Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (C) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Chin-Ti Chen' _publ_contact_author_email CCHEN@CHEM.SINICA.EDU.TW _publ_section_title ; Achieving High-Efficiency Non-Doped Blue Organic Light-Emitting Diodes: Charge-Balance Control of Bipolar Blue Fluorescent Materials with Reduced Hole-Mobility ; _publ_author_name 'Chin-Ti Chen' # Attachment 'i7740.cif' data_i7740 _database_code_depnum_ccdc_archive 'CCDC 682902' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H35 Cl2 N3' _chemical_formula_sum 'C50 H35 Cl2 N3' _chemical_formula_weight 748.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl Cl 0.1484 0.1585 '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' 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' _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 12.5133(3) _cell_length_b 34.5307(8) _cell_length_c 8.9169(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.493(2) _cell_angle_gamma 90.00 _cell_volume 3788.50(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used 3528 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 21.57 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.967 _exptl_absorpt_correction_T_max 0.9967 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(1) _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 27836 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.1049 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6695 _reflns_number_gt 3432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0382P)^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 0.00157(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6695 _refine_ls_number_parameters 497 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0782 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0851 _refine_ls_wR_factor_gt 0.0801 _refine_ls_goodness_of_fit_ref 0.776 _refine_ls_restrained_S_all 0.776 _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 Cl1 Cl 0.92595(6) 0.20841(2) 0.92686(8) 0.0672(2) Uani 1 1 d . . . Cl2 Cl 0.93365(7) 0.17971(3) 1.23360(10) 0.0891(3) Uani 1 1 d . . . N1 N 2.14459(13) 0.11565(5) 1.7514(2) 0.0275(5) Uani 1 1 d . . . N25 N 1.65778(14) 0.14888(6) 2.0068(2) 0.0337(5) Uani 1 1 d . . . N31 N 1.64168(15) 0.20827(6) 1.7483(2) 0.0372(5) Uani 1 1 d . . . C1 C 1.73542(16) 0.11172(6) 1.6527(2) 0.0188(5) Uani 1 1 d . . . C2 C 1.85013(16) 0.09924(6) 1.6387(2) 0.0198(5) Uani 1 1 d . . . C3 C 1.94733(16) 0.11459(6) 1.7114(2) 0.0226(5) Uani 1 1 d . . . H3 H 1.9484 0.1352 1.7787 0.027 Uiso 1 1 calc R . . C4 C 2.04410(16) 0.09880(6) 1.6828(2) 0.0232(5) Uani 1 1 d . . . C5 C 2.04121(18) 0.06770(6) 1.5839(2) 0.0272(6) Uani 1 1 d . . . H5 H 2.1060 0.0575 1.5640 0.033 Uiso 1 1 calc R . . C6 C 1.94368(17) 0.05159(6) 1.5145(2) 0.0263(5) Uani 1 1 d . . . H6 H 1.9427 0.0304 1.4500 0.032 Uiso 1 1 calc R . . C7 C 1.84724(16) 0.06740(6) 1.5419(2) 0.0199(5) Uani 1 1 d . . . C8 C 1.66696(16) 0.08329(6) 1.5435(2) 0.0182(5) Uani 1 1 d . . . C9 C 1.55554(16) 0.08164(6) 1.5026(2) 0.0215(5) Uani 1 1 d . . . H9 H 1.5122 0.0998 1.5402 0.026 Uiso 1 1 calc R . . C10 C 1.50818(16) 0.05226(6) 1.4036(2) 0.0209(5) Uani 1 1 d . . . C11 C 1.57639(17) 0.02482(6) 1.3558(2) 0.0236(5) Uani 1 1 d . . . H11 H 1.5453 0.0042 1.2962 0.028 Uiso 1 1 calc R . . C12 C 1.68798(17) 0.02692(6) 1.3932(2) 0.0229(5) Uani 1 1 d . . . H12 H 1.7315 0.0085 1.3573 0.027 Uiso 1 1 calc R . . C13 C 1.73391(16) 0.05709(6) 1.4856(2) 0.0192(5) Uani 1 1 d . . . C14 C 1.39096(16) 0.04819(6) 1.3488(2) 0.0246(5) Uani 1 1 d . . . H14 H 1.3663 0.0228 1.3341 0.030 Uiso 1 1 calc R . . C15 C 1.31378(17) 0.07553(6) 1.3166(2) 0.0224(5) Uani 1 1 d . . . C20 C 0.8721(2) 0.21198(7) 1.0945(3) 0.0506(7) Uani 1 1 d . . . H20A H 0.8821 0.2382 1.1337 0.061 Uiso 1 1 calc R . . H20B H 0.7947 0.2068 1.0712 0.061 Uiso 1 1 calc R . . C21 C 1.71511(15) 0.10810(6) 1.8154(2) 0.0197(5) Uani 1 1 d . . . C22 C 1.72830(16) 0.07679(6) 1.9114(2) 0.0264(6) Uani 1 1 d . . . H22 H 1.7518 0.0531 1.8803 0.032 Uiso 1 1 calc R . . C23 C 1.70549(17) 0.08172(7) 2.0558(3) 0.0334(6) Uani 1 1 d . . . H23 H 1.7130 0.0612 2.1245 0.040 Uiso 1 1 calc R . . C24 C 1.67146(18) 0.11736(8) 2.0965(3) 0.0370(6) Uani 1 1 d . . . H24 H 1.6566 0.1199 2.1945 0.044 Uiso 1 1 calc R . . C26 C 1.67989(16) 0.14305(6) 1.8668(2) 