#------------------------------------------------------------------------------ #$Date: 2024-12-07 18:12:38 +0100 (Sat, 07 Dec 2024) $ #$Revision: 296787 $ #$URL: svn://www.crystallography.net/cod/cif/2/02/32/2023286.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2023286 loop_ _publ_author_name 'Inoue, Kazuki' 'Nakami, Shun' 'Kumasaki, Mieko' 'Matsumoto, Shinya' _publ_section_title ; Synthesis and crystal structure of 1H-1,2,4-triazole-3,5-diamine monohydrate ; _journal_coeditor_code DX2060 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E Crystallographic Communications' _journal_page_first 1161 _journal_page_last 1164 _journal_paper_doi 10.1107/S2056989024009265 _journal_volume 80 _journal_year 2024 _chemical_formula_iupac 'C2 H5 N5, H2 O' _chemical_formula_moiety 'C2 H5 N5, H2 O' _chemical_formula_sum 'C2 H7 N5 O' _chemical_formula_weight 117.13 _chemical_name_systematic ; 1H-1,2,4-Triazole-3,5-diamine monohydrate ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _cell_angle_alpha 90 _cell_angle_beta 92.9639(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 3.80560(5) _cell_length_b 9.49424(11) _cell_length_c 14.01599(15) _cell_measurement_reflns_used 2506 _cell_measurement_temperature 123.15 _cell_measurement_theta_max 72.5260 _cell_measurement_theta_min 6.3240 _cell_volume 505.738(10) _computing_cell_refinement ; CrysAlisPro 1.171.40.66a (Rigaku OD, 2019) ; _computing_data_collection ; CrysAlisPro 1.171.40.66a (Rigaku OD, 2019) ; _computing_data_reduction ; CrysAlisPro 1.171.40.66a (Rigaku OD, 2019) ; _computing_molecular_graphics ; Mercury (Macrae et al., 2020) ; _computing_publication_material ; PublCIF (Westrip, 2010) and OLEX2 1.5 (Dolomanov et al., 2009) ; _computing_structure_refinement ; SHELXL2019/3 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT2018/2 (Sheldrick, 2015a) ; _diffrn_ambient_temperature 123.15 _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa dual home/near' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_unetI/netI 0.0183 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2894 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.669 _diffrn_reflns_theta_min 5.631 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 