data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Charng-Hsing Liu' 'Min-Jie Huang' 'Chun-Jung Kuo' 'Ting-Yu Li' 'Chia- Chun Lien' 'Fang-Iy Wu' _publ_contact_author_name 'Charng-Hsing Liu' _publ_contact_author_email LIUCHS@MAIL.CHNA.EDU.TW _publ_section_title ; Bis(phenanthroimidazolyl)biphenyl derivatives as saturated blue emitters for electroluminescent devices ; # Attachment 'PPIP08JA60_0M.cif' data_08ja60_0m _database_code_depnum_ccdc_archive 'CCDC 714355' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H34 N4' _chemical_formula_sum 'C54 H34 N4' _chemical_formula_weight 738.85 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6874(2) _cell_length_b 13.4536(4) _cell_length_c 16.6938(5) _cell_angle_alpha 86.465(2) _cell_angle_beta 82.7850(10) _cell_angle_gamma 81.250(2) _cell_volume 1911.34(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5612 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Lamellar _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.80935 _exptl_absorpt_correction_T_max 0.95261 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35997 _diffrn_reflns_av_R_equivalents 0.1014 _diffrn_reflns_av_sigmaI/netI 0.0923 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 28.39 _reflns_number_total 9503 _reflns_number_gt 4013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'Shelxtl-97 (Sheldrick, 1990)' _computing_structure_refinement 'Shelxtl-97 (Sheldrick, 2000)' _computing_molecular_graphics 'Bruker Shelxtl' _computing_publication_material 'Bruker Shelxtl' _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^)+(0.1025P)^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 SHELXL _refine_ls_extinction_coef 0.109(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9503 _refine_ls_number_parameters 524 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1347 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.1900 _refine_ls_wR_factor_gt 0.1370 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.864 _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 0.9602(2) 0.49698(15) 0.16519(11) 0.0491(5) Uani 1 1 d . . . C2 C 0.8990(2) 0.40316(15) 0.18135(12) 0.0538(5) Uani 1 1 d . . . C3 C 0.7624(3) 0.38102(18) 0.15302(15) 0.0760(7) Uani 1 1 d . . . H3 H 0.7036 0.4299 0.1231 0.091 Uiso 1 1 calc R . . C4 C 0.7155(4) 0.2889(2) 0.16893(17) 0.0920(9) Uani 1 1 d . . . H4 H 0.6251 0.2753 0.1499 0.110 Uiso 1 1 calc R . . C5 C 0.8020(4) 0.21602(19) 0.21319(16) 0.0854(8) Uani 1 1 d . . . H5 H 0.7705 0.1529 0.2229 0.102 Uiso 1 1 calc R . . C6 C 0.9328(3) 0.23501(17) 0.24289(14) 0.0702(7) Uani 1 1 d . . . H6 H 0.9885 0.1847 0.2730 0.084 Uiso 