# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Suning Wang' 'Hiroshi Fukutani' 'Wen-Li Jia' 'Qin-De Liu' 'Theresa McCormick' 'Michael Motala' 'Ye Tao' 'Rui-Yao Wang' _publ_contact_author_name 'Prof Suning Wang' _publ_contact_author_address ; Chemistry Queen's University Kingston Ontario K7L 3N6 CANADA ; _publ_contact_author_email WANGS@CHEM.QUEENSU.CA _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; Diarylamino Functionalized Pyrene Derivatives for Use in Blue OLEDs and Complex Formation ; data_jia33ta _database_code_depnum_ccdc_archive 'CCDC 244022' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H25 N3' _chemical_formula_weight 523.61 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 22.742(7) _cell_length_b 10.668(3) _cell_length_c 10.704(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.893(6) _cell_angle_gamma 90.00 _cell_volume 2587.3(13) _cell_formula_units_Z 4 _cell_measurement_temperature 180(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 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type 'Psi Scan' _exptl_absorpt_correction_T_min 0.2337 _exptl_absorpt_correction_T_max 0.2838 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 18194 _diffrn_reflns_av_R_equivalents 0.1714 _diffrn_reflns_av_sigmaI/netI 0.3448 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.53 _reflns_number_total 6158 _reflns_number_gt 1577 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0203P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6158 _refine_ls_number_parameters 470 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2406 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 0.679 _refine_ls_restrained_S_all 0.679 _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 0.55950(16) 0.4122(3) 0.1597(3) 0.0295(10) Uani 1 1 d . . . C2 C 0.49894(17) 0.3874(3) 0.1214(3) 0.0268(9) Uani 1 1 d . . . C3 C 0.39496(17) 0.3965(3) 0.1599(3) 0.0281(9) Uani 1 1 d . . . C4 C 0.38263(18) 0.3312(4) 0.0481(4) 0.0339(11) Uani 1 1 d . . . H4 H 0.3408(13) 0.316(3) 0.031(3) 0.042(11) Uiso 1 1 d . . . C5 C 0.42618(19) 0.2977(3) -0.0270(4) 0.0341(11) Uani 1 1 d . . . H5 H 0.4168(12) 0.256(2) -0.108(3) 0.027(10) Uiso 1 1 d . . . C6 C 0.48445(16) 0.3229(3) 0.0084(3) 0.0279(9) Uani 1 1 d . . . C7 C 0.53067(19) 0.2826(4) -0.0632(4) 0.0320(10) Uani 1 1 d . . . H7 H 0.5182(12) 0.238(2) -0.137(3) 0.017(9) Uiso 1 1 d . . . C8 C 0.58687(19) 0.3020(4) -0.0265(4) 0.0344(11) Uani 1 1 d . . . H8 H 0.6153(13) 0.276(3) -0.075(3) 0.029(11) Uiso 1 1 d . . . C9 C 0.60374(17) 0.3683(3) 0.0853(4) 