1.070 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.88295 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlisPro; Rigaku OD, 2019) ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.538 _exptl_crystal_description block _exptl_crystal_F_000 248 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.189 _refine_diff_density_min -0.220 _refine_ls_extinction_coef 0.0108(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method ; SHELXL2019/2 (Sheldrick, 2015b) ; _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 102 _refine_ls_number_reflns 989 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.110 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0312 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+0.1848P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.0805 _reflns_number_gt 956 _reflns_number_total 989 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL 20240717datah2o-6_a.res in P2(1)/c 20240717datah2o-6.res created by SHELXL-2019/3 at 18:42:28 on 07-Aug-2024 REM Old TITL 20240717DATAH2O-6 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.124, Rweak 0.132, Alpha 0.011 REM 1.322 for 69 systematic absences, Orientation as input REM Formula found by SHELXT: C7 N CELL 1.54184 3.805599 9.49424 14.015994 90 92.9639 90 ZERR 4 0.000046 0.000105 0.000154 0 0.0011 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 8 28 20 4 L.S. 10 PLAN 14 SIZE 0.1 0.2 0.1 TEMP -150 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.040300 0.184800 EXTI 0.010777 FVAR 0.97788 O1 4 0.384919 0.753538 0.118406 11.00000 0.02674 0.01920 = 0.01617 -0.00106 -0.00365 0.00538 N2 3 0.728526 0.721500 0.301935 11.00000 0.01575 0.01332 = 0.01502 0.00015 -0.00102 0.00000 N4 3 0.768354 0.629220 0.445513 11.00000 0.01993 0.01471 = 0.01232 0.00033 -0.00138 0.00092 N3 3 0.915141 0.529317 0.386477 11.00000 0.01812 0.01423 = 0.01650 -0.00086 -0.00179 0.00111 N6 3 0.963796 0.525987 0.218300 11.00000 0.02111 0.01365 = 0.01691 -0.00051 0.00032 0.00118 N5 3 0.528187 0.860036 0.430968 11.00000 0.02386 0.01643 = 0.01565 0.00007 0.00110 0.00372 C8 1 0.663328 0.741096 0.394034 11.00000 0.01303 0.01439 = 0.01569 0.00017 -0.00222 -0.00212 C7 1 0.878798 0.590720 