1 1 calc R . . C7 C 0.9862(3) 0.32963(16) 0.22910(12) 0.0560(6) Uani 1 1 d . . . C8 C 1.1246(3) 0.35085(16) 0.26305(12) 0.0587(6) Uani 1 1 d . . . C9 C 1.2069(3) 0.28229(19) 0.31422(15) 0.0819(8) Uani 1 1 d . . . H9 H 1.1739 0.2201 0.3275 0.098 Uiso 1 1 calc R . . C10 C 1.3334(4) 0.3044(2) 0.34483(19) 0.1040(10) Uani 1 1 d . . . H10 H 1.3847 0.2576 0.3795 0.125 Uiso 1 1 calc R . . C11 C 1.3889(3) 0.3957(2) 0.32580(19) 0.1007(9) Uani 1 1 d . . . H11 H 1.4778 0.4090 0.3465 0.121 Uiso 1 1 calc R . . C12 C 1.3114(3) 0.46572(19) 0.27616(15) 0.0773(7) Uani 1 1 d . . . H12 H 1.3471 0.5271 0.2631 0.093 Uiso 1 1 calc R . . C13 C 1.1786(2) 0.44436(16) 0.24543(12) 0.0564(6) Uani 1 1 d . . . C14 C 1.0920(2) 0.51659(15) 0.19511(12) 0.0503(5) Uani 1 1 d . . . C15 C 1.0185(2) 0.64784(15) 0.12266(12) 0.0507(5) Uani 1 1 d . . . C16 C 1.0129(2) 0.74881(15) 0.08352(12) 0.0502(5) Uani 1 1 d . . . C17 C 1.0732(2) 0.82040(17) 0.11999(14) 0.0631(6) Uani 1 1 d . . . H17 H 1.1184 0.8031 0.1675 0.076 Uiso 1 1 calc R . . C18 C 1.0685(2) 0.91754(17) 0.08781(15) 0.0669(7) Uani 1 1 d . . . H18 H 1.1092 0.9643 0.1147 0.080 Uiso 1 1 calc R . . C19 C 1.0052(2) 0.94751(15) 0.01685(12) 0.0489(5) Uani 1 1 d . . . C20 C 0.9523(3) 0.87378(18) -0.02079(14) 0.0802(8) Uani 1 1 d . . . H20 H 0.9127 0.8901 -0.0699 0.096 Uiso 1 1 calc R . . C21 C 0.9551(3) 0.77720(18) 0.01075(15) 0.0813(8) Uani 1 1 d . . . H21 H 0.9176 0.7300 -0.0172 0.098 Uiso 1 1 calc R . . C22 C 0.7659(2) 0.60350(14) 0.08248(12) 0.0475(5) Uani 1 1 d . . . C23 C 0.6340(2) 0.64549(17) 0.12839(13) 0.0628(6) Uani 1 1 d . . . H23 H 0.6383 0.6601 0.1817 0.075 Uiso 1 1 calc R . . C24 C 0.4946(3) 0.6662(2) 0.09567(17) 0.0806(8) Uani 1 1 d . . . H24 H 0.4047 0.6952 0.1269 0.097 Uiso 1 1 calc R . . C25 C 0.4874(3) 0.6443(2) 0.01775(17) 0.0772(7) Uani 1 1 d . . . H25 H 0.3929 0.6590 -0.0043 0.093 Uiso 1 1 calc R . . C26 C 0.6178(3) 0.60121(19) -0.02753(15) 0.0759(7) Uani 1 1 d . . . H26 H 0.6125 0.5860 -0.0806 0.091 Uiso 1 1 calc R . . C27 C 0.7584(3) 0.57967(17) 0.00441(13) 0.0645(6) Uani 1 1 d . . . H27 H 0.8475 0.5492 -0.0267 0.077 Uiso 1 1 calc R . . C28 C 0.3094(2) 0.86806(17) 0.33434(13) 0.0551(6) Uani 1 1 d . . . C29 C 0.4668(2) 0.81348(18) 0.32644(14) 0.0638(6) Uani 1 1 d . . . C30 C 0.5206(3) 0.7308(2) 0.37578(17) 0.0917(9) Uani 1 1 d . . . H30 H 0.4509 0.7051 0.4158 0.110 Uiso 1 1 calc R . . C31 C 0.6747(4) 0.6871(3) 0.3659(2) 0.1128(11) Uani 1 1 d . . . H31 H 0.7084 0.6325 0.3995 0.135 Uiso 1 1 calc R . . C32 C 0.7781(3) 0.7227(3) 0.3081(2) 0.1037(11) Uani 1 1 d . . . H32 H 0.8823 0.6926 0.3019 0.124 Uiso 1 1 calc R . . C33 C 0.7295(3) 0.8026(2) 