# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Prof Qi Fang' _publ_contact_author_address ; State Key Laboratory of Crystal Materials Shandong University Jinan Shandong Province 250100 CHINA ; _publ_contact_author_email FANGQI@ICM.SDU.EDU.CN _publ_section_title ; Frequency up-conversion of s-triazine derivatives via two photon absorption and second-harmonic generation ; _publ_author_name 'Qi Fang' data_0318 _database_code_depnum_ccdc_archive 'CCDC 228998' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;2-methyl-4,6-dis(2-(4-N,N-diethylamino)phenylethenyl)-s- triazine ; _chemical_melting_point ? _chemical_formula_moiety 'C28 H35 N5' _chemical_formula_sum 'C28 H35 N5' _chemical_formula_weight 441.61 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8105(14) _cell_length_b 14.8249(18) _cell_length_c 14.7773(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.349(8) _cell_angle_gamma 90.00 _cell_volume 2579.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 4.81 _cell_measurement_theta_max 12.44 _exptl_crystal_description prism _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.137 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.818 _exptl_absorpt_correction_T_max 0.861 _exptl_absorpt_process_details 'Bruker XSCANS(Bruker,1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 P4' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.3 _diffrn_reflns_number 5991 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.1281 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4801 _reflns_number_gt 1653 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS(Bruker,1996)' _computing_cell_refinement 'Bruker XSCANS(Bruker,1996)' _computing_data_reduction 'Bruker SHELXTL (Bruker,1997)' _computing_structure_solution 'Bruker SHELXTL (Bruker,1997)' _computing_structure_refinement 'Bruker SHELXTL (Bruker,1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker,1997)' _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^)+(0.0638P)^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 SHELXL _refine_ls_extinction_coef 0.0042(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4801 _refine_ls_number_parameters 300 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.2107 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1836 _refine_ls_wR_factor_gt 0.1330 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.906 _refine_ls_shift/su_max 0.001 _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 0.2654(4) 0.1338(3) 0.6998(2) 0.0801(14) Uani 1 1 d . . . H1A H 0.3410 0.1105 0.6978 0.120 Uiso 1 1 calc R . . H1B H 0.2514 0.1781 0.6529 0.120 Uiso 1 1 calc R . . H1C H 0.2117 0.0854 0.6906 0.120 Uiso 1 1 calc R . . C2 C 0.2531(3) 0.1762(3) 0.7901(3) 0.0574(11) Uani 1 1 d . . . C3 C 0.2678(3) 0.1694(3) 0.9432(3) 0.0516(11) Uani 1 1 d . . . C4 C 0.2939(3) 0.1181(3) 1.0257(3) 0.0568(11) Uani 1 1 d . . . H4A H 0.2782 