0.302169 11.00000 0.01281 0.01285 = 0.01652 -0.00013 -0.00178 -0.00178 H4 2 0.764704 0.612442 0.507424 11.00000 0.02129 H5A 2 0.453845 0.850602 0.490240 11.00000 0.02329 H6A 2 1.064464 0.584659 0.178278 11.00000 0.03158 H6B 2 1.085186 0.447587 0.228432 11.00000 0.03125 H5B 2 0.401639 0.914188 0.388033 11.00000 0.03170 H1A 2 0.279736 0.835354 0.114855 11.00000 0.04126 H1B 2 0.495067 0.752934 0.176854 11.00000 0.04509 HKLF 4 REM 20240717datah2o-6_a.res in P2(1)/c REM wR2 = 0.0805, GooF = S = 1.110, Restrained GooF = 1.110 for all data REM R1 = 0.0312 for 956 Fo > 4sig(Fo) and 0.0318 for all 989 data REM 102 parameters refined using 0 restraints END WGHT 0.0402 0.1850 REM Highest difference peak 0.189, deepest hole -0.220, 1-sigma level 0.044 Q1 1 0.8639 0.4516 0.3868 11.00000 0.05 0.19 Q2 1 0.8093 0.6622 0.2974 11.00000 0.05 0.18 Q3 1 0.7142 0.6909 0.4206 11.00000 0.05 0.18 Q4 1 0.6456 0.7189 0.3423 11.00000 0.05 0.18 Q5 1 0.9159 0.5635 0.2588 11.00000 0.05 0.18 Q6 1 0.8473 0.5407 0.3404 11.00000 0.05 0.18 Q7 1 0.7294 0.7453 0.3422 11.00000 0.05 0.17 Q8 1 0.7470 0.7754 0.2557 11.00000 0.05 0.17 Q9 1 0.6367 0.8028 0.4119 11.00000 0.05 0.16 Q10 1 0.5248 0.7752 0.4091 11.00000 0.05 0.14 Q11 1 0.5060 0.7378 0.0573 11.00000 0.05 0.14 Q12 1 0.6257 0.7699 0.0872 11.00000 0.05 0.13 Q13 1 0.9524 0.7311 0.2808 11.00000 0.05 0.13 Q14 1 0.8280 0.5706 0.4191 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0312 for 956 Fo > 4sig(Fo) and 0.0318 for all 3002 data REM 102 parameters refined using n/a restraints REM Highest difference peak 0.19, deepest hole -0.22 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0318 REM R1_gt = 0.0312 REM wR_ref = 0.0805 REM GOOF = 1.110 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 3002 REM Reflections_gt = 956 REM Parameters = 102 REM Hole = -0.22 REM Peak = 0.19 REM Flack = n/a ; _cod_data_source_file dx2060.cif _cod_data_source_block I _cod_depositor_comments 'Adding full bibliography for 2023286.cif.' _cod_database_code 2023286 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.814 _shelx_estimated_absorpt_t_max 0.901 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.3849(2) 0.75354(9) 0.11841(6) 0.0209(3) Uani d 1 . . N N2 