Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2002 data_sx49 _database_code_CSD 192205 _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Baowen Zhang' 'P. Bugnon' 'Y. Cao' 'Chang-Qi Ma' 'F. Nuesch' 'Y. Qiu' 'M. Schaer' 'X. S. Wang' 'L. Q. Zhang' 'D. Q. Zhang' 'Jia-Hong Zhou' _publ_contact_author_name 'Prof Baowen Zhang' _publ_contact_author_address ; Group 5061 Technical Institute of Physics & Chemistry Chinese Academy of Sciences Beijing 100101 CHINA ; _publ_contact_author_email 'G203@IPC.AC.CN ' _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; 1,3-Diphenyl-5-(9-phenanthryl)-4,5-dihydro-1H-pyrazol (DPPhP): Structure, Properties, and Application in Organic Light-Emitting Diodes ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H22 N2' _chemical_formula_weight 398.49 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)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.3456(4) _cell_length_b 9.1508(3) _cell_length_c 27.9462(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.735(2) _cell_angle_gamma 90.00 _cell_volume 2133.24(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8146 _cell_measurement_theta_min 1.46 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type 'Empirical' _exptl_absorpt_correction_T_min 0.9605 _exptl_absorpt_correction_T_max 0.9751 _exptl_absorpt_process_details 'PSI scans' _exptl_special_details ; ABSCOR by T. Higashi ; _diffrn_ambient_temperature 293(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 R-AXIS RIPAD IP' _diffrn_measurement_method 'Oscillation' _diffrn_detector_area_resol_mean '100 X 100 microns' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8146 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4422 _reflns_number_gt 2416 _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 'SHELXTL (Siemens, 1994)' _computing_publication_material 'SHELXTL (Siemens, 1994)' _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^)+(0.0753P)^2^+0.0278P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4422 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1057 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1554 _refine_ls_wR_factor_gt 0.1342 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.2544(2) 0.18950(19) 0.15587(7) 0.0552(5) Uani 1 1 d . . . C2 C -0.3914(3) 0.1950(3) 0.12546(9) 0.0746(6) Uani 1 1 d . . . H2A H -0.3904 0.1469 0.0962 0.090 Uiso 1 1 calc R . . C3 C -0.5260(3) 0.2693(3) 0.13785(11) 0.0913(8) Uani 1 1 d . . . H3A H -0.6157 0.2708 0.1173 0.110 Uiso 1 1 calc R . . C4 C -0.5281(4) 0.3420(3) 0.18110(12) 0.0963(9) Uani 1 1 d . . . H4A H -0.6194 0.3930 0.1896 0.116 Uiso 1 1 calc R . . C5 C -0.3976(3) 0.3398(3) 0.21142(9) 0.0801(7) Uani 1 1 d . . . H5A H -0.4018 0.3891 0.2404 0.096 Uiso 1 1 calc R . . C6 C -0.2553(3) 0.2644(2) 0.20005(7) 0.0609(6) Uani 1 1 d . . . C7 C -0.1142(3) 0.2635(2) 0.23156(7) 