0.1442 1.0806 0.068 Uiso 1 1 calc R . . C5 C 0.3392(3) 0.0354(2) 1.0274(3) 0.0541(11) Uani 1 1 d . . . H5A H 0.3571 0.0127 0.9716 0.065 Uiso 1 1 calc R . . C6 C 0.3640(3) -0.0232(3) 1.1041(3) 0.0499(10) Uani 1 1 d . . . C7 C 0.3349(3) -0.0037(3) 1.1919(3) 0.0639(12) Uani 1 1 d . . . H7A H 0.3018 0.0518 1.2030 0.077 Uiso 1 1 calc R . . C8 C 0.3536(4) -0.0638(3) 1.2627(3) 0.0732(13) Uani 1 1 d . . . H8A H 0.3332 -0.0480 1.3201 0.088 Uiso 1 1 calc R . . C9 C 0.4033(4) -0.1487(3) 1.2492(3) 0.0674(13) Uani 1 1 d . . . C10 C 0.4343(4) -0.1675(3) 1.1625(3) 0.0681(13) Uani 1 1 d . . . H10A H 0.4686 -0.2224 1.1513 0.082 Uiso 1 1 calc R . . C11 C 0.4153(3) -0.1068(3) 1.0932(3) 0.0601(12) Uani 1 1 d . . . H11A H 0.4377 -0.1220 1.0362 0.072 Uiso 1 1 calc R . . C12 C 0.4747(4) -0.2968(3) 1.3074(3) 0.0887(16) Uani 1 1 d . . . H12A H 0.5089 -0.3169 1.3657 0.106 Uiso 1 1 calc R . . H12B H 0.5350 -0.2900 1.2669 0.106 Uiso 1 1 calc R . . C13 C 0.3925(4) -0.3690(4) 1.2694(4) 0.131(2) Uani 1 1 d U . . H13A H 0.4326 -0.4246 1.2631 0.197 Uiso 1 1 calc R . . H13B H 0.3593 -0.3502 1.2111 0.197 Uiso 1 1 calc R . . H13C H 0.3336 -0.3775 1.3100 0.197 Uiso 1 1 calc R . . C14 C 0.3839(5) -0.1915(4) 1.4086(4) 0.113(2) Uani 1 1 d . . . H14A H 0.3669 -0.2485 1.4367 0.136 Uiso 1 1 calc R . . H14B H 0.3144 -0.1564 1.4025 0.136 Uiso 1 1 calc R . . C15 C 0.4705(5) -0.1417(4) 1.4695(3) 0.139(2) Uani 1 1 d . . . H15A H 0.4409 -0.1317 1.5274 0.209 Uiso 1 1 calc R . . H15B H 0.4871 -0.0848 1.4425 0.209 Uiso 1 1 calc R . . H15C H 0.5387 -0.1769 1.4775 0.209 Uiso 1 1 calc R . . C16 C 0.2115(3) 0.2983(3) 0.8723(3) 0.0551(11) Uani 1 1 d . . . C17 C 0.1733(4) 0.3912(3) 0.8760(3) 0.0623(12) Uani 1 1 d . . . H17A H 0.1497 0.4188 0.8213 0.075 Uiso 1 1 calc R . . C18 C 0.1692(3) 0.4402(3) 0.9509(3) 0.0626(12) Uani 1 1 d . . . H18A H 0.1915 0.4115 1.0053 0.075 Uiso 1 1 calc R . . C19 C 0.1337(4) 0.5336(3) 0.9574(3) 0.0568(11) Uani 1 1 d . . . C20 C 0.1566(4) 0.5828(3) 1.0364(3) 0.0690(13) Uani 1 1 d . . . H20A H 0.1897 0.5530 1.0871 0.083 Uiso 1 1 calc R . . C21 C 0.1332(4) 0.6728(3) 1.0443(3) 0.0715(13) Uani 1 1 d . . . H21A H 0.1533 0.7030 1.0983 0.086 Uiso 1 1 calc R . . C22 C 0.0788(4) 0.7193(3) 0.9705(3) 0.0619(12) Uani 1 1 d . . . C23 C 0.0476(4) 0.6690(3) 0.8919(3) 0.0685(13) Uani 1 1 d . . . H23A H 0.0079 0.6969 0.8429 0.082 Uiso 1 1 calc R . . C24 C 0.0748(4) 0.5791(3) 0.8864(3) 0.0653(13) Uani 1 1 d . . . H24A H 0.0530 0.5477 0.8334 0.078 Uiso 1 1 calc R . . C25 C 0.1057(4) 0.8651(3) 1.0484(3) 0.0779(14) Uani 1 1 d . . . H25A H 0.1193 0.9253 1.0258 0.093 Uiso 1 1 calc R . . H25B H 0.1785 0.8395 1.0697 0.093 Uiso 1 1 calc R . . C26 C 0.0325(4) 0.8718(3) 1.1266(3) 0.1133(19) Uani 1 1 d . . . H26A H 0.0695 0.9087 1.1733 0.170 Uiso 1 1 calc R . . H26B H 0.0201 0.8125 1.1503 0.170 Uiso 1 1 calc R . . H26C H -0.0392 0.8983 1.1064 0.170 Uiso 1 1 calc R . . C27 C -0.0014(4) 