0.25875(18) 0.0864(9) Uani 1 1 d . . . H33 H 0.8023 0.8262 0.2193 0.104 Uiso 1 1 calc R . . C34 C 0.5728(2) 0.85101(19) 0.26527(15) 0.0666(7) Uani 1 1 d . . . C35 C 0.5234(2) 0.9376(2) 0.21238(14) 0.0668(7) Uani 1 1 d . . . C36 C 0.6233(3) 0.9724(3) 0.14842(18) 0.0949(9) Uani 1 1 d . . . H36 H 0.7248 0.9385 0.1379 0.114 Uiso 1 1 calc R . . C37 C 0.5770(4) 1.0544(3) 0.10099(19) 0.1039(10) Uani 1 1 d . . . H37 H 0.6465 1.0751 0.0585 0.125 Uiso 1 1 calc R . . C38 C 0.4278(3) 1.1072(2) 0.11531(16) 0.0891(8) Uani 1 1 d . . . H38 H 0.3973 1.1642 0.0834 0.107 Uiso 1 1 calc R . . C39 C 0.3254(3) 1.07491(19) 0.17686(14) 0.0681(7) Uani 1 1 d . . . H39 H 0.2246 1.1101 0.1865 0.082 Uiso 1 1 calc R . . C40 C 0.3701(2) 0.99013(18) 0.22517(13) 0.0567(6) Uani 1 1 d . . . C41 C 0.2638(2) 0.95150(16) 0.28765(12) 0.0510(5) Uani 1 1 d . . . C42 C 0.0602(2) 0.92940(15) 0.36945(12) 0.0486(5) Uani 1 1 d . . . C43 C -0.1010(2) 0.94496(14) 0.41026(11) 0.0451(5) Uani 1 1 d . . . C44 C -0.2180(2) 0.99363(15) 0.36689(12) 0.0509(5) Uani 1 1 d . . . H44 H -0.1923 1.0127 0.3129 0.061 Uiso 1 1 calc R . . C45 C -0.3714(2) 1.01475(15) 0.40115(12) 0.0525(5) Uani 1 1 d . . . H45 H -0.4463 1.0475 0.3697 0.063 Uiso 1 1 calc R . . C46 C -0.4170(2) 0.98859(14) 0.48113(11) 0.0422(5) Uani 1 1 d . . . C47 C -0.2982(2) 0.94005(16) 0.52453(12) 0.0560(6) Uani 1 1 d . . . H47 H -0.3234 0.9214 0.5786 0.067 Uiso 1 1 calc R . . C48 C -0.1451(2) 0.91874(16) 0.49033(12) 0.0586(6) Uani 1 1 d . . . H48 H -0.0698 0.8861 0.5217 0.070 Uiso 1 1 calc R . . C49 C 0.1666(2) 0.76697(16) 0.44133(13) 0.0540(5) Uani 1 1 d . . . C50 C 0.1341(3) 0.6811(2) 0.41195(18) 0.0825(8) Uani 1 1 d . . . H50 H 0.1118 0.6805 0.3589 0.099 Uiso 1 1 calc R . . C51 C 0.1345(4) 0.5958(3) 0.4609(3) 0.1191(11) Uani 1 1 d . . . H51 H 0.1132 0.5368 0.4410 0.143 Uiso 1 1 calc R . . C52 C 0.1660(4) 0.5969(3) 0.5388(3) 0.1258(14) Uani 1 1 d . . . H52 H 0.1633 0.5392 0.5724 0.151 Uiso 1 1 calc R . . C53 C 0.2016(3) 0.6823(3) 0.56774(17) 0.1011(10) Uani 1 1 d . . . H53 H 0.2255 0.6823 0.6205 0.121 Uiso 1 1 calc R . . C54 C 0.2022(3) 0.7690(2) 0.51859(14) 0.0713(7) Uani 1 1 d . . . H54 H 0.2263 0.8275 0.5378 0.086 Uiso 1 1 calc R . . N1 N 1.12688(18) 0.61023(13) 0.16886(10) 0.0549(5) Uani 1 1 d . . . N2 N 0.91198(18) 0.58176(12) 0.11751(9) 0.0506(4) Uani 1 1 d . . . N3 N 0.10926(17) 0.99000(13) 0.30994(10) 0.0514(4) Uani 1 1 d . . . N4 N 0.17734(18) 0.85300(13) 0.38748(10) 0.0536(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 0.0543(12) 0.0426(12) 0.0456(12) 0.0072(9) 0.0000(9) -0.0007(9) C2 0.0675(14) 0.0430(13) 0.0484(12) 0.0069(10) -0.0029(10) -0.0065(11) C3 