# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_datam2 _database_code_depnum_ccdc_archive 'CCDC 851866' #TrackingRef '2,4-Diamino-6-phenyl-1,3,5-triazine+1,3-Phenylenediacetic acid.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic '2,4-Diamino-6-phenyl-1,3,5-triazine+1,3-Phenylenediacetic acid' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 O4, 2(C9 H9 N5)' _chemical_formula_sum 'C28 H28 N10 O4' _chemical_formula_weight 568.60 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 31.500(7) _cell_length_b 12.412(3) _cell_length_c 7.016(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2743.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker, APEX CCD area detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18397 _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.23 _reflns_number_total 2487 _reflns_number_gt 2109 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0741P)^2^+1.4753P] 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 2487 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1686 _refine_ls_wR_factor_gt 0.1617 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 C1 C 0.77960(7) 0.76027(15) 0.1148(3) 0.0377(5) Uani 1 1 d . . . C2 C 0.71837(7) 0.85472(14) 0.1304(3) 0.0369(5) Uani 1 1 d . . . C3 C 0.78128(7) 0.94403(15) 0.1360(3) 0.0397(5) Uani 1 1 d . . . C4 C 0.67142(7) 0.85753(15) 0.1310(3) 0.0382(5) Uani 1 1 d . . . C5 C 0.64788(7) 0.77852(17) 0.0356(3) 0.0447(5) Uani 1 1 d . . . H5A H 0.6618 0.7225 -0.0264 0.054 Uiso 1 1 calc R . . C6 C 0.60421(8) 0.7833(2) 0.0331(4) 0.0557(6) Uani 1 1 d . . . H6 H 0.5902(9) 0.733(2) -0.033(4) 0.071(9) Uiso 1 1 d . . . C7 C 0.58322(9) 0.8654(2) 0.1258(4) 0.0612(7) Uani 1 1 d . . . H7 H 0.5537(9) 0.871(2) 0.125(4) 0.062(8) Uiso 1 1 d . . . C8 C 0.60601(8) 0.9434(2) 0.2229(4) 0.0558(6) Uani 1 1 d . . . H8 H 0.5919(8) 0.998(2) 0.285(4) 0.058(7) Uiso 1 1 d . . . C9 C 0.64952(7) 0.94001(17) 0.2252(3) 0.0446(5) Uani 1 1 d . . . H9 H 0.6660(7) 0.991(2) 0.295(4) 0.050(6) Uiso 1 1 d . . . C10 C 0.59129(9) 0.3980(2) 0.0265(4) 0.0661(7) Uani 1 1 d . . . C11 C 0.54736(9) 0.3674(3) -0.0370(5) 0.0760(9) Uani 1 1 d . . . H11A H 0.5494 0.3254 -0.1532 0.091 Uiso 1 1 calc R . . H11B H 0.5316 0.4325 -0.0662 0.091 Uiso 1 1 calc R . . C12 C 0.52294(7) 0.3030(2) 0.1102(4) 0.0598(7) Uani 1 1 d . . . C13 C 0.52319(9) 0.1914(3) 0.1134(5) 0.0715(8) Uani 1 1 d . . . H13 H 0.5398(11) 0.159(2) 0.017(5) 0.085(10) Uiso 1 1 d . . . C14 C 0.5000 0.1370(4) 0.2500 0.0786(13) Uani 1 2 d S . . H14 H 0.5000 0.060(4) 0.2500 0.080(13) Uiso 1 2 d S . . C15 C 0.5000 0.3564(3) 0.2500 0.0587(9) Uani 1 2 d S . . H15 H 0.5000 0.432(3) 0.2500 0.056(10) Uiso 1 2 d S . . N1 N 0.80051(7) 0.66712(15) 0.1032(3) 0.0472(5) Uani 1 1 d . . . H1B H 0.8285(8) 0.6727(18) 0.098(3) 0.042(6) Uiso 1 1 d . . . H1A H 0.7862(8) 0.606(2) 0.107(4) 0.053(7) Uiso 1 1 d . . . N2 N 0.80370(6) 1.03431(14) 0.1449(3) 0.0538(6) Uani 1 1 d . . . H2A H 0.7910 1.0954 0.1527 0.065 Uiso 1 1 calc R . . H2B H 0.8310 1.0317 0.1429 0.065 Uiso 1 1 calc R . . N3 N 0.80312(6) 0.85071(13) 0.1220(3) 0.0428(5) Uani 1 1 d . . . N4 N 0.73695(5) 0.75786(12) 0.1193(2) 0.0385(4) Uani 1 1 d . . . N5 N 0.73861(5) 0.94968(13) 0.1393(3) 0.0403(5) Uani 1 1 d . . . O1 O 0.60194(8) 0.4893(2) 0.0637(5) 0.1117(10) Uani 1 1 d . . . O2 O 0.61584(7) 0.31715(16) 0.0405(4) 0.0876(7) Uani 1 1 d . . . H2W H 0.6403 0.3379 0.0575 0.16(2) Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0472(12) 0.0297(10) 0.0361(11) 0.0013(8) 0.0008(9) 0.0004(8) C2 0.0497(12) 0.0302(10) 0.0307(10) 0.0008(8) 0.0017(8) 0.0011(8) C3 0.0492(12) 0.0297(10) 0.0402(12) 0.0012(8) -0.0010(9) -0.0009(8) C4 0.0477(12) 0.0327(10) 0.0344(11) 0.0049(8) 0.0015(9) 0.0020(8) C5 0.0532(13) 0.0396(11) 0.0414(12) -0.0012(9) 0.0000(10) -0.0021(9) C6 0.0542(14) 0.0590(15) 0.0539(15) -0.0015(12) -0.0091(12) -0.0054(12) C7 0.0445(14) 0.0765(18) 0.0625(17) 0.0053(13) -0.0006(12) 0.0060(12) C8 0.0558(14) 0.0568(15) 0.0547(15) -0.0008(12) 0.0078(12) 0.0144(12) C9 0.0541(13) 0.0372(11) 0.0425(12) -0.0005(9) 0.0022(10) 0.0035(9) C10 0.0659(17) 0.0618(17) 0.0706(18) 0.0097(14) 0.0075(13) 0.0055(13) C11 0.0524(15) 0.106(2) 0.0696(19) 0.0163(17) 0.0023(14) 0.0066(14) C12 0.0380(12) 0.0790(19) 0.0623(16) 0.0021(14) -0.0072(11) 0.0051(12) C13 0.0595(17) 0.081(2) 0.074(2) -0.0093(17) -0.0042(15) 0.0134(15) C14 0.074(3) 0.062(3) 0.100(4) 0.000 -0.015(3) 0.000 C15 0.0435(18) 0.064(2) 0.068(2) 0.000 -0.0085(17) 0.000 N1 0.0432(11) 0.0291(9) 0.0694(14) -0.0006(9) 0.0035(9) 0.0012(8) N2 0.0490(11) 0.0300(9) 0.0823(15) -0.0001(9) -0.0028(10) -0.0014(8) N3 0.0457(10) 0.0295(9) 0.0532(11) 0.0029(8) 0.0002(8) 0.0000(7) N4 0.0461(10) 0.0266(8) 0.0427(10) 0.0000(7) 0.0005(7) 0.0012(7) N5 0.0473(10) 0.0274(9) 0.0462(11) -0.0003(7) 0.0006(8) 0.0010(7) O1 0.0903(16) 0.0683(15) 0.177(3) -0.0079(17) -0.0099(18) 0.0135(13) O2 0.0590(12) 0.0574(12) 0.146(2) -0.0032(13) -0.0143(14) 0.0048(9) _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 C1 N1 1.333(3) . ? C1 N4 1.344(3) . ? C1 N3 1.346(3) . ? C2 N4 1.339(2) . ? C2 N5 1.341(2) . ? C2 C4 1.479(3) . ? C3 N2 1.326(3) . ? C3 N5 1.346(3) . ? C3 N3 1.351(3) . ? C4 C5 1.400(3) . ? C4 C9 1.400(3) . ? C5 C6 1.377(3) . ? C5 H5A 0.9300 . ? C6 C7 1.378(4) . ? C6 H6 0.89(3) . ? C7 C8 1.384(4) . ? C7 H7 0.93(3) . ? C8 C9 1.371(3) . ? C8 H8 0.92(3) . ? C9 H9 0.96(3) . ? C10 O1 1.210(4) . ? C10 O2 1.271(3) . ? C10 C11 1.503(4) . ? C11 C12 1.516(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.385(4) . ? C12 C15 1.387(3) . ? C13 C14 1.382(4) . ? C13 H13 0.94(4) . ? C14 C13 1.382(4) 3_655 ? C14 H14 0.96(4) . ? C15 C12 1.387(3) 3_655 ? C15 H15 0.94(4) . ? N1 H1B 0.89(2) . ? N1 H1A 0.88(3) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? O2 H2W 0.8200 . ? 