0.8577(3) 0.8980(3) 0.0785(14) Uani 1 1 d . . . H27A H -0.0386 0.9107 0.9203 0.094 Uiso 1 1 calc R . . H27B H -0.0596 0.8190 0.8690 0.094 Uiso 1 1 calc R . . C28 C 0.0790(4) 0.8866(3) 0.8280(3) 0.1091(18) Uani 1 1 d . . . H28A H 0.0369 0.9172 0.7790 0.164 Uiso 1 1 calc R . . H28B H 0.1153 0.8344 0.8050 0.164 Uiso 1 1 calc R . . H28C H 0.1354 0.9265 0.8557 0.164 Uiso 1 1 calc R . . N1 N 0.2195(3) 0.2629(2) 0.7898(2) 0.0618(10) Uani 1 1 d . . . N2 N 0.2362(3) 0.2552(2) 0.9520(2) 0.0586(9) Uani 1 1 d . . . N3 N 0.2781(3) 0.1267(2) 0.8635(2) 0.0588(9) Uani 1 1 d . . . N4 N 0.4210(3) -0.2088(3) 1.3191(3) 0.0826(12) Uani 1 1 d . . . N5 N 0.0552(3) 0.8100(2) 0.9744(2) 0.0701(11) 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 0.108(4) 0.072(3) 0.059(3) -0.009(3) -0.004(3) 0.013(3) C2 0.056(3) 0.060(3) 0.057(3) -0.011(2) 0.010(2) 0.002(2) C3 0.047(3) 0.057(3) 0.049(3) -0.001(2) -0.007(2) -0.004(2) C4 0.064(3) 0.051(3) 0.054(3) 0.001(2) -0.004(2) -0.001(2) C5 0.062(3) 0.046(2) 0.054(3) 0.004(2) 0.006(2) -0.002(2) C6 0.051(3) 0.049(3) 0.049(2) 0.003(2) 0.004(2) -0.002(2) C7 0.071(3) 0.048(2) 0.073(3) 0.003(2) 0.009(3) 0.007(2) C8 0.091(4) 0.062(3) 0.068(3) 0.009(3) 0.011(3) 0.015(3) C9 0.067(3) 0.063(3) 0.071(3) 0.020(3) 0.000(3) 0.012(3) C10 0.073(3) 0.052(3) 0.080(3) 0.002(3) 0.009(3) 0.013(3) C11 0.066(3) 0.049(3) 0.066(3) -0.001(2) 0.011(2) -0.003(2) C12 0.074(4) 0.079(4) 0.112(4) 0.026(3) -0.003(3) 0.019(3) C13 0.103(4) 0.096(4) 0.191(5) 0.028(4) -0.008(4) -0.003(4) C14 0.125(5) 0.120(5) 0.099(4) 0.063(4) 0.044(4) 0.039(4) C15 0.150(6) 0.181(7) 0.087(4) 0.002(4) 0.008(4) 0.036(6) C16 0.063(3) 0.053(3) 0.051(3) 0.004(2) 0.010(2) -0.010(2) C17 0.089(3) 0.043(3) 0.055(3) 0.005(2) 0.005(2) -0.002(2) C18 0.077(3) 0.050(3) 0.059(3) 0.007(2) -0.004(2) -0.006(3) C19 0.077(3) 0.044(2) 0.050(3) 0.004(2) 0.013(2) -0.006(2) C20 0.101(4) 0.057(3) 0.050(3) 0.002(2) 0.007(3) -0.002(3) C21 0.100(4) 0.056(3) 0.057(3) -0.006(2) 0.002(3) 0.000(3) C22 0.068(3) 0.046(3) 0.072(3) -0.006(2) 0.011(2) 0.001(2) C23 0.086(3) 0.053(3) 0.065(3) 0.004(2) -0.006(3) 0.002(3) C24 0.085(3) 0.049(3) 0.061(3) -0.001(2) -0.007(3) -0.001(3) C25 0.065(3) 0.059(3) 0.109(4) -0.017(3) 0.003(3) -0.002(3) C26 0.119(5) 0.114(4) 0.111(4) -0.046(4) 0.035(4) 0.001(4) C27 0.070(3) 0.058(3) 0.106(4) -0.013(3) 0.000(3) 0.012(3) C28 0.116(5) 0.094(4) 0.116(4) 0.015(3) -0.001(4) 0.014(4) N1 0.085(3) 0.051(2) 0.050(2) -0.0037(18) 0.0081(19) 0.010(2) N2 0.078(3) 0.042(2) 0.055(2) -0.0018(17) 0.0017(19) -0.005(2) N3 0.069(2) 0.052(2) 0.054(2) -0.0036(19) -0.0033(19) 0.0008(19) N4 0.086(3) 0.082(3) 0.082(3) 0.034(2) 0.018(2) 0.033(2) N5 0.086(3) 0.051(2) 0.070(2) -0.007(2) -0.012(2) 0.002(2) _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 1.493(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N3 1.324(5) . ? C2 N1 1.345(5) . ? C3 N2 1.335(4) . ? C3 N3 1.351(4) . ? C3 C4 