# Supplementary Material (ESI) for PCCP # This journal is (c) the Owner Societies 2010 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _journal_year 2010 _journal_volume 12 _journal_page_first ? _publ_contact_author_name 'Yuan Wang' _publ_contact_author_email WANGY@PKU.EDU.CN _publ_section_title ; A europium complex with enhanced long-wavelength sensitized luminescent properties ; loop_ _publ_author_name 'Yuan Wang.' 'Li-Min Fu.' 'Rui Hao.' 'Yan Ma.' 'Guangsheng Shao.' ; Minxian Tang ; 'Fumin Xue.' 'Jian-Ping Zhang.' data_ligand _database_code_depnum_ccdc_archive 'CCDC 749810' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;2-(N,N-diethylanilin-4-yl)-4,6-bis(pyrazol-1-yl)-1,3,5- triazine ; _chemical_melting_point 433-436 _chemical_formula_moiety 'C19 H20 N8' _chemical_formula_sum 'C19 H20 N8' _chemical_formula_weight 360.43 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 P2(1)/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 5.8827(12) _cell_length_b 17.349(3) _cell_length_c 18.563(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.90(3) _cell_angle_gamma 90.00 _cell_volume 1839.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 15762 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9678 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details 'ABSCOR by T.Higashi 8 March, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku raxis Rapid IP Area Detector' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9616 _diffrn_reflns_av_R_equivalents 0.1029 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3208 _reflns_number_gt 2825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _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^)+(0.0522P)^2^+0.8521P] 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_number_reflns 3208 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0891 _refine_ls_wR_factor_ref 0.1885 _refine_ls_wR_factor_gt 0.1823 _refine_ls_goodness_of_fit_ref 1.330 _refine_ls_restrained_S_all 1.330 _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 -0.1828(4) 0.13941(15) 0.08675(14) 0.0456(6) Uani 1 1 d . . . N2 N 0.8129(4) 0.18358(15) 0.31487(13) 0.0434(6) Uani 1 1 d . . . N3 N 1.1498(4) 0.26468(14) 0.33207(13) 0.0431(6) Uani 1 1 d . . . N4 N 0.8179(4) 0.28909(14) 0.23324(13) 0.0432(6) Uani 1 1 d . . . N5 N 1.1483(4) 0.16049(15) 0.40843(13) 0.0461(6) Uani 1 1 d . . . N6 N 1.0335(5) 0.11323(19) 0.44603(16) 0.0672(9) Uani 1 1 d . . . N7 N 1.1414(4) 0.36786(14) 0.25183(13) 0.0425(6) Uani 1 1 d . . . N8 N 1.3722(4) 0.38317(15) 0.28250(16) 0.0532(7) Uani 1 1 d . . . C1 C -0.1994(7) -0.0040(2) 0.0796(2) 0.0662(10) Uani 1 1 d . . . H1A H -0.2816 -0.0475 0.0929 0.099 Uiso 1 1 calc R . . H1B H -0.0358 -0.0083 0.1032 0.099 Uiso 1 1 calc R . . H1C H -0.2199 -0.0028 0.0267 0.099 Uiso 1 1 calc R . . C2 C -0.2955(5) 0.0693(2) 0.10478(19) 0.0520(8) Uani 1 1 d . . . H2B H -0.4619 0.0722 0.0819 