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 N1 C1 N4 118.43(18) . . ? N1 C1 N3 117.0(2) . . ? N4 C1 N3 124.61(17) . . ? N4 C2 N5 125.7(2) . . ? N4 C2 C4 117.26(17) . . ? N5 C2 C4 117.02(17) . . ? N2 C3 N5 119.14(18) . . ? N2 C3 N3 117.18(19) . . ? N5 C3 N3 123.68(18) . . ? C5 C4 C9 118.5(2) . . ? C5 C4 C2 120.78(18) . . ? C9 C4 C2 120.72(19) . . ? C6 C5 C4 120.3(2) . . ? C6 C5 H5A 119.8 . . ? C4 C5 H5A 119.8 . . ? C5 C6 C7 120.4(2) . . ? C5 C6 H6 118.0(19) . . ? C7 C6 H6 121.6(19) . . ? C6 C7 C8 120.0(3) . . ? C6 C7 H7 121.8(17) . . ? C8 C7 H7 118.1(17) . . ? C9 C8 C7 120.2(2) . . ? C9 C8 H8 120.1(16) . . ? C7 C8 H8 119.7(16) . . ? C8 C9 C4 120.6(2) . . ? C8 C9 H9 121.9(14) . . ? C4 C9 H9 117.4(14) . . ? O1 C10 O2 123.6(3) . . ? O1 C10 C11 123.8(3) . . ? O2 C10 C11 112.5(3) . . ? C10 C11 C12 113.5(2) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C15 118.0(3) . . ? C13 C12 C11 122.4(3) . . ? C15 C12 C11 119.6(3) . . ? C14 C13 C12 119.8(3) . . ? C14 C13 H13 125.3(19) . . ? C12 C13 H13 114.9(19) . . ? C13 C14 C13 121.5(4) . 3_655 ? C13 C14 H14 119.3(2) . . ? C13 C14 H14 119.3(2) 3_655 . ? C12 C15 C12 122.8(4) 3_655 . ? C12 C15 H15 118.58(19) 3_655 . ? C12 C15 H15 118.58(19) . . ? C1 N1 H1B 115.3(14) . . ? C1 N1 H1A 119.3(17) . . ? H1B N1 H1A 125(2) . . ? C3 N2 H2A 120.0 . . ? C3 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 N3 C3 115.94(18) . . ? C2 N4 C1 114.72(16) . . ? C2 N5 C3 115.34(17) . . ? C10 O2 H2W 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.23 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.420 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.072 data_datam3 _database_code_depnum_ccdc_archive 'CCDC 851867' #TrackingRef '2,4-Diamino-6-phenyl-1,3,5-triazine+1,4-Phenylenediacetic acid.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic '2,4-Diamino-6-phenyl-1,3,5-triazine+1,4-Phenylenediacetic acid' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C9 H9 N5), C10 H10 O4' _chemical_formula_sum 'C28 H28 N10 O4' _chemical_formula_weight 568.60 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.405(4) _cell_length_b 6.948(2) _cell_length_c 31.402(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2706.5(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker, APEX CCD area detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18044 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.29 _reflns_number_total 2459 _reflns_number_gt 2152 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0799P)^2^+1.8497P] 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 2459 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1904 _refine_ls_wR_factor_gt 0.1856 _refine_ls_goodness_of_fit_ref 1.292 _refine_ls_restrained_S_all 1.292 _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 C1 C 0.4584(3) -0.1218(5) 0.46972(10) 0.0520(8) Uani 1 1 d . . . C2 C 0.3920(2) -0.0002(5) 0.49218(9) 0.0509(8) Uani 1 1 d . . . H2C H 0.3183 -0.0023 0.4867 0.061 Uiso 1 1 calc R . . C3 C 0.4309(2) 0.1250(4) 0.52268(8) 0.0444(7) Uani 1 1 d . . . C4 C 0.3561(3) 0.2564(6) 0.54695(9) 0.0585(9) Uani 1 1 d . . . H4A H 0.3875 0.3842 0.5479 0.070 Uiso 1 1 calc R . . H4B H 0.2883 0.2655 0.5317 0.070 Uiso 1 1 calc R . . C5 C 0.3339(2) 0.1909(5) 0.59162(9) 0.0485(8) Uani 1 1 d . . . C6 C 0.98698(18) 0.1114(4) 0.77989(8) 0.0298(5) Uani 1 1 d . . . C7 C 0.89394(17) 0.0969(4) 0.71810(8) 0.0293(6) Uani 1 1 d . . . C8 C 0.80354(18) 0.0902(4) 0.78089(8) 0.0326(6) Uani 1 1 d . . . C9 C 0.89245(18) 0.0959(4) 0.67105(8) 0.0310(6) Uani 1 1 d . . . C10 C 0.9723(2) 0.1895(4) 0.64772(8) 0.0370(6) Uani 1 1 d . . . H10 H 1.026(2) 0.257(5) 0.6633(10) 0.044(8) Uiso 1 1 d . . . C11 C 0.9694(2) 0.1910(5) 0.60373(9) 0.0458(7) Uani 1 1 d . . . H11 H 1.024(3) 0.256(5) 0.5890(11) 0.055(9) Uiso 1 1 d . . . C12 C 0.8875(3) 0.0956(5) 0.58258(10) 0.0499(8) Uani 1 1 d . . . H12 H 0.887(3) 0.097(5) 0.5522(13) 0.066(11) Uiso 1 1 d . . . C13 C 0.8084(2) -0.0003(5) 0.60531(9) 0.0463(7) Uani 1 1 d . . . H13 H 0.755(3) -0.060(5) 0.5904(11) 0.062(10) Uiso 1 1 d . . . C14 C 0.8105(2) -0.0004(4) 0.64915(8) 0.0371(6) Uani 1 1 d . . . H14 H 0.759(3) -0.070(5) 0.6663(10) 0.050(8) Uiso 1 1 d . . . N1 N 0.71271(18) 0.0799(4) 0.80306(8) 0.0447(7) Uani 1 1 d . . . H1B H 0.719(2) 0.099(5) 0.8307(11) 0.045(8) Uiso 1 1 d . . . N2 N 1.07993(17) 0.1228(4) 0.80110(8) 0.0392(6) Uani 1 1 d . . . H2B H 1.077(2) 0.126(4) 0.8295(11) 0.036(7) Uiso 1 1 d . . . N3 N 0.99046(15) 0.1079(3) 0.73711(6) 0.0314(5) Uani 1 1 d . . . N4 N 0.89621(15) 0.1038(3) 0.80317(7) 0.0347(5) Uani 1 1 d . . . N5 N 0.79867(15) 0.0873(3) 0.73806(6) 0.0333(5) Uani 1 1 d . . . O1 O 0.24617(19) 0.1436(5) 0.60402(7) 0.0766(9) Uani 1 1 d . . . O2 O 0.41943(17) 0.1917(5) 0.61579(7) 0.0706(8) Uani 1 1 d . . . H2W H 0.405(3) 0.156(7) 0.6431(17) 0.091(14) Uiso 1 1 d . . . H1 H 0.432(2) -0.209(4) 0.4504(10) 0.040(8) Uiso 1 1 d . . . H2A H 1.141(3) 0.123(5) 0.7864(10) 0.049(9) Uiso 1 1 d . . . H1A H 0.651(3) 0.082(5) 0.7892(10) 0.052(9) 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 C1 0.0499(18) 0.067(2) 0.0391(15) -0.0080(15) -0.0051(13) -0.0103(16) C2 0.0371(15) 0.079(2) 0.0368(15) 0.0038(15) -0.0017(11) -0.0070(14) C3 0.0462(16) 0.0588(19) 0.0282(13) 0.0090(12) 0.0015(11) -0.0003(13) C4 0.065(2) 0.070(2) 0.0399(16) 