############################################################################## ### ### ### 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 2010-10-18 _journal_date_accepted 2010-10-20 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2010 _journal_volume 66 _journal_issue 11 _journal_page_first o2950 _journal_page_last o2951 _journal_paper_category QO _journal_coeditor_code FJ2355 _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 ; 2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium 2-carboxy-4,6-dinitrophenolate monohydrate ; 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 ; 2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium 2-carboxy-4,6-dinitrophenolate monohydrate ; _chemical_name_common ? _chemical_formula_moiety 'C8 H13 N2 O +, C7 H3 N2 O7 -, H2 O' _chemical_formula_sum 'C15 H18 N4 O9' _chemical_formula_iupac 'C8 H13 N2 O +, C7 H3 N2 O7 -, H2 O' _chemical_formula_weight 398.33 _chemical_melting_point ? _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6691(3) _cell_length_b 11.3831(4) _cell_length_c 12.2900(5) _cell_angle_alpha 89.727(2) _cell_angle_beta 76.771(2) _cell_angle_gamma 76.930(2) _cell_volume 883.62(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6994 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 31.63 _cell_measurement_temperature 100.00(10) _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_absorpt_correction_T_min 0.9374 _exptl_absorpt_correction_T_max 0.9872 _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' _diffrn_detector_area_resol_mean . _diffrn_reflns_number 17014 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _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 4061 _reflns_number_gt 3279 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_gt 0.0950 _refine_ls_wR_factor_ref 0.1045 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_number_reflns 4061 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.3946P] 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 ? _refine_ls_shift/su_max_lt 0.001 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.533 _refine_diff_density_min -0.303 _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 O O1 0.30537(18) -0.17099(10) 0.14974(9) 0.0223(2) Uani d . 1 . . O O2 0.5667(2) -0.35714(10) 0.01344(10) 0.0310(3) Uani d . 1 . . O O3 0.4865(2) -0.36692(10) -0.14689(10) 0.0308(3) Uani d . 1 . . O O4 0.36257(17) -0.00307(10) -0.33888(9) 0.0231(3) Uani d . 1 . . O O5 0.23770(18) 0.16989(10) -0.24573(9) 0.0251(3) Uani d . 1 . . O O6 0.07237(17) 0.19149(9) 0.16326(9) 0.0200(2) Uani d . 1 . . O O7 0.14505(18) 0.02269(10) 0.25242(9) 0.0213(2) Uani d . 1 . . H H7 0.1960 -0.0493 0.2360 0.032 Uiso calc R 1 . . O O8 0.31892(18) 0.38518(9) 0.41955(9) 0.0220(2) Uani d . 1 . . N N1 0.30166(19) 0.05932(11) -0.25097(10) 0.0182(3) Uani d . 1 . . N N2 0.4862(2) -0.31082(11) -0.06121(11) 0.0206(3) Uani d . 1 . . N N3 0.11901(19) 0.64262(11) 0.66450(10) 0.0148(3) Uani d . 