1.450(5) . ? C4 C5 1.336(5) . ? C4 H4A 0.9300 . ? C5 C6 1.441(5) . ? C5 H5A 0.9300 . ? C6 C11 1.394(5) . ? C6 C7 1.398(5) . ? C7 C8 1.379(5) . ? C7 H7A 0.9300 . ? C8 C9 1.410(5) . ? C8 H8A 0.9300 . ? C9 N4 1.367(5) . ? C9 C10 1.387(5) . ? C10 C11 1.369(5) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 N4 1.466(5) . ? C12 C13 1.523(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N4 1.447(5) . ? C14 C15 1.504(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N1 1.336(4) . ? C16 N2 1.352(4) . ? C16 C17 1.452(5) . ? C17 C18 1.328(5) . ? C17 H17A 0.9300 . ? C18 C19 1.452(5) . ? C18 H18A 0.9300 . ? C19 C24 1.388(5) . ? C19 C20 1.387(5) . ? C20 C21 1.369(5) . ? C20 H20A 0.9300 . ? C21 C22 1.403(5) . ? C21 H21A 0.9300 . ? C22 N5 1.375(5) . ? C22 C23 1.406(5) . ? C23 C24 1.374(5) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 N5 1.458(4) . ? C25 C26 1.498(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 N5 1.451(5) . ? C27 C28 1.518(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 N1 125.5(4) . . ? N3 C2 C1 117.9(4) . . ? N1 C2 C1 116.7(4) . . ? N2 C3 N3 125.2(4) . . ? N2 C3 C4 117.5(4) . . ? N3 C3 C4 117.3(4) . . ? C5 C4 C3 123.8(4) . . ? C5 C4 H4A 118.1 . . ? C3 C4 H4A 118.1 . . ? C4 C5 C6 128.7(4) . . ? C4 C5 H5A 115.7 . . ? C6 C5 H5A 115.7 . . ? C11 C6 C7 115.5(4) . . ? C11 C6 C5 120.7(4) . . ? C7 C6 C5 123.8(4) . . ? C8 C7 C6 122.3(4) . . ? C8 C7 H7A 118.9 . . ? C6 C7 H7A 118.9 . . ? C7 C8 C9 121.0(4) . . ? C7 C8 H8A 119.5 . . ? C9 C8 H8A 119.5 . . ? N4 C9 C10 122.0(4) . . ? N4 C9 C8 121.1(4) . . ? C10 C9 C8 116.8(4) . . ? C11 C10 C9 121.3(4) . . ? C11 C10 H10A 119.4 . . ? C9 C10 H10A 119.4 . . ? C10 C11 C6 123.1(4) . . ? C10 C11 H11A 118.5 . . ? C6 C11 H11A 118.5 . . ? N4 C12 C13 113.5(4) . . ? N4 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? N4 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C14 C15 113.3(5) . . ? N4 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? N4 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 N2 125.7(4) . . ? N1 C16 C17 116.8(4) . . ? N2 C16 C17 117.6(4) . . ? C18 C17 C16 125.6(4) . . ? C18 C17 H17A 117.2 . . ? C16 C17 H17A 117.2 . . ? C17 C18 C19 127.2(4) . . ? C17 C18 H18A 116.4 . . ? C19 C18 H18A 116.4 . . ? C24 C19 C20 115.8(4) . . ? C24 C19 C18 123.0(4) . . ? C20 C19 C18 121.2(4) . . ? C21 C20 C19 123.8(4) . . ? C21 C20 H20A 118.1 . . ? C19 C20 H20A 118.1 . . ? C20 C21 C22 119.7(4) . . ? C20 C21 H21A 120.1 . . ? C22 C21 H21A 120.1 . . ? N5 C22 C21 122.0(4) . . ? N5 C22 C23 120.7(4) . . ? C21 C22 C23 117.2(4) . . ? C24 C23 C22 121.0(4) . . ? C24 C23 H23A 119.5 . . ? C22 C23 H23A 119.5 . . ? C23 C24 C19 122.2(4) . . ? C23 C24 H24A 118.9 . . ? C19 C24 H24A 118.9 . . ? N5 C25 C26 112.8(4) . . ? N5 C25 H25A 109.0 . . ? C26 C25 H25A 109.0 . . ? N5 C25 H25B 109.0 . . ? C26 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N5 C27 C28 113.1(4) . . ? N5 C27 H27A 109.0 . . ? C28 C27 H27A 109.0 . . ? N5 C27 H27B 109.0 . . ? C28 C27 H27B 109.0 . . ? H27A C27 H27B 107.