0.0055(15) 0.0011(14) 0.0164(18) C5 0.0455(17) 0.064(2) 0.0355(14) -0.0021(13) 0.0008(12) 0.0098(15) C6 0.0187(11) 0.0360(13) 0.0347(12) -0.0004(10) -0.0017(9) 0.0012(9) C7 0.0183(11) 0.0345(13) 0.0350(13) -0.0014(10) -0.0018(9) 0.0007(9) C8 0.0197(12) 0.0415(14) 0.0365(13) 0.0008(11) -0.0012(9) 0.0014(10) C9 0.0218(11) 0.0374(14) 0.0338(13) 0.0009(11) -0.0014(9) 0.0055(10) C10 0.0272(12) 0.0445(15) 0.0395(14) 0.0004(12) -0.0015(11) 0.0009(11) C11 0.0424(15) 0.0543(18) 0.0408(15) 0.0072(13) 0.0046(12) 0.0005(14) C12 0.0576(19) 0.0599(19) 0.0322(14) -0.0002(14) -0.0052(13) 0.0026(15) C13 0.0430(16) 0.0541(18) 0.0417(15) -0.0076(13) -0.0116(13) 0.0003(13) C14 0.0262(13) 0.0442(15) 0.0409(14) -0.0018(12) -0.0039(11) 0.0007(11) N1 0.0179(10) 0.0808(19) 0.0353(13) -0.0022(12) 0.0009(9) -0.0016(11) N2 0.0169(10) 0.0671(17) 0.0337(12) -0.0033(11) -0.0019(9) -0.0020(10) N3 0.0162(10) 0.0444(13) 0.0338(11) -0.0005(9) -0.0017(8) 0.0012(8) N4 0.0176(10) 0.0538(14) 0.0327(11) -0.0008(10) -0.0009(7) 0.0021(9) N5 0.0170(10) 0.0475(13) 0.0353(11) -0.0028(9) -0.0012(8) 0.0005(9) O1 0.0432(13) 0.134(3) 0.0523(13) 0.0078(14) -0.0038(11) -0.0137(14) O2 0.0367(11) 0.137(3) 0.0377(12) 0.0135(14) 0.0010(9) -0.0026(14) _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 C1 C2 1.375(5) . ? C1 C3 1.393(4) 5_656 ? C1 H1 0.92(3) . ? C2 C3 1.381(4) . ? C2 H2C 0.9300 . ? C3 C1 1.393(4) 5_656 ? C3 C4 1.509(4) . ? C4 C5 1.500(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O1 1.201(4) . ? C5 O2 1.305(4) . ? C6 N2 1.334(3) . ? C6 N4 1.344(3) . ? C6 N3 1.344(3) . ? C7 N5 1.339(3) . ? C7 N3 1.340(3) . ? C7 C9 1.478(4) . ? C8 N1 1.327(3) . ? C8 N5 1.346(3) . ? C8 N4 1.349(3) . ? C9 C10 1.393(4) . ? C9 C14 1.398(4) . ? C10 C11 1.382(4) . ? C10 H10 0.95(3) . ? C11 C12 1.383(4) . ? C11 H11 0.94(3) . ? C12 C13 1.384(5) . ? C12 H12 0.95(4) . ? C13 C14 1.377(4) . ? C13 H13 0.91(4) . ? C14 H14 0.97(3) . ? N1 H1B 0.88(3) . ? N1 H1A 0.88(4) . ? N2 H2B 0.89(3) . ? N2 H2A 0.89(3) . ? O2 H2W 0.91(5) . ? 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 C2 C1 C3 120.8(3) . 5_656 ? C2 C1 H1 122.1(18) . . ? C3 C1 H1 117.0(18) 5_656 . ? C1 C2 C3 122.2(3) . . ? C1 C2 H2C 118.9 . . ? C3 C2 H2C 118.9 . . ? C2 C3 C1 117.0(3) . 5_656 ? C2 C3 C4 121.1(3) . . ? C1 C3 C4 122.0(3) 5_656 . ? C5 C4 C3 113.7(3) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? O1 C5 O2 123.3(3) . . ? O1 C5 C4 123.5(3) . . ? O2 C5 C4 113.2(3) . . ? N2 C6 N4 117.1(2) . . ? N2 C6 N3 118.2(2) . . ? N4 C6 N3 124.7(2) . . ? N5 C7 N3 125.7(2) . . ? N5 C7 C9 117.2(2) . . ? N3 C7 C9 117.2(2) . . ? N1 C8 N5 119.0(2) . . ? N1 C8 N4 117.1(2) . . ? N5 C8 N4 123.9(2) . . ? C10 C9 C14 118.8(2) . . ? C10 C9 C7 121.0(2) . . ? C14 C9 C7 120.2(2) . . ? C11 C10 C9 120.7(3) . . ? C11 C10 H10 121.8(18) . . ? C9 C10 H10 117.4(18) . . ? C10 C11 C12 119.7(3) . . ? C10 C11 H11 119(2) . . ? C12 C11 H11 122(2) . . ? C11 C12 C13 120.2(3) . . ? C11 C12 H12 119(2) . . ? C13 C12 H12 121(2) . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13 122(2) . . ? C12 C13 H13 118(2) . . ? C13 C14 C9 120.4(3) . . ? C13 C14 H14 123.0(19) . . ? C9 C14 H14 116.6(19) . . ? C8 N1 H1B 116(2) . . ? C8 N1 H1A 118(2) . . ? H1B N1 H1A 124(3) . . ? C6 N2 H2B 117.7(18) . . ? C6 N2 H2A 119(2) . . ? H2B N2 H2A 124(3) . . ? C7 N3 C6 114.67(19) . . ? C6 N4 C8 115.8(2) . . ? C7 N5 C8 115.28(19) . . ? C5 O2 H2W 113(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.29 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.264 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.078 data_datam4 _database_code_depnum_ccdc_archive 'CCDC 851868' #TrackingRef '2,4-Diamino-6-phenyl-1,3,5-triazine+Isophthalic Acid.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic '2,4-Diamino-6-phenyl-1,3,5-triazine+Isophthalic Acid' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N5, C8 H6 O4' _chemical_formula_sum 'C17 H15 N5 O4' _chemical_formula_weight 353.34 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.504(6) _cell_length_b 10.199(7) _cell_length_c 10.258(7) _cell_angle_alpha 108.530(10) _cell_angle_beta 91.790(10) _cell_angle_gamma 92.960(10) _cell_volume 841.4(10) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker, APEX CCD area detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4255 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0716 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2967 _reflns_number_gt 1693 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0980P)^2^+0.0000P] 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 2967 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1127 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1886 _refine_ls_wR_factor_gt 0.1387 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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 C1 C 0.3511(4) 0.5731(4) 0.6571(3) 0.0415(9) Uani 1 1 d . . . C2 C 0.4585(4) 0.6228(3) 0.7836(3) 0.0385(8) Uani 1 1 d . . . C3 C 0.0856(4) 0.4140(3) 0.2995(3) 0.0368(8) Uani 1 1 d . . . C4 C 0.5574(4) 0.5351(4) 0.8204(3) 0.0387(8) Uani 1 1 d . . . C5 C 0.0146(4) 0.2261(3) 0.1138(3) 0.0391(8) Uani 1 1 d . . . C6 C 0.1365(4) 0.1977(3) 0.3027(3) 0.0390(8) Uani 1 1 d . . . C7 C 0.1946(4) 0.1053(4) 0.3773(4) 0.0480(10) Uani 1 1 d . . . C8 C 0.6429(4) 0.7203(4) 1.0279(4) 0.0500(10) Uani 1 1 d . . . C9 C 0.7599(4) 0.4888(4) 0.9775(3) 0.0412(9) Uani 1 1 d . . . C10 C 0.4522(5) 0.7598(4) 0.8692(4) 0.0528(10) Uani 1 1 d . . . C11 C 0.6521(4) 0.5840(3) 0.9429(3) 0.0391(8) Uani 1 1 d . . . C12 C 