0.0243(5) Uani 1 1 d . . . C27 C 1.70860(16) 0.15402(6) 1.6205(2) 0.0223(5) Uani 1 1 d . . . C28 C 1.71368(18) 0.17575(7) 1.4938(3) 0.0330(6) Uani 1 1 d . . . H28 H 1.7381 0.1653 1.4101 0.040 Uiso 1 1 calc R . . C29 C 1.68087(19) 0.21395(7) 1.4956(3) 0.0412(7) Uani 1 1 d . . . H29 H 1.6829 0.2298 1.4119 0.049 Uiso 1 1 calc R . . C30 C 1.64518(19) 0.22847(7) 1.6215(3) 0.0432(7) Uani 1 1 d . . . H30 H 1.6219 0.2541 1.6180 0.052 Uiso 1 1 calc R . . C32 C 1.67359(16) 0.17154(6) 1.7437(2) 0.0262(5) Uani 1 1 d . . . C41 C 2.23544(17) 0.09204(6) 1.8098(2) 0.0234(5) Uani 1 1 d . . . C42 C 2.22243(18) 0.05752(6) 1.8831(2) 0.0266(6) Uani 1 1 d . . . H42 H 2.1532 0.0491 1.8917 0.032 Uiso 1 1 calc R . . C43 C 2.31178(19) 0.03561(6) 1.9433(2) 0.0310(6) Uani 1 1 d . . . H43 H 2.3024 0.0123 1.9915 0.037 Uiso 1 1 calc R . . C44 C 2.41525(18) 0.04787(7) 1.9328(2) 0.0311(6) Uani 1 1 d . . . H44 H 2.4755 0.0332 1.9754 0.037 Uiso 1 1 calc R . . C45 C 2.42794(18) 0.08172(7) 1.8590(2) 0.0292(6) Uani 1 1 d . . . H45 H 2.4973 0.0900 1.8504 0.035 Uiso 1 1 calc R . . C46 C 2.33946(17) 0.10371(6) 1.7974(2) 0.0275(6) Uani 1 1 d . . . H46 H 2.3494 0.1266 1.7470 0.033 Uiso 1 1 calc R . . C51 C 2.15328(16) 0.15659(6) 1.7590(2) 0.0254(6) Uani 1 1 d . . . C52 C 2.10284(17) 0.17895(7) 1.6376(3) 0.0308(6) Uani 1 1 d . . . H52 H 2.0634 0.1671 1.5514 0.037 Uiso 1 1 calc R . . C53 C 2.11083(18) 0.21867(7) 1.6438(3) 0.0391(6) Uani 1 1 d . . . H53 H 2.0762 0.2335 1.5620 0.047 Uiso 1 1 calc R . . C54 C 2.16936(19) 0.23661(7) 1.7693(3) 0.0442(7) Uani 1 1 d . . . H54 H 2.1746 0.2635 1.7731 0.053 Uiso 1 1 calc R . . C55 C 2.22038(19) 0.21452(7) 1.8897(3) 0.0424(7) Uani 1 1 d . . . H55 H 2.2611 0.2266 1.9745 0.051 Uiso 1 1 calc R . . C56 C 2.21195(17) 0.17474(7) 1.8861(3) 0.0327(6) Uani 1 1 d . . . H56 H 2.2456 0.1601 1.9690 0.039 Uiso 1 1 calc R . . C61 C 1.34248(16) 0.11742(6) 1.3239(2) 0.0228(5) Uani 1 1 d . . . C62 C 1.30399(17) 0.14261(7) 1.4225(2) 0.0303(6) Uani 1 1 d . . . H62 H 1.2563 0.1336 1.4833 0.036 Uiso 1 1 calc R . . C63 C 1.33553(19) 0.18089(7) 1.4316(3) 0.0392(6) Uani 1 1 d . . . H63 H 1.3110 0.1973 1.5007 0.047 Uiso 1 1 calc R . . C64 C 1.4034(2) 0.19485(7) 1.3383(3) 0.0433(7) Uani 1 1 d . . . H64 H 1.4246 0.2207 1.3443 0.052 Uiso 1 1 calc R . . C65 C 1.43984(18) 0.17051(7) 1.2365(3) 0.0367(6) Uani 1 1 d . . . H65 H 1.4847 0.1799 1.1723 0.044 Uiso 1 1 calc R . . C66 C 1.40981(17) 0.13221(7) 1.2299(2) 0.0296(6) Uani 1 1 d . . . H66 H 1.4350 0.1159 1.1611 0.035 Uiso 1 1 calc R . . C71 C 1.19888(17) 0.06477(6) 1.2586(2) 0.0234(5) Uani 1 1 d . . . C72 C 1.16163(17) 0.02693(7) 1.2645(2) 0.0280(6) Uani 1 1 d . . . H72 H 1.2084 0.0082 1.3146 0.034 Uiso 1 1 calc R . . C73 C 1.05771(17) 0.01641(7) 1.1983(2) 0.0314(6) Uani 1 1 d . . . H73 H 1.0359 -0.0093 1.2011 0.038 Uiso 1 1 calc R . . C74 C 0.98588(18) 0.04393(7) 1.1278(2) 0.0343(6) Uani 1 1 d . . . H74 H 0.9155 0.0369 1.0832 0.041 Uiso 1 1 calc R . . C75 C 1.01901(18) 0.08180(7) 1.1239(2) 0.0362(6) Uani 1 1 d . . . H75 H 0.9704 0.1005 1.0780 0.043 Uiso 1 1 calc R . . C76 C 1.12436(17) 0.09224(7) 1.1879(2) 0.0296(6) Uani 1 1 d . . . H76 H 1.1458 0.1180 1.1839 0.035 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 Cl1 0.0637(5) 0.0684(6) 0.0726(5) -0.0287(4) 0.0207(4) -0.0213(4) Cl2 0.0862(7) 0.0901(7) 0.0832(6) 0.0126(5) -0.0047(5) 0.0059(5) N1 0.0177(11) 0.0210(12) 0.0413(12) -0.0003(9) -0.0010(9) -0.0007(9) N25 0.0283(12) 0.0461(14) 0.0282(12) -0.0117(11) 0.0089(9) -0.0059(10) N31 0.0348(13) 0.0246(13) 0.0502(14) -0.0069(11) 0.0025(10) 0.0025(10) C1 0.0171(12) 0.0189(13) 0.0203(12) -0.0024(10) 0.0032(9) 0.0013(10) C2 0.0179(12) 0.0225(13) 0.0193(12) 0.0029(10) 0.0043(10) -0.0001(10) C3 0.0236(13) 0.0227(13) 0.0217(12) -0.0037(10) 0.0042(10) -0.0004(11) C4 0.0176(13) 0.0242(14) 0.0272(13) 0.0024(11) 0.0026(10) -0.0007(11) C5 0.0196(13) 0.0318(14) 0.0316(14) 0.0007(12) 0.0081(11) 0.0033(11) C6 0.0286(14) 0.0244(13) 0.0264(13) -0.0019(11) 0.0067(11) 0.0021(11) C7 0.0188(13) 0.0210(13) 0.0196(12) -0.0001(10) 0.0029(10) 0.0007(10) C8 0.0202(13) 0.0185(12) 0.0155(12) 0.0012(9) 0.0021(10) -0.0013(10) C9 0.0219(13) 0.0203(13) 0.0223(12) 0.0000(10) 0.0043(10) 0.0036(10) C10 0.0204(13) 0.0219(13) 0.0191(12) 0.0026(10) 0.0002(10) -0.0015(10) C11 0.0276(14) 0.0189(13) 0.0225(13) -0.0038(10) -0.0001(10) -0.0022(11) C12 