############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_global _audit_creation_method 'form.cif (version 2.0)' _journal_data_validation_number ? _journal_date_recd_electronic 2010-09-28 _journal_date_accepted 2010-09-29 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2010 _journal_volume 66 _journal_issue 11 _journal_page_first o2747 _journal_page_last o2747 _journal_paper_category QO _journal_coeditor_code HB5660 _publ_contact_author_name 'Prof. Fun, Hoong-Kun' _publ_contact_author_address ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang MALAYSIA ; _publ_contact_author_email 'hkfun@usm.my' _publ_contact_author_fax '604 6579150' _publ_contact_author_phone '604 6533652' _publ_section_title ; 3,4-Diaminopyridinium 2-carboxy-4,6-dinitrophenolate ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Madhukar Hemamalini' ? ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang Malaysia ; 'Hoong-Kun Fun' ; Thomson Reuters ResearcherID: A-3561-2009. ; ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang Malaysia ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,4-Diaminopyridinium 2-carboxy-4,6-dinitrophenolate ; _chemical_name_common ? _chemical_formula_moiety 'C5 H8 N3 +, C7 H3 N2 O7 -' _chemical_formula_sum 'C12 H11 N5 O7' _chemical_formula_iupac 'C5 H8 N3 +, C7 H3 N2 O7 -' _chemical_formula_weight 337.26 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.1187(4) _cell_length_b 11.3569(5) _cell_length_c 13.1343(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.204(4) _cell_angle_gamma 90.00 _cell_volume 1346.27(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2307 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 28.61 _cell_measurement_temperature 100.00(10) _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_absorpt_correction_T_min 0.9309 _exptl_absorpt_correction_T_max 0.9863 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0(1) K. ; _diffrn_ambient_temperature 100.00(10) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker SMART APEXII CCD area-detector ; _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean . _diffrn_reflns_number 10195 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0656 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 26.50 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _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^ > 2\s(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. ; _reflns_number_total 2785 _reflns_number_gt 1979 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1047 _refine_ls_R_factor_gt 0.0702 _refine_ls_wR_factor_gt 0.1486 _refine_ls_wR_factor_ref 0.1622 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.020 _refine_ls_number_reflns 2785 _refine_ls_number_parameters 279 _refine_ls_number_restraints 526 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+2.4565P] 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_ls_shift/su_mean 0.000 _refine_diff_density_max 0.456 _refine_diff_density_min -0.282 _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 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' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N N1 0.1346(3) 0.4299(2) -0.0435(2) 0.0286(7) Uani d . 