0.2686(6) -0.0123(4) 0.3085(5) 0.0710(14) Uani 1 1 d . . . C13 C 0.1717(6) 0.1341(5) 0.5164(4) 0.0645(12) Uani 1 1 d . . . C14 C 0.2909(7) -0.0720(6) 0.5159(6) 0.119(3) Uani 1 1 d . . . H14 H 0.3249 -0.1312 0.5622 0.143 Uiso 1 1 calc R . . C15 C 0.5443(5) 0.8073(4) 0.9903(4) 0.0597(11) Uani 1 1 d . . . H15A H 0.5399 0.8985 1.0470 0.072 Uiso 1 1 calc R . . C16 C 0.3161(7) -0.1008(5) 0.3781(6) 0.101(2) Uani 1 1 d . . . H16A H 0.3656 -0.1803 0.3314 0.121 Uiso 1 1 calc R . . C17 C 0.2151(7) 0.0447(5) 0.5858(5) 0.0984(19) Uani 1 1 d . . . H17A H 0.1937 0.0626 0.6780 0.118 Uiso 1 1 calc R . . N1 N 0.1472(3) 0.3357(3) 0.3693(3) 0.0391(7) Uani 1 1 d . . . N2 N 0.0736(3) 0.1371(3) 0.1744(3) 0.0439(8) Uani 1 1 d . . . N3 N -0.0488(4) 0.1723(3) -0.0139(3) 0.0546(9) Uani 1 1 d . . . H3A H -0.0876 0.2255 -0.0553 0.065 Uiso 1 1 calc R . . H3B H -0.0509 0.0843 -0.0549 0.065 Uiso 1 1 calc R . . N4 N 0.0970(3) 0.5509(3) 0.3592(3) 0.0486(8) Uani 1 1 d . . . H4A H 0.1426 0.5864 0.4398 0.058 Uiso 1 1 calc R . . H4B H 0.0588 0.6038 0.3172 0.058 Uiso 1 1 calc R . . N5 N 0.0145(3) 0.3642(3) 0.1727(3) 0.0414(7) Uani 1 1 d . . . O1 O 0.3590(3) 0.4395(2) 0.5894(3) 0.0567(7) Uani 1 1 d . . . H100 H 0.3015 0.4181 0.5192 0.075(14) Uiso 1 1 calc R . . O2 O 0.2650(3) 0.6479(2) 0.6221(2) 0.0549(7) Uani 1 1 d . . . O3 O 0.7757(3) 0.3728(3) 0.8993(2) 0.0543(7) Uani 1 1 d . . . O4 O 0.8352(3) 0.5405(3) 1.0988(2) 0.0521(7) Uani 1 1 d . . . H400 H 0.8908 0.4824 1.1124 0.088(17) Uiso 1 1 calc R . . H1 H 0.377(4) 0.823(3) 0.846(3) 0.046(9) Uiso 1 1 d . . . H2 H 0.574(4) 0.439(4) 0.761(4) 0.061(11) Uiso 1 1 d . . . H5 H 0.702(4) 0.743(4) 1.115(4) 0.062(11) Uiso 1 1 d . . . H10 H 0.282(5) -0.029(4) 0.211(4) 0.073(13) Uiso 1 1 d . . . H13 H 0.126(5) 0.211(4) 0.575(4) 0.077(15) 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 C1 0.043(2) 0.036(2) 0.045(2) 0.0144(18) -0.0040(16) -0.0036(17) C2 0.0392(19) 0.0332(19) 0.0430(19) 0.0132(16) -0.0034(15) -0.0017(15) C3 0.0410(19) 0.035(2) 0.0366(18) 0.0146(16) -0.0045(15) 0.0035(15) C4 0.040(2) 0.037(2) 0.0383(19) 0.0119(17) -0.0046(15) 0.0009(16) C5 0.046(2) 0.036(2) 0.0380(19) 0.0161(16) -0.0070(15) 0.0042(16) C6 0.042(2) 0.035(2) 0.0395(19) 0.0112(16) -0.0024(15) 0.0008(15) C7 0.061(2) 0.033(2) 0.048(2) 0.0130(17) -0.0220(18) -0.0017(17) C8 0.053(2) 0.043(2) 0.045(2) 0.0039(18) -0.0148(18) 0.0038(18) C9 0.044(2) 0.041(2) 0.039(2) 0.0155(17) -0.0073(16) -0.0021(17) C10 0.056(2) 0.040(2) 0.058(2) 0.0118(19) -0.0137(19) 0.0080(19) C11 0.041(2) 0.037(2) 0.0394(19) 0.0132(16) -0.0026(15) 0.0005(15) C12 0.091(3) 0.045(3) 0.069(3) 0.010(2) -0.041(3) 0.006(2) C13 0.091(3) 0.051(3) 0.053(3) 0.023(2) -0.021(2) -0.010(2) C14 0.183(6) 0.053(3) 0.121(5) 0.044(3) -0.108(4) -0.036(4) C15 0.068(3) 0.038(2) 0.060(2) -0.0011(19) -0.018(2) 0.0071(19) C16 0.139(5) 0.038(3) 0.110(4) 0.009(3) -0.080(4) 0.007(3) C17 0.165(6) 0.063(3) 0.073(3) 0.042(3) -0.051(3) -0.039(3) N1 0.0457(17) 0.0348(16) 0.0367(15) 0.0117(13) -0.0053(13) 0.0031(13) N2 0.0567(19) 0.0359(17) 0.0363(16) 0.0093(13) -0.0106(13) -0.0001(14) N3 0.081(2) 0.0370(17) 0.0402(17) 0.0067(14) -0.0273(16) 0.0048(15) N4 0.070(2) 0.0337(17) 0.0403(16) 0.0097(13) -0.0159(14) 0.0115(14) N5 0.0497(17) 0.0362(17) 0.0370(16) 0.0106(13) -0.0103(13) 0.0063(13) O1 0.0708(18) 0.0411(16) 0.0520(16) 0.0091(13) -0.0284(14) 0.0031(12) O2 0.0634(17) 0.0420(15) 0.0597(16) 0.0182(13) -0.0225(13) 0.0098(13) O3 0.0721(18) 0.0380(15) 0.0485(15) 0.0091(13) -0.0194(12) 0.0068(13) O4 0.0618(17) 0.0489(16) 0.0423(14) 0.0115(13) -0.0199(12) 0.0085(14) _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 C1 O2 1.209(4) . ? C1 O1 1.325(4) . ? C1 C2 1.495(4) . ? C2 C4 1.387(5) . ? C2 C10 1.399(5) . ? C3 N4 1.331(4) . ? C3 N1 1.344(4) . ? C3 N5 1.348(4) . ? C4 C11 1.404(4) . ? C4 H2 0.99(4) . ? C5 N3 1.333(4) . ? C5 N5 1.345(4) . ? C5 N2 1.359(4) . ? C6 N2 1.344(4) . ? C6 N1 1.351(4) . ? C6 C7 1.483(5) . ? C7 C12 1.379(5) . ? C7 C13 1.385(5) . ? C8 C15 1.383(5) . ? C8 C11 1.395(5) . ? C8 H5 0.97(4) . ? C9 O3 1.217(4) . ? C9 O4 1.317(4) . ? C9 C11 1.483(5) . ? C10 C15 1.381(5) . ? C10 H1 1.01(3) . ? C12 C16 1.384(6) . ? C12 H10 0.98(4) . ? C13 C17 1.381(6) . ? C13 H13 0.93(4) . ? C14 C16 1.375(8) . ? C14 C17 1.382(8) . ? C14 H14 0.9300 . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? O1 H100 0.8200 . ? O4 H400 0.8200 . ? 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 O2 C1 O1 124.0(3) . . ? O2 C1 C2 122.9(3) . . ? O1 C1 C2 113.1(3) . . ? C4 C2 C10 119.9(3) . . ? C4 C2 C1 121.7(3) . . ? C10 C2 C1 118.4(3) . . ? N4 C3 N1 117.8(3) . . ? N4 C3 N5 117.4(3) . . ? N1 C3 N5 124.8(3) . . ? C2 C4 C11 120.1(3) . . ? C2 C4 H2 124(2) . . ? C11 C4 H2 116(2) . . ? N3 C5 N5 117.3(3) . . ? N3 C5 N2 117.5(3) . . ? N5 C5 N2 125.2(3) . . ? N2 C6 N1 124.9(3) . . ? N2 C6 C7 117.1(3) . . ? N1 C6 C7 118.0(3) . . ? C12 C7 C13 119.0(4) . . ? C12 C7 C6 120.6(3) . . ? C13 C7 C6 120.4(4) . . ? C15 C8 C11 120.3(3) . . ? C15 C8 H5 125(2) . . ? C11 C8 H5 114(2) . . ? O3 C9 O4 123.6(3) . . ? O3 C9 C11 122.0(3) . . ? O4 C9 C11 114.4(3) . . ? C15 C10 C2 120.0(3) . . ? C15 C10 H1 119.5(18) . . ? C2 C10 H1 120.4(18) . . ? C8 C11 C4 119.3(3) . . ? C8 C11 C9 121.9(3) . . ? C4 C11 C9 118.8(3) . . ? C7 C12 C16 120.0(5) . . ? C7 C12 H10 116(2) . . ? C16 C12 H10 124(2) . . ? C17 C13 C7 121.5(5) . . ? C17 C13 H13 111(3) . . ? C7 C13 H13 127(3) . . ? C16 C14 C17 120.2(5) . . ? C16 C14 H14 119.9 . . ? C17 C14 H14 119.9 . . ? C10 C15 C8 120.5(3) . . ? C10 C15 H15A 119.8 . . ? C8 C15 H15A 119.8 . . ? C14 C16 C12 120.5(5) . . ? C14 C16 H16A 119.7 . . ? C12 C16 H16A 119.7 . . ? C13 C17 C14 118.8(5) . . ? C13 C17 H17A 120.6 . . ? C14 C17 H17A 120.6 . . ? C3 N1 C6 115.5(3) . . ? C6 N2 C5 114.6(3) . . ? C5 N3 H3A 120.0 . . ? C5 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C3 N4 H4A 120.0 . . ? C3 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C5 N5 C3 115.0(3) . . ? C1 O1 H100 109.5 . . ? C9 O4 H400 109.5 . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.254 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.079 data_datam5 _database_code_depnum_ccdc_archive 'CCDC 851869' #TrackingRef '2,4-Diamino-6-phenyl-1,3,5-triazine+Phthalic Acid.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic '2,4-Diamino-6-phenyl-1,3,5-triazine+Phthalic Acid' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H10 N5, C8 H5 O4' _chemical_formula_sum 'C17 H15 N5 O4' _chemical_formula_weight 353.34 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.162(2) _cell_length_b 10.042(2) _cell_length_c 12.835(3) _cell_angle_alpha 68.270(10) _cell_angle_beta 85.450(10) _cell_angle_gamma 71.460(10) _cell_volume 812.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Rod Shaped' _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker, APEX CCD area detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4143 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0766 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2883 _reflns_number_gt 1607 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1071P)^2^+0.0000P] 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 2883 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1222 _refine_ls_R_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.2119 _refine_ls_wR_factor_gt 0.1624 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 C1 C 0.0624(5) 0.6837(4) 0.8257(3) 0.0337(9) Uani 1 1 d . . . C2 C 0.1145(7) 0.5657(5) 0.7869(4) 0.0470(11) Uani 1 1 d . . . H4 H 0.167(6) 0.474(5) 0.838(3) 0.043(12) Uiso 1 1 d . . . C3 C 0.0761(7) 0.5849(6) 0.6782(4) 0.0536(13) Uani 1 1 d . . . H10 H 0.116(7) 0.507(5) 0.655(4) 0.063(15) Uiso 1 1 d . . . C4 C -0.0129(7) 0.7284(5) 0.6024(4) 0.0526(12) Uani 1 1 d . . . H4C H -0.0370 0.7439 0.5280 0.063 Uiso 1 1 calc R . . C5 C -0.0650(6) 0.8470(5) 0.6377(3) 0.0467(11) Uani 1 1 d . . . H5A H -0.1256 0.9431 0.5859 0.056 Uiso 1 1 calc R . . C6 C -0.0316(5) 0.8312(4) 0.7486(3) 0.0341(9) Uani 1 1 d . . . C7 C -0.1014(6) 0.9774(4) 0.7696(3) 0.0409(10) Uani 1 1 d . . . C8 C 0.1170(6) 0.6389(4) 0.9487(3) 0.0374(10) Uani 1 1 d . . . C9 C 0.5429(6) 0.1851(5) 0.1141(3) 0.0424(11) Uani 1 1 d . . . H9A H 0.4960 0.2851 0.0656 0.051 Uiso 1 1 calc R . . C10 C 0.6132(7) 0.0719(6) 0.0711(4) 0.0530(12) Uani 1 1 d . . . H13 H 0.608(6) 0.100(5) -0.012(4) 0.061(13) Uiso 1 1 d . . . C11 C 0.6823(7) -0.0768(5) 0.1413(4) 0.0569(13) Uani 1 1 d . . . H11A H 0.7304 -0.1526 0.1121 0.068 Uiso 1 1 calc R . . C12 C 0.6791(7) -0.1114(5) 0.2547(4) 0.0618(14) Uani 1 1 d . . . H12A H 0.7244 -0.2119 0.3026 0.074 Uiso 1 1 calc R . . C13 C 0.6103(7) -0.0005(5) 0.2993(4) 0.0515(12) Uani 1 1 d . . . H14 H 0.608(8) -0.019(7) 0.378(5) 0.11(2) Uiso 1 1 d . . . C14 C 0.5418(6) 0.1510(4) 0.2280(3) 0.0371(10) Uani 1 1 d . . . C15 C 0.4865(6) 0.2667(4) 0.2787(3) 0.0355(10) Uani 1 1 d . . . C16 C 0.3435(6) 0.5205(4) 0.2629(3) 0.0363(10) Uani 1 1 d . . . C17 C 0.5024(6) 0.3406(4) 0.4234(3) 0.0389(10) Uani 1 1 d . . . N1 N 0.3834(5) 0.4127(3) 0.2164(3) 0.0355(8) Uani 1 1 d . . . H3 H 0.343(6) 0.439(4) 0.143(4) 0.048(12) Uiso 1 1 d . . . N2 N 0.4043(5) 0.4864(3) 0.3674(3) 0.0418(9) Uani 1 1 d . . . N3 N 0.5436(5) 0.2277(3) 0.3830(3) 0.0416(9) Uani 1 1 d . . . N4 N 0.5656(5) 0.3017(4) 0.5279(3) 0.0513(10) Uani 1 1 d . . . H4A H 0.5433 0.3689 0.5576 0.062 Uiso 1 1 calc R . . H4B H 0.6290 0.2091 0.5661 0.062 Uiso 1 1 calc R . . N5 N 0.2409(6) 0.6592(4) 0.2024(3) 0.0541(11) Uani 1 1 d . . . H1 H 0.207(7) 0.689(5) 0.128(4) 0.063(14) Uiso 1 1 d . . . H2 H 0.242(6) 0.731(5) 0.223(3) 0.044(13) Uiso 1 1 d . . . O1 O -0.1153(5) 0.9776(4) 0.8701(2) 0.0558(9) Uani 1 1 d . . . H1A H -0.0500 0.8950 0.9140 0.14(3) Uiso 1 1 calc R . . O2 O -0.1451(5) 1.0980(3) 0.6904(3) 0.0607(10) Uani 1 1 d . . . O3 O 0.0320(4) 0.7259(3) 1.0007(2) 0.0498(8) Uani 1 1 d . . . O4 O 0.2439(4) 0.5157(3) 0.9952(2) 0.0543(9) Uani 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 C1 0.035(2) 0.039(2) 0.029(2) -0.0116(18) -0.0016(17) -0.0129(18) C2 0.057(3) 0.038(3) 0.044(3) -0.016(2) -0.003(2) -0.009(2) C3 0.063(3) 0.051(3) 0.055(3) -0.031(3) -0.001(2) -0.013(3) C4 0.060(3) 0.066(3) 0.036(2) -0.024(2) -0.002(2) -0.016(3) C5 0.053(3) 0.046(3) 0.034(2) -0.009(2) -0.0045(19) -0.011(2) C6 0.035(2) 0.034(2) 0.030(2) -0.0072(17) -0.0063(16) -0.0095(18) C7 0.039(2) 0.036(2) 0.040(2) -0.0089(19) -0.0123(19) -0.0040(19) C8 0.043(2) 0.032(2) 0.031(2) -0.0041(19) -0.0050(18) -0.0113(19) C9 0.049(3) 0.037(2) 0.039(2) -0.015(2) -0.0035(19) -0.009(2) C10 0.063(3) 0.061(3) 0.048(3) -0.034(3) 0.004(2) -0.021(3) C11 0.056(3) 0.048(3) 0.071(3) -0.034(3) 0.008(2) -0.008(2) C12 0.079(4) 0.034(3) 0.068(3) -0.019(2) 0.007(3) -0.012(2) C13 0.066(3) 0.037(3) 0.047(3) -0.016(2) -0.002(2) -0.008(2) C14 0.038(2) 0.036(2) 0.043(2) -0.0205(19) 0.0012(18) -0.0108(19) C15 0.039(2) 0.031(2) 0.034(2) -0.0096(17) -0.0029(18) -0.0095(18) C16 0.047(2) 0.027(2) 0.032(2) -0.0097(18) -0.0066(18) -0.0071(18) C17 0.050(3) 0.030(2) 0.030(2) -0.0073(18) -0.0074(18) -0.0065(19) N1 0.048(2) 0.0306(18) 0.0276(18) -0.0126(15) -0.0061(15) -0.0080(15) N2 