0.0329(10) Uani 1 1 d . . . C10 C 0.66237(18) 0.3945(4) 0.1246(4) 0.0391(11) Uani 1 1 d . . . H10 H 0.6943(14) 0.359(3) 0.070(3) 0.048(12) Uiso 1 1 d . . . C11 C 0.6769(2) 0.4579(4) 0.2344(4) 0.0444(12) Uani 1 1 d . . . H11 H 0.7198(15) 0.470(3) 0.255(3) 0.055(13) Uiso 1 1 d . . . C12 C 0.6342(2) 0.5005(4) 0.3048(4) 0.0447(12) Uani 1 1 d . . . H12 H 0.6428(11) 0.551(2) 0.383(3) 0.018(9) Uiso 1 1 d . . . C13 C 0.57490(17) 0.4800(3) 0.2693(4) 0.0317(10) Uani 1 1 d . . . C14 C 0.5295(2) 0.5212(4) 0.3406(4) 0.0393(12) Uani 1 1 d . . . H14 H 0.5390(14) 0.573(3) 0.413(3) 0.043(11) Uiso 1 1 d . . . C15 C 0.47212(18) 0.4978(3) 0.3083(4) 0.0333(11) Uani 1 1 d . . . H15 H 0.4394(12) 0.528(3) 0.360(3) 0.031(10) Uiso 1 1 d . . . C16 C 0.45412(17) 0.4285(3) 0.1957(3) 0.0316(10) Uani 1 1 d . . . C17 C 0.34653(16) 0.4258(4) 0.2372(3) 0.0299(10) Uani 1 1 d . . . C18 C 0.30946(17) 0.3307(4) 0.2716(3) 0.0310(10) Uani 1 1 d . . . H18 H 0.3145(12) 0.247(3) 0.238(3) 0.032(11) Uiso 1 1 d . . . C19 C 0.26520(17) 0.3518(4) 0.3498(4) 0.0337(10) Uani 1 1 d . . . H19 H 0.2417(12) 0.284(3) 0.367(2) 0.017(10) Uiso 1 1 d . . . C20 C 0.25712(16) 0.4700(4) 0.3983(3) 0.0289(10) Uani 1 1 d . . . C21 C 0.29238(17) 0.5651(4) 0.3599(4) 0.0364(10) Uani 1 1 d . . . H21 H 0.2884(12) 0.653(3) 0.393(3) 0.028(10) Uiso 1 1 d . . . C22 C 0.33636(18) 0.5442(4) 0.2828(4) 0.0345(10) Uani 1 1 d . . . H22 H 0.3613(14) 0.610(3) 0.255(3) 0.042(12) Uiso 1 1 d . . . C23 C 0.21346(16) 0.4950(4) 0.4892(3) 0.0308(10) Uani 1 1 d . . . C24 C 0.18730(18) 0.6117(4) 0.4972(4) 0.0392(11) Uani 1 1 d . . . H24 H 0.1965(13) 0.677(3) 0.441(3) 0.028(10) Uiso 1 1 d . . . C25 C 0.15140(18) 0.6395(4) 0.5907(4) 0.0390(11) Uani 1 1 d . . . H25 H 0.1346(14) 0.719(3) 0.593(3) 0.046(12) Uiso 1 1 d . . . C26 C 0.14007(15) 0.5505(4) 0.6778(3) 0.0331(10) Uani 1 1 d . . . C27 C 0.16305(16) 0.4311(4) 0.6697(4) 0.0347(10) Uani 1 1 d . . . H27 H 0.1537(13) 0.365(3) 0.732(3) 0.042(11) Uiso 1 1 d . . . C28 C 0.19980(16) 0.4048(4) 0.5758(4) 0.0319(10) Uani 1 1 d . . . H28 H 0.2182(13) 0.316(3) 0.577(3) 0.050(12) Uiso 1 1 d . . . C29 C 0.04688(16) 0.6373(4) 0.7343(3) 0.0320(10) Uani 1 1 d . . . C30 C 0.02562(18) 0.7395(4) 0.7927(4) 0.0361(11) Uani 1 1 d . . . H30 H 0.0482(12) 0.776(2) 0.871(3) 0.024(9) Uiso 1 1 d . . . C31 C -0.02784(18) 0.7884(4) 0.7472(4) 0.0386(11) Uani 1 1 d . . . H31 H -0.0441(14) 0.876(3) 0.780(3) 0.052(12) Uiso 1 1 d . . . C32 C -0.05832(19) 0.7309(4) 0.6458(4) 0.0389(11) Uani 1 1 d . . . H32 H -0.0966(15) 0.769(3) 0.603(3) 0.074(15) Uiso 1 1 d . . . C33 C -0.03345(17) 0.6302(4) 0.5931(4) 0.0353(10) Uani 1 1 d . . . H33 H -0.0517(14) 0.584(3) 0.510(3) 0.058(12) Uiso 1 1 d . . . C34 C 0.11769(18) 0.5520(3) 0.8991(3) 0.0340(10) Uani 1 1 d . . . C35 C 0.1745(2) 0.5352(5) 0.9384(5) 0.0376(14) Uani 1 1 d . . . H35 H 0.1925(14) 0.545(4) 0.907(3) 0.010(14) Uiso 1 1 d . . . C36 C 0.1880(2) 0.5015(5) 1.0589(5) 0.0566(14) Uani 1 1 d . . . H36 H 0.2299(14) 0.493(3) 1.082(3) 0.063(14) Uiso 1 1 d . . . C37 C 0.1465(2) 0.4888(5) 1.1409(5) 0.0556(14) Uani 1 1 d . . . H37 H 0.1549(19) 0.455(4) 1.215(4) 0.10(2) Uiso 1 1 d . . . C38 C 0.0893(2) 0.5091(4) 1.0992(4) 0.0460(12) Uani 1 1 d . . . H38 H 0.0534(15) 0.499(3) 1.152(3) 0.062(13) Uiso 1 1 d . . . N1 N 0.01850(13) 0.5795(3) 0.6361(3) 0.0354(9) Uani 1 1 d . . . N2 N 0.07267(15) 0.5405(3) 0.9754(3) 0.0525(10) Uani 1 1 d . . . N3 N 0.10225(13) 0.5816(3) 0.7729(3) 0.0341(8) 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 0.031(3) 0.030(2) 0.028(2) 0.0039(18) 0.003(2) -0.001(2) C2 0.033(3) 0.021(2) 0.025(2) 0.0036(17) -0.0020(19) -0.0012(19) C3 0.033(2) 0.024(2) 0.027(2) 0.0025(18) 0.000(2) 0.002(2) C4 0.027(3) 0.041(3) 0.033(3) 0.006(2) -0.002(2) -0.001(2) C5 0.041(3) 0.033(3) 0.028(3) -0.003(2) 0.001(2) -0.002(2) C6 0.030(3) 0.027(2) 0.026(2) 0.0046(18) -0.001(2) -0.001(2) C7 0.041(3) 0.027(2) 0.029(3) -0.0004(19) 0.003(2) -0.007(2) C8 0.033(3) 0.035(3) 0.037(3) -0.001(2) 0.012(2) 0.001(2) C9 0.031(3) 0.026(2) 0.041(3) 0.008(2) 0.000(2) -0.006(2) C10 0.031(3) 0.036(3) 0.051(3) 0.007(2) 0.007(2) 0.000(2) C11 0.034(3) 0.046(3) 0.053(3) 0.005(2) 0.000(3) -0.002(3) C12 0.050(3) 0.045(3) 0.038(3) -0.005(2) -0.007(3) -0.010(3) C13 0.029(3) 0.030(2) 0.036(3) 0.0012(19) -0.002(2) -0.005(2) C14 0.049(3) 0.035(3) 0.033(3) -0.005(2) -0.005(2) -0.005(2) C15 0.037(3) 0.032(3) 0.031(3) -0.0056(19) 0.000(2) 0.001(2) C16 0.042(3) 0.028(2) 0.024(2) 0.0049(18) -0.001(2) 0.001(2) C17 0.030(3) 0.032(3) 0.027(2) 0.0045(19) 0.0004(19) -0.001(2) C18 0.028(3) 0.038(3) 0.026(2) -0.005(2) -0.0036(19) 0.004(2) C19 0.029(3) 0.032(3) 0.040(3) 0.004(2) 0.000(2) -0.006(2) C20 0.027(2) 0.035(3) 0.025(2) 0.0040(19) 0.0010(18) 0.003(2) C21 0.036(3) 0.032(3) 0.041(3) 0.000(2) 0.003(2) 0.004(2) C22 0.033(3) 0.030(3) 0.041(3) 0.000(2) 0.008(2) -0.002(2) C23 0.026(2) 0.035(3) 0.031(2) -0.0014(19) -0.0016(19) 0.001(2) C24 0.039(3) 0.043(3) 0.036(3) 0.007(2) 0.007(2) 0.006(2) C25 0.040(3) 0.034(3) 0.043(3) 0.008(2) 0.006(2) 0.009(2) C26 0.023(2) 0.046(3) 0.030(2) -0.001(2) -0.0001(19) 0.005(2) C27 0.025(2) 0.037(3) 0.042(3) 0.006(2) 