0.7285(2) 0.72150(10) 0.30194(7) 0.0148(3) Uani d 1 . . N N4 0.7684(2) 0.62922(10) 0.44551(7) 0.0157(3) Uani d 1 . . N N3 0.9151(3) 0.52932(10) 0.38648(7) 0.0164(3) Uani d 1 . . N N6 0.9638(3) 0.52599(11) 0.21830(7) 0.0172(3) Uani d 1 . . N N5 0.5282(3) 0.86004(11) 0.43097(8) 0.0186(3) Uani d 1 . . C C8 0.6633(3) 0.74110(12) 0.39403(8) 0.0145(3) Uani d 1 . . C C7 0.8788(3) 0.59072(12) 0.30217(8) 0.0141(3) Uani d 1 . . H H4 0.765(4) 0.6124(16) 0.5074(12) 0.021(4) Uiso d 1 . . H H5A 0.454(4) 0.8506(17) 0.4902(12) 0.023(4) Uiso d 1 . . H H6A 1.064(4) 0.5847(19) 0.1783(12) 0.032(4) Uiso d 1 . . H H6B 1.085(4) 0.448(2) 0.2284(12) 0.031(4) Uiso d 1 . . H H5B 0.402(4) 0.9142(19) 0.3880(12) 0.032(4) Uiso d 1 . . H H1A 0.280(5) 0.835(2) 0.1149(13) 0.041(5) Uiso d 1 . . H H1B 0.495(5) 0.753(2) 0.1769(16) 0.045(5) 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 0.0267(5) 0.0192(5) 0.0162(5) 0.0054(4) -0.0036(4) -0.0011(3) N2 0.0157(5) 0.0133(5) 0.0150(5) 0.0000(4) -0.0010(4) 0.0002(4) N4 0.0199(5) 0.0147(5) 0.0123(5) 0.0009(4) -0.0014(4) 0.0003(4) N3 0.0181(5) 0.0142(5) 0.0165(5) 0.0011(4) -0.0018(4) -0.0009(4) N6 0.0211(5) 0.0136(5) 0.0169(5) 0.0012(4) 0.0003(4) -0.0005(4) N5 0.0239(5) 0.0164(5) 0.0156(5) 0.0037(4) 0.0011(4) 0.0001(4) C8 0.0130(5) 0.0144(6) 0.0157(5) -0.0021(4) -0.0022(4) 0.0002(4) C7 0.0128(5) 0.0128(5) 0.0165(6) -0.0018(4) -0.0018(4) -0.0001(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_refln_index_h _diffrn_refln_index_k _diffrn_refln_index_l 0 0 -2 0 0 -3 0 0 -4 0 0 -5 0 0 -6 0 0 -7 0 0 -8 0 0 -9 0 0 -9 0 0 -10 0 0 -10 0 0 -11 0 0 -11 0 0 -12 0 0 -12 0 0 -13 0 0 -13 0 0 -14 0 0 -14 0 0 -15 0 0 -15 0 0 -16 0 0 -17 0 1 0 0 1 -1 0 -1 -1 0 1 -1 0 1 -1 0 -1 -2 0 1 -2 0 1 -2 0 1 -2 0 1 -3 0 1 -3 0 -1 -3 0 -1 -3 0 1 -4 0 -1 -4 0 1 -4 0 -1 -4 0 1 -5 0 -1 -5 0 -1 -5 0 1 -6 0 -1 -6 0 -1 -6 0 1 -6 0 1 -7 0 1 -7 0 -1 -7 0 -1 -7 0 1 -8 0 1 -8 0 -1 -8 0 1 -9 0 -1 -9 0 1 -9 0 1 -9 0 1 -9 0 1 -10 0 1 -10 0 1 -10 0 1 -11 0 1 -11 0 -1 -11 0 -1 -11 0 1 11 0 1 -11 0 -1 -12 0 1 -12 0 1 12 0 1 -12 0 1 -12 0 -1 -12 0 1 -13 0 -1 -13 0 1 -13 0 -1 -13 0 1 -13 0 -1 -14 0 1 -14 0 1 -14 0 1 -14 0 -1 -14 0 1 -15 0 1 -15 0 -1 -15 0 -1 -15 0 1 -15 0 1 -16 0 1 -16 0 -1 -16 0 -1 -17 0 2 0 0 2 0 0 2 1 0 2 -1 0 2 1 0 -2 -2 0 2 -2 0 2 -2 0 2 -2 0 -2 -3 0 2 -3 0 2 -3 0 2 -3 0 2 -4 0 -2 -4 0 2 -4 0 2 -4 0 -2 -5 0 2 -5 0 2 -5 0 2 -5 0 2 -6 0 2 -6 0 -2 -6 0 2 -7 0 2 -7 0 -2 -7 0 -2 -8 0 2 -8 0 2 9 0 2 -9 0 -2 -9 0 2 -9 0 2 -10 0 2 10 0 2 -10 0 -2 -10 0 2 -11 0 -2 -11 0 2 -11 0 2 -11 0 -2 -11 0 2 11 0 2 -12 0 -2 -12 0 2 12 0 2 -12 0 2 -12 0 -2 -12 0 2 -13 0 -2 -13 0 2 13 0 -2 -13 0 2 -13 0 2 -13 0 2 -14 0 2 -14 0 -2 -14 0 -2 -14 0 2 -14 0 2 -15 0 -2 -15 0 2 -15 0 2 -15 0 2 -16 0 3 0 0 3 -1 0 3 1 0 3 -1 0 3 1 0 3 2 0 3 -2 0 3 -2 0 3 2 0 3 -3 0 3 -3 0 -3 -4 0 3 -4 0 3 -4 0 3 -4 0 3 -5 0 -3 -5 0 3 -5 0 3 -5 0 3 -6 0 3 -6 0 -3 -6 0 3 -6 0 3 -7 0 3 8 0 3 8 0 3 -8 0 -3 -8 0 3 -8 0 3 8 0 -3 -9 0 3 -9 0 3 -9 0 3 9 0 3 -9 0 3 9 0 -3 -9 0 -3 -10 0 3 -10 0 -3 -10 0 3 -10 0 3 10 0 3 11 0 3 -11 0 -3 -11 0 -3 -11 0 3 -12 0 -3 -12 0 3 12 0 3 12 0 -3 -12 0 3 -12 0 -3 -13 0 -3 -13 0 3 13 0 3 -13 0 3 -13 0 3 14 0 3 -14 0 -3 -14 0 -3 -14 0 3 -14 0 3 -15 0 -3 -15 0 -3 -16 0 3 -16 0 4 0 0 4 0 0 4 1 0 4 -1 0 4 -1 0 4 -2 0 4 -2 0 4 2 0 4 3 0 4 -3 0 4 -3 0 4 -4 0 4 -4 0 4 4 0 4 -5 0 4 5 0 4 6 0 4 -6 0 4 7 0 4 -7 0 4 7 0 4 7 0 4 -7 0 -4 -7 0 4 7 0 4 8 0 4 8 0 4 8 0 -4 -8 0 4 -8 0 4 -8 0 4 8 0 4 9 0 4 -9 0 -4 -9 0 4 9 0 4 9 0 4 9 0 4 -9 0 4 10 0 4 10 0 4 -10 0 4 -10 0 -4 -10 0 4 10 0 4 -11 0 -4 -11 0 4 11 0 4 12 0 4 -12 0 4 -12 0 -4 -12 0 4 -13 0 -4 -13 0 4 -13 0 4 13 0 4 14 0 -4 -14 0 4 15 0 -4 -15 0 -4 -16 0 4 -16 0 5 0 0 5 -1 0 5 1 0 5 2 0 5 -2 0 5 3 0 5 -3 0 5 -4 0 5 4 0 5 5 0 5 5 0 5 5 0 5 5 0 5 5 0 5 -5 0 5 6 0 5 -6 0 5 -6 0 5 6 0 5 6 0 5 6 0 5 -6 0 5 6 0 5 -7 0 5 7 0 5 7 0 5 7 0 5 -7 0 5 -8 0 5 8 0 5 8 0 5 8 0 5 -8 0 5 8 0 5 9 0 5 9 0 5 -9 0 5 9 0 5 9 0 -5 -9 0 5 -9 0 5 10 0 5 10 0 5 -10 0 -5 -10 0 5 -10 0 5 10 0 5 11 0 5 -11 0 5 11 0 -5 -11 0 5 12 0 -5 -12 0 5 -13 0 -5 -13 0 5 13 0 5 -14 0 -5 -14 0 5 14 0 5 -15 0 -5 -15 0 6 0 0 6 0 0 6 1 0 6 1 0 6 -1 0 6 1 0 6 1 0 6 -1 0 6 2 0 6 -2 0 6 2 0 6 -2 0 6 2 0 6 3 0 6 3 0 6 3 0 6 3 0 6 3 0 6 -3 0 6 4 0 6 4 0 6 4 0 6 4 0 6 4 0 6 -5 0 6 5 0 6 5 0 6 5 0 6 5 0 6 6 0 6 -6 0 6 6 0 6 6 0 6 6 0 6 7 0 6 7 0 6 7 0 6 7 0 6 7 0 6 8 0 6 8 0 6 8 0 6 -8 0 6 -9 0 6 9 0 6 9 0 6 9 0 6 -10 0 6 10 0 6 10 0 6 11 0 6 -11 0 6 11 0 6 12 0 6 -12 0 