 C21 C20 0.6(3) . . . . no C21 N6 C17 C18 -1.3(3) . . . . no N1 C1 C2 C10 179.06(17) . . . . no N1 C1 C2 C3 0.5(2) . . . . no C10 C2 C3 C4 -0.1(4) . . . . no C10 C2 C3 C8 -178.73(19) . . . . no C1 C2 C10 N2 178.00(18) . . . . no C3 C2 C10 N2 -3.8(3) . . . . no C1 C2 C3 C4 178.3(2) . . . . no C1 C2 C3 C8 -0.3(2) . . . . no C2 C3 C4 C5 -178.7(2) . . . . no C2 C3 C8 C7 179.29(18) . . . . no C4 C3 C8 N1 -178.88(16) . . . . no C4 C3 C8 C7 0.4(3) . . . . no C8 C3 C4 C5 -0.2(3) . . . . no C2 C3 C8 N1 0.0(2) . . . . no C3 C4 C5 O1 179.70(18) . . . . no C3 C4 C5 C6 0.7(3) . . . . no O1 C5 C6 C7 179.45(18) . . . . no C4 C5 C6 C7 -1.4(3) . . . . no C5 C6 C7 C8 1.6(3) . . . . no C6 C7 C8 C3 -1.1(3) . . . . no C6 C7 C8 N1 178.01(19) . . . . no N5 C12 C13 C14 174.38(17) . . . . no C12 C13 C14 C15 179.94(18) . . . . no C13 C14 C15 C16 177.43(19) . . . . no N6 C17 C18 C19 0.5(3) . . . . no N6 C17 C18 C22 -179.16(18) . . . . no C17 C18 C19 C20 1.0(3) . . . . no C22 C18 C19 C20 -179.31(19) . . . . no C17 C18 C22 O2 -20.3(3) . . . . no C17 C18 C22 O3 159.61(19) . . . . no C19 C18 C22 O2 160.09(19) . . . . no C19 C18 C22 O3 -20.0(3) . . . . no C18 C19 C20 C21 -1.7(3) . . . . no C19 C20 C21 N6 0.9(3) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O4 H411 N6 0.9100 1.9000 2.795(2) 169.00 4_555 yes N1 H11 O2 0.9300 1.8500 2.757(2) 163.00 2_545 yes N3 H3 O3 0.8400 1.9100 2.745(2) 177.00 1_655 yes N4 H41 O4 0.9000 2.0400 2.914(2) 163.00 . yes N4 H42 O2 0.9200 1.9400 2.861(2) 174.00 1_655 yes C1 H1 O4 0.9500 2.3900 3.289(2) 157.00 2_645 yes C9 H91 O1 0.9500 2.4200 3.282(3) 150.00 3_556 yes # End of CIF #============================================================================== # Attachment 'Tegegaserod freebase.cif' #============================================================================== data___Tegaserodfreebase _database_code_depnum_ccdc_archive 'CCDC 653783' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C16 H23 N5 O ' _chemical_formula_moiety 'C16 H23 N5 O ' _chemical_formula_weight 301.39 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z #------------------------------------------------------------------------------ _cell_length_a 7.395(4) _cell_length_b 11.218(6) _cell_length_c 20.202(10) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1675.9(15) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5279 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 27.3 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648.00 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.987 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 17553 _diffrn_reflns_av_R_equivalents 0.087 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2197 _reflns_number_gt 929 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.0975 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2197 _refine_ls_number_parameters 222 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 2140.2800 2913.0300 779.5100 ; _refine_ls_shift/su_max 0.0092 _refine_diff_density_max 0.31 _refine_diff_density_min -0.30 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.7191(4) 0.5070(3) 0.13643(15) 1.000 0.0717(12) . . N1 N Uani 0.1394(5) 0.5136(3) 0.30476(16) 1.000 0.0572(11) . . N2 N Uani 0.1316(4) 0.2496(2) 0.12792(14) 1.000 0.0419(10) . . N3 N Uani 0.0273(4) 0.1627(2) 0.09465(15) 1.000 0.0455(10) . . N4 N Uani 0.2553(5) 0.1799(3) 0.01404(17) 1.000 0.0710(14) . . N5 N Uani 0.0131(5) 0.0537(3) -0.00094(16) 1.000 0.0558(11) . . C1 C Uani 0.0404(6) 0.4262(3) 0.27754(18) 1.000 0.0523(12) . . C2 C Uani 0.1268(5) 0.3780(3) 0.22346(18) 1.000 0.0425(11) . . C3 