data_General _audit_creation_date 2014-04-29 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'ENTER NAME' _publ_contact_author_email 'ENTER EMAIL ADDRESS' _publ_contact_author_fax 'ENTER FAX NUMBER' _publ_contact_author_phone 'ENTER PHONE NUMBER' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal 'ENTER JOURNAL NAME HERE' _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku (2010). CrystalStructure. Version 4.0. Rigaku Corporation, Tokyo, Japan. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. SHELX97 Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #============================================================================== data_User-defined #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C21 H20 N4 O5' _chemical_formula_moiety 'C21 H20 N4 O5' _chemical_formula_weight 408.41 _chemical_melting_point ? #============================================================================== # 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 11.251(2) _cell_length_b 10.0262(18) _cell_length_c 17.905(4) _cell_angle_alpha 90.0000 _cell_angle_beta 90.013(7) _cell_angle_gamma 90.0000 _cell_volume 2019.7(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4061 _cell_measurement_theta_min 3.55 _cell_measurement_theta_max 24.97 _cell_measurement_temperature 293 #------------------------------------------------------------------------------ _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.060 _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856.00 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.409 _exptl_absorpt_correction_T_max 0.994 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 10853 _diffrn_reflns_av_R_equivalents 0.1004 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measured_fraction_theta_full 0.984 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # 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 3500 _reflns_number_gt 1533 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1411 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3500 _refine_ls_number_parameters 274 _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.180 _refine_diff_density_min -0.200 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'H' 'H' 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; 'N' 'N' 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'O' 'O' 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.5904(2) 1.1066(3) 0.32734(15) 0.0785(9) Uani 1.0 4 d . . . O2 O 0.4861(3) 0.9286(3) 0.29192(16) 0.0904(11) Uani 1.0 4 d . . . O3 O 0.51496(19) 0.78380(19) 0.43660(14) 0.0714(8) Uani 1.0 4 d . . . O4 O 0.35060(18) 0.75381(18) 0.50582(13) 0.0625(8) Uani 1.0 4 d . . . O5 O -0.17449(19) 0.9774(2) 0.81217(14) 0.0718(8) Uani 1.0 4 d . . . N1 N 0.2794(2) 1.1508(2) 0.45315(15) 0.0483(8) Uani 1.0 4 d . . . N2 N 0.3579(3) 1.1672(3) 0.39584(16) 0.0547(8) Uani 1.0 4 d . . . N3 N -0.0304(3) 1.4017(3) 0.5631(2) 0.0947(14) Uani 1.0 4 d . . . N4 N 0.2022(3) 1.3617(2) 0.43318(16) 0.0645(10) Uani 1.0 4 d . . . C1 C 0.4135(3) 1.0500(3) 0.39230(19) 0.0502(10) Uani 