0.0940(19) 0.0553(16) 0.0853(17) 0.0195(13) -0.0324(14) -0.0229(13) C4 0.119(2) 0.0650(18) 0.104(2) 0.0278(16) -0.0440(18) -0.0392(16) C5 0.122(2) 0.0558(17) 0.0852(19) 0.0180(14) -0.0261(17) -0.0332(16) C6 0.0935(19) 0.0489(15) 0.0625(15) 0.0153(12) -0.0028(13) -0.0039(13) C7 0.0659(14) 0.0481(14) 0.0487(12) 0.0073(10) 0.0011(10) -0.0023(10) C8 0.0653(14) 0.0503(14) 0.0528(13) 0.0089(11) 0.0004(11) 0.0061(11) C9 0.0897(19) 0.0645(17) 0.0889(19) 0.0209(14) -0.0262(15) -0.0001(14) C10 0.107(2) 0.082(2) 0.121(3) 0.0347(19) -0.047(2) 0.0022(18) C11 0.0784(19) 0.098(2) 0.127(2) 0.020(2) -0.0451(17) 0.0004(17) C12 0.0645(15) 0.0718(18) 0.0938(18) 0.0139(14) -0.0224(13) -0.0002(13) C13 0.0500(12) 0.0568(15) 0.0555(13) 0.0053(11) -0.0012(10) 0.0071(10) C14 0.0471(12) 0.0473(13) 0.0516(12) 0.0050(10) 0.0020(9) -0.0005(9) C15 0.0442(11) 0.0473(13) 0.0565(13) 0.0071(10) 0.0030(9) -0.0048(10) C16 0.0414(11) 0.0448(13) 0.0598(13) 0.0081(10) 0.0041(9) -0.0040(9) C17 0.0500(13) 0.0598(15) 0.0833(16) 0.0232(13) -0.0242(11) -0.0170(11) C18 0.0602(14) 0.0562(15) 0.0912(17) 0.0210(13) -0.0294(12) -0.0237(11) C19 0.0377(11) 0.0490(13) 0.0568(13) 0.0115(10) 0.0037(9) -0.0094(9) C20 0.132(2) 0.0567(16) 0.0573(14) 0.0147(12) -0.0245(15) -0.0279(15) C21 0.135(2) 0.0523(16) 0.0637(15) 0.0104(13) -0.0258(15) -0.0292(15) C22 0.0499(12) 0.0392(12) 0.0521(13) 0.0057(9) -0.0058(10) -0.0056(9) C23 0.0540(14) 0.0737(16) 0.0619(14) -0.0128(12) 0.0000(11) -0.0148(11) C24 0.0489(14) 0.093(2) 0.100(2) -0.0171(16) -0.0048(13) -0.0093(13) C25 0.0625(16) 0.0835(19) 0.090(2) 0.0078(16) -0.0256(14) -0.0168(14) C26 0.0837(18) 0.0849(19) 0.0624(15) 0.0019(14) -0.0236(14) -0.0120(15) C27 0.0690(15) 0.0665(16) 0.0547(14) -0.0026(12) -0.0077(11) 0.0012(12) C28 0.0401(11) 0.0625(15) 0.0592(13) -0.0080(11) -0.0013(10) 0.0012(10) C29 0.0431(12) 0.0732(17) 0.0726(15) -0.0208(13) -0.0092(11) 0.0083(11) C30 0.0588(15) 0.105(2) 0.099(2) 0.0010(17) -0.0106(14) 0.0258(14) C31 0.070(2) 0.136(3) 0.118(3) -0.016(2) -0.0202(19) 0.0444(19) C32 0.0476(16) 0.140(3) 0.119(3) -0.051(2) -0.0230(17) 0.0292(17) C33 0.0434(14) 0.115(2) 0.101(2) -0.0521(19) -0.0007(13) 0.0000(14) C34 0.0402(12) 0.0829(18) 0.0776(16) -0.0356(14) -0.0018(11) -0.0030(11) C35 0.0439(12) 0.0860(19) 0.0716(16) -0.0297(14) 0.0092(11) -0.0150(12) C36 0.0558(16) 0.121(3) 0.103(2) -0.024(2) 0.0276(15) -0.0188(16) C37 0.080(2) 0.131(3) 0.097(2) -0.008(2) 0.0347(17) -0.037(2) C38 0.0812(19) 0.100(2) 0.0842(19) 0.0023(16) 0.0172(15) -0.0321(16) C39 0.0563(14) 0.0820(18) 0.0657(15) -0.0072(14) 0.0080(12) -0.0198(12) C40 0.0459(12) 0.0697(16) 0.0556(13) -0.0150(12) 