# 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 'Dr K Bhanuprakash' _publ_contact_author_address ; Inorganic and Physical Chemistry Division Indian Institute of Chemical Technology (IICT) Uppal Road Habsiguda Hyderabad Andhra Pradesh 500 007 INDIA ; _publ_contact_author_email BHANU2505@YAHOO.CO.IN _publ_section_title ; First Hyperpolarizability of some Nonconjugated Donor Acceptor 3D Molecules: Noncentrosymmetric Crystal through Conformational Flexibility. ; loop_ _publ_author_name 'Bhanuprakash Kotamarthi' 'S. Philip Anthony' 'K. Ravi Kumar' 'T. P. Radhakrishan' ; R.Vaidya Jayathirtha ; 'Sanyasi Sitha' 'K. Srinivas' data_hr04 _database_code_depnum_ccdc_archive 'CCDC 250341' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,6-tris(4-fluorobenzylamino)-1,3,5-triazine ; _chemical_formula_sum 'C24 H21 F3 N6' _chemical_formula_weight 450.47 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 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 12.0367(11) _cell_length_b 20.9059(18) _cell_length_c 8.6999(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2189.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3086 _cell_measurement_theta_min 2.534 _cell_measurement_theta_max 23.693 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_special_details ; All H atoms were positioned using SHELXL97 HFIX instructions (Sheldrick, 1997) and treated as riding atoms with C-H distances in the range 0.93-0.98\%A and N-H distance 0.86\%A. The absolute structure could not be refined because of the absence of significant anomalous effects; Friedel pairs were mereged before the final cycles of the refinement. ; _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 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 12595 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.98 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.969 _reflns_number_total 2719 _reflns_number_gt 1924 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003) ' _computing_publication_material SHELXL97 _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^)+(0.0501P)^2^+0.1105P] 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 2719 _refine_ls_number_parameters 301 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.155 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.034 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 N4 N 0.06953(16) 0.25966(10) -0.0468(3) 0.0464(5) Uani 1 1 d . . . N2 N 0.26760(16) 0.26094(10) -0.0532(2) 0.0426(5) Uani 1 1 d . . . N6 N 0.17227(16) 0.17399(10) 0.0678(3) 0.0453(5) Uani 1 1 d . . . C5 C 0.0778(2) 0.20355(12) 0.0283(3) 0.0443(6) Uani 1 1 d . . . N7 N 0.36161(18) 0.17758(11) 0.0540(3) 0.0497(6) Uani 1 1 d . . . H7 H 0.4212 0.1989 0.0351 0.082(11) Uiso 1 1 calc R . . C1 C 0.2637(2) 0.20440(12) 0.0211(3) 0.0409(6) Uani 1 1 d . . . C13 C 0.3813(2) 0.11266(13) 0.2919(3) 0.0454(7) Uani 1 1 d . . . N9 N -0.01791(19) 0.17523(11) 0.0683(3) 0.0579(6) Uani 