6 12 0 6 -13 0 6 13 0 6 -14 0 7 0 0 7 0 0 7 -1 0 7 1 0 7 -1 0 7 1 0 7 1 0 7 -2 0 7 -2 0 7 2 0 7 -2 0 7 3 0 7 -3 0 7 3 0 7 4 0 7 4 0 7 4 0 7 4 0 7 -4 0 7 5 0 7 5 0 7 5 0 7 -5 0 7 5 0 7 5 0 7 6 0 7 -6 0 7 6 0 7 6 0 7 6 0 7 7 0 7 7 0 7 -7 0 7 7 0 7 7 0 7 7 0 7 8 0 7 8 0 7 8 0 7 9 0 7 9 0 7 9 0 7 10 0 7 -10 0 7 11 0 7 11 0 7 -11 0 7 12 0 7 -12 0 7 -13 0 8 0 0 8 0 0 8 0 0 8 1 0 8 1 0 8 -1 0 8 -1 0 8 1 0 8 2 0 8 -2 0 8 2 0 8 -2 0 8 3 0 8 -3 0 8 3 0 8 4 0 8 4 0 8 -4 0 8 4 0 8 5 0 8 5 0 8 5 0 8 6 0 8 -6 0 8 6 0 8 7 0 8 -7 0 8 8 0 8 8 0 8 9 0 8 9 0 8 9 0 8 10 0 8 11 0 8 12 0 9 0 0 9 0 0 9 -1 0 9 1 0 9 1 0 9 1 0 9 -1 0 9 2 0 9 2 0 9 2 0 9 -2 0 9 -2 0 9 3 0 9 -3 0 9 3 0 9 4 0 9 4 0 9 -5 0 9 5 0 9 5 0 9 5 0 9 6 0 9 6 0 9 6 0 9 -6 0 9 7 0 9 7 0 9 7 0 9 8 0 9 8 0 9 9 0 9 9 0 9 10 0 9 11 0 10 0 0 10 0 0 10 1 0 10 -1 0 10 1 0 10 -1 0 10 2 0 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-1 1 3 1 1 -3 -1 -2 3 1 2 3 -1 2 3 1 2 3 -1 2 3 1 2 3 -1 2 -3 -1 -3 3 1 3 3 -1 3 3 1 3 3 -1 3 3 1 4 3 -1 4 3 1 4 3 -1 4 -3 1 -5 3 1 5 3 -1 5 3 1 5 3 -1 5 -3 1 -6 3 1 6 3 1 6 3 -1 6 3 -1 6 -3 1 -7 -3 1 -8 -3 1 -9 -3 1 -10 -3 -1 -10 -3 1 -11 -3 1 -11 -3 -1 -11 -3 1 -12 -3 -1 -12 3 2 -13 -3 2 13 3 -2 -12 3 2 -12 3 -2 -11 3 2 -11 3 -2 -10 3 2 -10 3 -2 -9 3 -2 -9 3 -2 -8 3 -2 -7 3 2 -7 3 2 -6 3 2 -6 -3 -2 6 3 2 -5 3 2 -5 -3 -2 5 -3 -2 4 3 2 -4 3 2 -4 3 2 -4 -3 -2 3 3 2 -3 3 2 -3 -3 2 3 3 2 -3 3 2 -3 -3 -2 2 3 -2 -2 3 2 -2 -3 2 2 3 2 -2 3 2 -2 3 2 -2 -3 -2 1 3 2 -1 3 -2 -1 3 2 -1 -3 2 1 3 2 -1 3 2 -1 -3 -2 0 3 2 0 3 2 0 3 -2 0 -3 2 0 3 2 0 3 2 0 -3 -2 -1 3 -2 1 3 2 1 3 2 1 -3 -2 -2 3 2 2 3 -2 2 3 2 2 3 -2 2 3 2 2 -3 -2 -3 3 2 3 3 -2 3 3 2 3 3 -2 3 3 2 3 -3 2 -4 3 2 4 3 -2 4 3 2 4 -3 2 -5 3 2 5 3 -2 5 -3 2 -6 -3 2 -7 -3 2 -8 -3 2 -9 -3 2 -10 -3 2 -10 -3 2 -11 -3 -2 -11 -3 2 -12 -3 -2 -12 3 3 -13 3 3 -13 3 3 -12 -3 3 12 3 3 -11 3 3 -11 -3 3 11 3 3 -10 3 3 -10 3 3 -9 3 3 -9 3 3 -8 3 3 -8 3 3 -7 3 3 -7 3 3 -6 3 3 -6 -3 -3 5 3 3 -5 3 3 -5 3 3 -5 -3 -3 4 3 3 -4 3 3 -4 -3 3 4 -3 -3 3 3 3 -3 -3 3 3 3 3 -3 3 3 -3 -3 -3 2 3 3 -2 -3 3 2 3 3 -2 3 3 -2 3 3 -1 3 -3 -1 3 3 -1 -3 3 1 3 3 -1 3 3 -1 -3 -3 0 3 3 0 3 -3 0 3 3 0 -3 3 0 3 3 0 -3 -3 -1 3 3 1 3 3 1 3 -3 1 -3 3 -1 3 3 1 -3 -3 -2 3 3 2 3 3 2 3 -3 2 -3 3 -2 3 3 