0.0229(13) 0.0234(13) 0.0222(13) -0.0022(10) 0.0039(10) 0.0055(10) C13 0.0198(13) 0.0198(13) 0.0178(12) 0.0014(10) 0.0028(10) 0.0016(10) C14 0.0235(13) 0.0250(14) 0.0242(13) -0.0025(10) 0.0013(10) -0.0044(11) C15 0.0216(13) 0.0270(14) 0.0179(12) -0.0010(10) 0.0014(10) 0.0008(11) C20 0.0426(17) 0.0464(18) 0.0631(19) -0.0142(14) 0.0102(14) 0.0049(14) C21 0.0133(12) 0.0241(14) 0.0210(12) -0.0021(10) 0.0016(9) -0.0033(10) C22 0.0186(13) 0.0327(15) 0.0269(14) -0.0002(11) 0.0016(10) 0.0012(11) C23 0.0247(14) 0.0472(17) 0.0278(15) 0.0067(12) 0.0031(11) -0.0019(12) C24 0.0302(15) 0.062(2) 0.0198(14) -0.0071(14) 0.0056(11) -0.0109(14) C26 0.0178(13) 0.0300(15) 0.0248(14) -0.0051(11) 0.0028(10) -0.0035(10) C27 0.0177(13) 0.0216(13) 0.0262(13) -0.0032(11) 0.0000(10) -0.0017(10) C28 0.0376(15) 0.0283(15) 0.0308(14) -0.0010(12) 0.0001(12) -0.0050(12) C29 0.0508(18) 0.0290(17) 0.0382(16) 0.0074(13) -0.0070(13) -0.0068(13) C30 0.0446(17) 0.0178(15) 0.062(2) -0.0034(14) -0.0052(15) 0.0022(12) C32 0.0201(13) 0.0215(14) 0.0360(14) -0.0095(12) 0.0026(11) -0.0022(11) C41 0.0214(13) 0.0240(14) 0.0241(13) -0.0019(11) 0.0021(10) 0.0008(11) C42 0.0262(14) 0.0268(14) 0.0275(13) -0.0022(11) 0.0071(11) -0.0028(11) C43 0.0402(16) 0.0231(14) 0.0294(14) -0.0009(11) 0.0058(12) 0.0031(12) C44 0.0300(15) 0.0311(15) 0.0302(14) -0.0038(12) -0.0001(11) 0.0094(12) C45 0.0207(13) 0.0357(16) 0.0314(14) -0.0036(12) 0.0049(11) 0.0018(12) C46 0.0218(14) 0.0308(15) 0.0295(14) 0.0063(11) 0.0036(11) 0.0007(11) C51 0.0160(13) 0.0249(15) 0.0357(15) 0.0014(11) 0.0059(11) -0.0004(10) C52 0.0237(13) 0.0319(16) 0.0364(15) 0.0030(12) 0.0049(11) -0.0007(11) C53 0.0278(15) 0.0365(17) 0.0527(17) 0.0143(14) 0.0064(13) 0.0038(12) C54 0.0369(16) 0.0232(15) 0.072(2) 0.0023(14) 0.0092(15) -0.0031(12) C55 0.0343(16) 0.0339(17) 0.0563(18) -0.0088(14) 0.0011(13) -0.0047(13) C56 0.0255(14) 0.0301(16) 0.0404(15) 0.0019(12) 0.0002(12) 0.0014(12) C61 0.0184(13) 0.0267(14) 0.0207(12) 0.0010(11) -0.0035(10) 0.0042(11) C62 0.0288(14) 0.0302(16) 0.0318(14) 0.0014(11) 0.0053(11) 0.0043(12) C63 0.0395(16) 0.0313(17) 0.0447(16) -0.0083(13) 0.0021(13) 0.0072(13) C64 0.0356(16) 0.0269(16) 0.0640(19) 0.0034(14) 0.0002(14) -0.0008(13) C65 0.0288(15) 0.0334(17) 0.0477(17) 0.0108(13) 0.0069(13) 0.0005(12) C66 0.0278(14) 0.0313(16) 0.0287(14) 0.0016(11) 0.0030(11) 0.0025(12) C71 0.0205(13) 0.0303(14) 0.0198(12) -0.0030(10) 0.0047(10) -0.0008(11) C72 0.0226(14) 0.0349(16) 0.0256(13) 0.0017(11) 0.0024(11) -0.0001(11) C73 0.0274(15) 0.0371(15) 0.0297(14) -0.0028(12) 0.0050(11) -0.0054(12) C74 0.0215(14) 0.0462(18) 0.0337(15) -0.0026(13) 0.0016(11) -0.0030(13) C75 0.0253(15) 0.0475(18) 0.0338(15) 0.0028(12) -0.0004(11) 0.0088(13) C76 0.0253(14) 0.0339(15) 0.0278(13) -0.0011(11) 0.0004(11) 0.0021(11) _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 Cl1 C20 1.752(3) . ? Cl2 C20 1.740(3) . ? N1 C51 1.419(3) . ? N1 C4 1.419(2) . ? N1 C41 1.418(2) . ? N25 C26 1.342(3) . ? N25 C24 1.343(3) . ? N31 C32 1.332(3) . ? N31 C30 1.336(3) . ? C1 C27 1.514(3) . ? C1 C21 1.523(3) . ? C1 C2 1.525(3) . ? C1 C8 1.531(3) . ? C2 C3 1.376(3) . ? C2 C7 1.395(3) . ? C3 C4 1.393(3) . ? C3 H3 0.9300 . ? C4 C5 1.386(3) . ? C5 C6 1.381(3) . ? C5 H5 0.9300 . ? C6 C7 1.386(3) . ? C6 H6 0.9300 . ? C7 C13 1.460(3) . ? C8 C9 1.377(3) . ? C8 C13 1.394(3) . ? C9 C10 1.403(3) . ? C9 H9 0.9300 . ? C10 C11 1.393(3) . ? C10 C14 1.466(3) . ? C11 C12 1.377(3) . ? C11 H11 0.9300 . ? C12 C13 1.386(3) . ? C12 H12 0.9300 . ? C14 C15 1.344(3) . ? C14 H14 0.9300 . ? C15 C71 1.484(3) . ? C15 C61 1.489(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.370(3) . ? C21 C26 1.391(3) . ? C22 C23 1.379(3) . ? C22 H22 0.9300 . ? C23 C24 1.373(3) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C26 C32 1.465(3) . ? C27 C28 1.368(3) . ? C27 C32 1.393(3) . ? C28 C29 1.382(3) . ? C28 H28 0.9300 . ? C29 C30 1.376(3) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C41 C42 1.383(3) . ? C41 C46 1.386(3) . ? C42 C43 1.376(3) . ? C42 H42 0.9300 . ? C43 C44 1.382(3) . ? C43 H43 0.9300 . ? C44 C45 1.364(3) . ? C44 H44 0.9300 . ? C45 C46 1.372(3) . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? C51 C56 1.383(3) . ? C51 C52 1.385(3) . ? C52 C53 1.375(3) . ? C52 H52 0.9300 . ? C53 C54 1.369(3) . ? C53 H53 0.9300 . ? C54 C55 1.375(3) . ? C54 H54 0.9300 . ? C55 C56 1.377(3) . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? C61 C62 1.384(3) . ? C61 C66 1.390(3) . ? C62 C63 1.378(3) . ? C62 H62 0.9300 . ? C63 C64 1.380(3) . ? C63 H63 0.9300 . ? C64 C65 1.374(3) . ? C64 H64 0.9300 . ? C65 C66 1.373(3) . ? C65 H65 0.9300 . ? C66 H66 0.9300 . ? C71 C72 1.391(3) . ? C71 C76 1.397(3) . ? C72 C73 1.375(3) . ? C72 H72 0.9300 . ? C73 C74 1.379(3) . ? C73 H73 0.9300 . ? C74 C75 1.374(3) . ? C74 H74 0.9300 . ? C75 C76 1.386(3) . ? C75 H75 0.9300 . ? C76 H76 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 C51 N1 C4 118.90(17) . . ? C51 N1 C41 120.38(17) . . ? C4 N1 C41 120.71(17) . . ? C26 N25 C24 114.0(2) . . ? C32 N31 C30 114.5(2) . . ? C27 C1 C21 100.95(16) . . ? C27 C1 C2 115.88(17) . . ? C21 C1 C2 112.18(16) . . ? C27 C1 C8 114.77(16) . . ? C21 C1 C8 112.49(16) . . ? C2 C1 C8 101.10(16) . . ? C3 C2 C7 121.08(19) . . ? C3 C2 C1 128.10(18) . . ? C7 C2 C1 110.78(17) . . ? C2 C3 C4 119.11(19) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 119.79(19) . . ? C5 C4 N1 120.68(19) . . ? C3 C4 N1 119.49(19) . . ? C6 C5 C4 121.0(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.3(2) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C6 C7 C2 119.63(19) . . ? C6 C7 C13 131.75(19) . . ? C2 C7 C13 108.62(18) . . ? C9 C8 C13 121.54(19) . . ? C9 C8 C1 128.13(18) . . ? C13 C8 C1 110.33(17) . . ? C8 C9 C10 119.20(19) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 118.17(19) . . ? C11 C10 C14 117.67(19) . . ? C9 C10 C14 124.15(19) . . ? C12 C11 C10 122.75(19) . . ? C12 C11 H11 118.6 . . ? C10 C11 H11 118.6 . . ? C11 C12 C13 118.40(19) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C12 C13 C8 119.70(19) . . ? C12 C13 C7 131.25(19) . . ? C8 C13 C7 109.03(17) . . ? C15 C14 C10 129.8(2) . . ? C15 C14 H14 115.1 . . ? C10 C14 H14 115.1 . . ? C14 C15 C71 120.77(19) . . ? C14 C15 C61 121.00(19) . . ? C71 C15 C61 117.99(18) . . ? Cl2 C20 Cl1 111.97(14) . . ? Cl2 C20 H20A 109.2 . . ? Cl1 C20 H20A 109.2 . . ? Cl2 C20 H20B 109.2 . . ? Cl1 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C22 C21 C26 119.22(19) . . ? C22 C21 C1 129.64(19) . . ? C26 C21 C1 111.13(18) . . ? C21 C22 C23 117.7(2) . . ? C21 C22 H22 121.2 . . ? C23 C22 H22 121.2 . . ? C24 C23 C22 119.0(2) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? N25 C24 C23 125.5(2) . . ? N25 C24 H24 117.2 . . ? C23 C24 H24 117.2 . . ? N25 C26 C21 124.6(2) . . ? N25 C26 C32 127.1(2) . . ? C21 C26 C32 108.24(18) . . ? C28 C27 C32 118.8(2) . . ? C28 C27 C1 130.1(2) . . ? C32 C27 C1 111.13(18) . . ? C27 C28 C29 117.1(2) . . ? C27 C28 H28 121.5 . . ? C29 C28 H28 121.5 . . ? C30 C29 C28 119.9(2) . . ? C30 C29 H29 120.1 . . ? C28 C29 H29 120.1 . . ? N31 C30 C29 124.4(2) . . ? N31 C30 H30 117.8 . . ? C29 C30 H30 117.8 . . ? N31 C32 C27 125.2(2) . . ? N31 C32 C26 126.3(2) . . ? C27 C32 C26 108.48(19) . . ? C42 C41 C46 118.8(2) . . ? C42 C41 N1 120.87(19) . . ? C46 C41 N1 120.36(19) . . ? C43 C42 C41 120.1(2) . . ? C43 C42 H42 120.0 . . ? C41 C42 H42 120.0 . . ? C42 C43 C44 120.7(2) . . ? C42 C43 H43 119.7 . . ? C44 C43 H43 119.7 . . ? C45 C44 C43 119.2(2) . . ? C45 C44 H44 120.4 . . ? C43 C44 H44 120.4 . . ? C44 C45 C46 120.7(2) . . ? C44 C45 H45 119.6 . . ? C46 C45 H45 119.6 . . ? C45 C46 C41 120.6(2) . . ? C45 C46 H46 119.7 . . ? C41 C46 H46 119.7 . . ? C56 C51 C52 119.1(2) . . ? C56 C51 N1 121.0(2) . . ? C52 C51 N1 119.9(2) . . ? C53 C52 C51 120.3(2) . . ? C53 C52 H52 119.8 . . ? C51 C52 H52 119.8 . . ? C54 C53 C52 120.5(2) . . ? C54 C53 H53 119.7 . . ? C52 C53 H53 119.7 . . ? C53 C54 C55 119.3(2) . . ? C53 C54 H54 120.3 . . ? C55 C54 H54 120.3 . . ? C56 C55 C54 120.8(2) . . ? C56 C55 H55 119.6 . . ? C54 C55 H55 119.6 . . ? C55 C56 C51 119.9(2) . . ? C55 C56 H56 120.1 . . ? C51 C56 H56 120.1 . . ? C62 C61 C66 118.1(2) . . ? C62 C61 C15 122.0(2) . . ? C66 C61 C15 119.9(2) . . ? C63 C62 C61 120.7(2) . . ? C63 C62 H62 119.6 . . ? C61 C62 H62 119.6 . . ? C64 C63 C62 120.1(2) . . ? C64 C63 H63 120.0 . . ? C62 C63 H63 120.0 . . ? C65 C64 C63 120.0(2) . . ? C65 C64 H64 120.0 . . ? C63 C64 H64 120.0 . . ? C66 C65 C64 119.8(2) . . ? C66 C65 H65 120.1 . . ? C64 C65 H65 120.1 . . ? C65 C66 C61 121.3(2) . . ? C65 C66 H66 119.4 . . ? C61 C66 H66 119.4 . . ? C72 C71 C76 117.0(2) . . ? C72 C71 C15 122.14(19) . . ? C76 C71 C15 120.8(2) . . ? C73 C72 C71 121.9(2) . . ? C73 C72 H72 119.0 . . ? C71 C72 H72 119.0 . . ? C72 C73 C74 120.0(2) . . ? C72 C73 H73 120.0 . . ? C74 C73 H73 120.0 . . ? C75 C74 C73 119.5(2) . . ? C75 C74 H74 120.2 . . ? C73 C74 H74 120.2 . . ? C74 C75 C76 120.4(2) . . ? C74 C75 H75 119.8 . . ? C76 C75 H75 119.8 . . ? C75 C76 C71 121.1(2) . . ? C75 C76 H76 119.5 . . ? C71 C76 H76 119.