0.062 Uiso 1 1 calc R . . H2C H -0.2769 0.0670 0.1581 0.062 Uiso 1 1 calc R . . C3 C -0.2988(5) 0.1812(2) 0.01985(18) 0.0548(9) Uani 1 1 d . . . H3B H -0.2692 0.2359 0.0282 0.066 Uiso 1 1 calc R . . H3C H -0.4665 0.1732 0.0111 0.066 Uiso 1 1 calc R . . C4 C -0.2213(7) 0.1576(2) -0.0487(2) 0.0691(10) Uani 1 1 d . . . H4B H -0.3043 0.1874 -0.0903 0.104 Uiso 1 1 calc R . . H4C H -0.2540 0.1038 -0.0583 0.104 Uiso 1 1 calc R . . H4D H -0.0561 0.1664 -0.0411 0.104 Uiso 1 1 calc R . . C5 C 0.0347(5) 0.16006(17) 0.12716(16) 0.0409(7) Uani 1 1 d . . . C6 C 0.1484(5) 0.11957(17) 0.19135(15) 0.0392(7) Uani 1 1 d . . . H6B H 0.0762 0.0767 0.2061 0.047 Uiso 1 1 calc R . . C7 C 0.3637(5) 0.14219(17) 0.23247(16) 0.0407(7) Uani 1 1 d . . . H7A H 0.4336 0.1144 0.2749 0.049 Uiso 1 1 calc R . . C8 C 0.4812(5) 0.20571(16) 0.21259(15) 0.0390(7) Uani 1 1 d . . . C9 C 0.3704(5) 0.24605(17) 0.14918(16) 0.0449(7) Uani 1 1 d . . . H9A H 0.4441 0.2889 0.1349 0.054 Uiso 1 1 calc R . . C10 C 0.1552(5) 0.22429(18) 0.10708(17) 0.0462(8) Uani 1 1 d . . . H10A H 0.0871 0.2522 0.0646 0.055 Uiso 1 1 calc R . . C11 C 0.7129(5) 0.22765(17) 0.25573(15) 0.0388(7) Uani 1 1 d . . . C12 C 1.0278(5) 0.20522(17) 0.34846(15) 0.0408(7) Uani 1 1 d . . . C13 C 1.0298(5) 0.30341(16) 0.27363(15) 0.0391(7) Uani 1 1 d . . . C14 C 1.2042(7) 0.0815(3) 0.4964(2) 0.0779(13) Uani 1 1 d . . . H14A H 1.1798 0.0467 0.5319 0.093 Uiso 1 1 calc R . . C15 C 1.4249(7) 0.1055(2) 0.4909(2) 0.0699(11) Uani 1 1 d . . . H15A H 1.5691 0.0899 0.5200 0.084 Uiso 1 1 calc R . . C16 C 1.3847(6) 0.15613(19) 0.43428(18) 0.0556(9) Uani 1 1 d . . . H16A H 1.4966 0.1829 0.4164 0.067 Uiso 1 1 calc R . . C17 C 1.4119(6) 0.44595(19) 0.2478(2) 0.0586(9) Uani 1 1 d . . . H17A H 1.5566 0.4705 0.2568 0.070 Uiso 1 1 calc R . . C18 C 1.2141(7) 0.4718(2) 0.1961(2) 0.0610(9) Uani 1 1 d . . . H18A H 1.2017 0.5150 0.1658 0.073 Uiso 1 1 calc R . . C19 C 1.0446(6) 0.42073(19) 0.19964(18) 0.0546(8) Uani 1 1 d . . . H19A H 0.8907 0.4216 0.1716 0.066 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 0.0401(14) 0.0473(16) 0.0474(14) 0.0027(12) 0.0067(11) -0.0007(11) N2 0.0457(14) 0.0407(15) 0.0446(14) -0.0048(11) 0.0128(11) -0.0046(11) N3 0.0470(14) 0.0375(14) 0.0461(14) -0.0042(11) 0.0136(11) -0.0056(11) N4 0.0433(14) 0.0387(14) 0.0489(14) -0.0042(11) 0.0138(12) -0.0035(11) N5 0.0497(15) 0.0435(15) 0.0429(13) 0.0007(12) 0.0069(11) -0.0088(12) N6 0.0662(19) 0.080(2) 0.0529(16) 0.0187(16) 0.0098(15) -0.0215(16) N7 0.0465(14) 0.0346(14) 0.0473(14) -0.0064(11) 0.0133(11) -0.0052(11) N8 0.0531(16) 0.0390(15) 0.0681(17) -0.0041(13) 0.0159(14) -0.0120(12) C1 0.086(3) 0.052(2) 0.065(2) -0.0086(18) 0.0266(19) -0.0143(19) C2 0.0403(16) 0.057(2) 0.0587(19) -0.0021(16) 0.0113(14) -0.0083(15) C3 0.0425(17) 0.056(2) 0.061(2) 0.0024(16) 0.0022(15) 0.0051(15) C4 0.079(3) 0.069(3) 0.057(2) 0.0091(19) 0.0115(19) 0.002(2) C5 0.0431(16) 0.0380(17) 