data_1 _iucr_refine_instructions_details ; TITL 5329 in P2(1)/n CELL 0.71073 7.3326 19.4897 8.6586 90.000 106.069 90.000 ZERR 4.00 0.0005 0.0014 0.0006 0.000 0.002 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N UNIT 44 52 28 OMIT -1.00 55.00 L.S. 4 ACTA BOND FMAP 2 PLAN 20 SIZE 0.70 0.40 0.20 HTAB N1 N5_$2 HTAB N1 N7_$1 HTAB HTAB N2 N6_$3 EQIV $1 -x-1/2, y+1/2, -z+1/2 EQIV $2 x+1/2, -y+1/2, z+1/2 EQIV $3 x+1/2, -y+1/2, z+1/2 TEMP 22 BOND $H WGHT 0.064200 0.237400 FVAR 0.55340 N1 3 0.126574 0.306152 0.566785 11.00000 0.03976 0.03852 = 0.04785 -0.01207 -0.01254 0.00777 H1A 2 0.215791 0.330128 0.635069 11.00000 0.04835 H1B 2 0.008266 0.322197 0.532001 11.00000 0.05096 N2 3 0.314400 0.209674 0.597970 11.00000 0.03294 0.03639 = 0.03148 -0.00660 -0.00751 0.00284 N3 3 0.209575 0.114353 0.442747 11.00000 0.02849 0.03056 = 0.03407 -0.00231 -0.00147 0.00070 N4 3 0.193873 0.047483 0.393216 11.00000 0.03190 0.03026 = 0.03970 -0.00395 0.00375 -0.00149 N5 3 -0.071546 0.108222 0.272223 11.00000 0.03417 0.03460 = 0.03636 -0.00386 -0.00420 -0.00085 N6 3 0.027075 0.217352 0.393401 11.00000 0.03935 0.03328 = 0.03741 -0.00377 -0.01182 0.00533 N7 3 -0.227810 -0.127533 0.016868 11.00000 0.05330 0.05116 = 0.06164 -0.02088 0.01692 -0.01726 C1 1 0.157197 0.243681 0.517124 11.00000 0.03343 0.03218 = 0.03081 -0.00001 -0.00159 0.00212 C2 1 0.383725 0.147814 0.537472 11.00000 0.02662 0.03381 = 0.03138 -0.00339 -0.00054 -0.00091 C3 1 0.052394 0.149822 0.368704 11.00000 0.03085 0.03479 = 0.03002 0.00058 -0.00374 0.00185 C4 1 0.021686 0.047203 0.291764 11.00000 0.03053 0.03334 = 0.03337 -0.00181 0.00584 -0.00322 C5 1 -0.062916 -0.013804 0.200621 11.00000 0.03000 0.03740 = 0.03935 -0.00529 0.01126 -0.00621 C6 1 0.000460 -0.079583 0.246043 11.00000 0.03304 0.03980 = 0.05787 -0.00540 0.00891 -0.00160 AFIX 43 H6 2 0.098776 -0.087030 0.338761 11.00000 -1.20000 AFIX 0 C7 1 -0.084905 -0.133960 0.151225 11.00000 0.04730 0.03812 = 0.08055 -0.01131 0.01984 -0.00369 AFIX 43 H7 2 -0.040294 -0.177889 0.182683 11.00000 -1.20000 AFIX 0 C8 1 -0.286326 -0.063984 -0.024487 11.00000 0.05081 0.05539 = 0.04068 -0.01015 0.00931 -0.01736 AFIX 43 H8 2 -0.385086 -0.058009 -0.117612 11.00000 -1.20000 AFIX 0 C9 1 -0.210633 -0.006387 0.061208 11.00000 0.04344 0.04395 = 0.03739 -0.00225 0.00689 -0.00907 AFIX 43 H9 2 -0.257709 0.036910 0.026284 11.00000 -1.20000 AFIX 0 C10 1 0.485660 0.102282 0.676399 11.00000 0.03155 0.04634 = 0.03781 0.00170 -0.00159 0.00740 AFIX 137 H10A 2 0.591712 0.126650 0.744110 11.00000 -1.50000 H10B 2 0.530013 0.061660 0.635520 11.00000 -1.50000 H10C 2 0.399844 0.089686 0.737598 11.00000 -1.50000 AFIX 0 C11 1 0.508637 0.165366 0.429132 11.00000 0.04531 0.05521 = 0.04688 -0.00265 0.01395 -0.00966 AFIX 137 H11A 2 