1 1 d . . . H9 H -0.0797 0.1944 0.0499 0.072(10) Uiso 1 1 calc R . . C12 C -0.0196(2) 0.11305(13) 0.1420(4) 0.0592(8) Uani 1 1 d . . . H9A H 0.0282 0.0843 0.0846 0.071 Uiso 1 1 calc R . . H9B H -0.0946 0.0961 0.1367 0.071 Uiso 1 1 calc R . . C10 C 0.3718(2) 0.11476(13) 0.1197(3) 0.0534(7) Uani 1 1 d . . . H10A H 0.4369 0.0943 0.0760 0.064 Uiso 1 1 calc R . . H10B H 0.3075 0.0898 0.0894 0.064 Uiso 1 1 calc R . . N8 N 0.1618(2) 0.34001(13) -0.1647(3) 0.0601(7) Uani 1 1 d . . . H8 H 0.0970 0.3566 -0.1764 0.074(10) Uiso 1 1 calc R . . C19 C 0.2363(2) 0.38544(14) -0.4016(4) 0.0508(7) Uani 1 1 d . . . C25 C 0.0170(2) 0.11321(13) 0.3068(4) 0.0528(7) Uani 1 1 d . . . C3 C 0.1678(2) 0.28516(12) -0.0847(3) 0.0419(6) Uani 1 1 d . . . C20 C 0.2548(2) 0.44459(14) -0.4648(4) 0.0606(8) Uani 1 1 d . . . H15 H 0.2800 0.4776 -0.4023 0.073 Uiso 1 1 calc R . . C18 C 0.4170(3) 0.05673(15) 0.3597(4) 0.0628(8) Uani 1 1 d . . . H16 H 0.4331 0.0216 0.2979 0.075 Uiso 1 1 calc R . . F31 F 0.4218(2) 0.09872(13) 0.7601(2) 0.1033(8) Uani 1 1 d . . . C14 C 0.3569(3) 0.16311(14) 0.3865(4) 0.0628(9) Uani 1 1 d . . . H17 H 0.3311 0.2010 0.3435 0.075 Uiso 1 1 calc R . . C17 C 0.4295(3) 0.05144(17) 0.5164(4) 0.0733(10) Uani 1 1 d . . . H18 H 0.4528 0.0132 0.5607 0.088 Uiso 1 1 calc R . . F32 F 0.1840(2) 0.41904(17) -0.8601(3) 0.1283(10) Uani 1 1 d . . . C26 C 0.0038(3) 0.16452(15) 0.4029(4) 0.0669(9) Uani 1 1 d . . . H20 H -0.0277 0.2019 0.3645 0.080 Uiso 1 1 calc R . . C21 C 0.2368(3) 0.45636(19) -0.6198(4) 0.0757(11) Uani 1 1 d . . . H21 H 0.2491 0.4967 -0.6615 0.091 Uiso 1 1 calc R . . C22 C 0.2009(3) 0.4073(2) -0.7082(4) 0.0767(11) Uani 1 1 d . . . C27 C 0.0360(3) 0.16244(19) 0.5547(5) 0.0824(11) Uani 1 1 d . . . H23 H 0.0256 0.1975 0.6189 0.099 Uiso 1 1 calc R . . C11 C 0.2545(3) 0.37379(16) -0.2330(4) 0.0637(9) Uani 1 1 d . . . H24A H 0.3218 0.3489 -0.2191 0.076 Uiso 1 1 calc R . . H24B H 0.2643 0.4144 -0.1811 0.076 Uiso 1 1 calc R . . F33 F 0.1164(3) 0.10526(15) 0.7589(3) 0.1324(10) Uani 1 1 d . . . C29 C 0.0981(3) 0.05594(18) 0.5179(5) 0.0860(12) Uani 1 1 d . . . H26 H 0.1306 0.0190 0.5571 0.103 Uiso 1 1 calc R . . C16 C 0.4070(3) 0.10324(18) 0.6045(4) 0.0683(9) Uani 1 1 d . . . C24 C 0.1990(3) 0.33747(17) -0.4983(4) 0.0691(9) Uani 1 1 d . . . H28 H 0.1854 0.2970 -0.4583 0.083 Uiso 1 1 calc R . . C15 C 0.3696(3) 0.15920(17) 0.5438(4) 0.0747(10) Uani 1 1 d . . . H29 H 0.3531 0.1939 0.6066 0.090 Uiso 1 1 calc R . . C30 C 0.0647(3) 0.05867(16) 0.3676(4) 0.0706(9) Uani 1 1 d . . . H30 H 0.0743 0.0230 0.3050 0.085 Uiso 1 1 calc R . . C28 C 0.0832(3) 0.1078(2) 0.6083(5) 0.0839(11) Uani 1 1 d . . . C23 C 0.1816(3) 0.3484(2) -0.6529(5) 0.0828(11) Uani 1 1 d . . . H32 H 0.1571 0.3157 -0.7171 0.099 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 N4 0.0311(12) 0.0604(13) 0.0476(13) 0.0115(12) -0.0001(10) 0.0021(9) N2 0.0328(12) 0.0534(12) 0.0416(13) 0.0093(11) 0.0014(10) 0.0002(9) N6 0.0332(11) 