0.0442(16) -0.0046(13) 0.0156(13) 0.0034(13) C6 0.0420(16) 0.0331(16) 0.0441(16) 0.0005(13) 0.0134(13) -0.0036(12) C7 0.0469(17) 0.0364(16) 0.0402(15) -0.0012(12) 0.0134(13) 0.0053(13) C8 0.0404(15) 0.0361(16) 0.0428(16) -0.0067(13) 0.0145(13) 0.0019(12) C9 0.0525(18) 0.0342(17) 0.0511(17) -0.0006(14) 0.0182(15) -0.0068(13) C10 0.0504(18) 0.0423(18) 0.0444(16) 0.0054(14) 0.0085(14) -0.0023(14) C11 0.0472(17) 0.0335(16) 0.0390(15) -0.0070(12) 0.0165(13) -0.0005(13) C12 0.0466(17) 0.0370(17) 0.0405(15) -0.0066(13) 0.0137(13) -0.0024(13) C13 0.0482(17) 0.0311(15) 0.0416(15) -0.0085(13) 0.0182(14) -0.0026(13) C14 0.092(3) 0.080(3) 0.053(2) 0.022(2) -0.001(2) -0.021(2) C15 0.067(2) 0.066(3) 0.063(2) 0.0096(19) -0.0113(18) -0.0116(19) C16 0.053(2) 0.052(2) 0.057(2) 0.0025(17) 0.0038(16) -0.0143(16) C17 0.062(2) 0.0393(19) 0.077(2) -0.0056(17) 0.0217(19) -0.0186(16) C18 0.086(3) 0.0389(19) 0.061(2) 0.0066(16) 0.0227(19) -0.0132(18) C19 0.063(2) 0.045(2) 0.0538(19) 0.0037(15) 0.0102(16) -0.0050(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 N1 C5 1.366(4) . ? N1 C3 1.458(4) . ? N1 C2 1.462(4) . ? N2 C12 1.323(4) . ? N2 C11 1.351(4) . ? N3 C13 1.326(4) . ? N3 C12 1.333(4) . ? N4 C13 1.315(4) . ? N4 C11 1.348(4) . ? N5 N6 1.357(4) . ? N5 C16 1.360(4) . ? N5 C12 1.402(4) . ? N6 C14 1.317(4) . ? N7 C19 1.356(4) . ? N7 N8 1.366(3) . ? N7 C13 1.405(4) . ? N8 C17 1.315(4) . ? C1 C2 1.511(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? C3 C4 1.508(5) . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C4 H4D 0.9600 . ? C5 C6 1.406(4) . ? C5 C10 1.418(4) . ? C6 C7 1.369(4) . ? C6 H6B 0.9300 . ? C7 C8 1.397(4) . ? C7 H7A 0.9300 . ? C8 C9 1.390(4) . ? C8 C11 1.456(4) . ? C9 C10 1.371(4) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C14 C15 1.390(5) . ? C14 H14A 0.9300 . ? C15 C16 1.346(5) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C18 1.392(5) . ? C17 H17A 0.9300 . ? C18 C19 1.347(5) . ? C18 H18A 0.9300 . ? C19 H19A 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 C5 N1 C3 121.5(3) . . ? C5 N1 C2 120.6(2) . . ? C3 N1 C2 117.6(2) . . ? C12 N2 C11 113.8(3) . . ? C13 N3 C12 111.6(2) . . ? C13 N4 C11 114.5(2) . . ? N6 N5 C16 112.2(3) . . ? N6 N5 C12 121.6(2) . . ? C16 N5 C12 126.2(3) . . ? C14 N6 N5 103.2(3) . . ? C19 N7 N8 111.8(3) . . ? C19 N7 C13 126.8(3) . . ? N8 N7 C13 121.4(2) . . ? C17 N8 N7 103.4(3) . . ? 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 . . ? N1 C2 C1 113.9(3) . . ? N1 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? N1 C2 H2C 108.8 . . ? C1 C2 H2C 108.8 . . ? H2B C2 H2C 107.7 . . ? N1 C3 C4 114.1(3) . . ? N1 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? N1 C3 H3C 108.7 . . ? C4 C3 H3C 108.7 . . ? H3B C3 H3C 107.6 . . ? C3 C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C4 H4D 109.5 . . ? H4B C4 H4D 109.5 . . ? H4C C4 H4D 109.5 . . ? N1 C5 C6 121.8(3) . . ? N1 C5 C10 