0.0617(6) Uani 1 1 d . . . C8 C -0.1011(4) 0.3456(3) 0.27397(9) 0.0859(8) Uani 1 1 d . . . H8A H -0.1868 0.4036 0.2829 0.103 Uiso 1 1 calc R . . C9 C 0.0349(5) 0.3420(3) 0.30237(10) 0.1033(10) Uani 1 1 d . . . H9A H 0.0401 0.3964 0.3305 0.124 Uiso 1 1 calc R . . C10 C 0.1655(4) 0.2581(3) 0.28981(10) 0.0981(9) Uani 1 1 d . . . H10A H 0.2578 0.2566 0.3093 0.118 Uiso 1 1 calc R . . C11 C 0.1577(3) 0.1775(3) 0.24848(8) 0.0773(7) Uani 1 1 d . . . H11A H 0.2449 0.1204 0.2402 0.093 Uiso 1 1 calc R . . C12 C 0.0201(3) 0.1800(2) 0.21850(7) 0.0575(5) Uani 1 1 d . . . C13 C 0.0160(2) 0.1039(2) 0.17412(7) 0.0557(5) Uani 1 1 d . . . H13A H 0.1044 0.0481 0.1661 0.067 Uiso 1 1 calc R . . C14 C -0.1110(2) 0.10938(19) 0.14329(7) 0.0521(5) Uani 1 1 d . . . C15 C 0.2071(3) 0.2033(2) 0.01356(7) 0.0602(5) Uani 1 1 d . . . C16 C 0.1648(3) 0.3401(2) -0.00357(8) 0.0759(7) Uani 1 1 d . . . H16A H 0.0666 0.3799 0.0044 0.091 Uiso 1 1 calc R . . C17 C 0.2648(4) 0.4186(3) -0.03218(10) 0.0960(9) Uani 1 1 d . . . H17A H 0.2337 0.5109 -0.0428 0.115 Uiso 1 1 calc R . . C18 C 0.4073(4) 0.3638(3) -0.04502(13) 0.1130(11) Uani 1 1 d . . . H18A H 0.4743 0.4178 -0.0643 0.136 Uiso 1 1 calc R . . C19 C 0.4521(4) 0.2267(3) -0.02925(14) 0.1344(14) Uani 1 1 d . . . H19A H 0.5490 0.1869 -0.0384 0.161 Uiso 1 1 calc R . . C20 C 0.3538(3) 0.1486(3) -0.00004(11) 0.1016(10) Uani 1 1 d . . . H20A H 0.3864 0.0570 0.0108 0.122 Uiso 1 1 calc R . . C21 C 0.0297(2) -0.2034(2) 0.10496(7) 0.0562(5) Uani 1 1 d . . . C22 C 0.1473(3) -0.3003(2) 0.09112(7) 0.0635(6) Uani 1 1 d . . . H22A H 0.2256 -0.2701 0.0703 0.076 Uiso 1 1 calc R . . C23 C 0.1479(3) -0.4415(2) 0.10834(8) 0.0759(7) Uani 1 1 d . . . H23A H 0.2269 -0.5060 0.0988 0.091 Uiso 1 1 calc R . . C24 C 0.0344(3) -0.4887(3) 0.13922(9) 0.0830(7) Uani 1 1 d . . . H24A H 0.0366 -0.5839 0.1509 0.100 Uiso 1 1 calc R . . C25 C -0.0827(3) -0.3928(3) 0.15256(9) 0.0845(7) Uani 1 1 d . . . H25A H -0.1611 -0.4240 0.1732 0.101 Uiso 1 1 calc R . . C26 C -0.0858(3) -0.2519(2) 0.13594(8) 0.0738(7) Uani 1 1 d . . . H26A H -0.1657 -0.1884 0.1455 0.089 Uiso 1 1 calc R . . C27 C -0.1057(3) 0.0432(2) 0.09349(7) 0.0588(5) Uani 1 1 d . . . H27A H -0.2082 -0.0037 0.0849 0.071 Uiso 1 1 calc R . . C28 C -0.0650(3) 0.1602(2) 0.05616(7) 0.0646(6) Uani 1 1 d . . . H28A H -0.1378 0.1555 0.0285 0.078 Uiso 1 1 calc R . . H28B H -0.0681 0.2576 0.0698 0.078 Uiso 1 1 calc R . . C29 C 0.1023(2) 0.1180(2) 0.04343(6) 0.0549(5) Uani 1 1 d . . . N1 N 0.1455(2) -0.00731(16) 0.06076(5) 0.0570(4) Uani 1 1 d . . . N2 N 0.0267(2) -0.06031(17) 0.08844(6) 0.0639(5) 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 0.0570(14) 0.0446(10) 0.0646(12) 0.0026(9) 0.0130(10) 0.0085(8) C2 0.0679(17) 0.0677(14) 0.0884(16) -0.0045(12) 0.0041(13) 0.0214(11) C3 0.0691(19) 0.0825(18) 0.122(2) -0.0021(16) 0.0037(15) 0.0269(13) C4 0.075(2) 0.0855(19) 