1 . . N N4 0.23843(18) 0.58272(10) 0.47925(10) 0.0144(3) Uani d . 1 . . C C1 0.3103(2) -0.11927(13) 0.05577(12) 0.0151(3) Uani d . 1 . . C C2 0.3897(2) -0.18173(13) -0.05146(12) 0.0156(3) Uani d . 1 . . C C3 0.3840(2) -0.12442(13) -0.15046(12) 0.0158(3) Uani d . 1 . . H H3A 0.4330 -0.1682 -0.2188 0.019 Uiso calc R 1 . . C C4 0.3044(2) -0.00117(13) -0.14625(12) 0.0153(3) Uani d . 1 . . C C5 0.2283(2) 0.06623(13) -0.04535(12) 0.0150(3) Uani d . 1 . . H H5A 0.1774 0.1494 -0.0446 0.018 Uiso calc R 1 . . C C6 0.2289(2) 0.00879(13) 0.05385(12) 0.0139(3) Uani d . 1 . . C C7 0.1427(2) 0.08136(13) 0.16144(12) 0.0157(3) Uani d . 1 . . C C8 0.2598(2) 0.45827(13) 0.49893(12) 0.0158(3) Uani d . 1 . . C C9 0.2071(2) 0.43350(13) 0.61585(12) 0.0159(3) Uani d . 1 . . H H9A 0.2214 0.3538 0.6364 0.019 Uiso calc R 1 . . C C10 0.1374(2) 0.52333(13) 0.69601(12) 0.0159(3) Uani d . 1 . . C C11 0.1694(2) 0.67070(13) 0.55878(12) 0.0142(3) Uani d . 1 . . C C12 0.1447(2) 0.80024(12) 0.52940(12) 0.0151(3) Uani d . 1 . . H H12A 0.1079 0.8501 0.5990 0.018 Uiso calc R 1 . . C C13 -0.0376(2) 0.83580(14) 0.47027(14) 0.0221(3) Uani d . 1 . . H H13A -0.1654 0.8227 0.5181 0.033 Uiso calc R 1 . . H H13B -0.0048 0.7874 0.4020 0.033 Uiso calc R 1 . . H H13C -0.0568 0.9195 0.4537 0.033 Uiso calc R 1 . . C C14 0.3510(2) 0.82287(13) 0.45724(13) 0.0192(3) Uani d . 1 . . H H14A 0.4628 0.7980 0.4955 0.029 Uiso calc R 1 . . H H14B 0.3331 0.9073 0.4438 0.029 Uiso calc R 1 . . H H14C 0.3864 0.7774 0.3871 0.029 Uiso calc R 1 . . C C15 0.0772(3) 0.50606(14) 0.81836(13) 0.0215(3) Uani d . 1 . . H H15A 0.0965 0.4214 0.8310 0.032 Uiso calc R 1 . . H H15B -0.0686 0.5459 0.8474 0.032 Uiso calc R 1 . . H H15C 0.1647 0.5398 0.8555 0.032 Uiso calc R 1 . . O O1W 0.3284(2) 0.60970(11) 0.25362(10) 0.0271(3) Uani d . 1 . . H H1N3 0.066(3) 0.7030(18) 0.7187(16) 0.028(5) Uiso d . 1 . . H H1N4 0.271(3) 0.5992(18) 0.4063(17) 0.032(5) Uiso d . 1 . . H H2W1 0.339(3) 0.667(2) 0.2096(17) 0.035(5) Uiso d . 1 . . H H1W1 0.377(4) 0.544(2) 0.2154(19) 0.044(6) Uiso d . 1 . . 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 0.0296(6) 0.0173(5) 0.0173(5) -0.0039(5) -0.0015(4) 0.0032(4) O2 0.0424(7) 0.0207(6) 0.0229(6) 0.0050(5) -0.0056(5) 0.0036(5) O3 0.0487(8) 0.0171(6) 0.0231(6) -0.0034(5) -0.0054(5) -0.0076(5) O4 0.0289(6) 0.0268(6) 0.0137(5) -0.0082(5) -0.0031(4) -0.0002(5) O5 0.0344(6) 0.0173(6) 0.0230(6) -0.0043(5) -0.0075(5) 0.0060(5) O6 0.0244(6) 0.0138(5) 0.0183(5) -0.0014(4) -0.0006(4) -0.0027(4) O7 0.0287(6) 0.0153(5) 0.0149(5) -0.0002(5) 0.0004(4) -0.0004(4) O8 0.0323(6) 0.0137(5) 0.0175(6) -0.0029(5) -0.0031(5) -0.0019(4) N1 0.0184(6) 0.0198(7) 0.0179(7) -0.0074(5) -0.0047(5) 0.0035(5) N2 0.0240(7) 0.0153(6) 0.0186(7) -0.0035(5) 0.0018(5) 0.0001(5) N3 0.0166(6) 0.0122(6) 0.0140(6) -0.0024(5) -0.0017(5) -0.0006(5) N4 0.0171(6) 0.0116(6) 0.0130(6) -0.0026(5) -0.0013(5) 0.0010(5) C1 0.0136(7) 0.0169(7) 0.0151(7) -0.0059(5) -0.0014(5) 