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.504 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.043 # Attachment 'i8175.cif' data_i8175 _database_code_depnum_ccdc_archive 'CCDC 682903' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C49 H35 N3' _chemical_formula_sum 'C49 H35 N3' _chemical_formula_weight 665.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _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 13.1622(6) _cell_length_b 25.6042(11) _cell_length_c 10.9596(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.046(2) _cell_angle_gamma 90.00 _cell_volume 3531.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used 3382 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 20.67 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_correction_T_min 0.7906 _exptl_absorpt_correction_T_max 1.0000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(1) _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 27399 _diffrn_reflns_av_R_equivalents 0.0745 _diffrn_reflns_av_sigmaI/netI 0.1708 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.03 _reflns_number_total 6169 _reflns_number_gt 2476 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0335P)^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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0028(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6169 _refine_ls_number_parameters 470 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1094 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0797 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 0.685 _refine_ls_restrained_S_all 0.685 _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 N15 N 0.50746(13) 0.27277(7) 0.63792(18) 0.0415(5) Uani 1 1 d . . . N21 N 0.46490(13) 0.37722(7) 0.86559(17) 0.0394(5) Uani 1 1 d . . . N27 N 0.30049(12) 0.44055(6) 0.41763(16) 0.0349(5) Uani 1 1 d . . . C1 C 0.58999(14) 0.35008(8) 0.75580(18) 0.0254(5) Uani 1 1 d . . . C2 C 0.54219(15) 0.37997(7) 0.63247(19) 0.0275(5) Uani 1 1 d . . . C3 C 0.43664(15) 0.39238(8) 0.57748(19) 0.0318(6) Uani 1 1 d . . . H3 H 0.3849 0.3796 0.6119 0.038 Uiso 1 1 calc R . . C4 C 0.40859(16) 0.42419(8) 0.4704(2) 0.0324(6) Uani 1 1 d . . . C5 C 0.48541(16) 0.44145(8) 0.41609(19) 0.0340(6) Uani 1 1 d . . . H5 H 0.4659 0.4627 0.3442 0.041 Uiso 1 1 calc R . . C6 C 0.59106(15) 0.42729(8) 0.46812(19) 0.0313(6) Uani 1 1 d . . . H6 H 0.6420 0.4380 0.4298 0.038 Uiso 1 1 calc R . . C7 C 0.61999(15) 0.39691(8) 0.57812(19) 0.0286(5) Uani 1 1 d . . . C8 C 0.72297(15) 0.37708(7) 0.65683(19) 0.0275(5) Uani 1 1 d . . . C9 C 0.82480(15) 0.37956(8) 0.6428(2) 0.0363(6) Uani 1 1 d . . . H9 H 0.8366 0.3967 0.5733 0.044 Uiso 1 1 calc R . . C10 C 0.90844(15) 0.35607(8) 0.7342(2) 0.0359(6) Uani 1 1 d . . . H10 H 0.9761 0.3574 0.7240 0.043 Uiso 1 1 calc R . . C11 C 0.89464(15) 0.33075(8) 0.8401(2) 0.0320(6) Uani 1 1 d . . . C12 C 0.79077(15) 0.32776(7) 0.85156(19) 0.0320(6) Uani 1 1 d . . . H12 H 0.7785 0.3102 0.9202 0.038 Uiso 1 1 calc R . . C13 C 0.70811(15) 0.35068(8) 0.76158(19) 0.0272(5) Uani 1 1 d . . . C14 C 0.55264(14) 0.29332(8) 0.7529(2) 0.0268(5) Uani 1 1 d . . . C16 C 0.48001(16) 0.22185(10) 0.6343(2) 0.0456(6) Uani 1 1 d . . . H16 H 0.4473 0.2070 0.5551 0.055 Uiso 1 1 calc R . . C17 C 0.49710(16) 0.19114(9) 0.7387(2) 0.0413(6) Uani 1 1 d . . . H17 H 0.4785 0.1560 0.7310 0.050 Uiso 1 1 calc R . . C18 C 0.54236(16) 0.21305(10) 0.8558(2) 0.0439(6) Uani 1 1 d . . . H18 H 0.5540 0.1932 0.9297 0.053 Uiso 1 1 calc R . . C19 C 0.57035(14) 0.26485(9) 0.8624(2) 0.0339(6) Uani 1 1 d . . . H19 H 0.6013 0.2805 0.9411 0.041 Uiso 1 1 calc R . . C20 C 0.56629(16) 0.38036(8) 0.86456(19) 0.0283(5) Uani 1 1 d . . . C22 C 0.43685(17) 0.40430(9) 0.9542(2) 0.0444(6) Uani 1 1 d . . . H22 H 0.3665 0.4021 0.9550 0.053 Uiso 1 1 calc R . . C23 C 0.50377(19) 0.43491(9) 1.0434(2) 0.0497(7) Uani 1 1 d . . . H23 H 0.4805 0.4532 