0.056(2) 0.0322(19) 0.0333(19) -0.0130(15) -0.0130(16) -0.0035(16) N3 0.054(2) 0.0300(18) 0.035(2) -0.0103(15) -0.0089(16) -0.0053(16) N4 0.082(3) 0.0316(19) 0.0320(19) -0.0089(15) -0.0180(18) -0.0057(18) N5 0.087(3) 0.031(2) 0.038(2) -0.0120(18) -0.023(2) -0.005(2) O1 0.076(2) 0.0442(19) 0.0396(18) -0.0190(16) -0.0006(16) -0.0033(17) O2 0.084(2) 0.0273(16) 0.0500(19) 0.0000(14) -0.0291(17) 0.0008(15) O3 0.067(2) 0.0424(17) 0.0320(16) -0.0141(14) -0.0053(14) -0.0044(15) O4 0.064(2) 0.0429(18) 0.0432(18) -0.0097(14) -0.0192(15) -0.0013(16) _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 C1 C2 1.385(6) . ? C1 C6 1.418(5) . ? C1 C8 1.519(5) . ? C2 C3 1.373(6) . ? C2 H4 0.89(4) . ? C3 C4 1.380(6) . ? C3 H10 0.90(5) . ? C4 C5 1.362(6) . ? C4 H4C 0.9300 . ? C5 C6 1.404(5) . ? C5 H5A 0.9300 . ? C6 C7 1.511(6) . ? C7 O2 1.223(4) . ? C7 O1 1.287(5) . ? C8 O4 1.240(4) . ? C8 O3 1.268(5) . ? C9 C14 1.372(5) . ? C9 C10 1.381(6) . ? C9 H9A 0.9300 . ? C10 C11 1.376(6) . ? C10 H13 1.00(4) . ? C11 C12 1.365(6) . ? C11 H11A 0.9300 . ? C12 C13 1.375(6) . ? C12 H12A 0.9300 . ? C13 C14 1.400(6) . ? C13 H14 0.95(6) . ? C14 C15 1.468(5) . ? C15 N3 1.308(5) . ? C15 N1 1.368(5) . ? C16 N5 1.312(5) . ? C16 N2 1.327(5) . ? C16 N1 1.366(5) . ? C17 N4 1.324(5) . ? C17 N2 1.342(5) . ? C17 N3 1.356(5) . ? N1 H3 0.92(4) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? N5 H1 0.92(5) . ? N5 H2 0.86(4) . ? O1 H1A 0.8200 . ? 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 C2 C1 C6 118.1(4) . . ? C2 C1 C8 114.9(3) . . ? C6 C1 C8 127.0(4) . . ? C3 C2 C1 123.0(4) . . ? C3 C2 H4 121(3) . . ? C1 C2 H4 116(3) . . ? C2 C3 C4 119.2(5) . . ? C2 C3 H10 121(3) . . ? C4 C3 H10 120(3) . . ? C5 C4 C3 119.3(4) . . ? C5 C4 H4C 120.4 . . ? C3 C4 H4C 120.4 . . ? C4 C5 C6 123.1(4) . . ? C4 C5 H5A 118.5 . . ? C6 C5 H5A 118.5 . . ? C5 C6 C1 117.3(4) . . ? C5 C6 C7 114.3(3) . . ? C1 C6 C7 128.4(3) . . ? O2 C7 O1 119.0(4) . . ? O2 C7 C6 120.0(4) . . ? O1 C7 C6 121.0(3) . . ? O4 C8 O3 122.2(4) . . ? O4 C8 C1 117.8(4) . . ? O3 C8 C1 120.0(3) . . ? C14 C9 C10 120.5(4) . . ? C14 C9 H9A 119.8 . . ? C10 C9 H9A 119.8 . . ? C11 C10 C9 120.7(5) . . ? C11 C10 H13 121(2) . . ? C9 C10 H13 118(2) . . ? C12 C11 C10 119.0(5) . . ? C12 C11 H11A 120.5 . . ? C10 C11 H11A 120.5 . . ? C11 C12 C13 121.2(5) . . ? C11 C12 H12A 119.4 . . ? C13 C12 H12A 119.4 . . ? C12 C13 C14 119.9(5) . . ? C12 C13 H14 124(4) . . ? C14 C13 H14 116(4) . . ? C9 C14 C13 118.7(4) . . ? C9 C14 C15 123.0(4) . . ? C13 C14 C15 118.1(4) . . ? N3 C15 N1 121.2(4) . . ? N3 C15 C14 118.5(3) . . ? N1 C15 C14 120.3(3) . . ? N5 C16 N2 120.4(4) . . ? N5 C16 N1 118.4(4) . . ? N2 C16 N1 121.2(3) . . ? N4 C17 N2 117.7(4) . . ? N4 C17 N3 116.3(3) . . ? N2 C17 N3 126.0(3) . . ? C16 N1 C15 119.5(3) . . ? C16 N1 H3 120(2) . . ? C15 N1 H3 121(2) . . ? C16 N2 C17 115.8(3) . . ? C15 N3 C17 116.3(3) . . ? C17 N4 H4A 120.0 . . ? C17 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C16 N5 H1 123(3) . . ? C16 N5 H2 118(3) . . ? H1 N5 H2 115(4) . . ? C7 O1 H1A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.265 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.070 data_datam6 _database_code_depnum_ccdc_archive 'CCDC 851870' #TrackingRef '2,4-Diamino-6-phenyl-1,3,5-triazine+benzoic acid.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic '2,4-Diamino-6-phenyl-1,3,5-triazine+benzoic acid' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N5, C7 H6 O2' _chemical_formula_sum 'C16 H15 N5 O2' _chemical_formula_weight 309.33 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 9.821(3) _cell_length_b 7.135(2) _cell_length_c 12.126(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.60(2) _cell_angle_gamma 90.00 _cell_volume 759.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker, APEX CCD area detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7108 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.29 _reflns_number_total 2748 _reflns_number_gt 2498 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_ls_number_reflns 2748 _refine_ls_number_parameters 210 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0931 _refine_ls_R_factor_gt 0.0869 _refine_ls_wR_factor_ref 0.2213 _refine_ls_wR_factor_gt 0.2169 _refine_ls_goodness_of_fit_ref 1.576 _refine_ls_restrained_S_all 1.576 _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 C1 C 0.1834(5) -1.1257(6) -0.4103(4) 0.0503(11) Uani 1 1 d . . . C2 C 0.2673(4) -1.3012(6) -0.4062(4) 0.0465(9) Uani 1 1 d . . . C3 C 0.3318(7) -1.3321(9) -0.4854(5) 0.0815(17) Uani 1 1 d . . . H3A H 0.3215 -1.2434 -0.5449 0.098 Uiso 1 1 calc R . . C4 C 0.4117(11) -1.4955(13) -0.4753(6) 0.117(3) Uani 1 1 d . . . H4A H 0.4505 -1.5190 -0.5313 0.141 Uiso 1 1 calc R . . C5 C 0.4344(9) -1.6209(11) -0.3867(6) 0.105(3) Uani 1 1 d . . . H5A H 0.4920 -1.7274 -0.3804 0.126 Uiso 1 1 calc R . . C6 C 0.3742(7) -1.5958(8) -0.3041(5) 0.0799(18) Uani 1 1 d . . . H6A H 0.3884 -1.6854 -0.2442 0.096 Uiso 1 1 calc R . . C7 C 0.2913(6) -1.4320(6) -0.3131(5) 0.0590(12) Uani 1 1 d . . . H7A H 0.2522 -1.4100 -0.2572 0.071 Uiso 1 1 calc R . . C8 C 0.9576(5) -0.3516(5) 0.0652(3) 0.0450(10) Uani 1 1 d . . . C9 C 0.9611(5) -0.3809(5) -0.1211(4) 0.0408(8) Uani 1 1 d . . . C10 C 0.8488(4) -0.6071(5) -0.0597(4) 0.0377(9) Uani 1 1 d . . . C11 C 0.7618(4) -0.7851(6) -0.0813(3) 0.0432(9) Uani 1 1 d . . . C12 C 0.6947(7) -0.8282(9) -0.0064(5) 0.0714(15) Uani 1 1 d . . . H12A H 0.7059 -0.7478 0.0575 0.086 Uiso 1 1 calc R . . C13 C 0.6112(10) -0.9897(11) -0.0259(6) 0.108(3) Uani 