1.0 4 d . . . C2 C 0.3730(3) 0.9581(3) 0.44617(19) 0.0504(10) Uani 1.0 4 d . . . C3 C 0.2841(3) 1.0256(3) 0.48560(18) 0.0485(10) Uani 1.0 4 d . . . C4 C 0.2076(3) 0.9986(3) 0.54602(18) 0.0494(10) Uani 1.0 4 d . . . C5 C 0.1294(3) 1.0936(3) 0.56967(19) 0.0480(10) Uani 1.0 4 d . . . C6 C 0.1266(3) 1.2200(3) 0.53305(19) 0.0507(10) Uani 1.0 4 d . . . C7 C 0.2011(3) 1.2492(3) 0.4735(2) 0.0512(10) Uani 1.0 4 d . . . C8 C 0.5085(3) 1.0333(3) 0.3344(2) 0.0592(11) Uani 1.0 4 d . . . C9 C 0.5768(4) 0.8914(4) 0.2373(3) 0.1067(19) Uani 1.0 4 d . . . C10 C 0.6493(4) 0.7797(5) 0.2681(3) 0.1137(18) Uani 1.0 4 d . . . C11 C 0.4215(3) 0.8250(3) 0.4611(2) 0.0559(10) Uani 1.0 4 d . . . C12 C 0.3938(4) 0.6231(3) 0.5281(3) 0.0720(12) Uani 1.0 4 d . . . C13 C 0.3113(4) 0.5691(4) 0.5861(3) 0.0943(15) Uani 1.0 4 d . . . C14 C 0.0475(3) 1.0644(3) 0.63337(19) 0.0481(9) Uani 1.0 4 d . . . C15 C -0.0153(3) 0.9458(3) 0.6338(2) 0.0597(11) Uani 1.0 4 d . . . C16 C -0.0919(3) 0.9139(3) 0.6923(3) 0.0623(11) Uani 1.0 4 d . . . C17 C -0.1041(3) 0.9995(3) 0.7512(2) 0.0546(10) Uani 1.0 4 d . . . C18 C -0.0403(3) 1.1188(3) 0.7520(2) 0.0609(11) Uani 1.0 4 d . . . C19 C 0.0327(3) 1.1504(3) 0.6932(2) 0.0579(11) Uani 1.0 4 d . . . C20 C -0.2367(4) 0.8535(4) 0.8144(3) 0.0876(15) Uani 1.0 4 d . . . C21 C 0.0379(3) 1.3189(3) 0.5504(2) 0.0660(12) Uani 1.0 4 d . . . H4 H 0.2104 0.9161 0.5697 0.0593 Uiso 1.0 4 calc R . . H4A H 0.2507 1.3699 0.3963 0.0774 Uiso 1.0 4 calc R . . H4B H 0.1545 1.4257 0.4442 0.0774 Uiso 1.0 4 calc R . . H9A H 0.6275 0.9674 0.2268 0.1280 Uiso 1.0 4 calc R . . H9B H 0.5393 0.8639 0.1910 0.1280 Uiso 1.0 4 calc R . . H10A H 0.7029 0.7479 0.2304 0.1365 Uiso 1.0 4 calc R . . H10B H 0.5977 0.7085 0.2833 0.1365 Uiso 1.0 4 calc R . . H10C H 0.6939 0.8107 0.3104 0.1365 Uiso 1.0 4 calc R . . H12A H 0.4736 0.6304 0.5482 0.0864 Uiso 1.0 4 calc R . . H12B H 0.3960 0.5639 0.4853 0.0864 Uiso 1.0 4 calc R . . H13A H 0.3359 0.4807 0.5998 0.1132 Uiso 1.0 4 calc R . . H13B H 0.2320 0.5662 0.5664 0.1132 Uiso 1.0 4 calc R . . H13C H 0.3131 0.6257 0.6293 0.1132 Uiso 1.0 4 calc R . . H15 H -0.0063 0.8863 0.5943 0.0716 Uiso 1.0 4 calc R . . H16 H -0.1345 0.8344 0.6913 0.0747 Uiso 1.0 4 calc R . . H18 H -0.0472 1.1768 0.7923 0.0731 Uiso 1.0 4 calc R . . H19 H 0.0731 1.2313 0.6935 0.0695 Uiso 1.0 4 calc R . . H20A H -0.1814 0.7816 0.8074 0.1052 Uiso 1.0 4 calc R . . H20B H -0.2951 0.8515 0.7753 0.1052 Uiso 1.0 4 calc R . . H20C H -0.2753 0.8440 0.8619 0.1052 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0713(16) 0.0738(15) 0.090(3) -0.0075(13) 0.0347(17) -0.0030(14) O2 0.104(2) 0.0823(16) 0.085(3) -0.0132(15) 0.0531(19) -0.0241(16) O3 0.0683(15) 0.0679(13) 0.078(3) 0.0135(12) 0.0254(15) -0.0018(13) O4 0.0718(15) 0.0480(12) 0.068(2) 0.0103(11) 0.0228(14) 0.0057(11) O5 0.0774(16) 0.0758(15) 0.062(2) -0.0122(13) 0.0384(15) -0.0034(13) N1 0.0512(15) 0.0463(13) 0.047(2) 0.0006(13) 0.0194(15) 0.0017(13) N2 0.0586(16) 0.0527(15) 0.053(3) 0.0064(14) 0.0197(16) 0.0004(13) N3 0.100(3) 0.0777(19) 0.106(4) 0.030(2) 0.052(3) 0.0253(19) N4 