121.5(3) . . ? C6 C5 C10 116.7(3) . . ? C7 C6 C5 121.1(3) . . ? C7 C6 H6B 119.4 . . ? C5 C6 H6B 119.4 . . ? C6 C7 C8 121.9(3) . . ? C6 C7 H7A 119.0 . . ? C8 C7 H7A 119.0 . . ? C9 C8 C7 117.4(3) . . ? C9 C8 C11 121.4(3) . . ? C7 C8 C11 121.2(3) . . ? C10 C9 C8 121.7(3) . . ? C10 C9 H9A 119.2 . . ? C8 C9 H9A 119.2 . . ? C9 C10 C5 121.2(3) . . ? C9 C10 H10A 119.4 . . ? C5 C10 H10A 119.4 . . ? N4 C11 N2 123.8(3) . . ? N4 C11 C8 118.3(3) . . ? N2 C11 C8 117.8(3) . . ? N2 C12 N3 128.2(3) . . ? N2 C12 N5 117.4(3) . . ? N3 C12 N5 114.4(2) . . ? N4 C13 N3 128.0(3) . . ? N4 C13 N7 115.5(3) . . ? N3 C13 N7 116.4(3) . . ? N6 C14 C15 112.9(3) . . ? N6 C14 H14A 123.6 . . ? C15 C14 H14A 123.6 . . ? C16 C15 C14 105.1(3) . . ? C16 C15 H15A 127.4 . . ? C14 C15 H15A 127.4 . . ? C15 C16 N5 106.5(3) . . ? C15 C16 H16A 126.7 . . ? N5 C16 H16A 126.7 . . ? N8 C17 C18 112.8(3) . . ? N8 C17 H17A 123.6 . . ? C18 C17 H17A 123.6 . . ? C19 C18 C17 105.1(3) . . ? C19 C18 H18A 127.4 . . ? C17 C18 H18A 127.4 . . ? C18 C19 N7 106.9(3) . . ? C18 C19 H19A 126.6 . . ? N7 C19 H19A 126.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N5 N6 C14 1.5(4) . . . . ? C12 N5 N6 C14 179.3(3) . . . . ? C19 N7 N8 C17 -0.1(3) . . . . ? C13 N7 N8 C17 179.1(3) . . . . ? C5 N1 C2 C1 -76.3(4) . . . . ? C3 N1 C2 C1 97.1(3) . . . . ? C5 N1 C3 C4 81.7(4) . . . . ? C2 N1 C3 C4 -91.7(4) . . . . ? C3 N1 C5 C6 -179.4(3) . . . . ? C2 N1 C5 C6 -6.3(4) . . . . ? C3 N1 C5 C10 1.7(4) . . . . ? C2 N1 C5 C10 174.9(3) . . . . ? N1 C5 C6 C7 -178.2(3) . . . . ? C10 C5 C6 C7 0.8(4) . . . . ? C5 C6 C7 C8 -0.5(4) . . . . ? C6 C7 C8 C9 0.4(4) . . . . ? C6 C7 C8 C11 -178.2(3) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C11 C8 C9 C10 178.0(3) . . . . ? C8 C9 C10 C5 0.9(5) . . . . ? N1 C5 C10 C9 178.0(3) . . . . ? C6 C5 C10 C9 -0.9(4) . . . . ? C13 N4 C11 N2 0.2(4) . . . . ? C13 N4 C11 C8 -177.7(2) . . . . ? C12 N2 C11 N4 -1.3(4) . . . . ? C12 N2 C11 C8 176.6(2) . . . . ? C9 C8 C11 N4 0.8(4) . . . . ? C7 C8 C11 N4 179.4(2) . . . . ? C9 C8 C11 N2 -177.3(3) . . . . ? C7 C8 C11 N2 1.3(4) . . . . ? C11 N2 C12 N3 1.8(4) . . . . ? C11 N2 C12 N5 -177.3(2) . . . . ? C13 N3 C12 N2 -0.9(4) . . . . ? C13 N3 C12 N5 178.1(2) . . . . ? N6 N5 C12 N2 -20.5(4) . . . . ? C16 N5 C12 N2 156.9(3) . . . . ? N6 N5 C12 N3 160.3(3) . . . . ? C16 N5 C12 N3 -22.2(4) . . . . ? C11 N4 C13 N3 0.8(4) . . . . ? C11 N4 C13 N7 -179.1(2) . . . . ? C12 N3 C13 N4 -0.5(4) . . . . ? C12 N3 C13 N7 179.5(2) . . . . ? C19 N7 C13 N4 7.9(4) . . . . ? N8 N7 C13 N4 -171.1(2) . . . . ? C19 N7 C13 N3 -172.0(3) . . . . ? N8 N7 C13 N3 9.0(4) . . . . ? N5 N6 C14 C15 -1.6(5) . . . . ? N6 C14 C15 C16 1.1(5) . . . . ? C14 C15 C16 N5 -0.2(4) . . . . ? N6 N5 C16 C15 -0.9(4) . . . . ? C12 N5 C16 C15 -178.5(3) . . . . ? N7 N8 C17 C18 0.4(4) . . . . ? N8 C17 C18 C19 -0.5(4) . . . . ? C17 C18 C19 N7 0.5(4) . . . . ? N8 N7 C19 C18 -0.3(4) . . . . ? C13 N7 C19 C18 -179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.226 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.053 # Attachment 'CIF file of dpbt.cif' data_ligand_dpbt _database_code_depnum_ccdc_archive 'CCDC 759053' #TrackingRef 'CIF file of dpbt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 N8' _chemical_formula_sum 'C23 H28 N8' _chemical_formula_weight 416.53 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 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 16.807(3) _cell_length_b 16.647(3) _cell_length_c 7.6875(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2150.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9631 _exptl_absorpt_correction_T_max 0.9878 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1489 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 23.00 _reflns_number_total 1489 _reflns_number_gt 808 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (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^)+(0.0910P)^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_number_reflns 1489 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1644 _refine_ls_wR_factor_gt 0.1517 _refine_ls_goodness_of_fit_ref 0.875 _refine_ls_restrained_S_all 0.875 _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 0.0000 0.3227(2) 0.7500 0.0701(13) Uani 1 2 d S . . N2 N 0.06447(15) -0.05507(16) 0.6869(4) 0.0484(8) Uani 1 1 d . . . N3 N 0.0000 -0.1794(2) 0.7500 0.0484(10) Uani 1 2 d S . . N4 N 0.12388(17) -0.17645(15) 0.6163(4) 0.0492(8) Uani 1 1 d . . . N5 N 0.12364(18) -0.25844(16) 0.6211(4) 0.0576(9) Uani 1 1 d . . . C1 C 0.0000 0.2414(3) 0.7500 0.0539(14) Uani 1 2 d S . . C2 C 0.0584(2) 0.1961(2) 0.6644(5) 0.0602(11) Uani 1 1 d . . . H2 H 0.0985 0.2229 0.6047 0.072 Uiso 1 1 calc R . . C3 C 0.05880(19) 0.1149(2) 0.6650(5) 0.0521(10) Uani 1 1 d . . . H3 H 0.0993 0.0877 0.6072 0.062 Uiso 1 1 calc R . . C4 C 0.0000 0.0709(3) 0.7500 0.0449(12) Uani 1 2 d S . . C5 C 0.0000 -0.0172(3) 0.7500 0.0448(12) Uani 1 2 d S . . C6 C 0.0594(2) -0.1341(2) 0.6875(4) 0.0452(9) Uani 1 1 d . . . C7 C 0.2090(2) -0.0606(2) 0.5000(6) 0.0715(12) Uani 1 1 d . . . H7A H 0.1690 -0.0274 0.5527 0.107 Uiso 1 1 calc R . . H7B H 0.2105 -0.0506 0.3771 0.107 Uiso 1 1 calc R . . H7C H 0.2599 -0.0482 0.5500 0.107 Uiso 1 1 calc R . . C8 C 0.1899(2) -0.1466(2) 0.5316(5) 0.0531(10) Uani 1 1 d . . . C9 C 0.2313(2) -0.2128(2) 0.4830(5) 0.0612(10) Uani 1 1 d . . . H9 H 0.2792 -0.2133 0.4226 0.073 Uiso 1 1 calc R . . C10 C 0.1895(2) -0.2793(2) 0.5395(5) 0.0623(11) Uani 1 1 d . . . C11 C 0.2109(3) -0.3663(2) 0.5221(6) 0.0895(15) Uani 1 1 d . . . H11A H 0.1704 -0.3986 0.5756 0.134 Uiso 1 1 calc R . . H11B H 0.2609 -0.3760 0.5785 0.134 Uiso 1 1 calc R . . H11C H 0.2150 -0.3800 0.4012 0.134 Uiso 1 1 calc R . . C12 C 0.0629(3) 0.3704(3) 0.6633(7) 0.1016(17) Uani 1 1 d . . . H12A H 0.1135 0.3431 0.6759 0.122 Uiso 1 1 calc R . . H12B H 0.0671 