C Uani 0.2971(6) 0.4415(3) 0.21825(17) 1.000 0.0428(11) . . C4 C Uani 0.4431(5) 0.4358(3) 0.17583(18) 1.000 0.0461(11) . . C5 C Uani 0.5838(6) 0.5159(4) 0.1834(2) 1.000 0.0533(12) . . C6 C Uani 0.5794(7) 0.6024(4) 0.2340(2) 1.000 0.0613(14) . . C7 C Uani 0.4357(7) 0.6074(3) 0.2774(2) 1.000 0.0653(16) . . C8 C Uani 0.2972(6) 0.5283(3) 0.26993(18) 1.000 0.0469(11) . . C9 C Uani 0.8583(7) 0.5953(5) 0.1382(2) 1.000 0.088(2) . . C10 C Uani 0.0517(5) 0.2899(3) 0.18048(19) 1.000 0.0457(12) . . C11 C Uani 0.0988(5) 0.1356(3) 0.03790(18) 1.000 0.0433(12) . . C12 C Uani -0.1518(6) -0.0047(4) 0.0213(2) 1.000 0.0630(14) . . C13 C Uani -0.2266(7) -0.0871(4) -0.0279(2) 1.000 0.0703(17) . . C14 C Uani -0.1224(6) -0.1934(4) -0.0474(2) 1.000 0.0617(14) . . C15 C Uani -0.2045(8) -0.2710(5) -0.0996(2) 1.000 0.100(2) . . C16 C Uani -0.0948(8) -0.3782(5) -0.1180(3) 1.000 0.111(3) . . H1 H Uiso -0.07510 0.40120 0.29270 1.000 0.0630 calc R H4 H Uiso 0.44610 0.37810 0.14140 1.000 0.0560 calc R H6 H Uiso 0.67760 0.65640 0.23830 1.000 0.0740 calc R H7 H Uiso 0.43290 0.66470 0.31210 1.000 0.0780 calc R H10 H Uiso -0.06330 0.25790 0.19160 1.000 0.0550 calc R H11 H Uiso 0.11030 0.56070 0.33530 1.000 0.0680 calc R H41 H Uiso 0.30110 0.24620 0.03840 1.000 0.0850 calc R H42 H Uiso 0.29640 0.16280 -0.02000 1.000 0.0850 calc R H51 H Uiso 0.06250 0.03190 -0.03530 1.000 0.0670 calc R H91 H Uiso 0.82570 0.66050 0.11070 1.000 0.1050 calc R H92 H Uiso 0.96700 0.56040 0.12230 1.000 0.1050 calc R H93 H Uiso 0.87610 0.62270 0.18220 1.000 0.1050 calc R H121 H Uiso -0.12540 -0.04980 0.06000 1.000 0.0760 calc R H122 H Uiso -0.23810 0.05520 0.03170 1.000 0.0760 calc R H131 H Uiso -0.24190 -0.04180 -0.06720 1.000 0.0850 calc R H132 H Uiso -0.34130 -0.11330 -0.01240 1.000 0.0840 calc R H141 H Uiso -0.00730 -0.16860 -0.06300 1.000 0.0740 calc R H142 H Uiso -0.10760 -0.24030 -0.00860 1.000 0.0740 calc R H151 H Uiso -0.31780 -0.29850 -0.08360 1.000 0.1200 calc R H152 H Uiso -0.22290 -0.22380 -0.13810 1.000 0.1200 calc R H161 H Uiso -0.01590 -0.35740 -0.15320 1.000 0.1330 calc R H162 H Uiso -0.17050 -0.44220 -0.13140 1.000 0.1330 calc R H163 H Uiso -0.02560 -0.40190 -0.08060 1.000 0.1330 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.053(2) 0.094(2) 0.068(2) 0.002(2) 0.0090(17) -0.020(2) N1 0.081(2) 0.0461(19) 0.0444(18) -0.0167(17) 0.005(2) 0.004(2) N2 0.051(2) 0.0411(16) 0.0337(15) -0.0061(14) 0.0039(15) -0.0081(16) N3 0.053(2) 0.0475(18) 0.0360(16) 0.0001(15) -0.0001(16) -0.0127(18) N4 0.073(2) 0.089(3) 0.051(2) -0.021(2) 0.028(2) -0.030(2) N5 0.064(2) 0.062(2) 0.0413(17) -0.0098(17) 0.0092(18) -0.014(2) C1 0.063(2) 0.054(2) 0.040(2) 0.005(2) 0.016(2) 0.001(2) C2 0.048(2) 0.042(2) 0.0374(19) 0.0060(17) 0.0022(18) -0.0050(19) C3 0.057(2) 0.0366(19) 0.0347(18) 0.0015(16) -0.0048(18) 0.0138(19) C4 0.056(2) 0.048(2) 0.0344(18) 0.0009(18) -0.0011(19) 0.002(2) C5 0.047(2) 0.061(2) 0.052(2) 0.010(2) -0.006(2) -0.006(2) C6 0.061(3) 0.062(2) 0.061(2) -0.004(2) -0.017(2) -0.011(2) C7 0.099(4) 0.045(2) 0.052(2) -0.012(2) -0.007(2) -0.005(2) C8 0.067(2) 0.038(2) 0.0357(19) -0.0030(17) 0.000(2) 0.004(2) C9 0.059(3) 0.112(4) 0.092(4) 0.031(3) -0.002(3) -0.017(3) C10 0.043(2) 0.047(2) 0.047(2) -0.0017(18) 0.0105(19) -0.0061(19) C11 0.047(2) 0.043(2) 0.040(2) 0.0015(17) -0.0051(18) -0.0052(19) C12 0.060(3) 0.063(2) 0.066(2) -0.014(2) 0.010(2) -0.021(2) C13 0.062(3) 0.075(3) 0.074(3) -0.022(2) 0.012(2) -0.020(2) C14 0.067(3) 0.052(2) 0.066(2) -0.008(2) 0.004(2) -0.004(2) C15 0.092(4) 0.088(4) 0.119(4) -0.053(3) 0.000(4) 0.000(3) C16 0.095(4) 0.104(4) 0.133(5) -0.071(4) -0.028(4) 0.018(4) #=============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR2004 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8.1' _computing_molecular_graphics 'X-seed 2.