0.0035(10) -0.0145(11) C41 0.0375(11) 0.0598(14) 0.0539(12) -0.0062(11) -0.0006(9) -0.0044(9) C42 0.0395(11) 0.0509(13) 0.0523(12) 0.0029(10) -0.0047(9) 0.0004(9) C43 0.0364(10) 0.0438(12) 0.0530(12) 0.0022(9) -0.0013(9) -0.0034(8) C44 0.0437(11) 0.0572(14) 0.0480(12) 0.0081(10) -0.0011(9) -0.0027(9) C45 0.0382(11) 0.0605(14) 0.0551(13) 0.0097(10) -0.0072(9) 0.0015(9) C46 0.0360(9) 0.0402(11) 0.0502(12) 0.0030(9) -0.0045(8) -0.0068(8) C47 0.0446(12) 0.0668(15) 0.0504(12) 0.0160(11) 0.0004(9) -0.0008(10) C48 0.0399(11) 0.0709(15) 0.0586(14) 0.0165(11) -0.0053(10) 0.0042(10) C49 0.0455(11) 0.0495(14) 0.0638(14) 0.0026(11) -0.0093(10) 0.0035(10) C50 0.0831(18) 0.0628(18) 0.105(2) 0.0012(17) -0.0282(15) -0.0095(14) C51 0.125(3) 0.068(2) 0.166(4) 0.009(2) -0.021(3) -0.0208(19) C52 0.125(3) 0.078(3) 0.152(4) 0.045(3) 0.018(3) 0.011(2) C53 0.099(2) 0.110(3) 0.0684(18) 0.0229(19) 0.0046(15) 0.042(2) C54 0.0712(16) 0.0700(17) 0.0655(16) -0.0045(13) -0.0109(12) 0.0152(12) N1 0.0445(10) 0.0514(11) 0.0642(11) 0.0116(9) -0.0012(8) -0.0021(8) N2 0.0535(10) 0.0420(10) 0.0538(10) 0.0083(8) -0.0049(8) -0.0047(8) N3 0.0383(9) 0.0573(11) 0.0546(10) 0.0018(9) 0.0024(7) -0.0023(8) N4 0.0397(9) 0.0546(11) 0.0613(11) 0.0064(9) -0.0019(8) 0.0029(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 C14 1.372(3) . ? C1 N2 1.392(2) . ? C1 C2 1.440(3) . ? C2 C3 1.409(3) . ? C2 C7 1.419(3) . ? C3 C4 1.363(3) . ? C3 H3 0.9300 . ? C4 C5 1.378(3) . ? C4 H4 0.9300 . ? C5 C6 1.359(3) . ? C5 H5 0.9300 . ? C6 C7 1.416(3) . ? C6 H6 0.9300 . ? C7 C8 1.465(3) . ? C8 C9 1.396(3) . ? C8 C13 1.410(3) . ? C9 C10 1.348(4) . ? C9 H9 0.9300 . ? C10 C11 1.391(4) . ? C10 H10 0.9300 . ? C11 C12 1.371(3) . ? C11 H11 0.9300 . ? C12 C13 1.394(3) . ? C12 H12 0.9300 . ? C13 C14 1.433(3) . ? C14 N1 1.373(2) . ? C15 N1 1.314(2) . ? C15 N2 1.391(2) . ? C15 C16 1.467(3) . ? C16 C17 1.371(3) . ? C16 C21 1.382(3) . ? C17 C18 1.379(3) . ? C17 H17 0.9300 . ? C18 C19 1.380(3) . ? C18 H18 0.9300 . ? C19 C20 1.370(3) . ? C19 C19 1.482(4) 2_775 ? C20 C21 1.369(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.362(3) . ? C22 C27 1.373(3) . ? C22 N2 1.446(2) . ? C23 C24 1.374(3) . ? C23 H23 0.9300 . ? C24 C25 1.362(3) . ? C24 H24 0.9300 . ? C25 C26 1.353(3) . ? C25 H25 0.9300 . ? C26 C27 1.377(3) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C41 1.364(3) . ? C28 N4 1.392(2) . ? C28 C29 1.445(3) . ? C29 C30 1.400(3) . ? C29 C34 1.409(3) . ? C30 C31 1.372(4) . ? C30 H30 0.9300 . ? C31 C32 1.351(4) . ? C31 H31 0.9300 . ? C32 C33 1.360(4) . ? C32 H32 0.9300 . ? C33 C34 1.411(3) . ? C33 H33 0.9300 . ? C34 C35 1.462(3) . ? C35 C36 