0.0016(6) C2 0.0161(7) 0.0122(7) 0.0174(7) -0.0032(5) -0.0020(5) -0.0006(5) C3 0.0166(7) 0.0179(7) 0.0137(7) -0.0072(6) -0.0016(5) -0.0019(6) C4 0.0152(7) 0.0195(7) 0.0130(7) -0.0076(6) -0.0032(5) 0.0034(6) C5 0.0132(7) 0.0135(7) 0.0186(7) -0.0046(5) -0.0028(5) 0.0008(6) C6 0.0116(6) 0.0149(7) 0.0151(7) -0.0043(5) -0.0014(5) -0.0007(5) C7 0.0134(7) 0.0169(7) 0.0159(7) -0.0047(5) -0.0003(5) -0.0009(6) C8 0.0156(7) 0.0132(7) 0.0182(7) -0.0028(5) -0.0035(5) 0.0004(6) C9 0.0178(7) 0.0112(7) 0.0181(7) -0.0030(5) -0.0036(6) 0.0036(6) C10 0.0147(7) 0.0157(7) 0.0175(7) -0.0039(6) -0.0041(5) 0.0033(6) C11 0.0117(6) 0.0143(7) 0.0163(7) -0.0028(5) -0.0027(5) -0.0001(5) C12 0.0183(7) 0.0105(7) 0.0154(7) -0.0033(5) -0.0019(5) -0.0001(5) C13 0.0222(8) 0.0136(7) 0.0319(9) -0.0033(6) -0.0099(7) 0.0055(6) C14 0.0203(7) 0.0138(7) 0.0221(8) -0.0051(6) -0.0008(6) 0.0007(6) C15 0.0267(8) 0.0189(8) 0.0176(8) -0.0048(6) -0.0031(6) 0.0021(6) O1W 0.0475(8) 0.0128(6) 0.0158(6) -0.0038(5) -0.0005(5) 0.0009(5) _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 O1 C1 . 1.2909(17) ? O2 N2 . 1.2250(17) ? O3 N2 . 1.2334(17) ? O4 N1 . 1.2299(16) ? O5 N1 . 1.2311(16) ? O6 C7 . 1.2335(17) ? O7 C7 . 1.3010(17) ? O7 H7 . 0.8200 ? O8 C8 . 1.2177(18) ? N1 C4 . 1.4586(18) ? N2 C2 . 1.4581(18) ? N3 C11 . 1.3221(18) ? N3 C10 . 1.3965(18) ? N3 H1N3 . 0.91(2) ? N4 C11 . 1.3285(19) ? N4 C8 . 1.4166(18) ? N4 H1N4 . 0.90(2) ? C1 C2 . 1.429(2) ? C1 C6 . 1.438(2) ? C2 C3 . 1.382(2) ? C3 C4 . 1.380(2) ? C3 H3A . 0.9300 ? C4 C5 . 1.389(2) ? C5 C6 . 1.3811(19) ? C5 H5A . 0.9300 ? C6 C7 . 1.486(2) ? C8 C9 . 1.441(2) ? C9 C10 . 1.348(2) ? C9 H9A . 0.9300 ? C10 C15 . 1.489(2) ? C11 C12 . 1.4981(19) ? C12 C14 . 1.5314(19) ? C12 C13 . 1.533(2) ? C12 H12A . 0.9800 ? C13 H13A . 0.9600 ? C13 H13B . 0.9600 ? C13 H13C . 0.9600 ? C14 H14A . 0.9600 ? C14 H14B . 0.9600 ? C14 H14C . 0.9600 ? C15 H15A . 0.9600 ? C15 H15B . 0.9600 ? C15 H15C . 0.9600 ? O1W H2W1 . 0.85(2) ? O1W H1W1 . 0.84(2) ? 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 C7 O7 H7 . . 109.5 ? O4 N1 O5 . . 124.05(12) ? O4 N1 C4 . . 118.14(12) ? O5 N1 C4 . . 117.81(12) ? O2 N2 O3 . . 123.54(13) ? O2 N2 C2 . . 119.12(12) ? O3 N2 C2 . . 117.31(12) ? C11 N3 C10 . . 122.35(13) ? C11 N3 H1N3 . . 119.1(12) ? C10 N3 H1N3 . . 118.5(12) ? C11 N4 C8 . . 124.54(12) ? C11 N4 H1N4 . . 121.1(12) ? C8 N4 H1N4 . . 114.3(12) ? O1 C1 C2 . . 124.18(13) ? O1 C1 C6 . . 120.48(13) ? C2 C1 C6 . . 115.33(12) ? C3 C2 C1 . . 122.73(13) ? C3 C2 N2 . . 116.52(13) ? C1 C2 N2 . . 120.74(12) ? C4 C3 C2 . . 118.90(13) ? C4 C3 H3A . . 120.5 ? C2 C3 H3A . . 120.5 ? C3 C4 C5 . . 121.76(13) ? C3 C4 N1 . . 118.76(13) ? C5 C4 N1 . . 119.48(13) ? C6 C5 C4 . . 119.48(13) ? C6 C5 H5A . . 120.3 ? C4 C5 H5A . . 120.3 ? C5 C6 C1 . . 121.77(13) ? C5 C6 C7 . . 119.05(13) ? C1 C6 C7 . . 119.18(12) ? O6 C7 O7 . . 122.30(13) ? O6 C7 C6 . . 121.12(13) ? O7 C7 C6 . . 116.58(12) ? O8 C8 N4 . . 