0.436255 0.191022 0.338082 11.00000 -1.50000 H11B 2 0.553834 0.123818 0.392891 11.00000 -1.50000 H11C 2 0.614692 0.192341 0.488014 11.00000 -1.50000 AFIX 0 H2 2 0.382814 0.227959 0.682180 11.00000 0.04139 HKLF 4 REM 5329 in P2(1)/n REM R1 = 0.0476 for 2282 Fo > 4sig(Fo) and 0.0582 for all 2736 data REM 177 parameters refined using 0 restraints END WGHT 0.0642 0.2374 REM Highest difference peak 0.268, deepest hole -0.213, 1-sigma level 0.042 Q1 1 0.4423 0.1546 0.4818 11.00000 0.05 0.27 Q2 1 -0.0121 0.0190 0.2428 11.00000 0.05 0.24 Q3 1 0.3013 0.1284 0.4948 11.00000 0.05 0.23 Q4 1 0.1713 0.2882 0.5056 11.00000 0.05 0.20 Q5 1 0.4379 0.1262 0.5982 11.00000 0.05 0.20 Q6 1 0.0132 -0.0457 0.1852 11.00000 0.05 0.20 Q7 1 0.0049 0.0806 0.2362 11.00000 0.05 0.18 Q8 1 0.3588 0.1833 0.5584 11.00000 0.05 0.18 Q9 1 -0.0636 -0.0454 0.2354 11.00000 0.05 0.17 Q10 1 0.1129 0.2664 0.5881 11.00000 0.05 0.17 Q11 1 -0.0046 0.1827 0.4070 11.00000 0.05 0.17 Q12 1 0.3057 0.1685 0.6036 11.00000 0.05 0.17 Q13 1 0.0037 0.1374 0.2862 11.00000 0.05 0.16 Q14 1 0.1192 0.1240 0.4806 11.00000 0.05 0.16 Q15 1 0.1509 0.1374 0.3723 11.00000 0.05 0.16 Q16 1 -0.1599 -0.0109 0.1514 11.00000 0.05 0.16 Q17 1 -0.0569 0.2423 0.3521 11.00000 0.05 0.15 Q18 1 -0.1990 -0.0348 -0.0038 11.00000 0.05 0.15 Q19 1 -0.0483 0.0701 0.3123 11.00000 0.05 0.15 Q20 1 0.2295 0.1815 0.6613 11.00000 0.05 0.15 ; _audit_update_record ; 2011-05-11 # Formatted by publCIF ; _publ_contact_author_name 'Anton V. Dolzhenko' _publ_contact_author_email phada@nus.edu.sg loop_ _publ_author_name _publ_author_address ' Dolzhenko, Anton V.' '' _audit_creation_method SHELXL-97 _chemical_name_systematic ;\ 7,7-dimethyl-2-pyridin-4-yl-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-\ amine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 N7' _chemical_formula_weight 243.28 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3326(5) _cell_length_b 19.4897(14) _cell_length_c 8.6586(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.069(2) _cell_angle_gamma 90.00 _cell_volume 1189.06(14) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2409 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 26.03 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9388 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 295(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8323 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2736 _reflns_number_gt 2282 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97' _computing_structure_refinement 'SHELXL-97' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2sigma(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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.2374P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2736 