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.383(5) . . yes O1 C9 1.429(6) . . yes N1 C1 1.342(5) . . yes N1 C8 1.373(6) . . yes N2 N3 1.413(4) . . yes N2 C10 1.297(5) . . yes N3 C11 1.299(5) . . yes N4 C11 1.349(5) . . yes N5 C11 1.364(5) . . yes N5 C12 1.455(6) . . yes N1 H11 0.8400 . . no N4 H41 0.9500 . . no N4 H42 0.7800 . . no N5 H51 0.8200 . . no C1 C2 1.376(5) . . no C2 C10 1.428(5) . . no C2 C3 1.451(6) . . no C3 C8 1.428(5) . . no C3 C4 1.380(6) . . no C4 C5 1.383(6) . . no C5 C6 1.410(6) . . no C6 C7 1.379(7) . . no C7 C8 1.364(6) . . no C12 C13 1.466(6) . . no C13 C14 1.473(6) . . no C14 C15 1.496(7) . . no C15 C16 1.498(8) . . no C1 H1 0.9500 . . no C4 H4 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C9 H91 0.9500 . . no C9 H92 0.9500 . . no C9 H93 0.9500 . . no C10 H10 0.9500 . . no C12 H121 0.9500 . . no C12 H122 0.9500 . . no C13 H131 0.9500 . . no C13 H132 0.9500 . . no C14 H141 0.9500 . . no C14 H142 0.9500 . . no C15 H151 0.9500 . . no C15 H152 0.9500 . . no C16 H161 0.9500 . . no C16 H162 0.9500 . . no C16 H163 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O1 C9 117.0(3) . . . yes C1 N1 C8 110.0(3) . . . yes N3 N2 C10 112.4(3) . . . yes N2 N3 C11 111.1(3) . . . yes C11 N5 C12 121.0(3) . . . yes C8 N1 H11 121.00 . . . no C1 N1 H11 128.00 . . . no C11 N4 H41 114.00 . . . no H41 N4 H42 121.00 . . . no C11 N4 H42 124.00 . . . no C11 N5 H51 119.00 . . . no C12 N5 H51 120.00 . . . no N1 C1 C2 111.1(4) . . . yes C1 C2 C3 105.5(3) . . . no C1 C2 C10 125.0(3) . . . no C3 C2 C10 129.3(3) . . . no C2 C3 C4 134.6(3) . . . no C2 C3 C8 106.4(3) . . . no C4 C3 C8 119.0(4) . . . no C3 C4 C5 119.3(3) . . . no O1 C5 C4 114.9(4) . . . yes O1 C5 C6 124.3(4) . . . yes C4 C5 C6 120.7(4) . . . no C5 C6 C7 120.5(4) . . . no C6 C7 C8 118.8(4) . . . no C3 C8 C7 121.7(4) . . . no N1 C8 C3 107.0(3) . . . yes N1 C8 C7 131.3(4) . . . yes N2 C10 C2 124.2(3) . . . yes N3 C11 N4 125.4(3) . . . yes N3 C11 N5 118.4(3) . . . yes N4 C11 N5 116.2(3) . . . yes N5 C12 C13 113.0(4) . . . yes C12 C13 C14 119.6(4) . . . no C13 C14 C15 116.6(4) . . . no C14 C15 C16 115.0(5) . . . no N1 C1 H1 125.00 . . . no C2 C1 H1 124.00 . . . no C3 C4 H4 120.00 . . . no C5 C4 H4 120.00 . . . no C5 C6 H6 119.00 . . . no C7 C6 H6 120.00 . . . no C6 C7 H7 121.00 . . . no C8 C7 H7 120.00 . . . no O1 C9 H91 110.00 . . . no O1 C9 H92 108.00 . . . no O1 C9 H93 110.00 . . . no H91 C9 H92 110.00 . . . no H91 C9 H93 109.00 . . . no H92 C9 H93 109.00 . . . no N2 C10 H10 118.00 . . . no C2 C10 H10 118.00 . . . no N5 C12 H121 109.00 . . . no N5 C12 H122 108.00 . . . no C13 C12 H121 107.00 . . . no C13 C12 H122 110.00 . . . no H121 C12 H122 109.00 . . . no C12 C13 H131 106.00 . . . no C12 C13 H132 108.00 . . . no C14 C13 H131 106.00 . . . no C14 C13 H132 108.00 . . . no H131 C13 H132 110.00 . . . no C13 C14 H141 109.00 . . . no C13 C14 H142 107.00 . . . no C15 C14 H141 107.00 . . . no C15 C14 H142 108.00 . . . no H141 C14 H142 109.00 . . . no C14 C15 H151 108.00 . . . no C14 C15 H152 108.00 . . . no C16 C15 H151 108.00 . . . no C16 C15 H152 109.00 . . . no H151 C15 H152 109.00 . . . no C15 C16 H161 109.00 . . . no C15 C16 H162 111.00 . . . no C15 C16 H163 109.00 . . . no H161 C16 H162 110.00 . . . no H161 C16 H163 109.00 . . . no H162 C16 H163 109.00 . . . no 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 C9 O1 C5 C4 174.0(4) . . . . no C9 O1 