119.20(13) ? O8 C8 C9 . . 127.19(13) ? N4 C8 C9 . . 113.61(12) ? C10 C9 C8 . . 121.41(13) ? C10 C9 H9A . . 119.3 ? C8 C9 H9A . . 119.3 ? C9 C10 N3 . . 118.94(13) ? C9 C10 C15 . . 124.98(13) ? N3 C10 C15 . . 116.08(13) ? N3 C11 N4 . . 119.11(13) ? N3 C11 C12 . . 120.22(13) ? N4 C11 C12 . . 120.66(12) ? C11 C12 C14 . . 111.37(12) ? C11 C12 C13 . . 109.34(11) ? C14 C12 C13 . . 111.33(12) ? C11 C12 H12A . . 108.2 ? C14 C12 H12A . . 108.2 ? C13 C12 H12A . . 108.2 ? C12 C13 H13A . . 109.5 ? C12 C13 H13B . . 109.5 ? H13A C13 H13B . . 109.5 ? C12 C13 H13C . . 109.5 ? H13A C13 H13C . . 109.5 ? H13B C13 H13C . . 109.5 ? C12 C14 H14A . . 109.5 ? C12 C14 H14B . . 109.5 ? H14A C14 H14B . . 109.5 ? C12 C14 H14C . . 109.5 ? H14A C14 H14C . . 109.5 ? H14B C14 H14C . . 109.5 ? C10 C15 H15A . . 109.5 ? C10 C15 H15B . . 109.5 ? H15A C15 H15B . . 109.5 ? C10 C15 H15C . . 109.5 ? H15A C15 H15C . . 109.5 ? H15B C15 H15C . . 109.5 ? H2W1 O1W H1W1 . . 108(2) ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C1 C2 C3 . . . . 177.02(13) ? C6 C1 C2 C3 . . . . -1.7(2) ? O1 C1 C2 N2 . . . . -4.3(2) ? C6 C1 C2 N2 . . . . 176.93(12) ? O2 N2 C2 C3 . . . . 153.14(14) ? O3 N2 C2 C3 . . . . -24.99(19) ? O2 N2 C2 C1 . . . . -25.6(2) ? O3 N2 C2 C1 . . . . 156.26(13) ? C1 C2 C3 C4 . . . . 2.0(2) ? N2 C2 C3 C4 . . . . -176.69(12) ? C2 C3 C4 C5 . . . . -0.6(2) ? C2 C3 C4 N1 . . . . 179.06(12) ? O4 N1 C4 C3 . . . . 2.98(19) ? O5 N1 C4 C3 . . . . -177.24(13) ? O4 N1 C4 C5 . . . . -177.33(12) ? O5 N1 C4 C5 . . . . 2.45(19) ? C3 C4 C5 C6 . . . . -1.0(2) ? N1 C4 C5 C6 . . . . 179.34(12) ? C4 C5 C6 C1 . . . . 1.2(2) ? C4 C5 C6 C7 . . . . -178.63(12) ? O1 C1 C6 C5 . . . . -178.73(13) ? C2 C1 C6 C5 . . . . 0.07(19) ? O1 C1 C6 C7 . . . . 1.1(2) ? C2 C1 C6 C7 . . . . 179.94(12) ? C5 C6 C7 O6 . . . . -0.5(2) ? C1 C6 C7 O6 . . . . 179.66(13) ? C5 C6 C7 O7 . . . . 179.34(12) ? C1 C6 C7 O7 . . . . -0.53(19) ? C11 N4 C8 O8 . . . . 177.87(13) ? C11 N4 C8 C9 . . . . -2.37(19) ? O8 C8 C9 C10 . . . . -178.07(15) ? N4 C8 C9 C10 . . . . 2.18(19) ? C8 C9 C10 N3 . . . . -0.8(2) ? C8 C9 C10 C15 . . . . 179.28(13) ? C11 N3 C10 C9 . . . . -0.6(2) ? C11 N3 C10 C15 . . . . 179.26(13) ? C10 N3 C11 N4 . . . . 0.5(2) ? C10 N3 C11 C12 . . . . 179.41(12) ? C8 N4 C11 N3 . . . . 1.1(2) ? C8 N4 C11 C12 . . . . -177.78(12) ? N3 C11 C12 C14 . . . . 126.27(14) ? N4 C11 C12 C14 . . . . -54.87(17) ? N3 C11 C12 C13 . . . . -110.27(15) ? N4 C11 C12 C13 . . . . 68.59(17) ? 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 N3 H1N3 O6 2_566 0.91(2) 1.817(19) 2.7180(16) 170(2) yes N4 H1N4 O1W . 0.90(2) 1.84(2) 2.7309(17) 171(2) yes O1W H2W1 O1 1_565 0.85(2) 1.97(2) 2.7878(16) 162(2) yes O1W H1W1 O3 2_655 0.84(2) 2.11(2) 2.9381(17) 170(2) yes O7 H7 O1 . 0.82 1.67 2.4370(16) 156 yes C9 H9A O5 1_556 0.93 2.54 3.4312(18) 161 yes C12 H12A O7 2_566 0.98 2.41 3.3023(18) 152 yes C14 H14B O4 2_665 0.96 2.60 3.2318(19) 124 yes C15 H15C O3 1_566 0.96 2.60 3.471(2) 152 yes