1 1 d . . . H13A H 0.5637 -1.0173 0.0234 0.129 Uiso 1 1 calc R . . C14 C 0.5978(7) -1.1120(9) -0.1192(6) 0.084(2) Uani 1 1 d . . . H14A H 0.5435 -1.2232 -0.1315 0.101 Uiso 1 1 calc R . . C15 C 0.6640(7) -1.0680(8) -0.1916(5) 0.0726(15) Uani 1 1 d . . . H15A H 0.6540 -1.1489 -0.2550 0.087 Uiso 1 1 calc R . . C16 C 0.7457(5) -0.9064(6) -0.1737(4) 0.0525(11) Uani 1 1 d . . . H16A H 0.7908 -0.8786 -0.2248 0.063 Uiso 1 1 calc R . . N1 N 0.9955(5) -0.2586(6) 0.1698(4) 0.0653(11) Uani 1 1 d . . . H1A H 0.9721 -0.3032 0.2250 0.078 Uiso 1 1 calc R . . H1B H 1.0433 -0.1537 0.1823 0.078 Uiso 1 1 calc R . . N2 N 0.9989(5) -0.3083(5) -0.2054(4) 0.0632(11) Uani 1 1 d . . . H2A H 0.9765 -0.3675 -0.2731 0.076 Uiso 1 1 calc R . . H2B H 1.0455 -0.2025 -0.1918 0.076 Uiso 1 1 calc R . . N3 N 0.8833(4) -0.5147(4) 0.0450(3) 0.0424(8) Uani 1 1 d . . . N4 N 1.0018(4) -0.2780(5) -0.0150(3) 0.0523(9) Uani 1 1 d . . . N5 N 0.8869(4) -0.5500(5) -0.1478(3) 0.0448(8) Uani 1 1 d . . . O1 O 0.1533(5) -1.0259(4) -0.5064(4) 0.0740(11) Uani 1 1 d . . . H1W H 0.1100 -0.9295 -0.5029 0.056(14) Uiso 1 1 calc R . . O2 O 0.1493(4) -1.0855(5) -0.3277(3) 0.0678(10) Uani 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 C1 0.065(3) 0.036(2) 0.057(3) -0.008(2) 0.032(2) -0.0108(19) C2 0.042(2) 0.048(2) 0.047(2) -0.0159(18) 0.0179(17) -0.0072(17) C3 0.116(4) 0.079(4) 0.062(3) -0.005(3) 0.051(3) 0.032(3) C4 0.152(7) 0.137(6) 0.061(4) 0.004(4) 0.046(4) 0.094(6) C5 0.135(6) 0.092(5) 0.063(4) -0.003(3) 0.024(4) 0.074(4) C6 0.094(4) 0.058(3) 0.064(3) 0.006(3) 0.014(3) 0.021(3) C7 0.065(3) 0.051(3) 0.056(3) -0.003(2) 0.022(2) -0.008(2) C8 0.067(3) 0.038(2) 0.042(2) -0.0026(18) 0.035(2) 0.0006(18) C9 0.059(2) 0.0307(18) 0.0419(19) 0.0029(16) 0.0307(17) 0.0046(16) C10 0.0360(19) 0.0373(19) 0.045(2) 0.0128(17) 0.0229(16) 0.0058(16) C11 0.050(2) 0.043(2) 0.0348(19) 0.0075(16) 0.0171(17) -0.0024(18) C12 0.090(3) 0.086(4) 0.051(2) -0.016(3) 0.043(3) -0.048(3) C13 0.141(6) 0.122(5) 0.073(4) -0.003(4) 0.060(5) -0.075(5) C14 0.096(4) 0.082(4) 0.059(3) 0.002(3) 0.020(3) -0.050(4) C15 0.074(4) 0.057(3) 0.069(3) -0.012(2) 0.016(3) -0.012(2) C16 0.063(3) 0.047(2) 0.052(3) -0.0022(19) 0.030(2) 0.0007(19) N1 0.107(3) 0.047(2) 0.063(2) 0.0075(17) 0.057(2) -0.0033(19) N2 0.102(3) 0.046(2) 0.070(2) 0.0080(18) 0.064(2) -0.005(2) N3 0.065(2) 0.0310(15) 0.0408(17) 0.0044(13) 0.0324(16) -0.0018(14) N4 0.071(2) 0.043(2) 0.056(2) 0.0155(17) 0.0400(19) 0.0035(16) N5 0.058(2) 0.051(2) 0.0357(16) 0.0060(15) 0.0298(16) 0.0010(16) O1 0.116(3) 0.0397(17) 0.090(3) 0.0063(18) 0.067(2) 0.0183(19) O2 0.104(3) 0.0550(19) 0.074(2) 0.0024(17) 0.066(2) 0.0090(18) _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 C1 O2 1.223(5) . ? C1 O1 1.282(6) . ? C1 C2 1.488(6) . ? C2 C3 1.384(7) . ? C2 C7 1.401(7) . ? C3 C4 1.380(8) . ? C3 H3A 0.9300 . ? C4 C5 1.339(12) . ? C4 H4A 0.9300 . ? C5 C6 1.383(10) . ? C5 H5A 0.9300 . ? C6 C7 1.400(8) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 N1 1.328(6) . ? C8 N3 1.337(5) . ? C8 N4 1.337(5) . ? C9 N2 1.337(5) . ? C9 N5 1.371(5) . ? C9 N4 1.376(5) . ? C10 N3 1.333(5) . ? C10 N5 1.344(5) . ? C10 C11 1.487(5) . ? C11 C16 1.368(6) . ? C11 C12 1.375(6) . ? C12 C13 1.372(8) . ? C12 H12A 0.9300 . ? C13 C14 1.388(11) . ? C13 H13A 0.9300 . ? C14 C15 1.342(9) . ? C14 H14A 0.9300 . ? C15 C16 1.366(7) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? O1 H1W 0.8200 . ? 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 O2 C1 O1 125.3(4) . . ? O2 C1 C2 121.4(4) . . ? O1 C1 C2 113.3(4) . . ? C3 C2 C7 119.2(5) . . ? C3 C2 C1 122.0(5) . . ? C7 C2 C1 118.6(4) . . ? C4 C3 C2 119.5(7) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C5 C4 C3 121.3(7) . . ? C5 C4 H4A 119.4 . . ? C3 C4 H4A 119.4 . . ? C4 C5 C6 121.6(5) . . ? C4 C5 H5A 119.2 . . ? C6 C5 H5A 119.2 . . ? C5 C6 C7 118.2(6) . . ? C5 C6 H6A 120.9 . . ? C7 C6 H6A 120.9 . . ? C6 C7 C2 120.1(5) . . ? C6 C7 H7A 119.9 . . ? C2 C7 H7A 119.9 . . ? N1 C8 N3 120.4(3) . . ? N1 C8 N4 117.0(3) . . ? N3 C8 N4 122.5(3) . . ? N2 C9 N5 117.4(4) . . ? N2 C9 N4 116.4(4) . . ? N5 C9 N4 126.2(3) . . ? N3 C10 N5 124.4(3) . . ? N3 C10 C11 118.1(3) . . ? N5 C10 C11 117.5(3) . . ? C16 C11 C12 119.1(4) . . ? C16 C11 C10 122.1(4) . . ? C12 C11 C10 118.8(4) . . ? C13 C12 C11 120.0(5) . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C12 C13 C14 120.0(6) . . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C15 C14 C13 119.3(5) . . ? C15 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? C14 C15 C16 121.0(5) . . ? C14 C15 H15A 119.5 . . ? C16 C15 H15A 119.5 . . ? C15 C16 C11 120.6(5) . . ? C15 C16 H16A 119.7 . . ? C11 C16 H16A 119.7 . . ? C8 N1 H1A 120.0 . . ? C8 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C9 N2 H2A 120.0 . . ? C9 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C10 N3 C8 119.4(3) . . ? C8 N4 C9 114.7(3) . . ? C10 N5 C9 112.8(3) . . ? C1 O1 H1W 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.29 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.483 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.079 data_datam _database_code_depnum_ccdc_archive 'CCDC 851871' #TrackingRef '2,4-Diamino-6-phenyl-1,3,5-triazine+terephthalic acid.