0.078(2) 0.0512(15) 0.064(3) 0.0096(14) 0.0301(18) 0.0125(15) C1 0.052(2) 0.0534(17) 0.045(3) 0.0021(16) 0.0085(19) -0.0047(17) C2 0.057(2) 0.0453(16) 0.048(3) 0.0059(16) 0.0146(19) 0.0001(16) C3 0.053(2) 0.0452(17) 0.047(3) 0.0022(15) 0.0093(19) 0.0037(16) C4 0.056(2) 0.0458(16) 0.046(3) -0.0005(16) 0.0139(19) 0.0040(15) C5 0.0500(19) 0.0468(16) 0.047(3) 0.0017(15) 0.0116(18) -0.0022(16) C6 0.0508(19) 0.0495(17) 0.052(3) 0.0026(16) 0.0186(18) -0.0015(16) C7 0.0506(19) 0.0468(17) 0.056(3) 0.0037(16) 0.0107(19) -0.0045(16) C8 0.070(3) 0.053(2) 0.055(3) 0.0104(19) 0.017(3) 0.0090(19) C9 0.136(4) 0.096(3) 0.088(5) 0.004(3) 0.067(4) -0.021(3) C10 0.087(3) 0.150(4) 0.105(5) 0.003(3) 0.026(3) -0.037(4) C11 0.064(3) 0.060(2) 0.044(3) 0.0015(19) 0.011(2) -0.0060(17) C12 0.091(3) 0.051(2) 0.074(4) 0.0116(18) 0.012(3) 0.0048(18) C13 0.125(4) 0.067(3) 0.090(4) -0.006(3) 0.019(3) 0.012(3) C14 0.0512(19) 0.0472(17) 0.046(3) 0.0047(16) 0.0085(18) 0.0019(16) C15 0.072(3) 0.0609(19) 0.047(3) -0.0069(18) 0.014(2) -0.0091(18) C16 0.060(3) 0.064(2) 0.063(3) -0.0128(18) 0.017(3) -0.0014(19) C17 0.056(2) 0.0599(19) 0.048(3) 0.0058(17) 0.014(2) -0.0013(18) C18 0.072(3) 0.060(2) 0.050(3) 0.0060(18) 0.017(2) -0.0082(17) C19 0.067(3) 0.0518(17) 0.054(3) -0.0039(17) 0.017(2) -0.0046(17) C20 0.086(3) 0.093(3) 0.084(4) -0.020(3) 0.041(3) 0.005(3) C21 0.074(3) 0.0536(19) 0.071(4) 0.0105(18) 0.032(3) 0.0104(18) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O1 C8 1.185(4) yes . . O2 C8 1.321(5) yes . . O2 C9 1.462(6) yes . . O3 C11 1.212(4) yes . . O4 C11 1.337(4) yes . . O4 C12 1.453(4) yes . . O5 C17 1.367(5) yes . . O5 C20 1.426(4) yes . . N1 N2 1.364(4) yes . . N1 C3 1.384(4) yes . . N1 C7 1.371(4) yes . . N2 C1 1.333(4) yes . . N3 C21 1.153(5) yes . . N4 C7 1.338(4) yes . . C1 C2 1.410(5) yes . . C1 C8 1.499(5) yes . . C2 C3 1.398(5) yes . . C2 C11 1.467(4) yes . . C3 C4 1.409(5) yes . . C4 C5 1.364(4) yes . . C5 C6 1.428(4) yes . . C5 C14 1.496(5) yes . . C6 C7 1.388(5) yes . . C6 C21 1.440(5) yes . . C9 C10 1.491(6) yes . . C12 C13 1.495(6) yes . . C14 C15 1.383(4) yes . . C14 C19 1.385(5) yes . . C15 C16 1.394(5) yes . . C16 C17 1.366(5) yes . . C17 C18 1.396(5) yes . . C18 C19 1.374(5) yes . . N4 H4A 0.860 no . . N4 H4B 0.860 no . . C4 H4 0.930 no . . C9 H9A 0.970 no . . C9 H9B 0.970 no . . C10 H10A 0.960 no . . C10 H10B 0.960 no . . C10 H10C 0.960 no . . C12 H12A 0.970 no . . C12 H12B 0.970 no . . C13 H13A 0.960 no . . C13 H13B 0.960 no . . C13 H13C 0.960 no . . C15 H15 0.930 no . . C16 H16 0.930 no . . C18 H18 0.930 no . . C19 H19 0.930 no . . C20 H20A 0.960 no . . C20 H20B 0.960 no . . C20 H20C 0.960 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C8 O2 C9 117.1(3) yes . . . C11 O4 C12 116.5(3) yes . . . C17 O5 C20 116.6(3) yes . . . N2 N1 C3 113.6(3) yes . . . N2 N1 C7 121.9(3) yes . . . C3 N1 C7 124.5(3) yes . . . N1 N2 C1 103.5(3) yes . . . N2 C1 C2 113.1(3) yes . . . N2 C1 C8 117.8(3) yes . . . C2 C1 C8 129.1(3) yes . . . C1 C2 C3 105.1(3) yes . . . C1 C2 C11 126.8(3) yes . . . C3 C2 C11 127.9(3) yes . . . N1 C3 C2 104.8(3) yes . . . N1 C3 C4 118.2(3) yes . . . C2 C3 C4 137.0(3) yes . . . C3 C4 C5 119.9(3) yes . . . C4 C5 C6 119.5(3) yes . . . C4 C5 C14 119.8(3) yes . . . C6 C5 C14 120.7(3) yes . . . C5 C6 C7 121.8(3) yes . . . C5 C6 C21 121.8(3) yes . . . C7 C6 C21 116.1(3) yes . . . N1 C7 N4 117.2(3) yes . . . N1 C7 C6 116.1(3) yes . . . N4 C7 C6 126.7(3) yes . . . O1 C8 O2 125.4(4) yes . . . O1 C8 C1 124.0(3) yes . . . O2 C8 C1 110.6(3) yes . . . O2 C9 C10 109.0(4) yes . . . O3 C11 O4 123.5(3) yes . . . O3 C11 C2 124.6(3) yes . . . O4 C11 C2 111.9(3) yes . . . O4 C12 C13 108.0(3) yes . . . C5 C14 C15 119.2(3) yes . . . C5 C14 C19 122.8(3) yes . . . C15 C14 C19 118.0(3) yes . . . C14 C15 C16 121.1(3) yes . . . C15 C16 C17 119.9(3) yes . . . O5 C17 C16 124.9(3) yes . . . O5 C17 C18 115.4(3) yes . . . C16 C17 C18 119.7(4) yes . . . C17 C18 C19 119.8(4) yes . . . C14 C19 C18 121.5(3) yes . . . N3 C21 C6 177.3(4) yes . . . C7 N4 H4A 120.002 no . . . C7 N4 H4B 119.999 no . . . H4A N4 H4B 119.998 no . . . C3 C4 H4 120.062 no . . . C5 C4 H4 120.069 no . . . O2 C9 H9A 109.876 no . . . O2 C9 H9B 109.876 no . . . C10 C9 H9A 109.876 no . . . C10 C9 H9B 109.880 no . . . H9A C9 H9B 108.285 no . . . C9 C10 H10A 109.473 no . . . C9 C10 H10B 109.471 no . . . C9 C10 H10C 109.474 no . . . H10A C10 H10B 109.467 no . . . H10A C10 H10C 109.470 no . . . H10B C10 H10C 109.472 no . . . O4 C12 H12A 110.098 no . . . O4 C12 H12B 110.088 no . . . C13 C12 H12A 110.102 no . . . C13 C12 H12B 110.089 no . . . H12A C12 H12B 108.423 no . . . C12 C13 H13A 109.476 no . . . C12 C13 H13B 109.473 no . . . C12 C13 H13C 109.467 no . . . H13A C13 H13B 109.475 no . . . H13A C13 H13C 109.465 no . . . H13B C13 H13C 109.471 no . . . C14 C15 H15 119.425 no . . . C16 C15 H15 119.425 no . . . C15 C16 H16 120.059 no . . . C17 C16 H16 120.064 no . . . C17 C18 H18 120.114 no . . . C19 C18 H18 120.110 no . . . C14 C19 H19 119.257 no . . . C18 C19 H19 119.268 no . . . O5 C20 H20A 109.468 no . . . O5 C20 H20B 109.469 no . . . O5 C20 H20C 109.471 no . . . H20A C20 H20B 109.476 no . . . H20A C20 H20C 109.468 no . . . H20B C20 H20C 109.476 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C8 O2 C9 C10 99.0(4) no . . . . C9 O2 C8 O1 7.4(5) no . . . . C9 O2 C8 C1 -174.2(3) no . . . . C11 O4 C12 C13 171.8(3) no . . . . C12 O4 C11 O3 3.3(5) no . . . . C12 O4 C11 C2 -176.3(3) no . . . . C20 O5 C17 C16 1.7(5) no . . . . C20 O5 C17 C18 -177.3(3) no . . . . N2 N1 C3 C2 0.4(3) no . . . . N2 N1 C3 C4 179.3(3) no . . . . C3 N1 N2 C1 -0.2(3) no . . . . N2 N1 C7 N4 1.9(4) no . . . . N2 N1 C7 C6 -179.6(3) no . . . . C7 N1 N2 C1 -177.8(3) no . . . . C3 N1 C7 N4 -175.5(3) no . . . . C3 N1 C7 C6 3.0(5) no . . . . C7 N1 C3 C2 178.0(3) no . . . . C7 N1 C3 C4 -3.2(5) no . . . . N1 N2 C1 C2 -0.2(4) no . . . . N1 N2 C1 C8 -179.5(3) no . . . . N2 C1 C2 C3 0.4(4) no . . . . N2 C1 C2 C11 -174.9(3) no . . . . N2 C1 C8 O1 53.4(5) no . . . . N2 C1 C8 O2 -125.0(3) no . . . . C2 C1 C8 O1 -125.8(4) no . . . . C2 C1 C8 O2 55.8(5) no . . . . C8 C1 C2 C3 179.7(3) no . . . . C8 C1 C2 C11 4.4(6) no . . . . C1 C2 C3 N1 -0.5(3) no . . . . C1 C2 C3 C4 -179.0(3) no . . . . C1 C2 C11 O3 11.8(6) no . . . . C1 C2 C11 O4 -168.7(3) no . . . . C3 C2 C11 O3 -162.4(3) no . . . . C3 C2 C11 O4 17.1(5) no . . . . C11 C2 C3 N1 174.7(3) no . . . . C11 C2 C3 C4 -3.8(6) no . . . . N1 C3 C4 C5 1.7(4) no . . . . C2 C3 C4 C5 -180.0(4) no . . . . C3 C4 C5 C6 -0.4(5) no . . . . C3 C4 C5 C14 179.5(3) no . . . . C4 C5 C6 C7 0.3(5) no . . . . C4 C5 C6 C21 173.5(3) no . . . . C4 C5 C14 C15 -47.5(4) no . . . . C4 C5 C14 C19 131.5(3) no . . . . C6 C5 C14 C15 132.3(3) no . . . . C6 C5 C14 C19 -48.7(5) no . . . . C14 C5 C6 C7 -179.5(3) no . . . . C14 C5 C6 C21 -6.3(5) no . . . . C5 C6 C7 N1 -1.5(5) no . . . . C5 C6 C7 N4 176.8(3) no . . . . C21 C6 C7 N1 -175.1(3) no . . . . C21 C6 C7 N4 3.2(5) no . . . . C5 C14 C15 C16 179.4(3) no . . . . C5 C14 C19 C18 -177.9(3) no . . . . C15 C14 C19 C18 1.1(5) no . . . . C19 C14 C15 C16 0.4(5) no . . . . C14 C15 C16 C17 -1.1(5) no . . . . C15 C16 C17 O5 -178.6(3) no . . . . C15 C16 C17 C18 0.4(5) no . . . . O5 C17 C18 C19 -179.8(3) no . . . . C16 C17 C18 C19 1.1(5) no . . . . C17 C18 C19 C14 -1.9(5) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 N2 2.953(4) no . . O1 C2 3.568(4) no . . O1 C9 2.697(5) no . . O1 C10 3.508(5) no . . O2 O3 2.987(4) no . . O2 N2 3.357(4) no . . O2 C2 3.056(5) no . . O2 C11 3.284(5) no . . O3 C1 3.009(4) no . . O3 C8 3.100(4) no . . O3 C10 3.375(6) no . . O3 C12 2.672(4) no . . O4 C3 2.849(4) no . . O4 C4 3.021(4) no . . N1 C5 2.744(4) no . . N1 C8 3.544(5) no . . N2 N4 2.705(4) no . . N2 C4 3.598(4) no . . N3 N4 3.524(5) no . . N3 C5 3.576(4) no . . N3 C7 3.420(5) no . . N3 C19 3.503(5) no . . N4 C21 2.831(5) no . . C1 C7 3.437(5) no . . C2 C7 3.535(4) no . . C3 C6 2.768(4) no . . C4 C7 2.830(4) no . . C4 C11 3.336(5) no . . C4 C15 3.007(5) no . . C6 C19 3.134(5) no . . C8 C10 3.223(6) no . . C8 C11 3.235(5) no . . C14 C17 2.790(5) no . . C14 C21 2.954(5) no . . C15 C18 2.752(5) no . . C16 C19 2.755(5) no . . C16 C20 2.792(6) no . . C19 C21 3.064(5) no . . O1 O4 3.365(4) no . 3_676 O1 C4 3.379(4) no . 3_676 O1 C18 3.400(4) no . 4_574 O1 C19 3.483(4) no . 4_574 O3 N1 3.111(4) no . 3_676 O3 N2 3.360(4) no . 3_676 O3 C1 3.579(4) no . 3_676 O3 C2 3.562(4) no . 3_676 O3 C3 3.271(4) no . 3_676 O3 C7 3.592(4) no . 3_676 O4 O1 3.365(4) no . 3_676 O5 N4 3.037(4) no . 4_475 N1 O3 3.111(4) no . 3_676 N1 C15 3.491(4) no . 3_576 N1 C16 3.414(5) no . 3_576 N2 O3 3.360(4) no . 3_676 N2 C11 3.567(5) no . 3_676 N2 C16 3.480(5) no . 3_576 N2 C18 3.542(5) no . 4_574 N3 N3 3.076(5) no . 3_586 N3 N4 3.062(4) no . 3_586 N3 C20 3.452(6) no . 2_456 N3 C21 3.463(5) no . 3_586 N4 O5 3.037(4) no . 4_574 N4 N3 3.062(4) no . 3_586 C1 O3 3.579(4) no . 3_676 C1 C11 3.450(5) no . 3_676 C2 O3 3.562(4) no . 3_676 C2 C2 3.549(5) no . 3_676 C2 C11 3.582(5) no . 3_676 C3 O3 3.271(4) no . 3_676 C4 O1 3.379(4) no . 3_676 C7 O3 3.592(4) no . 3_676 C7 C15 3.447(5) no . 3_576 C11 N2 3.567(5) no . 3_676 C11 C1 3.450(5) no . 3_676 C11 C2 3.582(5) no . 