0.0535(12) 0.0492(13) 0.0118(10) 0.0003(10) -0.0015(9) C5 0.0337(14) 0.0596(15) 0.0398(14) 0.0044(13) 0.0018(11) -0.0033(11) N7 0.0310(12) 0.0602(14) 0.0578(15) 0.0163(12) 0.0009(10) 0.0055(10) C1 0.0350(14) 0.0520(14) 0.0357(13) 0.0021(12) -0.0014(11) 0.0024(10) C13 0.0340(14) 0.0506(16) 0.0517(17) 0.0067(13) 0.0019(12) 0.0010(11) N9 0.0334(13) 0.0701(15) 0.0702(16) 0.0170(13) 0.0010(12) -0.0043(10) C12 0.0424(16) 0.0614(17) 0.074(2) 0.0071(16) 0.0051(14) -0.0146(13) C10 0.0486(17) 0.0567(17) 0.0548(18) 0.0058(13) -0.0009(13) 0.0131(13) N8 0.0428(14) 0.0682(16) 0.0693(16) 0.0300(13) 0.0008(12) 0.0066(11) C19 0.0409(15) 0.0541(16) 0.0575(18) 0.0116(14) 0.0026(13) 0.0031(12) C25 0.0387(15) 0.0523(16) 0.0673(19) 0.0123(14) 0.0106(14) -0.0067(12) C3 0.0355(14) 0.0536(15) 0.0367(13) 0.0045(12) 0.0010(11) 0.0038(11) C20 0.0550(19) 0.0582(18) 0.069(2) 0.0165(17) 0.0055(15) -0.0006(13) C18 0.068(2) 0.0569(18) 0.063(2) 0.0079(15) 0.0054(16) 0.0127(15) F31 0.1202(19) 0.138(2) 0.0522(12) 0.0085(12) -0.0152(12) -0.0174(16) C14 0.071(2) 0.0518(17) 0.066(2) -0.0016(16) -0.0047(16) 0.0066(14) C17 0.083(2) 0.071(2) 0.065(2) 0.0247(19) -0.0059(18) 0.0107(17) F32 0.1160(19) 0.214(3) 0.0547(13) 0.0171(18) -0.0004(12) 0.0406(18) C26 0.064(2) 0.0562(17) 0.081(2) 0.0058(18) 0.0070(18) 0.0041(14) C21 0.072(2) 0.082(2) 0.074(3) 0.034(2) 0.0168(18) 0.0151(18) C22 0.061(2) 0.121(3) 0.048(2) 0.009(2) 0.0088(16) 0.022(2) C27 0.089(3) 0.084(3) 0.074(3) -0.012(2) 0.010(2) -0.005(2) C11 0.0532(19) 0.072(2) 0.066(2) 0.0237(17) -0.0056(14) -0.0102(14) F33 0.169(3) 0.155(3) 0.0731(17) 0.0103(15) -0.0253(18) -0.001(2) C29 0.096(3) 0.074(2) 0.088(3) 0.026(2) -0.015(2) 0.004(2) C16 0.068(2) 0.087(2) 0.050(2) 0.0089(18) -0.0077(16) -0.0114(18) C24 0.067(2) 0.0646(19) 0.076(3) 0.0063(17) 0.0004(17) -0.0029(16) C15 0.086(3) 0.075(2) 0.063(2) -0.0161(19) -0.001(2) -0.0037(18) C30 0.077(2) 0.0570(19) 0.078(3) 0.0014(17) 0.0016(18) 0.0039(16) C28 0.091(3) 0.096(3) 0.065(3) 0.014(2) -0.006(2) -0.006(2) C23 0.070(3) 0.110(3) 0.068(2) -0.019(2) -0.0039(19) 0.008(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 N4 C3 1.339(3) . ? N4 C5 1.346(3) . ? N2 C3 1.332(3) . ? N2 C1 1.348(3) . ? N6 C1 1.334(3) . ? N6 C5 1.339(3) . ? C5 N9 1.341(3) . ? N7 C1 1.336(3) . ? N7 C10 1.437(3) . ? N7 H7 0.8600 . ? C13 C14 1.370(4) . ? C13 C18 1.378(4) . ? C13 C10 1.503(4) . ? N9 C12 1.449(4) . ? N9 H9 0.8600 . ? C12 C25 1.500(5) . ? C12 H9A 0.9700 . ? C12 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N8 C3 1.343(3) . ? N8 C11 1.447(4) . ? N8 H8 0.8600 . ? C19 C20 1.372(4) . ? C19 C24 1.384(5) . ? C19 C11 1.502(4) . ? C25 C26 1.369(4) . ? C25 C30 1.382(4) . ? C20 C21 1.388(5) . ? C20 H15 0.9300 . ? C18 C17 1.375(4) . ? C18 H16 0.9300 . ? F31 C16 1.369(4) . ? C14 C15 1.379(5) . ? C14 H17 0.9300 . ? C17 C16 1.354(5) . ? C17 H18 0.9300 . ? F32 C22 1.359(4) . ? C26 C27 1.377(6) . ? C26 H20 0.9300 . ? C21 C22 1.353(5) . ? C21 H21 0.9300 . ? C22 C23 1.344(6) . ? C27 C28 1.358(5) . ? C27 H23 0.9300 . ? C11 H24A 0.9700 . ? C11 H24B 0.9700 . ? F33 C28 1.371(4) . ? C29 C28 1.352(5) . ? C29 C30 1.370(5) . ? C29 H26 0.9300 . ? C16 C15 1.360(5) . ? C24 C23 1.379(6) . ? C24 H28 0.9300 . ? C15 H29 0.9300 . ? C30 H30 0.9300 . ? C23 H32 0.9300 . ? 