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic '2,4-Diamino-6-phenyl-1,3,5-triazine+terephthalic acid' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C9 H9 N5), C8 H6 O4' _chemical_formula_sum 'C26 H24 N10 O4' _chemical_formula_weight 540.55 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.9430(10) _cell_length_b 7.007(2) _cell_length_c 12.152(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.780(10) _cell_angle_gamma 90.00 _cell_volume 2427.8(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Rectangular Blocks' _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker, APEX CCD area detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7497 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.27 _reflns_number_total 2210 _reflns_number_gt 1750 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+0.0000P] 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 2210 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1085 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.3098 _refine_ls_wR_factor_gt 0.2998 _refine_ls_goodness_of_fit_ref 2.037 _refine_ls_restrained_S_all 2.037 _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 C1 C 0.00905(18) 0.3762(7) 1.0945(4) 0.0204(12) Uani 1 1 d . . . C2 C 0.02267(17) 0.3279(7) 0.9974(4) 0.0174(11) Uani 1 1 d . . . C3 C 0.01343(18) 0.4534(7) 0.9043(4) 0.0173(11) Uani 1 1 d . . . H3 H 0.0239(18) 0.407(7) 0.850(5) 0.018(14) Uiso 1 1 d . . . C4 C 0.04653(17) 0.1419(7) 0.9907(4) 0.0186(12) Uani 1 1 d . . . C5 C 0.38584(16) 0.1255(7) 0.3213(4) 0.0145(11) Uani 1 1 d . . . C6 C 0.38463(16) 0.1478(7) 0.5072(4) 0.0165(11) Uani 1 1 d . . . C7 C 0.35120(16) -0.1045(7) 0.3967(4) 0.0159(11) Uani 1 1 d . . . C8 C 0.32506(17) -0.2876(7) 0.3858(4) 0.0197(12) Uani 1 1 d . . . C9 C 0.3036(2) -0.3389(9) 0.4670(5) 0.0428(18) Uani 1 1 d . . . H9A H 0.3063 -0.2599 0.5302 0.051 Uiso 1 1 calc R . . C10 C 0.2784(3) -0.5045(10) 0.4557(6) 0.055(2) Uani 1 1 d . . . H10A H 0.2638 -0.5356 0.5108 0.065 Uiso 1 1 calc R . . C11 C 0.2743(2) -0.6254(9) 0.3646(5) 0.0411(17) Uani 1 1 d . . . H11A H 0.2573 -0.7381 0.3582 0.049 Uiso 1 1 calc R . . C12 C 0.29543(19) -0.5787(8) 0.2828(5) 0.0287(14) Uani 1 1 d . . . H12 H 0.291(2) -0.650(8) 0.213(5) 0.037(17) Uiso 1 1 d . . . C13 C 0.32097(19) -0.4120(7) 0.2927(5) 0.0247(13) Uani 1 1 d . . . H13 H 0.3342(18) -0.380(7) 0.230(5) 0.022(14) Uiso 1 1 d . . . N1 N 0.39654(17) 0.1986(7) 0.2311(4) 0.0219(11) Uani 1 1 d . . . H1B H 0.385(2) 0.164(10) 0.156(6) 0.06(2) Uiso 1 1 d . . . N2 N 0.39529(15) 0.2418(6) 0.6071(3) 0.0207(11) Uani 1 1 d . . . H2A H 0.3872 0.1960 0.6639 0.025 Uiso 1 1 calc R . . H2B H 0.4102 0.3483 0.6148 0.025 Uiso 1 1 calc R . . N3 N 0.36263(14) -0.0425(6) 0.3046(3) 0.0164(10) Uani 1 1 d . . . N4 N 0.36144(14) -0.0168(5) 0.5000(3) 0.0159(10) Uani 1 1 d . . . N5 N 0.39824(14) 0.2249(5) 0.4206(3) 0.0155(10) Uani 1 1 d . . . O1 O 0.05718(13) 0.0399(5) 1.0853(3) 0.0215(9) Uani 1 1 d . . . H1W H 0.0700 -0.0591 1.0754 0.17(6) Uiso 1 1 calc R . . O2 O 0.05556(13) 0.0946(5) 0.9031(3) 0.0225(9) Uani 1 1 d . . . H1 H 0.013(2) 0.290(8) 1.151(5) 0.028(16) Uiso 1 1 d . . . H1A H 0.413(3) 0.306(12) 0.247(8) 0.09(3) 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 C1 0.025(3) 0.019(3) 0.017(3) 0.002(2) 0.007(2) -0.003(2) C2 0.018(3) 0.015(3) 0.018(3) -0.001(2) 0.004(2) -0.004(2) C3 0.018(3) 0.023(3) 0.012(2) -0.002(2) 0.008(2) 0.002(2) C4 0.019(3) 0.022(3) 0.017(3) 0.001(2) 0.009(2) -0.003(2) C5 0.016(2) 0.016(3) 0.013(2) 0.0022(19) 0.0066(19) 0.003(2) C6 0.017(3) 0.013(3) 0.021(3) 0.000(2) 0.007(2) 0.003(2) C7 0.014(2) 0.019(3) 0.016(2) 0.002(2) 0.0053(19) 0.002(2) C8 0.020(3) 0.022(3) 0.016(3) 0.005(2) 0.003(2) -0.002(2) C9 0.057(4) 0.050(4) 0.021(3) -0.006(3) 0.010(3) -0.029(3) C10 0.068(5) 0.069(5) 0.030(4) -0.003(3) 0.021(3) -0.049(4) C11 0.050(4) 0.038(4) 0.028(3) 0.001(3) 0.001(3) -0.026(3) C12 0.026(3) 0.022(3) 0.031(3) -0.002(2) -0.002(3) -0.001(2) C13 0.024(3) 0.020(3) 0.031(3) 0.003(2) 0.010(2) 0.002(2) N1 0.030(3) 0.019(2) 0.018(2) -0.0022(19) 0.010(2) -0.001(2) N2 0.033(3) 0.017(2) 0.017(2) 0.0001(17) 0.015(2) -0.0047(19) N3 0.016(2) 0.018(2) 0.016(2) -0.0001(17) 0.0062(17) -0.0006(17) N4 0.017(2) 0.015(2) 0.017(2) 0.0014(17) 0.0066(17) 0.0001(17) N5 0.018(2) 0.011(2) 0.018(2) 0.0013(16) 0.0071(18) 0.0001(16) O1 0.029(2) 0.022(2) 0.0166(19) 0.0065(15) 0.0115(16) 0.0058(17) O2 0.033(2) 0.0183(19) 0.021(2) 0.0011(15) 0.0161(17) 0.0037(16) _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 C1 C3 1.373(8) 5_567 ? C1 C2 1.403(7) . ? C2 C3 1.392(7) . ? C2 C4 1.500(7) . ? C3 C1 1.373(8) 5_567 ? C4 O2 1.222(6) . ? C4 O1 1.307(6) . ? C5 N1 1.334(6) . ? C5 N5 1.343(6) . ? C5 N3 1.350(6) . ? C6 N2 1.331(6) . ? C6 N4 1.336(6) . ? C6 N5 1.352(6) . ? C7 N3 1.338(6) . ? C7 N4 1.346(6) . ? C7 C8 1.488(7) . ? C8 C9 1.379(8) . ? C8 C13 1.404(7) . ? C9 C10 1.368(8) . ? C10 C11 1.369(9) . ? C11 C12 1.371(9) . ? C12 C13 1.382(7) . ? 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 C3 C1 C2 119.2(5) 5_567 . ? C3 C2 C1 119.6(5) . . ? C3 C2 C4 119.0(5) . . ? C1 C2 C4 121.4(4) . . ? C1 C3 C2 121.2(5) 5_567 . ? O2 C4 O1 124.0(5) . . ? O2 C4 C2 121.2(4) . . ? O1 C4 C2 114.8(4) . . ? N1 C5 N5 117.9(4) . . ? N1 C5 N3 116.9(4) . . ? N5 C5 N3 125.1(4) . . ? N2 C6 N4 117.5(4) . . ? N2 C6 N5 117.9(4) . . ? N4 C6 N5 124.6(4) . . ? N3 C7 N4 126.0(4) . . ? N3 C7 C8 117.9(4) . . ? N4 C7 C8 116.1(4) . . ? C9 C8 C13 118.1(5) . . ? C9 C8 C7 120.6(5) . . ? C13 C8 C7 121.4(5) . . ? C10 C9 C8 120.8(6) . . ? C9 C10 C11 121.1(6) . . ? C10 C11 C12 119.4(6) . . ? C11 C12 C13 120.3(6) . . ? C12 C13 C8 120.3(5) . . ? C7 N3 C5 114.1(4) . . ? C6 N4 C7 114.9(4) . . ? C5 N5 C6 115.2(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.27 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.554 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.109