1 . . H H1N1 0.2282 0.4863 -0.0241 0.034 Uiso d R 1 . . N N2 0.0269(3) 0.1468(3) 0.0541(2) 0.0370(8) Uani d . 1 . . H H2N2 -0.0550 0.1048 0.0573 0.044 Uiso d R 1 . . H H1N2 0.1048 0.1417 0.1192 0.044 Uiso d R 1 . . N N3 -0.1784(3) 0.1759(2) -0.1255(2) 0.0279(7) Uani d . 1 . . H H1N3 -0.1717 0.1109 -0.0876 0.034 Uiso d R 1 . . H H2N3 -0.2376 0.1940 -0.1942 0.034 Uiso d R 1 . . C C1 0.1297(4) 0.3365(3) 0.0206(3) 0.0283(8) Uani d . 1 . . H H1A 0.1953 0.3325 0.0816 0.034 Uiso calc R 1 . . C C2 0.0275(3) 0.2469(3) -0.0045(3) 0.0274(8) Uani d . 1 . . C C3 -0.0744(3) 0.2571(3) -0.0968(2) 0.0253(7) Uani d . 1 . . C C4 -0.0643(4) 0.3579(3) -0.1599(3) 0.0275(8) Uani d . 1 . . H H4A -0.1299 0.3671 -0.2204 0.033 Uiso calc R 1 . . C C5 0.0411(4) 0.4406(3) -0.1315(3) 0.0298(8) Uani d . 1 . . H H5A 0.0486 0.5054 -0.1737 0.036 Uiso calc R 1 . . O O1 0.3734(3) 0.5460(2) 0.06336(19) 0.0242(7) Uani d PDU 0.886(4) A 1 O O2 0.5011(3) 0.4686(2) 0.2297(2) 0.0278(7) Uani d PDU 0.886(4) A 1 H H2 0.4413 0.4777 0.1774 0.033 Uiso calc PR 0.886(4) A 1 O O3 0.6962(5) 0.5623(2) 0.3110(3) 0.0274(9) Uani d PDU 0.886(4) A 1 O O4 0.2470(6) 0.6533(5) -0.1085(5) 0.0309(11) Uani d PDU 0.886(4) A 1 O O5 0.3768(6) 0.7848(5) -0.1745(3) 0.0242(10) Uani d PDU 0.886(4) A 1 O O6 0.7238(3) 1.0170(3) 0.0450(3) 0.0246(7) Uani d PDU 0.886(4) A 1 O O7 0.8474(3) 0.9354(3) 0.1809(2) 0.0270(7) Uani d PDU 0.886(4) A 1 N N4 0.3541(10) 0.7207(7) -0.1015(5) 0.0204(9) Uani d PDU 0.886(4) A 1 N N5 0.7468(3) 0.9350(3) 0.1074(3) 0.0191(7) Uani d PDU 0.886(4) A 1 C C6 0.5497(8) 0.8229(5) 0.0041(4) 0.0177(14) Uani d PDU 0.886(4) A 1 H H6A 0.5442 0.8801 -0.0470 0.021 Uiso calc PR 0.886(4) A 1 C C7 0.4568(12) 0.7259(7) -0.0067(6) 0.0182(12) Uani d PDU 0.886(4) A 1 C C8 0.4606(6) 0.6350(4) 0.0699(4) 0.0179(9) Uani d PDU 0.886(4) A 1 C C9 0.5741(4) 0.6491(3) 0.1573(3) 0.0171(8) Uani d PDU 0.886(4) A 1 C C10 0.6650(4) 0.7456(3) 0.1681(3) 0.0162(7) Uani d PDU 0.886(4) A 1 H H10A 0.7364 0.7530 0.2259 0.019 Uiso calc PR 0.886(4) A 1 C C11 0.6506(5) 0.8326(4) 0.0926(3) 0.0158(8) Uani d PDU 0.886(4) A 1 C C12 0.5956(4) 0.5570(3) 0.2394(3) 0.0210(8) Uani d PDU 0.886(4) A 1 O O1B 0.703(2) 0.7054(19) 0.2650(14) 0.037(6) Uiso d PDU 0.114(4) A 2 O O2B 0.598(2) 0.512(2) 0.2943(15) 0.034(6) Uiso d PDU 0.114(4) A 2 H H2B 0.6584 0.5652 0.2956 0.01(17) Uiso calc PR 0.114(4) A 2 O O3B 0.409(3) 0.4439(19) 0.1805(19) 0.051(7) Uiso d PDU 0.114(4) A 2 O O4B 0.833(2) 0.892(2) 