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 N1 N 0.1266(2) 0.30615(7) 0.56678(17) 0.0470(4) Uani 1 1 d . . . H1A H 0.216(3) 0.3301(9) 0.635(2) 0.048(5) Uiso 1 1 d . . . H1B H 0.008(3) 0.3222(9) 0.532(2) 0.051(5) Uiso 1 1 d . . . N2 N 0.31440(17) 0.20967(6) 0.59797(15) 0.0369(3) Uani 1 1 d . . . N3 N 0.20958(16) 0.11435(6) 0.44275(14) 0.0331(3) Uani 1 1 d . . . N4 N 0.19387(17) 0.04748(6) 0.39322(15) 0.0352(3) Uani 1 1 d . . . N5 N -0.07155(17) 0.10822(6) 0.27222(15) 0.0378(3) Uani 1 1 d . . . N6 N 0.02707(18) 0.21735(6) 0.39340(15) 0.0412(3) Uani 1 1 d . . . N7 N -0.2278(2) -0.12753(8) 0.01687(19) 0.0552(4) Uani 1 1 d . . . C1 C 0.1572(2) 0.24368(7) 0.51712(16) 0.0342(3) Uani 1 1 d . . . C2 C 0.38373(19) 0.14781(7) 0.53747(16) 0.0323(3) Uani 1 1 d . . . C3 C 0.0524(2) 0.14982(7) 0.36870(16) 0.0343(3) Uani 1 1 d . . . C4 C 0.0217(2) 0.04720(7) 0.29176(16) 0.0330(3) Uani 1 1 d . . . C5 C -0.0629(2) -0.01380(7) 0.20062(18) 0.0352(3) Uani 1 1 d . . . C6 C 0.0005(2) -0.07958(8) 0.2460(2) 0.0443(4) Uani 1 1 d . . . H6 H 0.0988 -0.0870 0.3388 0.053 Uiso 1 1 calc R . . C7 C -0.0849(3) -0.13396(9) 0.1512(3) 0.0549(5) Uani 1 1 d . . . H7 H -0.0403 -0.1779 0.1827 0.066 Uiso 1 1 calc R . . C8 C -0.2863(3) -0.06398(9) -0.0245(2) 0.0496(4) Uani 1 1 d . . . H8 H -0.3851 -0.0580 -0.1176 0.060 Uiso 1 1 calc R . . C9 C -0.2106(2) -0.00639(9) 0.06121(18) 0.0425(4) Uani 1 1 d . . . H9 H -0.2577 0.0369 0.0263 0.051 Uiso 1 1 calc R . . C10 C 0.4857(2) 0.10228(8) 0.67640(18) 0.0408(4) Uani 1 1 d . . . H10A H 0.5917 0.1267 0.7441 0.061 Uiso 1 1 calc R . . H10B H 0.5300 0.0617 0.6355 0.061 Uiso 1 1 calc R . . H10C H 0.3998 0.0897 0.7376 0.061 Uiso 1 1 calc R . . C11 C 0.5086(2) 0.16537(9) 0.4291(2) 0.0489(4) Uani 1 1 d . . . H11A H 0.4363 0.1910 0.3381 0.073 Uiso 1 1 calc R . . H11B H 0.5538 0.1238 0.3929 0.073 Uiso 1 1 calc R . . H11C H 0.6147 0.1923 0.4880 0.073 Uiso 1 1 calc R . . H2 H 0.383(2) 0.2280(9) 0.682(2) 0.041(4) Uiso 1 1 d . . . 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 N1 0.0398(8) 0.0385(7) 0.0478(8) -0.0121(6) -0.0125(6) 0.0078(6) N2 0.0329(6) 0.0364(6) 0.0315(6) -0.0066(5) -0.0075(5) 0.0028(5) N3 0.0285(6) 0.0306(6) 0.0341(6) -0.0023(5) -0.0015(5) 0.0007(4) N4 0.0319(6) 0.0303(6) 0.0397(7) -0.0040(5) 0.0037(5) -0.0015(5) N5 0.0342(7) 0.0346(6) 0.0364(6) -0.0039(5) -0.0042(5) -0.0009(5) N6 0.0394(7) 0.0333(6) 0.0374(7) -0.0038(5) -0.0118(5) 0.0053(5) N7 0.0533(9) 0.0512(9) 0.0616(9) -0.0209(7) 0.0169(7) -0.0173(7) C1 0.0334(7) 0.0322(7) 0.0308(7) 0.0000(5) -0.0016(6) 0.0021(6) C2 0.0266(7) 0.0338(7) 0.0314(7) -0.0034(5) -0.0005(5) -0.0009(5) C3 0.0308(7) 0.0348(7) 0.0300(7) 0.0006(5) -0.0037(5) 0.0019(6) C4 0.0305(7) 0.0333(7) 0.0334(7) -0.0018(5) 