C5 C6 -2.9(6) . . . . no C8 N1 C1 C2 0.2(5) . . . . no C1 N1 C8 C3 -1.4(4) . . . . no C1 N1 C8 C7 177.7(4) . . . . no C10 N2 N3 C11 171.5(3) . . . . no N3 N2 C10 C2 179.8(3) . . . . no N2 N3 C11 N4 2.4(5) . . . . no N2 N3 C11 N5 -179.2(3) . . . . no C12 N5 C11 N3 -1.7(5) . . . . no C12 N5 C11 N4 176.8(3) . . . . no C11 N5 C12 C13 178.4(4) . . . . no N1 C1 C2 C3 1.1(4) . . . . no N1 C1 C2 C10 -174.9(3) . . . . no C1 C2 C3 C4 179.6(4) . . . . no C1 C2 C3 C8 -1.9(4) . . . . no C10 C2 C3 C4 -4.6(7) . . . . no C10 C2 C3 C8 173.9(4) . . . . no C1 C2 C10 N2 176.6(3) . . . . no C3 C2 C10 N2 1.5(6) . . . . no C2 C3 C4 C5 176.8(4) . . . . no C8 C3 C4 C5 -1.5(5) . . . . no C2 C3 C8 N1 2.0(4) . . . . no C2 C3 C8 C7 -177.1(4) . . . . no C4 C3 C8 N1 -179.2(3) . . . . no C4 C3 C8 C7 1.6(6) . . . . no C3 C4 C5 O1 -176.8(3) . . . . no C3 C4 C5 C6 0.3(6) . . . . no O1 C5 C6 C7 177.7(4) . . . . no C4 C5 C6 C7 0.9(7) . . . . no C5 C6 C7 C8 -0.8(6) . . . . no C6 C7 C8 N1 -179.3(4) . . . . no C6 C7 C8 C3 -0.4(6) . . . . no N5 C12 C13 C14 64.1(5) . . . . no C12 C13 C14 C15 -177.9(4) . . . . no C13 C14 C15 C16 -179.9(4) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N5 H51 O1 0.8200 2.3900 3.206(5) 173.00 3_455 yes N1 H11 N3 0.8400 2.0900 2.906(5) 166.00 4_555 yes # End of CIF #============================================================================== #============================================================================== data___Teg_Free_Mono_3 _database_code_depnum_ccdc_archive 'CCDC 653784' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C16 H25 N5 O2 ' _chemical_formula_moiety 'C16 H25 N5 O2 ' _chemical_formula_weight 319.41 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 7.111(3) _cell_length_b 10.857(5) _cell_length_c 23.106(10) _cell_angle_alpha 90.0000 _cell_angle_beta 93.241(4) _cell_angle_gamma 90.0000 _cell_volume 1780.8(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6428 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680.00 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.995 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 19687 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.983 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 0.5 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3625 _reflns_number_gt 1724 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.0989 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3191 _refine_ls_number_parameters 225 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 7901.0900 10916.3000 3160.0000 ; _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.32 _refine_diff_density_min -0.33 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 808(39) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani -0.1952(2) 0.22261(17) 0.83613(8) 1.000 0.0799(7) . . N1 N Uani 0.3798(2) 0.25836(18) 0.68901(7) 1.000 0.0631(7) . . N2 N Uani 0.4002(2) 0.49208(16) 0.85629(7) 1.000 0.0514(5) . . N3 N Uani 0.5041(2) 0.57179(17) 0.89477(7) 1.000 0.0571(6) . . N4 N Uani 0.2286(3) 0.5625(2) 0.94646(9) 1.000 0.0769(8) . . N5 N Uani 0.4838(3) 0.6737(2) 0.98117(8) 1.000 0.0810(9) . . C1 C Uani 0.4953(3) 0.3386(2) 0.72063(9) 1.000 0.0597(8) . . C2 C Uani 0.4101(3) 0.37498(19) 0.76948(8) 1.000 0.0514(7) . . C3 C Uani 0.2317(3) 0.31073(19) 0.76927(8) 1.000 0.0486(6) . . C4 C Uani 0.0886(3) 0.3046(2) 0.80765(9) 1.000 0.0534(7) . . C5 C Uani -0.0604(3) 0.2254(2) 0.79506(10) 1.000 0.0594(8) . . C6 C Uani -0.0716(3) 0.1547(2) 0.74490(11) 1.000 0.0702(9) . . C7 C Uani 0.0680(3) 0.1614(2) 0.70599(10) 1.000 0.0678(8) . . C8 C Uani 0.2207(3) 0.2377(2) 