2 -3 -3 -3 3 3 3 3 -3 3 3 3 3 3 -3 3 3 3 3 3 3 4 3 -3 4 -3 3 -4 -3 3 -4 3 3 4 3 -3 4 3 3 4 -3 3 -5 -3 3 -5 -3 3 -6 -3 3 -6 -3 3 -7 -3 3 -7 -3 3 -8 -3 3 -8 -3 3 -9 -3 3 -9 -3 3 -10 -3 3 -10 3 3 11 3 -3 11 -3 3 -11 -3 -3 -11 -3 3 -12 -3 -3 -12 3 4 -12 3 4 -11 -3 4 11 3 4 -10 3 4 -10 3 4 -9 3 4 -9 3 4 -8 3 4 -8 3 4 -7 3 4 -7 3 4 -6 3 4 -6 3 4 -6 3 4 -5 -3 4 5 3 4 -5 3 4 -4 3 4 -4 -3 4 4 -3 -4 3 3 4 -3 3 4 -3 -3 4 3 3 4 -3 -3 -4 2 3 4 -2 3 4 -2 -3 4 2 3 4 -2 3 4 -2 3 4 -1 -3 4 1 3 4 -1 3 4 -1 3 4 0 -3 4 0 3 4 0 3 4 0 3 4 1 -3 4 -1 3 4 1 3 4 1 3 4 2 3 4 2 3 4 2 -3 4 -3 -3 4 -3 -3 4 -4 -3 4 -4 -3 4 -5 3 -4 5 -3 4 -5 3 -4 6 -3 4 -6 -3 4 -6 -3 4 -7 -3 4 -7 -3 4 -8 -3 4 -8 -3 4 -9 -3 4 -9 -3 4 -10 -3 4 -11 -3 -4 -11 3 5 -11 3 5 -11 3 5 -10 3 5 -9 3 5 -9 3 5 -8 3 5 -8 3 5 -7 3 5 -7 3 5 -7 3 5 -6 3 5 -6 -3 5 6 3 5 -6 3 5 -5 3 5 -5 3 5 -5 3 5 -4 -3 5 4 3 5 -4 3 5 -4 3 5 -3 -3 5 3 3 5 -3 3 5 -2 -3 5 2 3 5 -2 -3 5 1 3 5 -1 -3 5 0 3 5 0 -3 5 -1 3 5 1 3 5 2 -3 5 -3 -3 5 -3 3 5 3 -3 5 -4 -3 5 -4 -3 5 -5 -3 5 -5 -3 5 -6 -3 5 -6 -3 5 -7 -3 5 -7 -3 5 -8 -3 5 -8 -3 5 -9 -3 5 -10 -3 6 9 3 6 -8 3 6 -7 3 6 -6 -3 6 6 3 6 -6 3 6 -5 -3 6 5 3 6 -5 3 6 -4 3 6 -4 3 6 -3 -3 6 3 3 6 -2 -3 6 2 3 6 -2 3 6 -1 -3 6 1 3 6 -1 3 6 0 -3 6 0 3 6 0 3 6 1 -3 6 -2 3 6 2 -3 6 -3 3 6 3 -3 6 -4 -3 6 -4 -3 6 -5 -3 6 -5 -3 6 -6 -3 6 -6 -3 6 -7 -3 6 -7 -3 6 -8 -3 6 -9 -3 7 8 -3 7 7 -3 7 6 3 7 -6 -3 7 5 3 7 -5 -3 7 4 3 7 -4 3 7 -3 -3 7 3 3 7 -2 3 7 -2 3 7 -1 3 7 -1 3 7 0 3 7 0 3 7 1 -3 7 -1 3 7 1 3 7 2 -3 7 -2 3 7 2 -3 7 -3 3 7 3 -3 7 -3 -3 7 -4 -3 7 -4 -3 7 -5 -3 7 -5 -3 7 -6 -3 7 -6 -3 7 -7 -3 8 6 -3 8 5 3 8 -5 -3 8 4 -3 8 4 3 8 -4 -3 8 3 -3 8 3 3 8 -3 -3 8 2 -3 8 2 -3 8 1 3 8 -1 -3 8 0 -3 8 0 3 8 0 -3 8 -1 3 8 1 3 8 2 -3 8 -3 -3 8 -3 -3 8 -4 -3 8 -4 -3 9 1 3 9 -1 -3 9 0 3 9 0 4 0 -9 4 0 -9 4 0 -8 4 0 -8 4 0 -7 4 0 -7 4 0 -6 4 0 -5 4 0 -4 4 0 -3 4 0 -2 4 0 -1 4 0 0 -4 0 -1 -4 0 -2 -4 0 -3 -4 0 -4 -4 0 -5 -4 0 -6 -4 0 -7 4 1 -9 4 -1 -9 4 1 -8 4 1 -8 4 -1 -8 4 1 -7 4 1 -7 4 -1 -7 4 1 -6 4 1 -5 4 1 -4 4 1 -3 4 1 -2 4 1 -1 4 1 0 -4 1 0 4 -1 1 4 1 1 -4 1 -1 4 1 2 4 -1 2 4 1 2 -4 -1 -2 4 1 3 4 -1 3 4 1 3 4 1 4 4 1 4 4 -1 4 -4 1 -4 4 1 5 4 -1 5 -4 1 -5 4 1 6 4 -1 6 -4 1 -6 4 1 7 4 -1 7 4 1 8 4 -1 8 -4 1 -8 -4 -1 -8 4 2 -9 