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C16 N1 C2 114.4(4) . . ? C3 N2 C16 114.2(3) . . ? C2 N3 C3 115.1(4) . . ? C9 N4 C14 122.3(4) . . ? C9 N4 C12 122.3(4) . . ? C14 N4 C12 115.4(4) . . ? C22 N5 C27 121.8(4) . . ? C22 N5 C25 120.4(4) . . ? C27 N5 C25 116.7(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.146 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.036 data_0319 _database_code_depnum_ccdc_archive 'CCDC 228999' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;2,4-dimethyl-6-(2-(4-N,N-diethylamino)phenylethenyl)-s- triazine ; _chemical_melting_point ? _chemical_formula_moiety 'C17 H22 N4' _chemical_formula_sum 'C17 H22 N4' _chemical_formula_weight 282.39 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 Cc 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' _cell_length_a 15.5368(15) _cell_length_b 14.0904(13) _cell_length_c 8.6146(8) _cell_angle_alpha 90.00 _cell_angle_beta 121.151(8) _cell_angle_gamma 90.00 _cell_volume 1614.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 5.247 _cell_measurement_theta_max 12.473 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.53204 _exptl_absorpt_correction_T_max 0.55962 _exptl_absorpt_process_details 'Bruker xscan(Bruker,1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 P4' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2229 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2059 _reflns_number_gt 1342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker xscan(Bruker,1996)' _computing_cell_refinement 'Bruker xscan(Bruker,1996)' _computing_data_reduction 'Bruker xscan(Bruker,1996)' _computing_structure_solution 'Bruker SHELXtl(Bruker,1997)' _computing_structure_refinement 'Bruker SHELXtl(Bruker,1997)' _computing_molecular_graphics 'Bruker SHELXtl(Bruker,1997)' _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^)+(0.0665P)^2^+0.1737P] 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 SHELXL _refine_ls_extinction_coef 0.0144(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(4) _refine_ls_number_reflns 2059 _refine_ls_number_parameters 193 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.980 _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 0.2007(2) 0.7173(2) 0.8593(4) 0.0695(8) Uani 1 1 d . . . N2 N 0.2129(2) 0.5532(2) 0.8227(5) 0.0759(9) Uani 1 1 d . . . N3 N 0.0769(2) 0.6137(2) 0.8404(5) 0.0728(8) Uani 1 1 d . . . N4 N 0.7633(2) 0.6191(2) 0.8478(4) 0.0679(8) Uani 1 1 d . . . C1 C 0.0624(3) 0.7822(3) 0.8722(7) 0.0922(13) Uani 1 1 d . . . H1B H 0.0983 0.8392 0.8806 0.138 Uiso 1 1 calc R . . H1C H 0.0582 0.7757 0.9790 0.138 Uiso 1 1 calc R . . H1D H -0.0042 0.7854 0.7672 0.138 Uiso 1 1 calc R . . C2 C 0.0878(4) 0.4450(3) 0.8112(9) 0.1071(16) Uani 1 1 d . . . H2B H 0.0716 0.4172 0.6975 0.161 