0.4224 0.7194 0.122 Uiso 1 1 calc R . . C13 C 0.0445(3) 0.3825(3) 0.4662(8) 0.127(2) Uani 1 1 d . . . H13A H 0.0862 0.4134 0.4136 0.190 Uiso 1 1 calc R . . H13B H -0.0052 0.4103 0.4535 0.190 Uiso 1 1 calc R . . H13C H 0.0411 0.3310 0.4101 0.190 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 0.080(3) 0.044(3) 0.087(4) 0.000 0.012(3) 0.000 N2 0.0470(18) 0.0409(17) 0.0573(19) -0.0001(14) -0.0026(14) -0.0009(14) N3 0.049(2) 0.048(2) 0.048(3) 0.000 0.001(2) 0.000 N4 0.0473(17) 0.0450(17) 0.0553(18) -0.0034(15) 0.0020(16) 0.0075(14) N5 0.056(2) 0.0484(18) 0.069(2) -0.0052(15) 0.0009(18) 0.0057(15) C1 0.054(3) 0.051(3) 0.057(3) 0.000 -0.008(3) 0.000 C2 0.060(3) 0.057(2) 0.064(3) 0.0052(19) -0.001(2) -0.0072(19) C3 0.049(2) 0.054(2) 0.054(2) 0.0008(18) -0.0014(18) -0.0061(18) C4 0.049(3) 0.045(3) 0.040(3) 0.000 -0.004(3) 0.000 C5 0.040(3) 0.055(3) 0.040(3) 0.000 -0.006(2) 0.000 C6 0.040(2) 0.059(2) 0.0365(19) -0.0011(17) -0.0052(16) 0.0037(18) C7 0.057(2) 0.067(2) 0.091(3) 0.003(2) 0.011(2) 0.001(2) C8 0.046(2) 0.060(2) 0.054(2) -0.0028(19) -0.0018(18) 0.0070(19) C9 0.049(2) 0.070(3) 0.064(2) 0.004(2) 0.0018(19) 0.012(2) C10 0.061(3) 0.059(3) 0.066(3) -0.001(2) -0.005(2) 0.016(2) C11 0.092(3) 0.068(3) 0.108(4) -0.014(3) -0.002(3) 0.023(2) C12 0.111(4) 0.075(3) 0.119(5) -0.004(3) -0.001(3) -0.001(3) C13 0.115(4) 0.124(4) 0.141(6) 0.058(4) 0.017(4) 0.007(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.354(6) . ? N1 C12 1.480(5) . ? N1 C12 1.480(5) 3_556 ? N2 C6 1.319(4) . ? N2 C5 1.344(3) . ? N3 C6 1.340(4) . ? N3 C6 1.340(4) 3_556 ? N4 N5 1.365(3) . ? N4 C8 1.379(4) . ? N4 C6 1.403(4) . ? N5 C10 1.318(4) . ? C1 C2 1.402(4) 3_556 ? C1 C2 1.402(4) . ? C2 C3 1.352(5) . ? C3 C4 1.393(4) . ? C4 C3 1.393(4) 3_556 ? C4 C5 1.467(6) . ? C5 N2 1.344(3) 3_556 ? C7 C8 1.487(5) . ? C8 C9 1.356(4) . ? C9 C10 1.382(5) . ? C10 C11 1.498(5) . ? C12 C13 1.560(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 C1 N1 C12 122.4(2) . . ? C1 N1 C12 122.4(2) . 3_556 ? C12 N1 C12 115.2(5) . 3_556 ? C6 N2 C5 114.5(3) . . ? C6 N3 C6 111.6(4) . 3_556 ? N5 N4 C8 112.0(3) . . ? N5 N4 C6 119.3(3) . . ? C8 N4 C6 128.6(3) . . ? C10 N5 N4 104.4(3) . . ? N1 C1 C2 122.6(2) . 3_556 ? N1 C1 C2 122.6(2) . . ? C2 C1 C2 114.8(5) 3_556 . ? C3 C2 C1 122.7(4) . . ? C2 C3 C4 121.6(4) . . ? C3 C4 C3 116.6(4) 3_556 . ? C3 C4 C5 121.7(2) 3_556 . ? C3 C4 C5 121.7(2) . . ? N2 C5 N2 124.1(4) 3_556 . ? N2 C5 C4 118.0(2) 3_556 . ? N2 C5 C4 118.0(2) . . ? N2 C6 N3 127.6(3) . . ? N2 C6 N4 116.7(3) . . ? N3 C6 N4 115.7(3) . . ? C9 C8 N4 104.5(3) . . ? C9 C8 C7 128.8(3) . . ? N4 C8 C7 126.7(3) . . ? C8 C9 C10 107.7(3) . . ? N5 C10 C9 111.4(3) . . ? N5 C10 C11 119.9(4) . . ? C9 C10 C11 128.6(4) . . ? N1 C12 C13 111.4(4) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 23.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.212 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.041