1.394(3) . ? C35 C40 1.407(3) . ? C36 C37 1.357(4) . ? C36 H36 0.9300 . ? C37 C38 1.380(4) . ? C37 H37 0.9300 . ? C38 C39 1.367(3) . ? C38 H38 0.9300 . ? C39 C40 1.390(3) . ? C39 H39 0.9300 . ? C40 C41 1.431(3) . ? C41 N3 1.377(2) . ? C42 N3 1.316(2) . ? C42 N4 1.380(2) . ? C42 C43 1.469(3) . ? C43 C44 1.382(2) . ? C43 C48 1.383(3) . ? C44 C45 1.377(3) . ? C44 H44 0.9300 . ? C45 C46 1.384(3) . ? C45 H45 0.9300 . ? C46 C47 1.393(2) . ? C46 C46 1.494(3) 2_476 ? C47 C48 1.375(3) . ? C47 H47 0.9300 . ? C48 H48 0.9300 . ? C49 C50 1.364(3) . ? C49 C54 1.366(3) . ? C49 N4 1.428(3) . ? C50 C51 1.367(4) . ? C50 H50 0.9300 . ? C51 C52 1.364(5) . ? C51 H51 0.9300 . ? C52 C53 1.365(5) . ? C52 H52 0.9300 . ? C53 C54 1.384(4) . ? C53 H53 0.9300 . ? C54 H54 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 C14 C1 N2 105.59(17) . . ? C14 C1 C2 123.04(18) . . ? N2 C1 C2 131.32(19) . . ? C3 C2 C7 119.5(2) . . ? C3 C2 C1 124.65(19) . . ? C7 C2 C1 115.80(19) . . ? C4 C3 C2 120.9(2) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.0(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.9(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 121.6(2) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C6 C7 C2 117.0(2) . . ? C6 C7 C8 121.5(2) . . ? C2 C7 C8 121.49(19) . . ? C9 C8 C13 117.2(2) . . ? C9 C8 C7 122.8(2) . . ? C13 C8 C7 120.08(19) . . ? C10 C9 C8 121.3(3) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 121.6(3) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C12 C11 C10 119.3(3) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 119.6(3) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C8 121.1(2) . . ? C12 C13 C14 121.3(2) . . ? C8 C13 C14 117.6(2) . . ? C1 C14 N1 111.16(17) . . ? C1 C14 C13 121.88(19) . . ? N1 C14 C13 126.95(19) . . ? N1 C15 N2 111.96(17) . . ? N1 C15 C16 122.50(18) . . ? N2 C15 C16 125.53(18) . . ? C17 C16 C21 116.8(2) . . ? C17 C16 C15 118.24(19) . . ? C21 C16 C15 125.0(2) . . ? C16 C17 C18 121.5(2) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C17 C18 C19 122.0(2) . . ? C17 C18 H18 119.0 . . ? C19 C18 H18 119.0 . . ? C20 C19 C18 115.7(2) . . ? C20 C19 C19 121.9(2) . 2_775 ? C18 C19 C19 122.4(2) . 2_775 ? C21 C20 C19 122.9(2) . . ? C21 C20 H20 118.5 . . ? C19 C20 H20 118.5 . . ? C20 C21 C16 121.0(2) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? C23 C22 C27 119.98(19) . . ? C23 C22 N2 119.39(18) . . ? C27 C22 N2 120.60(18) . . ? C22 C23 C24 119.8(2) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C25 C24 C23 120.4(2) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C26 C25 C24 119.9(2) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C25 