Uiso 1 1 calc R . . H2C H 0.0284 0.4475 0.8191 0.161 Uiso 1 1 calc R . . H2D H 0.1380 0.4072 0.9089 0.161 Uiso 1 1 calc R . . C3 C 0.1163(3) 0.6989(3) 0.8563(5) 0.0656(9) Uani 1 1 d . . . C4 C 0.1268(3) 0.5420(3) 0.8238(5) 0.0762(11) Uani 1 1 d . . . C5 C 0.2464(3) 0.6419(3) 0.8422(5) 0.0636(9) Uani 1 1 d . . . C6 C 0.3414(3) 0.6587(3) 0.8468(4) 0.0674(10) Uani 1 1 d . . . H6A H 0.3705 0.7185 0.8825 0.081 Uiso 1 1 calc R . . C7 C 0.3877(3) 0.5955(3) 0.8042(5) 0.0677(10) Uani 1 1 d . . . H7A H 0.3554 0.5373 0.7636 0.081 Uiso 1 1 calc R . . C8 C 0.4829(2) 0.6048(2) 0.8125(4) 0.0583(9) Uani 1 1 d . . . C9 C 0.5114(2) 0.5387(3) 0.7305(4) 0.0638(9) Uani 1 1 d . . . H9A H 0.4675 0.4893 0.6665 0.077 Uiso 1 1 calc R . . C10 C 0.6024(3) 0.5427(2) 0.7393(5) 0.0645(9) Uani 1 1 d . . . H10A H 0.6179 0.4967 0.6800 0.077 Uiso 1 1 calc R . . C11 C 0.6721(3) 0.6147(2) 0.8358(5) 0.0583(9) Uani 1 1 d . . . C12 C 0.6436(3) 0.6824(2) 0.9198(4) 0.0630(9) Uani 1 1 d . . . H12A H 0.6874 0.7316 0.9852 0.076 Uiso 1 1 calc R . . C13 C 0.5520(3) 0.6774(3) 0.9073(4) 0.0630(9) Uani 1 1 d . . . H13A H 0.5352 0.7239 0.9637 0.076 Uiso 1 1 calc R . . C14 C 0.8351(3) 0.6952(3) 0.9462(5) 0.0675(9) Uani 1 1 d . . . H14A H 0.9021 0.6729 0.9833 0.081 Uiso 1 1 calc R . . H14B H 0.8339 0.7093 1.0553 0.081 Uiso 1 1 calc R . . C15 C 0.8152(3) 0.7849(3) 0.8395(5) 0.0806(11) Uani 1 1 d . . . H15A H 0.8651 0.8314 0.9127 0.121 Uiso 1 1 calc R . . H15B H 0.7497 0.8085 0.8046 0.121 Uiso 1 1 calc R . . H15C H 0.8182 0.7722 0.7329 0.121 Uiso 1 1 calc R . . C16 C 0.7899(3) 0.5535(3) 0.7471(5) 0.0764(11) Uani 1 1 d . . . H16A H 0.8388 0.5839 0.7257 0.092 Uiso 1 1 calc R . . H16B H 0.7303 0.5408 0.6299 0.092 Uiso 1 1 calc R . . C17 C 0.8324(4) 0.4607(3) 0.8428(6) 0.0929(14) Uani 1 1 d . . . H17A H 0.8494 0.4218 0.7711 0.139 Uiso 1 1 calc R . . H17B H 0.7832 0.4286 0.8595 0.139 Uiso 1 1 calc R . . H17C H 0.8916 0.4724 0.9588 0.139 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 N1 0.0653(19) 0.0705(18) 0.0732(19) 0.0054(14) 0.0361(16) 0.0015(15) N2 0.0669(19) 0.075(2) 0.087(2) 0.0036(17) 0.0401(17) 0.0125(16) N3 0.0570(16) 0.0737(19) 0.090(2) -0.0030(17) 0.0400(15) -0.0018(16) N4 0.0685(19) 0.0649(18) 0.083(2) -0.0152(15) 0.0479(17) -0.0079(15) C1 0.094(3) 0.076(3) 0.118(3) -0.008(2) 0.063(3) 0.002(2) C2 0.094(3) 0.074(3) 0.165(5) -0.011(3) 0.075(3) -0.012(2) C3 0.055(2) 0.078(2) 0.061(2) 0.0009(17) 0.0277(16) 0.0001(18) C4 0.068(2) 0.075(3) 0.084(3) 0.000(2) 0.038(2) 0.003(2) C5 0.058(2) 0.067(2) 0.0571(18) 0.0108(18) 0.0243(17) -0.0004(19) C6 0.072(2) 0.060(2) 0.064(2) 0.0051(17) 0.030(2) -0.002(2) C7 0.065(2) 0.068(2) 0.063(2) 0.0068(18) 0.029(2) 0.0019(19) C8 0.051(2) 0.064(2) 0.055(2) 0.0095(17) 0.0236(17) 0.0044(16) C9 0.0547(19) 0.062(2) 0.064(2) -0.0034(16) 0.0237(17) -0.0052(16) C10 0.072(2) 0.056(2) 0.067(2) -0.0086(16) 0.0366(19) -0.0025(17) C11 0.060(2) 0.062(2) 