0.130(2) -0.0023(17) 0.0309(18) 0.0279(14) C5 0.084(2) 0.0664(15) 0.0917(17) -0.0088(12) 0.0390(15) 0.0122(12) C6 0.0708(16) 0.0450(10) 0.0686(13) 0.0030(9) 0.0273(11) 0.0052(9) C7 0.0822(16) 0.0476(11) 0.0566(12) 0.0022(9) 0.0235(11) -0.0051(9) C8 0.115(2) 0.0766(17) 0.0676(15) -0.0114(12) 0.0249(15) -0.0140(14) C9 0.145(3) 0.098(2) 0.0679(16) -0.0186(15) 0.0113(19) -0.025(2) C10 0.119(3) 0.096(2) 0.0779(18) 0.0039(15) -0.0207(17) -0.0252(18) C11 0.0836(18) 0.0707(15) 0.0771(16) 0.0081(12) -0.0043(13) -0.0057(12) C12 0.0688(15) 0.0468(11) 0.0573(12) 0.0088(9) 0.0071(10) -0.0034(9) C13 0.0581(14) 0.0473(10) 0.0624(12) 0.0058(9) 0.0114(10) 0.0104(8) C14 0.0584(13) 0.0400(9) 0.0586(11) 0.0018(8) 0.0128(10) 0.0086(8) C15 0.0681(15) 0.0471(11) 0.0650(12) 0.0064(9) -0.0061(10) 0.0067(9) C16 0.0913(18) 0.0628(14) 0.0736(14) 0.0164(11) 0.0045(13) 0.0187(12) C17 0.120(3) 0.0650(15) 0.1031(19) 0.0340(14) 0.0029(18) 0.0125(15) C18 0.089(2) 0.095(2) 0.156(3) 0.057(2) 0.012(2) -0.0058(16) C19 0.078(2) 0.105(2) 0.222(4) 0.079(2) 0.039(2) 0.0142(16) C20 0.0699(18) 0.0737(16) 0.162(3) 0.0527(17) 0.0200(17) 0.0163(13) C21 0.0713(14) 0.0423(10) 0.0554(11) -0.0022(8) 0.0095(10) 0.0067(9) C22 0.0727(15) 0.0495(11) 0.0690(13) 0.0051(9) 0.0122(10) 0.0122(9) C23 0.0885(18) 0.0498(12) 0.0897(16) 0.0069(11) 0.0100(13) 0.0174(11) C24 0.105(2) 0.0497(13) 0.0943(17) 0.0171(12) 0.0103(15) -0.0024(12) C25 0.098(2) 0.0604(14) 0.0970(17) 0.0090(13) 0.0307(15) -0.0040(13) C26 0.0844(18) 0.0570(13) 0.0814(15) -0.0023(11) 0.0263(13) 0.0054(11) C27 0.0626(14) 0.0517(11) 0.0624(11) -0.0043(9) 0.0067(10) 0.0166(9) C28 0.0784(16) 0.0605(12) 0.0550(11) -0.0012(9) 0.0022(10) 0.0258(10) C29 0.0659(14) 0.0452(10) 0.0536(10) 0.0000(8) -0.0013(9) 0.0129(9) N1 0.0660(12) 0.0438(9) 0.0615(10) 0.0018(7) 0.0079(8) 0.0106(7) N2 0.0755(13) 0.0471(9) 0.0706(10) 0.0055(8) 0.0278(9) 0.0189(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.405(3) . ? C1 C6 1.412(3) . ? C1 C14 1.456(2) . ? C2 C3 1.367(3) . ? C2 H2A 0.9300 . ? C3 C4 1.381(4) . ? C3 H3A 0.9300 . ? C4 C5 1.360(4) . ? C4 H4A 0.9300 . ? C5 C6 1.417(3) . ? C5 H5A 0.9300 . ? C6 C7 1.449(3) . ? C7 C8 1.405(3) . ? C7 C12 1.414(3) . ? C8 C9 1.366(4) . ? C8 H8A 0.9300 . ? C9 C10 1.387(4) . ? C9 H9A 0.9300 . ? C10 C11 1.370(3) . ? C10 H10A 0.9300 . ? C11 C12 1.401(3) . ? C11 H11A 0.9300 . ? C12 C13 1.422(3) . ? C13 C14 1.346(3) . ? C13 H13A 0.9300 . ? C14 C27 1.520(3) . ? C15 C16 1.382(3) . ? C15 C20 1.386(3) . ? C15 C29 1.454(3) . ? C16 C17 1.376(3) . ? C16 H16A 0.9300 . ? C17 C18 1.349(4) . ? C17 H17A 0.9300 . ? C18 C19 1.377(4) . ? C18 H18A 0.9300 . ? C19 C20 1.375(4) . ? C19 H19A 0.9300 . ? C20 H20A 0.9300 . ? C21 C22 1.386(3) . ? C21 C26 1.388(3) . ? C21 N2 1.388(2) . ? C22 C23 1.379(3) . ? C22 H22A 0.9300 . ? C23 C24 1.371(3) . ? C23 H23A 0.9300 . ? C24 C25 1.373(3) . ? C24 H24A 0.9300 . ? C25 C26 1.371(3) . ? C25 H25A 0.9300 . ? C26 H26A 0.9300 . ? C27 N2 1.466(2) . ? C27 C28 1.539(3) . ? C27 H27A 0.9800 . ? C28 C29 1.502(3) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 N1 1.292(2) . ? N1 N2 1.365(2) . ? 