0.71849(9) 1.000 0.0559(7) . . C9 C Uani -0.3323(4) 0.1272(2) 0.83163(13) 1.000 0.0897(11) . . C10 C Uani 0.4907(3) 0.45811(19) 0.81251(8) 1.000 0.0525(7) . . C11 C Uani 0.4060(3) 0.5998(2) 0.93933(9) 1.000 0.0588(8) . . C12 C Uani 0.6714(5) 0.7246(3) 0.98130(12) 1.000 0.1127(13) . . C13 C Uani 0.7719(9) 0.7829(5) 1.0317(2) 0.500 0.095(2) . . C13' C Uani 0.6400(12) 0.8223(8) 1.0370(2) 0.500 0.091(3) . . C14 C Uani 0.7333(13) 0.9105(5) 1.0410(2) 0.500 0.126(3) . . C14' C Uani 0.810(3) 0.9000(15) 1.0346(7) 0.500 0.214(9) . . C15 C Uani 0.7763(13) 0.9968(9) 1.1011(3) 0.500 0.156(4) . . C15' C Uani 0.812(3) 0.9790(12) 1.0879(5) 0.500 0.167(7) . . C16 C Uani 0.9290(13) 1.0779(10) 1.1006(3) 0.500 0.159(4) . . C16' C Uani 0.794(3) 1.1018(12) 1.0886(5) 0.500 0.161(7) . . O2 O Uani 0.8173(2) 0.4053(2) 0.92651(7) 1.000 0.0905(8) . . H1 H Uiso 0.61610 0.36480 0.71010 1.000 0.0720 calc R H4 H Uiso 0.09350 0.35390 0.84170 1.000 0.0640 calc R H6 H Uiso -0.17610 0.10150 0.73720 1.000 0.0840 calc R H7 H Uiso 0.06020 0.11400 0.67140 1.000 0.0810 calc R H10 H Uiso 0.61490 0.48810 0.80880 1.000 0.0630 calc R H11 H Uiso 0.41380 0.21110 0.66170 1.000 0.0760 calc R H41 H Uiso 0.18990 0.57200 0.98540 1.000 0.0930 calc R H42 H Uiso 0.18450 0.51450 0.91940 1.000 0.0930 calc R H51 H Uiso 0.42060 0.68180 1.01680 1.000 0.0980 calc R H91 H Uiso -0.43800 0.15520 0.80830 1.000 0.1090 calc R H92 H Uiso -0.37060 0.10740 0.86920 1.000 0.1090 calc R H93 H Uiso -0.28100 0.05600 0.81450 1.000 0.1090 calc R H121 H Uiso 0.74910 0.65270 0.97230 1.000 0.1350 calc R H122 H Uiso 0.69330 0.77370 0.94770 1.000 0.1350 calc R H21 H Uiso 0.80990 0.34540 0.89790 1.000 0.1090 calc R H22 H Uiso 0.74680 0.46340 0.91260 1.000 0.1090 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0635(10) 0.0847(13) 0.0932(12) -0.0270(10) 0.0201(9) -0.0178(9) N1 0.0817(13) 0.0645(12) 0.0442(9) -0.0110(9) 0.0131(9) 0.0104(10) N2 0.0605(10) 0.0512(10) 0.0427(8) -0.0025(7) 0.0048(7) -0.0037(8) N3 0.0743(12) 0.0567(11) 0.0406(9) -0.0023(8) 0.0070(8) -0.0117(9) N4 0.0781(14) 0.0991(17) 0.0553(11) -0.0148(11) 0.0203(10) -0.0064(12) N5 0.1169(19) 0.0746(14) 0.0518(11) -0.0138(10) 0.0081(11) -0.0122(13) C1 0.0779(15) 0.0569(13) 0.0453(11) -0.0002(10) 0.0123(10) 0.0034(11) C2 0.0653(13) 0.0468(12) 0.0426(10) -0.0021(9) 0.0070(9) 0.0033(10) C3 0.0584(12) 0.0464(11) 0.0405(9) -0.0050(8) -0.0003(8) 0.0081(9) C4 0.0614(13) 0.0496(12) 0.0495(11) -0.0101(9) 0.0047(9) 0.0039(10) C5 0.0518(12) 0.0621(14) 0.0645(13) -0.0131(11) 0.0047(10) 0.0030(10) C6 0.0600(14) 0.0676(15) 0.0817(16) -0.0246(13) -0.0081(12) 0.0015(12) C7 0.0751(16) 0.0676(15) 0.0597(13) -0.0247(12) -0.0038(11) 0.0093(13) C8 0.0662(14) 0.0556(13) 0.0454(11) -0.0092(10) -0.0013(10) 0.0112(11) C9 0.0792(18) 0.085(2) 0.106(2) -0.0080(17) 0.0146(16) -0.0213(16) C10 0.0635(13) 0.0522(12) 0.0423(10) 0.0013(9) 0.0083(9) -0.0033(10) C11 0.0823(16) 0.0530(13) 0.0415(11) -0.0009(9) 0.0062(10) -0.0024(12) C12 0.176(3) 0.093(2) 0.0676(17) -0.0052(16) -0.0053(19) -0.072(2) C13 0.131(5) 0.087(4) 0.067(3) -0.010(3) -0.006(3) -0.027(3) C13' 0.125(6) 0.085(5) 0.064(3) -0.021(3) 0.006(4) -0.021(4) C14 0.271(9) 0.046(3) 0.067(3) 0.006(2) 0.067(4) 0.008(4) C14' 0.33(2) 0.171(13) 0.148(11) -0.091(8) 0.087(11) -0.149(13) C15 0.138(7) 0.190(9) 0.141(7) -0.084(6) 0.020(5) -0.045(6) C15' 0.37(2) 0.073(5) 0.052(4) -0.005(4) -0.041(8) -0.083(9) C16 0.118(6) 0.187(9) 0.166(8) 0.010(7) -0.031(5) -0.022(6) C16' 0.253(18) 0.088(6) 0.139(8) -0.018(6) -0.008(10) 0.027(9) O2 0.0900(13) 0.1204(16) 0.0608(10) -0.0202(10) 0.0023(9) 