0.2101(17) 0.028(6) Uiso d PDU 0.114(4) A 2 O O5B 0.722(3) 0.995(2) 0.0788(19) 0.013(6) Uiso d PDU 0.114(4) A 2 O O6B 0.375(7) 0.811(4) -0.176(4) 0.045(16) Uiso d PDU 0.114(4) A 2 O O7B 0.250(6) 0.660(5) -0.132(4) 0.044(15) Uiso d PDU 0.114(4) A 2 N N4B 0.733(3) 0.908(2) 0.138(2) 0.032(7) Uiso d PDU 0.114(4) A 2 N N5B 0.353(10) 0.733(7) -0.115(4) 0.032(7) Uiso d PDU 0.114(4) A 2 C C6B 0.537(6) 0.824(4) 0.018(3) 0.011(6) Uiso d PDU 0.114(4) A 2 H H6BA 0.5362 0.8931 -0.0200 0.013 Uiso calc PR 0.114(4) A 2 C C7B 0.633(4) 0.811(3) 0.110(2) 0.011(6) Uiso d PDU 0.114(4) A 2 C C8B 0.620(3) 0.714(2) 0.1781(16) 0.007(6) Uiso d PDU 0.114(4) A 2 C C9B 0.520(3) 0.6226(19) 0.1401(17) 0.014(5) Uiso d PDU 0.114(4) A 2 C C10B 0.432(5) 0.633(3) 0.049(3) 0.014(5) Uiso d PDU 0.114(4) A 2 H H10B 0.3639 0.5746 0.0275 0.016 Uiso calc PR 0.114(4) A 2 C C11B 0.442(12) 0.732(7) -0.014(5) 0.026(6) Uiso d PDU 0.114(4) A 2 C C12B 0.499(3) 0.521(2) 0.2106(18) 0.026(6) Uiso d PDU 0.114(4) A 2 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 N1 0.0268(15) 0.0294(15) 0.0305(16) 0.0010(13) 0.0071(13) -0.0046(12) N2 0.0307(15) 0.0329(17) 0.0469(19) -0.0038(14) 0.0036(14) 0.0063(14) N3 0.0288(14) 0.0247(14) 0.0296(15) -0.0042(12) 0.0017(12) 0.0005(12) C1 0.0268(17) 0.0239(17) 0.037(2) 0.0027(15) 0.0138(15) -0.0011(15) C2 0.0254(17) 0.0312(18) 0.0262(17) 0.0103(15) 0.0055(14) -0.0011(14) C3 0.0219(16) 0.0277(18) 0.0282(18) 0.0005(14) 0.0098(14) -0.0089(14) C4 0.0260(16) 0.0239(17) 0.0346(19) 0.0016(14) 0.0110(15) -0.0036(14) C5 0.0318(18) 0.0268(18) 0.0319(19) 0.0035(15) 0.0089(15) 0.0015(14) O1 0.0243(13) 0.0203(13) 0.0282(14) -0.0050(11) 0.0047(11) -0.0006(10) O2 0.0340(15) 0.0211(15) 0.0283(15) -0.0031(12) 0.0053(12) 0.0083(12) O3 0.0300(15) 0.0260(19) 0.0258(16) 0.0037(12) 0.0021(15) 0.0078(11) O4 0.0240(18) 0.034(2) 0.033(3) -0.0167(12) -0.0016(18) 0.0034(19) O5 0.0281(19) 0.024(2) 0.0201(18) -0.0091(18) 0.0016(11) 0.0047(15) O6 0.0303(16) 0.0173(15) 0.0266(18) -0.0026(11) 0.0051(14) 0.0060(13) O7 0.0245(14) 0.0227(15) 0.0308(16) -0.0050(12) -0.0065(12) -0.0017(13) N4 0.0193(16) 0.023(3) 0.020(2) -0.0003(18) 0.0050(17) -0.0003(14) N5 0.0198(16) 0.0176(18) 0.0203(18) 0.0005(14) 0.0038(14) -0.0027(15) C6 0.019(2) 0.0193(19) 0.016(2) 0.0018(15) 0.009(2) -0.0020(16) C7 0.016(3) 0.020(2) 0.020(2) 0.002(2) 0.0068(14) -0.0020(14) C8 0.018(3) 0.0159(17) 0.021(3) 0.0011(16) 0.0086(17) -0.0020(16) C9 0.018(2) 0.0158(18) 0.0183(17) 0.0026(16) 0.0059(14) 0.0005(14) C10 0.0153(17) 0.0164(18) 0.0182(18) -0.0011(16) 0.0067(14) -0.0041(14) C11 0.018(2) 0.011(2) 0.020(2) -0.0012(14) 0.0103(16) -0.0006(14) C12 0.0255(19) 0.0153(16) 0.024(2) 0.0030(15) 0.0096(16) 0.0010(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C5 . 1.341(4) ? N1 C1 . 1.358(4) ? N1 H1N1 . 1.0684 ? N2 C2 . 1.373(4) ? N2 H2N2 . 