3_676 C12 C12 3.580(5) no . 3_666 C15 N1 3.491(4) no . 3_576 C15 C7 3.447(5) no . 3_576 C16 N1 3.414(5) no . 3_576 C16 N2 3.480(5) no . 3_576 C18 O1 3.400(4) no . 4_475 C18 N2 3.542(5) no . 4_475 C19 O1 3.483(4) no . 4_475 C20 N3 3.452(6) no . 2_446 C21 N3 3.463(5) no . 3_586 O1 H9A 2.3158 no . . O1 H9B 3.4939 no . . O1 H10C 3.2011 no . . O2 H10A 3.2324 no . . O2 H10B 2.5439 no . . O2 H10C 2.6400 no . . O3 H10B 2.9948 no . . O3 H10C 3.0392 no . . O3 H12A 2.5646 no . . O3 H12B 2.7222 no . . O4 H4 2.5387 no . . O4 H13A 3.2179 no . . O4 H13B 2.5488 no . . O4 H13C 2.5922 no . . O5 H16 2.6340 no . . O5 H18 2.4852 no . . N1 H4 3.2400 no . . N1 H4A 2.4417 no . . N1 H4B 3.0976 no . . N2 H4A 2.3628 no . . N2 H4B 3.5641 no . . N3 H4B 2.9867 no . . N3 H19 3.1175 no . . C2 H4 2.9012 no . . C4 H15 2.7947 no . . C5 H15 2.6167 no . . C5 H19 2.6873 no . . C6 H4 3.2568 no . . C6 H4A 3.1940 no . . C6 H4B 2.6239 no . . C6 H19 2.9366 no . . C8 H9A 2.4380 no . . C8 H9B 3.0977 no . . C8 H10B 3.5289 no . . C8 H10C 3.0851 no . . C11 H4 3.2028 no . . C11 H12A 2.5657 no . . C11 H12B 2.6687 no . . C14 H4 2.6211 no . . C14 H16 3.2537 no . . C14 H18 3.2419 no . . C15 H4 2.8028 no . . C15 H19 3.2132 no . . C16 H18 3.2264 no . . C16 H20A 2.6502 no . . C16 H20B 2.7977 no . . C17 H15 3.2226 no . . C17 H19 3.2322 no . . C17 H20A 2.5585 no . . C17 H20B 2.6464 no . . C17 H20C 3.1734 no . . C18 H16 3.2304 no . . C19 H15 3.2144 no . . C20 H16 2.4925 no . . C21 H4B 2.5480 no . . C21 H19 2.7353 no . . H4 H13B 3.5170 no . . H4 H13C 3.3095 no . . H4 H15 2.4960 no . . H9A H10A 2.3594 no . . H9A H10B 2.8065 no . . H9A H10C 2.2937 no . . H9B H10A 2.2890 no . . H9B H10B 2.3647 no . . H9B H10C 2.8060 no . . H12A H13A 2.3465 no . . H12A H13B 2.8124 no . . H12A H13C 2.3178 no . . H12B H13A 2.3150 no . . H12B H13B 2.3492 no . . H12B H13C 2.8123 no . . H15 H16 2.3167 no . . H16 H20A 2.2094 no . . H16 H20B 2.3572 no . . H16 H20C 3.4417 no . . H18 H19 2.2949 no . . O1 H4 2.9101 no . 3_676 O1 H10A 2.9124 no . 2_655 O1 H12A 3.5265 no . 3_676 O1 H13C 2.9976 no . 3_676 O1 H18 2.7397 no . 4_574 O1 H19 2.9028 no . 4_574 O2 H16 3.4695 no . 4_564 O2 H20A 2.8412 no . 4_564 O2 H20B 3.3057 no . 3_576 O3 H13A 3.2056 no . 3_666 O3 H20A 3.2646 no . 4_564 O4 H20A 3.5876 no . 4_564 O4 H20C 3.0997 no . 4_564 O5 H4A 2.3077 no . 4_475 O5 H4B 3.1989 no . 4_475 O5 H12B 3.2255 no . 4_465 N1 H12A 3.5408 no . 3_676 N1 H15 3.2090 no . 3_576 N1 H16 3.0611 no . 3_576 N2 H12A 2.9523 no . 3_676 N2 H16 2.9584 no . 3_576 N2 H18 2.6496 no . 4_574 N2 H20B 3.1502 no . 3_576 N3 H4A 3.4527 no . 3_586 N3 H4B 2.2277 no . 3_586 N3 H9B 3.3745 no . 4_475 N3 H13B 3.3822 no . 1_565 N3 H13B 3.2591 no . 3_576 N3 H20B 3.5333 no . 2_456 N3 H20C 2.6307 no . 2_456 N4 H9B 3.5110 no . 2_555 N4 H12B 3.1201 no . 1_565 N4 H13A 3.5472 no . 1_565 N4 H13B 3.1636 no . 1_565 N4 H15 3.3589 no . 3_576 N4 H16 3.0685 no . 3_576 N4 H20C 3.2255 no . 4_574 C1 H18 3.3016 no . 4_574 C1 H20B 3.4282 no . 3_576 C2 H20A 3.5097 no . 4_564 C3 H15 3.5491 no . 3_576 C4 H10C 3.3903 no . 3_676 C4 H15 3.5741 no . 3_576 C5 H10C 3.0794 no . 