0.0582(18) -0.0009(16) 0.0340(16) -0.0008(17) C12 0.065(2) 0.063(2) 0.069(2) -0.0087(17) 0.0397(19) -0.0070(17) C13 0.066(2) 0.068(2) 0.062(2) -0.0036(16) 0.0385(18) 0.0021(17) C14 0.0584(19) 0.075(2) 0.073(2) -0.0111(18) 0.0363(18) -0.0060(18) C15 0.077(3) 0.076(2) 0.090(3) -0.002(2) 0.045(2) -0.011(2) C16 0.078(3) 0.087(3) 0.083(3) -0.017(2) 0.055(2) -0.008(2) C17 0.089(3) 0.087(3) 0.111(4) -0.019(3) 0.058(3) 0.013(3) _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 C3 1.322(5) . ? N1 C5 1.327(5) . ? N2 C5 1.331(5) . ? N2 C4 1.351(5) . ? N3 C3 1.323(5) . ? N3 C4 1.326(5) . ? N4 C11 1.367(4) . ? N4 C14 1.461(5) . ? N4 C16 1.466(5) . ? C1 C3 1.489(5) . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 H1D 0.9600 . ? C2 C4 1.477(5) . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C2 H2D 0.9600 . ? C5 C6 1.474(5) . ? C6 C7 1.312(5) . ? C6 H6A 0.9300 . ? C7 C8 1.448(5) . ? C7 H7A 0.9300 . ? C8 C9 1.373(5) . ? C8 C13 1.400(5) . ? C9 C10 1.378(5) . ? C9 H9A 0.9300 . ? C10 C11 1.400(5) . ? C10 H10A 0.9300 . ? C11 C12 1.402(5) . ? C12 C13 1.372(5) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C15 1.498(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.504(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 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 C3 N1 C5 115.1(3) . . ? C5 N2 C4 115.6(3) . . ? C3 N3 C4 115.9(3) . . ? C11 N4 C14 121.9(3) . . ? C11 N4 C16 121.6(3) . . ? C14 N4 C16 116.2(3) . . ? C3 C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C1 H1D 109.5 . . ? H1B C1 H1D 109.5 . . ? H1C C1 H1D 109.5 . . ? C4 C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C2 H2D 109.5 . . ? H2B C2 H2D 109.5 . . ? H2C C2 H2D 109.5 . . ? N1 C3 N3 125.5(3) . . ? N1 C3 C1 116.3(4) . . ? N3 C3 C1 118.2(4) . . ? N3 C4 N2 123.3(4) . . ? N3 C4 C2 118.1(4) . . ? N2 C4 C2 118.6(4) . . ? N1 C5 N2 124.6(3) . . ? N1 C5 C6 117.0(3) . . ? N2 C5 C6 118.4(3) . . ? C7 C6 C5 124.8(3) . . ? C7 C6 H6A 117.6 . . ? C5 C6 H6A 117.6 . . ? C6 C7 C8 128.2(4) . . ? C6 C7 H7A 115.9 . . ? C8 C7 H7A 115.9 . . ? C9 C8 C13 116.2(3) . . ? C9 C8 C7 120.4(3) . . ? C13 C8 C7 123.4(3) . . ? C8 C9 C10 122.7(3) . . ? C8 C9 H9A 118.7 . . ? C10 C9 H9A 118.7 . . ? C9 C10 C11 121.2(3) . . ? C9 C10 H10A 119.4 . . ? C11 C10 H10A 119.4 . . ? N4 C11 C10 122.0(3) . . ? N4 C11 C12 121.5(3) . . ? C10 C11 C12 116.5(3) . . ? C13 C12 C11 121.1(3) . . ? C13 C12 H12A 119.4 . . ? C11 C12 H12A 119.4 . . ? C12 C13 C8 122.3(3) . . ? C12 C13 H13A 118.8 . . ? C8 C13 H13A 118.8 . . ? N4 C14 C15 114.2(3) . . ? N4 C14 H14A 108.7 . . ? C15 C14 H14A 108.7 . . ? N4 C14 H14B 108.7 . . ? C15 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N4 C16 C17 113.7(4) . . ? N4 C16 H16A 108.8 . . ? C17 C16 H16A 108.8 . . ? N4 C16 H16B 108.8 . . ? C17 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.157 _refine_diff_density_min -0.102 _refine_diff_density_rms 0.025