0.8919 ? N2 H1N2 . 1.0329 ? N3 C3 . 1.338(4) ? N3 H1N3 . 0.8875 ? N3 H2N3 . 1.0043 ? C1 C2 . 1.387(5) ? C1 H1A . 0.9300 ? C2 C3 . 1.423(4) ? C3 C4 . 1.424(5) ? C4 C5 . 1.357(5) ? C4 H4A . 0.9300 ? C5 H5A . 0.9300 ? O1 C8 . 1.282(5) ? O2 C12 . 1.317(4) ? O2 H2 . 0.8200 ? O3 C12 . 1.219(6) ? O4 N4 . 1.234(4) ? O5 N4 . 1.244(5) ? O6 N5 . 1.239(5) ? O7 N5 . 1.233(4) ? N4 C7 . 1.449(5) ? N5 C11 . 1.453(5) ? C6 C11 . 1.381(5) ? C6 C7 . 1.384(5) ? C6 H6A . 0.9300 ? C7 C8 . 1.438(5) ? C8 C9 . 1.441(5) ? C9 C10 . 1.369(5) ? C9 C12 . 1.494(5) ? C10 C11 . 1.393(5) ? C10 H10A . 0.9300 ? O1B C8B . 1.281(16) ? O2B C12B . 1.322(16) ? O2B H2B . 0.8200 ? O3B C12B . 1.229(17) ? O4B N4B . 1.230(17) ? O5B N4B . 1.249(17) ? O6B N5B . 1.237(18) ? O7B N5B . 1.246(18) ? N4B C7B . 1.445(16) ? N5B C11B . 1.454(17) ? C6B C11B . 1.386(18) ? C6B C7B . 1.388(18) ? C6B H6BA . 0.9300 ? C7B C8B . 1.436(16) ? C8B C9B . 1.424(16) ? C9B C10B . 1.348(16) ? C9B C12B . 1.507(16) ? C10B C11B . 1.398(18) ? C10B H10B . 0.9300 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 N1 C1 . . 122.1(3) ? C5 N1 H1N1 . . 122.6 ? C1 N1 H1N1 . . 114.6 ? C2 N2 H2N2 . . 122.6 ? C2 N2 H1N2 . . 116.9 ? H2N2 N2 H1N2 . . 114.3 ? C3 N3 H1N3 . . 115.2 ? C3 N3 H2N3 . . 112.3 ? H1N3 N3 H2N3 . . 131.3 ? N1 C1 C2 . . 120.4(3) ? N1 C1 H1A . . 119.8 ? C2 C1 H1A . . 119.8 ? N2 C2 C1 . . 122.0(3) ? N2 C2 C3 . . 119.4(3) ? C1 C2 C3 . . 118.5(3) ? N3 C3 C2 . . 122.3(3) ? N3 C3 C4 . . 119.5(3) ? C2 C3 C4 . . 118.3(3) ? C5 C4 C3 . . 119.9(3) ? C5 C4 H4A . . 120.1 ? C3 C4 H4A . . 120.1 ? N1 C5 C4 . . 120.8(3) ? N1 C5 H5A . . 119.6 ? C4 C5 H5A . . 119.6 ? C12 O2 H2 . . 109.5 ? O4 N4 O5 . . 121.5(4) ? O4 N4 C7 . . 119.8(4) ? O5 N4 C7 . . 118.7(4) ? O7 N5 O6 . . 123.5(3) ? O7 N5 C11 . . 118.3(4) ? O6 N5 C11 . . 118.1(3) ? C11 C6 C7 . . 118.3(4) ? C11 C6 H6A . . 120.9 ? C7 C6 H6A . . 120.9 ? C6 C7 C8 . . 123.1(4) ? C6 C7 N4 . . 115.5(4) ? C8 C7 N4 . . 121.3(4) ? O1 C8 C7 . . 124.5(4) ? O1 C8 C9 . . 120.6(4) ? C7 C8 C9 . . 114.9(3) ? C10 C9 C8 . . 121.8(3) ? C10 C9 C12 . . 118.0(3) ? C8 C9 C12 . . 120.2(3) ? C9 C10 C11 . . 120.0(3) ? C9 C10 H10A . . 120.0 ? C11 C10 H10A . . 120.0 ? C6 C11 C10 . . 121.8(4) ? C6 C11 N5 . . 119.6(4) ? C10 C11 N5 . . 118.6(3) ? O3 C12 O2 . . 121.5(3) ? O3 C12 C9 . . 122.0(3) ? O2 C12 C9 . . 116.5(3) ? C12B O2B H2B . . 109.5 ? O4B N4B O5B . . 126(2) ? O4B N4B C7B . . 116.9(19) ? O5B N4B C7B . . 116.5(18) ? O6B N5B O7B . . 123(3) ? O6B N5B C11B . . 119(2) ? O7B N5B C11B . . 118(3) ? C11B C6B C7B . . 118.0(19) ? C11B C6B H6BA . . 121.0 ? C7B C6B H6BA . . 121.0 ? C6B C7B C8B . . 121.6(17) ? C6B C7B N4B . . 115.9(18) ? C8B C7B N4B . . 121.9(17) ? O1B C8B C9B . . 121.6(16) ? O1B C8B C7B . . 121.6(17) ? C9B C8B C7B . . 116.4(15) ? C10B C9B C8B . . 120.9(16) ? C10B C9B C12B . . 120.2(17) ? C8B C9B C12B . . 118.2(15) ? C9B C10B C11B . . 