3_676 C5 H15 3.2528 no . 3_576 C6 H10C 3.4690 no . 3_676 C6 H15 2.8580 no . 3_576 C7 H13A 3.5777 no . 1_565 C7 H15 2.8502 no . 3_576 C7 H16 3.1579 no . 3_576 C8 H18 3.0669 no . 4_574 C8 H19 3.5309 no . 4_574 C8 H20B 3.3099 no . 3_576 C9 H13B 3.5487 no . 4_564 C9 H13C 3.2919 no . 4_564 C9 H16 3.3845 no . 4_564 C10 H13A 3.5270 no . 3_666 C10 H13C 3.2360 no . 4_564 C10 H19 3.2005 no . 3_676 C11 H20A 3.1705 no . 4_564 C11 H20C 3.3058 no . 4_564 C12 H12A 3.2490 no . 3_666 C12 H12B 3.0275 no . 3_666 C12 H20C 3.5472 no . 4_564 C13 H4B 3.4111 no . 1_545 C13 H9A 3.2802 no . 4_465 C13 H10A 3.3957 no . 4_465 C13 H18 3.5982 no . 2_546 C14 H10C 3.3237 no . 3_676 C15 H9B 3.3269 no . 4_465 C15 H10A 3.5762 no . 4_465 C15 H10B 3.3428 no . 4_465 C16 H9B 3.1516 no . 4_465 C16 H10B 2.9503 no . 4_465 C17 H4A 3.3376 no . 4_475 C17 H10B 3.1357 no . 4_465 C18 H4A 3.4953 no . 4_475 C18 H13C 3.3238 no . 2_556 C18 H20B 3.0185 no . 2_456 C19 H10A 3.4293 no . 3_676 C19 H10C 3.1015 no . 3_676 C19 H20B 3.3960 no . 2_456 C20 H4A 3.1411 no . 4_475 C20 H4B 3.4352 no . 4_475 C20 H12B 3.5033 no . 4_465 C20 H18 3.5634 no . 2_446 C21 H4B 3.3546 no . 3_586 C21 H13B 3.3169 no . 1_565 C21 H15 3.3283 no . 3_576 C21 H20C 3.3552 no . 2_456 H4 O1 2.9101 no . 3_676 H4 H10A 3.3145 no . 4_465 H4A O5 2.3077 no . 4_574 H4A N3 3.4527 no . 3_586 H4A C17 3.3376 no . 4_574 H4A C18 3.4953 no . 4_574 H4A C20 3.1411 no . 4_574 H4A H12A 3.2572 no . 3_676 H4A H12B 2.9993 no . 1_565 H4A H16 2.8923 no . 3_576 H4A H18 2.9760 no . 4_574 H4A H20B 3.5723 no . 4_574 H4A H20C 2.9492 no . 4_574 H4B O5 3.1989 no . 4_574 H4B N3 2.2277 no . 3_586 H4B C13 3.4111 no . 1_565 H4B C20 3.4352 no . 4_574 H4B C21 3.3546 no . 3_586 H4B H9B 3.3157 no . 2_555 H4B H12B 3.1376 no . 1_565 H4B H13A 3.4972 no . 1_565 H4B H13B 2.7449 no . 1_565 H4B H16 3.5691 no . 3_576 H4B H20C 2.8507 no . 4_574 H9A C13 3.2802 no . 4_564 H9A H10A 3.4834 no . 2_655 H9A H13A 3.3075 no . 4_564 H9A H13B 3.1215 no . 4_564 H9A H13C 2.8770 no . 4_564 H9A H19 3.1398 no . 4_574 H9B N3 3.3745 no . 4_574 H9B N4 3.5110 no . 2_545 H9B C15 3.3269 no . 4_564 H9B C16 3.1516 no . 4_564 H9B H4B 3.3157 no . 2_545 H9B H13B 3.1895 no . 4_564 H9B H13C 3.2749 no . 4_564 H9B H15 3.0909 no . 4_564 H9B H16 2.7883 no . 4_564 H9B H20A 3.5553 no . 4_564 H10A O1 2.9124 no . 2_645 H10A C13 3.3957 no . 4_564 H10A C15 3.5762 no . 4_564 H10A C19 3.4293 no . 3_676 H10A H4 3.3145 no . 4_564 H10A H9A 3.4834 no . 2_645 H10A H13B 3.4931 no . 4_564 H10A H13C 2.5334 no . 4_564 H10A H19 2.8727 no . 3_676 H10B C15 3.3428 no . 4_564 H10B C16 2.9503 no . 4_564 H10B C17 3.1357 no . 4_564 H10B H13A 2.9215 no . 3_666 H10B H16 3.1174 no . 4_564 H10B H20A 3.1717 no . 4_564 H10C C4 3.3903 no . 3_676 H10C C5 3.0794 no . 3_676 H10C C6 3.4690 no . 3_676 H10C C14 3.3237 no . 3_676 H10C C19 3.1015 no . 3_676 H10C H13A 3.3526 no . 3_666 H10C H13C 3.5654 no . 4_564 H10C H19 2.6564 no . 3_676 H12A O1 3.5265 no . 3_676 H12A N1 3.5408 no . 3_676 H12A N2 2.9523 no . 3_676 H12A C12 3.2490 no . 3_666 H12A H4A 3.2572 no . 3_676 H12A H12A 3.1898 no . 