1.1035 0.060 Uiso 1 1 calc R . . C24 C 0.60662(19) 0.43768(10) 1.0410(2) 0.0661(8) Uani 1 1 d . . . H24 H 0.6554 0.4580 1.1008 0.079 Uiso 1 1 calc R . . C25 C 0.63818(16) 0.41057(9) 0.9504(2) 0.0506(7) Uani 1 1 d . . . H25 H 0.7080 0.4128 0.9476 0.061 Uiso 1 1 calc R . . C28 C 0.23220(16) 0.44473(8) 0.4955(2) 0.0326(6) Uani 1 1 d . . . C29 C 0.26789(16) 0.46180(8) 0.6211(2) 0.0350(6) Uani 1 1 d . . . H29 H 0.3388 0.4712 0.6557 0.042 Uiso 1 1 calc R . . C30 C 0.19998(17) 0.46503(8) 0.6951(2) 0.0385(6) Uani 1 1 d . . . H30 H 0.2261 0.4755 0.7798 0.046 Uiso 1 1 calc R . . C31 C 0.09319(17) 0.45286(8) 0.6453(2) 0.0439(6) Uani 1 1 d . . . H31 H 0.0471 0.4557 0.6951 0.053 Uiso 1 1 calc R . . C32 C 0.05717(16) 0.43648(8) 0.5209(2) 0.0455(6) Uani 1 1 d . . . H32 H -0.0144 0.4283 0.4862 0.055 Uiso 1 1 calc R . . C33 C 0.12475(16) 0.43181(8) 0.4458(2) 0.0394(6) Uani 1 1 d . . . H33 H 0.0987 0.4201 0.3621 0.047 Uiso 1 1 calc R . . C34 C 0.25571(15) 0.44311(10) 0.2830(2) 0.0341(6) Uani 1 1 d . . . C35 C 0.25851(16) 0.40022(10) 0.2091(3) 0.0513(7) Uani 1 1 d . . . H35 H 0.2938 0.3700 0.2458 0.062 Uiso 1 1 calc R . . C36 C 0.2081(2) 0.40243(16) 0.0790(3) 0.0919(13) Uani 1 1 d . . . H36 H 0.2112 0.3735 0.0290 0.110 Uiso 1 1 calc R . . C37 C 0.1547(3) 0.4452(2) 0.0225(3) 0.1078(18) Uani 1 1 d . . . H37 H 0.1194 0.4454 -0.0644 0.129 Uiso 1 1 calc R . . C38 C 0.1539(2) 0.48862(14) 0.0970(3) 0.0892(12) Uani 1 1 d . . . H38 H 0.1194 0.5188 0.0593 0.107 Uiso 1 1 calc R . . C39 C 0.20398(17) 0.48768(10) 0.2271(2) 0.0549(7) Uani 1 1 d . . . H39 H 0.2027 0.5170 0.2765 0.066 Uiso 1 1 calc R . . C41 C 0.98381(14) 0.30504(8) 0.9329(2) 0.0373(6) Uani 1 1 d . . . H41 H 1.0369 0.2919 0.9011 0.045 Uiso 1 1 calc R . . C42 C 0.99824(14) 0.29807(8) 1.0580(2) 0.0330(6) Uani 1 1 d . . . C43 C 0.93176(15) 0.32384(10) 1.1296(2) 0.0345(6) Uani 1 1 d . . . C44 C 0.93103(15) 0.37732(10) 1.1413(2) 0.0448(6) Uani 1 1 d . . . H44 H 0.9708 0.3978 1.1020 0.054 Uiso 1 1 calc R . . C45 C 0.8713(2) 0.40089(11) 1.2114(2) 0.0636(8) Uani 1 1 d . . . H45 H 0.8723 0.4370 1.2202 0.076 Uiso 1 1 calc R . . C46 C 0.8107(2) 0.37107(15) 1.2679(2) 0.0757(10) Uani 1 1 d . . . H46 H 0.7701 0.3871 1.3139 0.091 Uiso 1 1 calc R . . C47 C 0.81022(19) 0.31784(14) 1.2565(3) 0.0742(9) Uani 1 1 d . . . H47 H 0.7688 0.2977 1.2941 0.089 Uiso 1 1 calc R . . C48 C 0.87133(17) 0.29407(10) 1.1890(2) 0.0551(7) Uani 1 1 d . . . H48 H 0.8721 0.2578 1.1832 0.066 Uiso 1 1 calc R . . C49 C 1.08794(15) 0.26580(9) 1.1362(2) 0.0341(6) Uani 1 1 d . . . C50 C 1.11392(17) 0.21882(9) 1.0895(2) 0.0448(6) Uani 1 1 d . . . H50 H 1.0739 0.2068 1.0098 0.054 Uiso 1 1 calc R . . C51 C 1.19922(18) 0.18978(9) 1.1612(3) 0.0536(7) Uani 1 1 d . . . H51 H 1.2157 0.1580 1.1304 0.064 Uiso 1 1 calc R . . C52 C 1.25944(17) 0.20789(11) 1.2778(3) 0.0567(7) Uani 1 1 d . . . H52 H 1.3187 0.1890 1.3236 0.068 Uiso 1 1 calc R . . C53 C 1.23383(17) 0.25349(10) 1.3283(2) 0.0479(7) Uani 1 1 d . . . H53 H 1.2740 0.2652 1.4082 0.057 Uiso 1 1 calc R . . C54 C 1.14628(16) 0.28156(8) 1.2566(2) 0.0420(6) Uani 1 1 d . . . H54 H 1.1265 0.3118 1.2908 0.050 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 N15 0.0399(12) 0.0422(14) 0.0400(14) -0.0029(11) 0.0082(10) -0.0050(10) N21 0.0281(12) 0.0482(13) 0.0456(13) -0.0056(11) 0.0166(10) -0.0056(9) N27 0.0204(11) 0.0544(13) 0.0273(12) 0.0070(10) 0.0027(10) 0.0082(9) C1 0.0142(12) 0.0358(14) 0.0243(13) 0.0008(12) 0.0028(10) -0.0027(10) C2 0.0223(13) 0.0326(14) 0.0276(14) -0.0014(11) 0.0074(11) -0.0027(11) C3 0.0189(13) 0.0430(15) 0.0337(14) 0.0023(12) 0.0081(11) -0.0024(11) C4 0.0246(14) 0.0416(15) 0.0287(14) 0.0022(12) 0.0044(12) 0.0019(11) C5 0.0329(14) 0.0398(15) 0.0304(14) 0.0060(12) 0.0111(12) 0.0036(12) C6 0.0225(13) 0.0404(15) 0.0334(14) 0.0043(12) 0.0120(11) -0.0008(11) C7 0.0199(13) 0.0364(15) 0.0289(14) -0.0017(12) 0.0059(11) -0.0034(11) C8 0.0175(13) 0.0330(14) 0.0319(14) -0.0027(12) 0.0071(11) -0.0027(10) C9 0.0257(14) 0.0474(16) 0.0373(15) 0.0017(12) 0.0114(12) -0.0038(12) C10 0.0180(13) 0.0506(16) 0.0394(15) 0.0019(13) 0.0091(12) -0.0002(11) C11 0.0183(13) 0.0407(15) 0.0361(15) -0.0017(13) 0.0069(12) 0.0030(11) C12 0.0244(13) 0.0354(14) 0.0366(14) 0.0008(12) 0.0096(12) 0.0012(11) C13 0.0167(13) 0.0329(14) 0.0299(14) -0.0001(12) 0.0037(11) 0.0000(10) C14 0.0135(12) 