121(2) ? C9B C10B H10B . . 119.5 ? C11B C10B H10B . . 119.5 ? C6B C11B C10B . . 121.0(19) ? C6B C11B N5B . . 121(2) ? C10B C11B N5B . . 118(2) ? O3B C12B O2B . . 124(2) ? O3B C12B C9B . . 119.1(17) ? O2B C12B C9B . . 116.2(17) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C5 N1 C1 C2 . . . . 1.0(5) ? N1 C1 C2 N2 . . . . 174.7(3) ? N1 C1 C2 C3 . . . . -1.9(5) ? N2 C2 C3 N3 . . . . 4.7(5) ? C1 C2 C3 N3 . . . . -178.6(3) ? N2 C2 C3 C4 . . . . -175.5(3) ? C1 C2 C3 C4 . . . . 1.2(4) ? N3 C3 C4 C5 . . . . -179.8(3) ? C2 C3 C4 C5 . . . . 0.4(5) ? C1 N1 C5 C4 . . . . 0.7(5) ? C3 C4 C5 N1 . . . . -1.4(5) ? C11 C6 C7 C8 . . . . 0.0(17) ? C11 C6 C7 N4 . . . . -179.7(9) ? O4 N4 C7 C6 . . . . -164.1(11) ? O5 N4 C7 C6 . . . . 16.1(17) ? O4 N4 C7 C8 . . . . 16.2(18) ? O5 N4 C7 C8 . . . . -163.6(11) ? C6 C7 C8 O1 . . . . 178.0(9) ? N4 C7 C8 O1 . . . . -2.3(17) ? C6 C7 C8 C9 . . . . -3.0(16) ? N4 C7 C8 C9 . . . . 176.7(10) ? O1 C8 C9 C10 . . . . -177.5(4) ? C7 C8 C9 C10 . . . . 3.5(9) ? O1 C8 C9 C12 . . . . 2.7(7) ? C7 C8 C9 C12 . . . . -176.4(7) ? C8 C9 C10 C11 . . . . -1.0(6) ? C12 C9 C10 C11 . . . . 178.9(4) ? C7 C6 C11 C10 . . . . 2.8(12) ? C7 C6 C11 N5 . . . . -178.3(9) ? C9 C10 C11 C6 . . . . -2.3(7) ? C9 C10 C11 N5 . . . . 178.7(4) ? O7 N5 C11 C6 . . . . -171.6(5) ? O6 N5 C11 C6 . . . . 7.8(7) ? O7 N5 C11 C10 . . . . 7.3(6) ? O6 N5 C11 C10 . . . . -173.2(4) ? C10 C9 C12 O3 . . . . -4.5(5) ? C8 C9 C12 O3 . . . . 175.3(4) ? C10 C9 C12 O2 . . . . 176.3(3) ? C8 C9 C12 O2 . . . . -3.8(5) ? C11B C6B C7B C8B . . . . -10(11) ? C11B C6B C7B N4B . . . . 178(8) ? O4B N4B C7B C6B . . . . -170(5) ? O5B N4B C7B C6B . . . . 1(7) ? O4B N4B C7B C8B . . . . 18(6) ? O5B N4B C7B C8B . . . . -171(4) ? C6B C7B C8B O1B . . . . -176(5) ? N4B C7B C8B O1B . . . . -5(6) ? C6B C7B C8B C9B . . . . 10(7) ? N4B C7B C8B C9B . . . . -179(4) ? O1B C8B C9B C10B . . . . 179(4) ? C7B C8B C9B C10B . . . . -7(6) ? O1B C8B C9B C12B . . . . 8(5) ? C7B C8B C9B C12B . . . . -178(3) ? C8B C9B C10B C11B . . . . 4(10) ? C12B C9B C10B C11B . . . . 175(8) ? C7B C6B C11B C10B . . . . 7(16) ? C7B C6B C11B N5B . . . . -172(10) ? C9B C10B C11B C6B . . . . -4(16) ? C9B C10B C11B N5B . . . . 175(9) ? O6B N5B C11B C6B . . . . 9(19) ? O7B N5B C11B C6B . . . . -167(12) ? O6B N5B C11B C10B . . . . -170(11) ? O7B N5B C11B C10B . . . . 15(18) ? C10B C9B C12B O3B . . . . 6(6) ? C8B C9B C12B O3B . . . . 177(3) ? C10B C9B C12B O2B . . . . 175(4) ? C8B C9B C12B O2B . . . . -14(4) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1N1 O1 . 1.07 1.76 2.753(4) 153 yes O2 H2 O1 . 0.82 1.72 2.485(4) 154 no N2 H2N2 O6 1_445 0.89 2.24 3.120(4) 171 yes N2 H1N2 O3 2_645 1.03 2.11 3.026(5) 146 yes N3 H1N3 O6 1_445 0.89 2.36 3.104(4) 142 yes N3 H2N3 O5 2_544 1.00 2.24 3.217(5) 163 yes C6 H6A O3 4_575 0.93 2.56 3.299(6) 136.4 yes