4 2 -8 4 2 -8 4 2 -7 4 -2 -7 4 2 -6 4 2 -6 4 2 -5 4 2 -4 4 2 -3 4 2 -2 4 2 -1 -4 2 1 4 2 0 -4 2 0 4 2 1 -4 2 -1 4 2 2 4 -2 2 4 2 2 -4 2 -2 4 2 3 4 -2 3 4 2 3 -4 2 -3 4 2 4 4 -2 4 -4 2 -4 4 2 5 4 -2 5 -4 2 -5 4 2 6 4 -2 6 4 2 7 4 -2 7 -4 2 -7 4 3 -8 4 3 -8 4 3 -7 4 3 -7 4 3 -6 4 3 -6 4 3 -5 4 3 -5 4 3 -4 4 3 -3 4 3 -2 -4 3 2 4 3 -1 -4 3 1 4 3 0 -4 3 0 4 3 1 -4 3 -1 4 3 2 -4 3 -2 4 3 3 -4 3 -3 -4 3 -4 4 -3 5 -4 3 -6 -4 3 -7 4 4 -7 4 4 -7 4 4 -6 4 4 -6 4 4 -5 4 4 -5 4 4 -4 4 4 -3 -4 4 2 -4 4 1 -4 4 0 4 4 1 -4 4 -1 4 4 2 -4 4 -2 4 4 3 -4 4 -3 4 4 4 4 4 5 -4 4 -5 4 4 6 -4 4 -6 4 5 -6 4 5 -5 4 5 -4 4 5 -3 4 5 -2 4 5 -1 -4 5 1 4 5 0 -4 5 0 4 5 1 -4 5 -1 4 5 2 -4 5 -2 4 5 3 -4 5 -3 4 5 4 -4 5 -4 4 6 -2 4 6 -1 -4 6 1 4 6 0 4 6 1 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 H1A O1 H1B . . 104.3(17) ? C8 N2 C7 . . 102.83(9) ? N3 N4 H4 . . 119.2(10) ? C8 N4 N3 . . 109.80(9) ? C8 N4 H4 . . 131.0(10) ? C7 N3 N4 . . 101.79(9) ? C7 N6 H6A . . 112.7(11) ? C7 N6 H6B . . 112.5(11) ? H6A N6 H6B . . 112.9(15) ? C8 N5 H5A . . 114.5(10) ? C8 N5 H5B . . 114.6(10) ? H5A N5 H5B . . 119.2(14) ? N2 C8 N5 . . 125.22(10) ? N4 C8 N2 . . 110.20(10) ? N4 C8 N5 . . 124.49(11) ? N2 C7 N6 . . 121.27(10) ? N3 C7 N2 . . 115.36(10) ? N3 C7 N6 . . 123.25(11) ? 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 H1A . 0.87(2) ? O1 H1B . 0.90(2) ? N2 C8 . 1.3400(15) ? N2 C7 . 1.3670(15) ? N4 N3 . 1.3943(13) ? N4 C8 . 1.3337(15) ? N4 H4 . 0.883(16) ? N3 C7 . 1.3185(15) ? N6 C7 . 1.3797(15) ? N6 H6A . 0.891(19) ? N6 H6B . 0.884(19) ? N5 C8 . 1.3547(15) ? N5 H5A . 0.896(17) ? N5 H5B . 0.910(18) ? 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 N5 H5A O1 4_576 0.895(17) 2.080(17) 2.9173(14) 155.4(14) O1 H1A N3 2_655 0.871(19) 1.988(19) 2.8558(13) 174.1(16) O1 H1B N2 . 0.90(2) 1.95(2) 2.8410(13) 171.5(18) N4 H4 N3 3_766 0.883(17) 2.306(16) 2.9947(14) 134.9(13) 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 N4 N3 C7 N2 . . . . 1.14(12) ? N4 N3 C7 N6 . . . . -174.87(10) ? N3 N4 C8 N2 . . . . 0.66(13) ? N3 N4 C8 N5 . . . . -176.03(10) ? C8 N2 C7 N3 . . . . -0.79(12) ? C8 N2 C7 N6 . . . . 175.30(10) ? C8 N4 N3 C7 . . . . -1.05(12) ? C7 N2 C8 N4 . . . . 0.04(12) ? C7 N2 C8 N5 . . . . 176.69(11) ?