C26 C27 120.5(2) . . ? C25 C26 H26 119.7 . . ? C27 C26 H26 119.7 . . ? C22 C27 C26 119.4(2) . . ? C22 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C41 C28 N4 105.55(17) . . ? C41 C28 C29 123.5(2) . . ? N4 C28 C29 131.0(2) . . ? C30 C29 C34 119.2(2) . . ? C30 C29 C28 125.3(2) . . ? C34 C29 C28 115.5(2) . . ? C31 C30 C29 120.9(3) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C32 C31 C30 120.7(3) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C31 C32 C33 119.9(3) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? C32 C33 C34 122.4(3) . . ? C32 C33 H33 118.8 . . ? C34 C33 H33 118.8 . . ? C29 C34 C33 116.9(3) . . ? C29 C34 C35 121.5(2) . . ? C33 C34 C35 121.6(2) . . ? C36 C35 C40 117.1(3) . . ? C36 C35 C34 122.6(2) . . ? C40 C35 C34 120.3(2) . . ? C37 C36 C35 122.0(3) . . ? C37 C36 H36 119.0 . . ? C35 C36 H36 119.0 . . ? C36 C37 C38 120.6(3) . . ? C36 C37 H37 119.7 . . ? C38 C37 H37 119.7 . . ? C39 C38 C37 119.3(3) . . ? C39 C38 H38 120.3 . . ? C37 C38 H38 120.3 . . ? C38 C39 C40 120.8(2) . . ? C38 C39 H39 119.6 . . ? C40 C39 H39 119.6 . . ? C39 C40 C35 120.2(2) . . ? C39 C40 C41 122.3(2) . . ? C35 C40 C41 117.5(2) . . ? C28 C41 N3 111.13(17) . . ? C28 C41 C40 121.56(19) . . ? N3 C41 C40 127.3(2) . . ? N3 C42 N4 111.87(16) . . ? N3 C42 C43 122.20(17) . . ? N4 C42 C43 125.92(18) . . ? C44 C43 C48 116.71(17) . . ? C44 C43 C42 118.01(17) . . ? C48 C43 C42 125.21(17) . . ? C45 C44 C43 121.97(18) . . ? C45 C44 H44 119.0 . . ? C43 C44 H44 119.0 . . ? C44 C45 C46 121.84(17) . . ? C44 C45 H45 119.1 . . ? C46 C45 H45 119.1 . . ? C45 C46 C47 115.81(17) . . ? C45 C46 C46 122.2(2) . 2_476 ? C47 C46 C46 122.0(2) . 2_476 ? C48 C47 C46 122.40(18) . . ? C48 C47 H47 118.8 . . ? C46 C47 H47 118.8 . . ? C47 C48 C43 121.27(18) . . ? C47 C48 H48 119.4 . . ? C43 C48 H48 119.4 . . ? C50 C49 C54 121.1(2) . . ? C50 C49 N4 118.6(2) . . ? C54 C49 N4 120.0(2) . . ? C49 C50 C51 119.6(3) . . ? C49 C50 H50 120.2 . . ? C51 C50 H50 120.2 . . ? C52 C51 C50 120.1(3) . . ? C52 C51 H51 119.9 . . ? C50 C51 H51 119.9 . . ? C51 C52 C53 120.3(3) . . ? C51 C52 H52 119.9 . . ? C53 C52 H52 119.9 . . ? C52 C53 C54 120.1(3) . . ? C52 C53 H53 120.0 . . ? C54 C53 H53 120.0 . . ? C49 C54 C53 118.8(3) . . ? C49 C54 H54 120.6 . . ? C53 C54 H54 120.6 . . ? C15 N1 C14 105.48(16) . . ? C15 N2 C1 105.81(15) . . ? C15 N2 C22 126.91(16) . . ? C1 N2 C22 126.40(16) . . ? C42 N3 C41 105.29(16) . . ? C42 N4 C28 106.15(17) . . ? C42 N4 C49 128.75(16) . . ? C28 N4 C49 124.63(16) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.748 _refine_diff_density_min -0.748 _refine_diff_density_rms 0.231