3_666 H12A H12B 2.5116 no . 3_666 H12A H13A 3.5866 no . 3_666 H12A H18 3.0084 no . 2_546 H12B O5 3.2255 no . 4_564 H12B N4 3.1201 no . 1_545 H12B C12 3.0275 no . 3_666 H12B C20 3.5033 no . 4_564 H12B H4A 2.9993 no . 1_545 H12B H4B 3.1376 no . 1_545 H12B H12A 2.5116 no . 3_666 H12B H12B 2.7194 no . 3_666 H12B H13A 3.4089 no . 3_666 H12B H20C 3.0735 no . 4_564 H13A O3 3.2056 no . 3_666 H13A N4 3.5472 no . 1_545 H13A C7 3.5777 no . 1_545 H13A C10 3.5270 no . 3_666 H13A H4B 3.4972 no . 1_545 H13A H9A 3.3075 no . 4_465 H13A H10B 2.9215 no . 3_666 H13A H10C 3.3526 no . 3_666 H13A H12A 3.5866 no . 3_666 H13A H12B 3.4089 no . 3_666 H13B N3 3.3822 no . 1_545 H13B N3 3.2591 no . 3_576 H13B N4 3.1636 no . 1_545 H13B C9 3.5487 no . 4_465 H13B C21 3.3169 no . 1_545 H13B H4B 2.7449 no . 1_545 H13B H9A 3.1215 no . 4_465 H13B H9B 3.1895 no . 4_465 H13B H10A 3.4931 no . 4_465 H13C O1 2.9976 no . 3_676 H13C C9 3.2919 no . 4_465 H13C C10 3.2360 no . 4_465 H13C C18 3.3238 no . 2_546 H13C H9A 2.8770 no . 4_465 H13C H9B 3.2749 no . 4_465 H13C H10A 2.5334 no . 4_465 H13C H10C 3.5654 no . 4_465 H13C H18 3.0275 no . 2_546 H13C H19 3.5814 no . 2_546 H15 N1 3.2090 no . 3_576 H15 N4 3.3589 no . 3_576 H15 C3 3.5491 no . 3_576 H15 C4 3.5741 no . 3_576 H15 C5 3.2528 no . 3_576 H15 C6 2.8580 no . 3_576 H15 C7 2.8502 no . 3_576 H15 C21 3.3283 no . 3_576 H15 H9B 3.0909 no . 4_465 H16 O2 3.4695 no . 4_465 H16 N1 3.0611 no . 3_576 H16 N2 2.9584 no . 3_576 H16 N4 3.0685 no . 3_576 H16 C7 3.1579 no . 3_576 H16 C9 3.3845 no . 4_465 H16 H4A 2.8923 no . 3_576 H16 H4B 3.5691 no . 3_576 H16 H9B 2.7883 no . 4_465 H16 H10B 3.1174 no . 4_465 H18 O1 2.7397 no . 4_475 H18 N2 2.6496 no . 4_475 H18 C1 3.3016 no . 4_475 H18 C8 3.0669 no . 4_475 H18 C13 3.5982 no . 2_556 H18 C20 3.5634 no . 2_456 H18 H4A 2.9760 no . 4_475 H18 H12A 3.0084 no . 2_556 H18 H13C 3.0275 no . 2_556 H18 H20B 2.7716 no . 2_456 H19 O1 2.9028 no . 4_475 H19 C8 3.5309 no . 4_475 H19 C10 3.2005 no . 3_676 H19 H9A 3.1398 no . 4_475 H19 H10A 2.8727 no . 3_676 H19 H10C 2.6564 no . 3_676 H19 H13C 3.5814 no . 2_556 H19 H20B 3.3984 no . 2_456 H20A O2 2.8412 no . 4_465 H20A O3 3.2646 no . 4_465 H20A O4 3.5876 no . 4_465 H20A C2 3.5097 no . 4_465 H20A C11 3.1705 no . 4_465 H20A H9B 3.5553 no . 4_465 H20A H10B 3.1717 no . 4_465 H20B O2 3.3057 no . 3_576 H20B N2 3.1502 no . 3_576 H20B N3 3.5333 no . 2_446 H20B C1 3.4282 no . 3_576 H20B C8 3.3099 no . 3_576 H20B C18 3.0185 no . 2_446 H20B C19 3.3960 no . 2_446 H20B H4A 3.5723 no . 4_475 H20B H18 2.7716 no . 2_446 H20B H19 3.3984 no . 2_446 H20C O4 3.0997 no . 4_465 H20C N3 2.6307 no . 2_446 H20C N4 3.2255 no . 4_475 H20C C11 3.3058 no . 4_465 H20C C12 3.5472 no . 4_465 H20C C21 3.3552 no . 2_446 H20C H4A 2.9492 no . 4_475 H20C H4B 2.8507 no . 4_475 H20C H12B 3.0735 no . 4_465 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N4 H4A O5 . . 4_574 3.037(4) 0.860 2.308 142.7 no N4 H4A N2 . . . 2.705(4) 0.860 2.363 104.1 no N4 H4B N3 . . 3_586 3.062(4) 0.860 2.228 163.4 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================