0.0402(16) 0.0276(14) -0.0001(14) 0.0074(11) 0.0008(11) C16 0.0494(16) 0.0402(18) 0.0428(18) -0.0068(15) 0.0066(13) -0.0111(13) C17 0.0400(15) 0.0345(16) 0.0547(17) -0.0006(16) 0.0224(14) -0.0093(12) C18 0.0548(17) 0.0409(18) 0.0385(17) 0.0063(14) 0.0174(14) 0.0075(13) C19 0.0341(14) 0.0366(16) 0.0280(15) -0.0004(13) 0.0044(11) 0.0010(12) C20 0.0202(13) 0.0330(14) 0.0289(14) 0.0033(12) 0.0027(11) 0.0003(11) C22 0.0361(15) 0.0488(17) 0.0544(18) -0.0017(15) 0.0231(14) 0.0007(13) C23 0.0489(18) 0.0562(18) 0.0429(17) -0.0076(14) 0.0114(14) 0.0159(14) C24 0.0383(17) 0.078(2) 0.071(2) -0.0393(17) -0.0016(15) 0.0030(14) C25 0.0236(14) 0.0637(18) 0.0599(18) -0.0267(15) 0.0048(14) 0.0009(13) C28 0.0237(14) 0.0382(15) 0.0344(15) 0.0075(13) 0.0061(12) 0.0039(11) C29 0.0242(13) 0.0390(15) 0.0392(16) 0.0007(13) 0.0052(12) -0.0028(11) C30 0.0382(16) 0.0422(16) 0.0360(15) 0.0005(12) 0.0122(13) 0.0025(12) C31 0.0295(15) 0.0577(18) 0.0467(17) 0.0006(14) 0.0146(13) 0.0039(12) C32 0.0257(14) 0.0661(18) 0.0436(17) 0.0033(15) 0.0082(13) -0.0026(12) C33 0.0258(14) 0.0549(17) 0.0342(15) -0.0018(12) 0.0038(12) -0.0013(12) C34 0.0225(13) 0.0465(17) 0.0333(16) 0.0005(15) 0.0082(12) -0.0064(12) C35 0.0219(14) 0.078(2) 0.057(2) -0.0167(17) 0.0171(14) -0.0095(13) C36 0.035(2) 0.197(4) 0.051(3) -0.052(3) 0.0234(17) -0.041(2) C37 0.035(2) 0.241(6) 0.039(2) 0.024(3) -0.0027(18) -0.048(3) C38 0.0403(19) 0.137(4) 0.072(3) 0.059(2) -0.012(2) -0.022(2) C39 0.0405(16) 0.0545(19) 0.059(2) 0.0175(16) -0.0015(14) -0.0055(14) C41 0.0152(13) 0.0496(16) 0.0451(16) -0.0018(14) 0.0056(12) 0.0033(11) C42 0.0167(13) 0.0408(15) 0.0402(15) 0.0017(13) 0.0064(12) 0.0015(11) C43 0.0233(13) 0.0415(17) 0.0343(14) 0.0028(14) 0.0015(11) 0.0104(12) C44 0.0247(14) 0.0554(19) 0.0461(16) -0.0093(15) -0.0023(12) 0.0077(13) C45 0.0450(18) 0.071(2) 0.060(2) -0.0241(18) -0.0083(15) 0.0211(16) C46 0.056(2) 0.123(3) 0.048(2) -0.002(2) 0.0162(16) 0.045(2) C47 0.0537(19) 0.113(3) 0.070(2) 0.033(2) 0.0390(16) 0.0348(19) C48 0.0445(16) 0.0666(19) 0.0612(18) 0.0220(16) 0.0264(15) 0.0201(14) C49 0.0197(13) 0.0423(17) 0.0393(16) 0.0006(13) 0.0069(12) 0.0052(12) C50 0.0308(15) 0.0499(17) 0.0519(17) -0.0046(15) 0.0092(13) 0.0040(13) C51 0.0383(16) 0.0525(19) 0.069(2) 0.0017(16) 0.0149(15) 0.0222(14) C52 0.0267(15) 0.071(2) 0.067(2) 0.0169(17) 0.0050(15) 0.0161(14) C53 0.0291(15) 0.0561(18) 0.0522(17) 0.0033(15) 0.0019(13) 0.0106(13) C54 0.0290(14) 0.0491(17) 0.0463(16) 0.0016(14) 0.0087(13) 0.0078(13) _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 N15 C14 1.334(2) . ? N15 C16 1.350(2) . ? N21 C22 1.330(2) . ? N21 C20 1.340(2) . ? N27 C28 1.414(2) . ? N27 C34 1.421(2) . ? N27 C4 1.432(2) . ? C1 C2 1.520(2) . ? C1 C20 1.529(3) . ? C1 C14 1.532(3) . ? C1 C13 1.537(2) . ? C2 C3 1.380(2) . ? C2 C7 1.396(2) . ? C3 C4 1.387(2) . ? C3 H3 0.9300 . ? C4 C5 1.387(2) . ? C5 C6 1.388(2) . ? C5 H5 0.9300 . ? C6 C7 1.391(2) . ? C6 H6 0.9300 . ? C7 C8 1.468(2) . ? C8 C9 1.395(2) . ? C8 C13 1.395(2) . ? C9 C10 1.390(2) . ? C9 H9 0.9300 . ? C10 C11 1.387(2) . ? C10 H10 0.9300 . ? C11 C12 1.411(2) . ? C11 C41 1.465(2) . ? C12 C13 1.368(2) . ? C12 H12 0.9300 . ? C14 C19 1.364(3) . ? C16 C17 1.351(3) . ? C16 H16 0.9300 . ? C17 C18 1.367(3) . ? C17 H17 0.9300 . ? C18 C19 1.373(2) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C25 1.363(2) . ? C22 C23 1.357(3) . ? C22 H22 0.9300 . ? C23 C24 1.364(3) . ? C23 H23 0.9300 . ? C24 C25 1.372(3) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C28 C29 1.388(2) . ? C28 C33 1.398(2) . ? C29 C30 1.374(2) . ? C29 H29 0.9300 . ? C30 C31 1.386(2) . ? C30 H30 0.9300 . ? C31 C32 1.372(3) . ? C31 H31 0.9300 . ? C32 C33 1.382(3) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? C34 C35 1.371(3) . ? C34 C39 1.377(3) . ? C35 C36 1.386(3) . ? C35 H35 0.9300 . ? C36 C37 1.349(4) . ? C36 H36 0.9300 . ? C37 C38 1.382(4) . ? C37 H37 0.9300 . ? C38 C39 1.384(3) . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C41 C42 1.340(2) . ? C41 H41 0.9300 . ? C42 C49 1.489(3) . ? C42 C43 1.490(3) . ? C43 C44 1.375(3) . ? C43 C48 1.393(3) . ? C44 C45 1.387(3) . ? C44 H44 0.9300 . ? C45 C46 1.376(3) . ? C45 H45 0.9300 . ? C46 C47 1.369(3) . ? C46 H46 0.9300 . ? C47 C48 1.383(3) . ? C47 H47 0.9300 . ? C48 H48 0.9300 . ? C49 C54 1.379(3) . ? C49 C50 1.389(3) . ? C50 C51 1.383(3) . ? C50 H50 0.9300 . ? C51 C52 1.372(3) . ? C51 H51 0.9300 . ? C52 C53 1.375(3) . ? C52 H52 0.9300 . ? C53 C54 1.389(3) . ? 