0.0227(11) #=============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR2004 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics X-seed #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.387(3) . . yes O1 C9 1.422(3) . . yes O2 H22 0.8600 . . no O2 H21 0.9300 . . no N1 C8 1.372(3) . . yes N1 C1 1.378(3) . . yes N2 C10 1.283(3) . . yes N2 N3 1.418(2) . . yes N3 C11 1.312(3) . . yes N4 C11 1.344(3) . . yes N5 C11 1.351(3) . . yes N5 C12 1.444(4) . . yes N1 H11 0.8600 . . no N4 H42 0.8600 . . no N4 H41 0.9600 . . no N5 H51 0.9600 . . no C1 C2 1.369(3) . . no C2 C3 1.448(3) . . no C2 C10 1.438(3) . . no C3 C8 1.415(3) . . no C3 C4 1.389(3) . . no C4 C5 1.383(3) . . no C5 C6 1.389(3) . . no C6 C7 1.378(3) . . no C7 C8 1.383(3) . . no C12 C13 1.474(6) . . no C12 C13' 1.692(7) . . no C13 C14 1.431(8) . . no C13 C14' 1.301(17) . . no C13 C13' 1.044(11) . . no C13' C14 1.166(11) . . no C13' C14' 1.48(2) . . no C14 C15 1.689(9) . . no C14 C14' 0.58(2) . . no C14 C15' 1.404(15) . . no C14' C15' 1.50(2) . . no C15 C16' 1.185(16) . . no C15 C16 1.399(14) . . no C15 C15' 0.451(18) . . no C15' C16' 1.340(19) . . no C15' C16 1.380(19) . . no C16 C16' 1.02(2) . . no C1 H1 0.9500 . . no C4 H4 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C9 H92 0.9500 . . no C9 H93 0.9500 . . no C9 H91 0.9500 . . no C10 H10 0.9500 . . no C12 H122 0.9600 . . no C12 H121 0.9900 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O1 C9 117.6(2) . . . yes H21 O2 H22 104.00 . . . no C1 N1 C8 108.88(17) . . . yes N3 N2 C10 113.76(15) . . . yes N2 N3 C11 110.63(15) . . . yes C11 N5 C12 124.8(2) . . . yes C1 N1 H11 126.00 . . . no C8 N1 H11 123.00 . . . no H41 N4 H42 129.00 . . . no C11 N4 H41 114.00 . . . no C11 N4 H42 114.00 . . . no C12 N5 H51 116.00 . . . no C11 N5 H51 118.00 . . . no N1 C1 C2 109.95(18) . . . yes C1 C2 C10 125.0(2) . . . no C3 C2 C10 128.31(18) . . . no C1 C2 C3 106.67(17) . . . no C2 C3 C4 134.00(18) . . . no C2 C3 C8 106.28(17) . . . no C4 C3 C8 119.65(19) . . . no C3 C4 C5 118.4(2) . . . no O1 C5 C4 114.88(19) . . . yes C4 C5 C6 121.8(2) . . . no O1 C5 C6 123.35(19) . . . yes C5 C6 C7 120.4(2) . . . no C6 C7 C8 118.8(2) . . . no C3 C8 C7 121.0(2) . . . no N1 C8 C3 108.17(18) . . . yes N1 C8 C7 130.9(2) . . . yes N2 C10 C2 121.83(19) . . . yes N4 C11 N5 116.2(2) . . . yes N3 C11 N4 124.8(2) . . . yes N3 C11 N5 119.02(19) . . . yes N5 C12 C13 124.9(3) . . . yes N5 C12 C13' 94.6(3) . . . yes C13 C12 C13' 37.7(4) . . . no C12 C13 C13' 82.5(5) . . . no C12 C13 C14 116.5(5) . . . no C13' C13 C14 53.5(6) . . . no C12 C13 C14' 123.4(8) . . . no C13' C13 C14' 77.3(11) . . . no C14 C13 C14' 24.1(10) . . . no C14 C13' C14' 21.7(8) . . . no C12 C13' C14 118.4(6) . . . no C12 C13' C14' 100.7(8) . . . no C12 C13' C13 59.7(4) . . . no C13 C13' C14' 59.2(9) . . . no C13 C13' C14 80.5(8) . . . no C13 C14 C13' 46.0(5) . . . no C13 C14 C14' 65.4(17) . . . no C13 C14 C15' 123.9(8) . . . no C13' C14 C14' 110.8(18) . . . no C13 C14 C15 129.3(5) . . . no C13' C14 C15' 134.1(8) . . . no C14' C14 C15' 88(2) . . . no C13' C14 C15 126.6(6) . . . no C14' C14 C15 100.8(18) . . . no C15 C14 C15' 13.1(9) . . . no C13' C14' C15' 105.4(14) . . . no C13 C14' C13' 43.6(7) . . . no C13 C14' C14 91(2) . . . no C13 C14' C15' 126.4(13) . . . no C14 C14' C15' 69.3(18) . . . no C13' C14' C14 47.5(15) . . . no C14 C15 C16 116.6(6) . . . no C14 C15 C16' 110.5(8) . . . no C14 C15 C15' 45(2) . . . no C15' C15 C16' 100(2) . . . no C16 C15 C16' 45.5(11) . . . no C15' C15 C16 78(2) . . . no C15 C15' C16' 61(2) . . . no C16 C15' C16' 43.9(11) . . . no C14 C15' C16 141.8(11) . . . no C14 