0.0058(6) -0.0032(6) C5 0.0300(7) 0.0374(8) 0.0393(8) -0.0053(6) 0.0113(6) -0.0062(6) C6 0.0330(8) 0.0398(8) 0.0579(10) -0.0054(7) 0.0089(7) -0.0016(6) C7 0.0473(10) 0.0381(9) 0.0805(13) -0.0113(8) 0.0198(9) -0.0037(7) C8 0.0508(10) 0.0554(10) 0.0407(9) -0.0102(7) 0.0093(7) -0.0174(8) C9 0.0434(8) 0.0439(8) 0.0374(8) -0.0022(6) 0.0069(7) -0.0091(7) C10 0.0316(7) 0.0463(9) 0.0378(8) 0.0017(6) -0.0016(6) 0.0074(6) C11 0.0453(9) 0.0552(10) 0.0469(9) -0.0026(7) 0.0139(7) -0.0097(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3308(19) . ? N1 H1A 0.88(2) . ? N1 H1B 0.89(2) . ? N2 C1 1.3459(17) . ? N2 C2 1.4607(18) . ? N2 H2 0.841(18) . ? N3 C3 1.3447(17) . ? N3 N4 1.3669(16) . ? N3 C2 1.4659(16) . ? N4 C4 1.3236(18) . ? N5 C3 1.3270(18) . ? N5 C4 1.3588(18) . ? N6 C1 1.3249(17) . ? N6 C3 1.3544(18) . ? N7 C8 1.327(2) . ? N7 C7 1.339(2) . ? C2 C10 1.5151(19) . ? C2 C11 1.520(2) . ? C4 C5 1.4664(19) . ? C5 C6 1.383(2) . ? C5 C9 1.388(2) . ? C6 C7 1.380(2) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.375(2) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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_3 _geom_angle_publ_flag C1 N1 H1A 122.7(12) . . ? C1 N1 H1B 116.5(12) . . ? H1A N1 H1B 120.7(16) . . ? C1 N2 C2 123.57(12) . . ? C1 N2 H2 117.5(11) . . ? C2 N2 H2 118.5(11) . . ? C3 N3 N4 110.73(11) . . ? C3 N3 C2 122.48(12) . . ? N4 N3 C2 125.76(11) . . ? C4 N4 N3 101.20(11) . . ? C3 N5 C4 102.89(11) . . ? C1 N6 C3 113.86(12) . . ? C8 N7 C7 116.02(14) . . ? N6 C1 N1 117.87(13) . . ? N6 C1 N2 123.45(13) . . ? N1 C1 N2 118.64(13) . . ? N2 C2 N3 103.42(11) . . ? N2 C2 C10 110.05(11) . . ? N3 C2 C10 110.22(12) . . ? N2 C2 C11 111.37(13) . . ? N3 C2 C11 109.58(12) . . ? C10 C2 C11 111.88(13) . . ? N5 C3 N3 109.47(12) . . ? N5 C3 N6 126.38(13) . . ? N3 C3 N6 124.13(12) . . ? N4 C4 N5 115.70(12) . . ? N4 C4 C5 122.97(13) . . ? N5 C4 C5 121.29(12) . . ? C6 C5 C9 117.62(14) . . ? C6 C5 C4 122.67(14) . . ? C9 C5 C4 119.70(13) . . ? C7 C6 C5 118.77(16) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? N7 C7 C6 124.20(17) . . ? N7 C7 H7 117.9 . . ? C6 C7 H7 117.9 . . ? N7 C8 C9 124.35(17) . . ? N7 C8 H8 117.8 . . ? C9 C8 H8 117.8 . . ? C8 C9 C5 119.04(16) . . ? C8 C9 H9 120.5 . . ? C5 C9 H9 120.5 . . ? C2 C10 H10A 109.5 . . ? C2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C2 C11 H11A 109.5 . . ? C2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 N1 H1A N5 0.88(2) 2.06(2) 2.9444(18) 173.6(17) 4_666 N1 H1B N7 0.89(2) 2.21(2) 3.094(2) 170.3(16) 2_455 N2 H2 N6 0.841(18) 2.128(18) 2.9648(17) 172.9(16) 4_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.268 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.042 _exptl_crystal_recrystallization_method 'recrystallized from ethanol'