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 N15 C16 116.73(19) . . ? C22 N21 C20 117.70(18) . . ? C28 N27 C34 118.70(16) . . ? C28 N27 C4 120.69(17) . . ? C34 N27 C4 119.55(17) . . ? C2 C1 C20 108.19(15) . . ? C2 C1 C14 114.38(16) . . ? C20 C1 C14 111.08(16) . . ? C2 C1 C13 100.46(15) . . ? C20 C1 C13 113.45(16) . . ? C14 C1 C13 108.95(15) . . ? C3 C2 C7 120.84(19) . . ? C3 C2 C1 127.29(18) . . ? C7 C2 C1 111.82(17) . . ? C2 C3 C4 119.28(18) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 120.23(19) . . ? C3 C4 N27 119.99(18) . . ? C5 C4 N27 119.75(19) . . ? C6 C5 C4 120.60(19) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.28(18) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C6 C7 C2 119.66(18) . . ? C6 C7 C8 132.38(18) . . ? C2 C7 C8 107.96(18) . . ? C9 C8 C13 118.96(18) . . ? C9 C8 C7 132.2(2) . . ? C13 C8 C7 108.86(17) . . ? C10 C9 C8 118.98(19) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 122.36(19) . . ? C9 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? C10 C11 C12 117.90(18) . . ? C10 C11 C41 121.08(18) . . ? C12 C11 C41 120.91(19) . . ? C13 C12 C11 119.93(19) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 121.84(18) . . ? C12 C13 C1 127.32(18) . . ? C8 C13 C1 110.80(17) . . ? N15 C14 C19 122.3(2) . . ? N15 C14 C1 116.44(19) . . ? C19 C14 C1 121.2(2) . . ? N15 C16 C17 124.1(2) . . ? N15 C16 H16 118.0 . . ? C17 C16 H16 118.0 . . ? C16 C17 C18 118.3(2) . . ? C16 C17 H17 120.8 . . ? C18 C17 H17 120.8 . . ? C17 C18 C19 118.8(2) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C14 C19 C18 119.7(2) . . ? C14 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? N21 C20 C25 121.3(2) . . ? N21 C20 C1 114.04(18) . . ? C25 C20 C1 124.54(19) . . ? N21 C22 C23 124.5(2) . . ? N21 C22 H22 117.7 . . ? C23 C22 H22 117.7 . . ? C22 C23 C24 117.0(2) . . ? C22 C23 H23 121.5 . . ? C24 C23 H23 121.5 . . ? C23 C24 C25 120.1(2) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C20 C25 C24 119.4(2) . . ? C20 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C29 C28 C33 118.08(19) . . ? C29 C28 N27 122.17(19) . . ? C33 C28 N27 119.75(19) . . ? C30 C29 C28 120.95(19) . . ? C30 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? C29 C30 C31 121.0(2) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C32 C31 C30 118.3(2) . . ? C32 C31 H31 120.8 . . ? C30 C31 H31 120.8 . . ? C31 C32 C33 121.5(2) . . ? C31 C32 H32 119.2 . . ? C33 C32 H32 119.2 . . ? C32 C33 C28 120.1(2) . . ? C32 C33 H33 120.0 . . ? C28 C33 H33 120.0 . . ? C35 C34 C39 119.8(2) . . ? C35 C34 N27 120.1(2) . . ? C39 C34 N27 120.0(2) . . ? C34 C35 C36 119.1(3) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 120.4 . . ? C37 C36 C35 122.2(3) . . ? C37 C36 H36 118.9 . . ? C35 C36 H36 118.9 . . ? C36 C37 C38 118.4(4) . . ? C36 C37 H37 120.8 . . ? C38 C37 H37 120.8 . . ? C39 C38 C37 120.7(3) . . ? C39 C38 H38 119.6 . . ? C37 C38 H38 119.6 . . ? C34 C39 C38 119.8(3) . . ? C34 C39 H39 120.1 . . ? C38 C39 H39 120.1 . . ? C42 C41 C11 127.94(19) . . ? C42 C41 H41 116.0 . . ? C11 C41 H41 116.0 . . ? C41 C42 C49 120.89(19) . . ? C41 C42 C43 123.44(19) . . ? C49 C42 C43 115.57(19) . . ? C44 C43 C48 118.7(2) . . ? C44 C43 C42 120.7(2) . . ? C48 C43 C42 120.5(2) . . ? C43 C44 C45 120.3(2) . . ? C43 C44 H44 119.8 . . ? C45 C44 H44 119.8 . . ? C46 C45 C44 120.3(3) . . ? C46 C45 H45 119.8 . . ? C44 C45 H45 119.8 . . ? C47 C46 C45 119.9(3) . . ? C47 C46 H46 120.0 . . ? C45 C46 H46 120.0 . . ? C46 C47 C48 119.9(3) . . ? C46 C47 H47 120.0 . . ? C48 C47 H47 120.0 . . ? C47 C48 C43 120.7(2) . . ? C47 C48 H48 119.7 . . ? C43 C48 H48 119.7 . . ? C54 C49 C50 118.6(2) . . ? C54 C49 C42 120.9(2) . . ? C50 C49 C42 120.5(2) . . ? C51 C50 C49 120.2(2) . . ? C51 C50 H50 119.9 . . ? C49 C50 H50 119.9 . . ? C52 C51 C50 119.9(2) . . ? C52 C51 H51 120.1 . . ? C50 C51 H51 120.1 . . ? C51 C52 C53 121.2(2) . . ? C51 C52 H52 119.4 . . ? C53 C52 H52 119.4 . . ? C52 C53 C54 118.2(2) . . ? C52 C53 H53 120.9 . . ? C54 C53 H53 120.9 . . ? C49 C54 C53 121.8(2) . . ? C49 C54 H54 119.1 . . ? C53 C54 H54 119.1 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.192 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.047