C15' C16' 120.2(12) . . . no C14' C15' C15 145(3) . . . no C14' C15' C16 126.7(15) . . . no C14' C15' C16' 125.6(12) . . . no C14 C15' C14' 22.9(9) . . . no C14 C15' C15 122(3) . . . no C15 C15' C16 83(2) . . . no C15 C16 C15' 18.7(8) . . . no C15 C16 C16' 56.1(10) . . . no C15' C16 C16' 65.9(12) . . . no C15 C16' C15' 19.4(8) . . . no C15 C16' C16 78.5(12) . . . no C15' C16' C16 70.1(14) . . . no N1 C1 H1 125.00 . . . no C2 C1 H1 125.00 . . . no C5 C4 H4 121.00 . . . no C3 C4 H4 121.00 . . . no C5 C6 H6 120.00 . . . no C7 C6 H6 120.00 . . . no C6 C7 H7 121.00 . . . no C8 C7 H7 121.00 . . . no O1 C9 H92 109.00 . . . no O1 C9 H93 110.00 . . . no H91 C9 H92 109.00 . . . no H91 C9 H93 110.00 . . . no H92 C9 H93 109.00 . . . no O1 C9 H91 109.00 . . . no N2 C10 H10 119.00 . . . no C2 C10 H10 119.00 . . . no N5 C12 H122 114.00 . . . no C13 C12 H121 105.00 . . . no C13 C12 H122 108.00 . . . no C13' C12 H121 139.00 . . . no C13' C12 H122 108.00 . . . no H121 C12 H122 99.00 . . . no N5 C12 H121 103.00 . . . no 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 C9 O1 C5 C4 -168.3(2) . . . . no C9 O1 C5 C6 11.6(3) . . . . no C8 N1 C1 C2 -2.5(2) . . . . no C1 N1 C8 C3 2.4(2) . . . . no C1 N1 C8 C7 -177.1(2) . . . . no C10 N2 N3 C11 -178.02(18) . . . . no N3 N2 C10 C2 178.52(18) . . . . no N2 N3 C11 N4 -2.6(3) . . . . no N2 N3 C11 N5 178.99(18) . . . . no C12 N5 C11 N3 -0.8(4) . . . . no C12 N5 C11 N4 -179.3(2) . . . . no C11 N5 C12 C13 -166.4(3) . . . . no C11 N5 C12 C13' 169.3(3) . . . . no N1 C1 C2 C3 1.6(2) . . . . no N1 C1 C2 C10 179.75(19) . . . . no C1 C2 C3 C4 176.5(2) . . . . no C1 C2 C3 C8 -0.2(2) . . . . no C10 C2 C3 C4 -1.5(4) . . . . no C10 C2 C3 C8 -178.2(2) . . . . no C1 C2 C10 N2 177.4(2) . . . . no C3 C2 C10 N2 -5.0(3) . . . . no C2 C3 C4 C5 -175.6(2) . . . . no C8 C3 C4 C5 0.7(3) . . . . no C2 C3 C8 N1 -1.3(2) . . . . no C2 C3 C8 C7 178.2(2) . . . . no C4 C3 C8 N1 -178.60(19) . . . . no C4 C3 C8 C7 0.9(3) . . . . no C3 C4 C5 O1 178.62(19) . . . . no C3 C4 C5 C6 -1.3(3) . . . . no O1 C5 C6 C7 -179.6(2) . . . . no C4 C5 C6 C7 0.3(3) . . . . no C5 C6 C7 C8 1.3(3) . . . . no C6 C7 C8 N1 177.5(2) . . . . no C6 C7 C8 C3 -2.0(3) . . . . no N5 C12 C13 C13' -42.0(6) . . . . no N5 C12 C13 C14 -84.6(6) . . . . no N5 C12 C13 C14' -111.3(12) . . . . no C13' C12 C13 C14 -42.6(6) . . . . no C13' C12 C13 C14' -69.3(12) . . . . no N5 C12 C13' C13 146.6(5) . . . . no N5 C12 C13' C14 -155.6(7) . . . . no N5 C12 C13' C14' -169.0(8) . . . . no C13 C12 C13' C14 57.8(7) . . . . no C13 C12 C13' C14' 44.4(8) . . . . no C12 C13 C13' C14 -131.1(4) . . . . no C12 C13 C13' C14' -126.8(8) . . . . no C14 C13 C13' C12 131.1(4) . . . . no C14 C13 C13' C14' 4.3(8) . . . . no C14' C13 C13' C12 126.8(8) . . . . no C14' C13 C13' C14 -4.3(8) . . . . no C12 C13 C14 C13' 56.7(5) . . . . no C12 C13 C14 C14' -113.1(19) . . . . no C12 C13 C14 C15 163.0(7) . . . . no C12 C13 C14 C15' 177.9(10) . . . . no C13' C13 C14 C14' -169.8(19) . . . . no C13' C13 C14 C15 106.4(9) . . . . no C13' C13 C14 C15' 121.2(12) . . . . no C14' C13 C14 C13' 169.8(19) . . . . no C14' C13 C14 C15 -84(2) . . . . no C14' C13 C14 C15' -69(2) . . . . no C12 C13 C14' C13' 72.0(9) . . . . no C12 C13 C14' C14 80.4(19) . . . . no C12 C13 C14' C15' 144.8(16) . . . . no C13' C13 C14' C14 8.4(16) . . . . no C13' C13 C14' C15' 72.8(19) . . . . no C14 C13 C14' C13' -8.4(16) . . . . no C14 C13 C14' C15' 64(2) . . . . no C12 C13' C14 C13 -47.8(5) . . . . no C12 C13' C14 C14' -38(2) . . . . no C12 C13' C14 C15 -160.1(6) . . . . no C12 C13' C14 C15' -146.0(13) . . . . no C13 C13' C14 C14' 