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 N4 C5 113.7(2) . . ? C3 N2 C1 113.6(2) . . ? C1 N6 C5 113.7(2) . . ? N6 C5 N9 117.3(2) . . ? N6 C5 N4 126.1(2) . . ? N9 C5 N4 116.6(2) . . ? C1 N7 C10 122.9(2) . . ? C1 N7 H7 118.5 . . ? C10 N7 H7 118.5 . . ? N6 C1 N7 117.5(2) . . ? N6 C1 N2 126.3(2) . . ? N7 C1 N2 116.1(2) . . ? C14 C13 C18 117.6(3) . . ? C14 C13 C10 124.1(3) . . ? C18 C13 C10 118.4(3) . . ? C5 N9 C12 121.5(2) . . ? C5 N9 H9 119.2 . . ? C12 N9 H9 119.2 . . ? N9 C12 C25 114.6(2) . . ? N9 C12 H9A 108.6 . . ? C25 C12 H9A 108.6 . . ? N9 C12 H9B 108.6 . . ? C25 C12 H9B 108.6 . . ? H9A C12 H9B 107.6 . . ? N7 C10 C13 115.4(2) . . ? N7 C10 H10A 108.4 . . ? C13 C10 H10A 108.4 . . ? N7 C10 H10B 108.4 . . ? C13 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? C3 N8 C11 126.0(2) . . ? C3 N8 H8 117.0 . . ? C11 N8 H8 117.0 . . ? C20 C19 C24 117.5(3) . . ? C20 C19 C11 120.9(3) . . ? C24 C19 C11 121.6(3) . . ? C26 C25 C30 117.5(3) . . ? C26 C25 C12 123.5(3) . . ? C30 C25 C12 119.0(3) . . ? N2 C3 N4 126.5(2) . . ? N2 C3 N8 118.6(2) . . ? N4 C3 N8 114.9(2) . . ? C19 C20 C21 121.6(3) . . ? C19 C20 H15 119.2 . . ? C21 C20 H15 119.2 . . ? C17 C18 C13 121.8(3) . . ? C17 C18 H16 119.1 . . ? C13 C18 H16 119.1 . . ? C13 C14 C15 121.8(3) . . ? C13 C14 H17 119.1 . . ? C15 C14 H17 119.1 . . ? C16 C17 C18 118.3(3) . . ? C16 C17 H18 120.8 . . ? C18 C17 H18 120.8 . . ? C25 C26 C27 121.9(3) . . ? C25 C26 H20 119.1 . . ? C27 C26 H20 119.1 . . ? C22 C21 C20 117.9(3) . . ? C22 C21 H21 121.0 . . ? C20 C21 H21 121.0 . . ? C23 C22 C21 123.1(3) . . ? C23 C22 F32 119.2(4) . . ? C21 C22 F32 117.7(4) . . ? C28 C27 C26 118.3(4) . . ? C28 C27 H23 120.9 . . ? C26 C27 H23 120.9 . . ? N8 C11 C19 111.6(3) . . ? N8 C11 H24A 109.3 . . ? C19 C11 H24A 109.3 . . ? N8 C11 H24B 109.3 . . ? C19 C11 H24B 109.3 . . ? H24A C11 H24B 108.0 . . ? C28 C29 C30 118.9(4) . . ? C28 C29 H26 120.6 . . ? C30 C29 H26 120.6 . . ? C17 C16 C15 122.3(3) . . ? C17 C16 F31 118.6(3) . . ? C15 C16 F31 119.1(4) . . ? C23 C24 C19 121.5(4) . . ? C23 C24 H28 119.3 . . ? C19 C24 H28 119.3 . . ? C16 C15 C14 118.2(3) . . ? C16 C15 H29 120.9 . . ? C14 C15 H29 120.9 . . ? C29 C30 C25 121.5(4) . . ? C29 C30 H30 119.3 . . ? C25 C30 H30 119.3 . . ? C29 C28 C27 122.0(4) . . ? C29 C28 F33 119.1(4) . . ? C27 C28 F33 118.9(4) . . ? C22 C23 C24 118.3(4) . . ? C22 C23 H32 120.8 . . ? C24 C23 H32 120.8 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7 N4 0.86 2.11 2.959(3) 169.6 3 N9 H9 N2 0.86 2.25 3.093(3) 167.2 3_455 N8 H8 F31 0.86 2.37 3.227(4) 173.3 3_454 _chemical_name_common 2,4,6-tris(4-fluorobenzylamino)-1,3,5-triazine