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 119.07(18) . . ? C2 C1 C14 122.13(18) . . ? C6 C1 C14 118.8(2) . . ? C3 C2 C1 121.7(2) . . ? C3 C2 H2A 119.2 . . ? C1 C2 H2A 119.2 . . ? C2 C3 C4 119.6(3) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C4 C5 C6 121.9(2) . . ? C4 C5 H5A 119.1 . . ? C6 C5 H5A 119.1 . . ? C1 C6 C5 117.3(2) . . ? C1 C6 C7 120.19(18) . . ? C5 C6 C7 122.5(2) . . ? C8 C7 C12 117.7(2) . . ? C8 C7 C6 123.4(2) . . ? C12 C7 C6 118.82(18) . . ? C9 C8 C7 121.3(3) . . ? C9 C8 H8A 119.4 . . ? C7 C8 H8A 119.4 . . ? C8 C9 C10 120.8(3) . . ? C8 C9 H9A 119.6 . . ? C10 C9 H9A 119.6 . . ? C11 C10 C9 119.6(3) . . ? C11 C10 H10A 120.2 . . ? C9 C10 H10A 120.2 . . ? C10 C11 C12 120.8(3) . . ? C10 C11 H11A 119.6 . . ? C12 C11 H11A 119.6 . . ? C11 C12 C7 119.7(2) . . ? C11 C12 C13 120.8(2) . . ? C7 C12 C13 119.5(2) . . ? C14 C13 C12 122.54(18) . . ? C14 C13 H13A 118.7 . . ? C12 C13 H13A 118.7 . . ? C13 C14 C1 120.07(17) . . ? C13 C14 C27 121.84(16) . . ? C1 C14 C27 117.94(18) . . ? C16 C15 C20 116.8(2) . . ? C16 C15 C29 122.2(2) . . ? C20 C15 C29 121.00(18) . . ? C17 C16 C15 121.4(2) . . ? C17 C16 H16A 119.3 . . ? C15 C16 H16A 119.3 . . ? C18 C17 C16 121.0(2) . . ? C18 C17 H17A 119.5 . . ? C16 C17 H17A 119.5 . . ? C17 C18 C19 119.1(3) . . ? C17 C18 H18A 120.4 . . ? C19 C18 H18A 120.4 . . ? C20 C19 C18 120.1(3) . . ? C20 C19 H19A 119.9 . . ? C18 C19 H19A 119.9 . . ? C19 C20 C15 121.5(2) . . ? C19 C20 H20A 119.2 . . ? C15 C20 H20A 119.2 . . ? C22 C21 C26 118.72(18) . . ? C22 C21 N2 121.06(17) . . ? C26 C21 N2 120.22(17) . . ? C23 C22 C21 119.8(2) . . ? C23 C22 H22A 120.1 . . ? C21 C22 H22A 120.1 . . ? C24 C23 C22 121.3(2) . . ? C24 C23 H23A 119.3 . . ? C22 C23 H23A 119.3 . . ? C23 C24 C25 118.7(2) . . ? C23 C24 H24A 120.6 . . ? C25 C24 H24A 120.6 . . ? C26 C25 C24 121.0(2) . . ? C26 C25 H25A 119.5 . . ? C24 C25 H25A 119.5 . . ? C25 C26 C21 120.4(2) . . ? C25 C26 H26A 119.8 . . ? C21 C26 H26A 119.8 . . ? N2 C27 C14 112.85(17) . . ? N2 C27 C28 101.63(15) . . ? C14 C27 C28 110.89(16) . . ? N2 C27 H27A 110.4 . . ? C14 C27 H27A 110.4 . . ? C28 C27 H27A 110.4 . . ? C29 C28 C27 102.00(15) . . ? C29 C28 H28A 111.4 . . ? C27 C28 H28A 111.4 . . ? C29 C28 H28B 111.4 . . ? C27 C28 H28B 111.4 . . ? H28A C28 H28B 109.2 . . ? N1 C29 C15 121.70(18) . . ? N1 C29 C28 112.97(17) . . ? C15 C29 C28 125.31(17) . . ? C29 N1 N2 109.16(15) . . ? N1 N2 C21 121.16(14) . . ? N1 N2 C27 112.82(15) . . ? C21 N2 C27 125.70(16) . . ? _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.906 _refine_diff_density_max 0.170 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.039