9.9(19) . . . . no C13 C13' C14 C15 -112.3(8) . . . . no C13 C13' C14 C15' -98.2(15) . . . . no C14' C13' C14 C13 -9.9(19) . . . . no C14' C13' C14 C15 -122(2) . . . . no C14' C13' C14 C15' -108(2) . . . . no C12 C13' C14' C13 -44.8(6) . . . . no C12 C13' C14' C14 146.7(17) . . . . no C12 C13' C14' C15' -171.9(10) . . . . no C13 C13' C14' C14 -169(2) . . . . no C13 C13' C14' C15' -127.1(13) . . . . no C14 C13' C14' C13 169(2) . . . . no C14 C13' C14' C15' 41.5(14) . . . . no C13 C14 C14' C13' 7.9(15) . . . . no C13 C14 C14' C15' -129.1(10) . . . . no C13' C14 C14' C13 -7.9(15) . . . . no C13' C14 C14' C15' -137.0(10) . . . . no C15 C14 C14' C13 128.4(8) . . . . no C15 C14 C14' C13' 136.3(12) . . . . no C15 C14 C14' C15' -0.7(7) . . . . no C15' C14 C14' C13 129.1(10) . . . . no C15' C14 C14' C13' 137.0(10) . . . . no C13 C14 C15 C15' 70(3) . . . . no C13 C14 C15 C16 104.2(10) . . . . no C13 C14 C15 C16' 153.6(13) . . . . no C13' C14 C15 C15' 129(3) . . . . no C13' C14 C15 C16 163.6(10) . . . . no C13' C14 C15 C16' -147.0(14) . . . . no C14' C14 C15 C15' 3(3) . . . . no C14' C14 C15 C16 37.2(19) . . . . no C14' C14 C15 C16' 87(2) . . . . no C15' C14 C15 C16 34(3) . . . . no C15' C14 C15 C16' 84(3) . . . . no C13 C14 C15' C14' 58.1(18) . . . . no C13 C14 C15' C15 -119(3) . . . . no C13 C14 C15' C16 117(2) . . . . no C13 C14 C15' C16' 169.0(14) . . . . no C13' C14 C15' C14' 117(2) . . . . no C13' C14 C15' C15 -60(3) . . . . no C13' C14 C15' C16 175.6(18) . . . . no C13' C14 C15' C16' -131.9(16) . . . . no C14' C14 C15' C15 -177(3) . . . . no C14' C14 C15' C16 58(3) . . . . no C14' C14 C15' C16' 111(2) . . . . no C15 C14 C15' C14' 177(3) . . . . no C15 C14 C15' C16 -125(4) . . . . no C15 C14 C15' C16' -72(3) . . . . no C13 C14' C15' C14 -75(2) . . . . no C13 C14' C15' C15 -70(5) . . . . no C13 C14' C15' C16 146.5(17) . . . . no C13 C14' C15' C16' -158(2) . . . . no C13' C14' C15' C14 -31.5(12) . . . . no C13' C14' C15' C15 -27(4) . . . . no C13' C14' C15' C16 -170.4(14) . . . . no C13' C14' C15' C16' -115(2) . . . . no C14 C14' C15' C15 4(5) . . . . no C14 C14' C15' C16 -139(2) . . . . no C14 C14' C15' C16' -84(3) . . . . no C14 C15 C15' C14' -2(2) . . . . no C14 C15 C15' C16 149(2) . . . . no C14 C15 C15' C16' 109(2) . . . . no C16 C15 C15' C14 -149(2) . . . . no C16 C15 C15' C14' -151(4) . . . . no C16 C15 C15' C16' -40.2(13) . . . . no C16' C15 C15' C14 -109(2) . . . . no C16' C15 C15' C14' -111(4) . . . . no C16' C15 C15' C16 40.2(13) . . . . no C14 C15 C16 C15' -24(2) . . . . no C14 C15 C16 C16' 93.3(11) . . . . no C15' C15 C16 C16' 117(2) . . . . no C16' C15 C16 C15' -117(2) . . . . no C14 C15 C16' C15' -45(2) . . . . no C14 C15 C16' C16 -107.6(9) . . . . no C15' C15 C16' C16 -62(3) . . . . no C16 C15 C16' C15' 62(3) . . . . no C14 C15' C16 C15 136(4) . . . . no C14 C15' C16 C16' 82(2) . . . . no C14' C15' C16 C15 160(3) . . . . no C14' C15' C16 C16' 105.9(18) . . . . no C15 C15' C16 C16' -54(2) . . . . no C16' C15' C16 C15 54(2) . . . . no C14 C15' C16' C15 112(4) . . . . no C14 C15' C16' C16 -134.9(17) . . . . no C14' C15' C16' C15 139(4) . . . . no C14' C15' C16' C16 -108(2) . . . . no C15 C15' C16' C16 113(3) . . . . no C16 C15' C16' C15 -113(3) . . . . no C15 C16 C16' C15' -18.2(7) . . . . no C15' C16 C16' C15 18.2(7) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N1 H11 N3 0.8600 2.1000 2.952(3) 170.00 2_646 yes O2 H21 O1 0.9300 1.9500 2.878(3) 177.00 1_655 yes O2 H22 N3 0.8600 2.1100 2.929(3) 160.00 . yes N4 H41 O2 0.9600 2.0500 2.992(3) 165.00 3_667 yes N5 H51 O2 0.9600 2.3900 3.223(3) 144.00 3_667 yes