0.001(2) -0.001(2) C28 0.021(2) 0.036(3) 0.038(3) 0.000(2) -0.002(2) 0.002(2) C29 0.028(2) 0.039(3) 0.029(2) -0.001(2) 0.0036(19) 0.004(2) C30 0.042(3) 0.036(3) 0.030(3) -0.011(2) 0.000(2) -0.001(2) C31 0.035(3) 0.031(3) 0.050(3) -0.008(2) 0.002(2) 0.004(2) C32 0.033(3) 0.043(3) 0.040(3) -0.004(2) 0.001(2) 0.006(2) C33 0.034(3) 0.041(3) 0.030(3) 0.003(2) -0.004(2) 0.005(2) C34 0.032(3) 0.044(3) 0.026(2) -0.001(2) 0.003(2) 0.000(2) C35 0.016(3) 0.063(4) 0.034(3) 0.006(2) 0.002(3) -0.003(3) C36 0.032(3) 0.087(4) 0.049(3) -0.001(3) -0.007(3) 0.015(3) C37 0.055(4) 0.071(4) 0.040(3) 0.008(3) -0.001(3) 0.004(3) C38 0.042(3) 0.061(3) 0.036(3) 0.005(2) 0.007(3) -0.004(3) N1 0.032(2) 0.040(2) 0.033(2) -0.0060(17) -0.0032(17) 0.0039(17) N2 0.052(3) 0.056(3) 0.050(2) 0.002(2) 0.010(2) -0.004(2) N3 0.029(2) 0.050(2) 0.0233(18) -0.0021(16) 0.0030(16) 0.0112(17) _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 C13 1.397(5) . ? C1 C9 1.415(4) . ? C1 C2 1.428(4) . ? C2 C6 1.406(4) . ? C2 C16 1.415(5) . ? C3 C4 1.393(5) . ? C3 C16 1.409(5) . ? C3 C17 1.466(5) . ? C4 C5 1.375(5) . ? C5 C6 1.373(4) . ? C6 C7 1.420(5) . ? C7 C8 1.321(5) . ? C8 C9 1.416(5) . ? C9 C10 1.391(5) . ? C10 C11 1.373(5) . ? C11 C12 1.357(5) . ? C12 C13 1.388(5) . ? C13 C14 1.406(5) . ? C14 C15 1.345(5) . ? C15 C16 1.443(5) . ? C17 C22 1.381(5) . ? C17 C18 1.388(5) . ? C18 C19 1.381(5) . ? C19 C20 1.381(5) . ? C20 C21 1.378(4) . ? C20 C23 1.472(4) . ? C21 C22 1.368(5) . ? C23 C24 1.385(5) . ? C23 C28 1.390(4) . ? C24 C25 1.377(5) . ? C25 C26 1.370(5) . ? C26 C27 1.382(5) . ? C26 N3 1.427(4) . ? C27 C28 1.389(5) . ? C29 N1 1.336(4) . ? C29 C30 1.365(4) . ? C29 N3 1.422(4) . ? C30 C31 1.373(5) . ? C31 C32 1.381(5) . ? C32 C33 1.358(5) . ? C33 N1 1.344(4) . ? C34 C35 1.336(6) . ? C34 N2 1.368(4) . ? C34 N3 1.402(4) . ? C35 C36 1.348(6) . ? C36 C37 1.349(6) . ? C37 C38 1.356(5) . ? C38 N2 1.388(5) . ? 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 C13 C1 C9 120.3(4) . . ? C13 C1 C2 120.2(4) . . ? C9 C1 C2 119.5(4) . . ? C6 C2 C16 120.5(4) . . ? C6 C2 C1 119.2(4) . . ? C16 C2 C1 120.3(4) . . ? C4 C3 C16 118.2(4) . . ? C4 C3 C17 119.0(4) . . ? C16 C3 C17 122.8(3) . . ? C5 C4 C3 122.0(4) . . ? C6 C5 C4 120.9(4) . . ? C5 C6 C2 118.9(4) . . ? C5 C6 C7 122.2(4) . . ? C2 C6 C7 118.9(4) . . ? C8 C7 C6 122.3(4) . . ? C7 C8 C9 121.0(4) . . ? C10 C9 C1 118.2(4) . . ? C10 C9 C8 122.6(4) . . ? C1 C9 C8 119.1(4) . . ? C11 C10 C9 120.8(4) . . ? C12 C11 C10 120.6(5) . . ? C11 C12 C13 121.3(4) . . ? C12 C13 C1 118.7(4) . . ? C12 C13 C14 122.9(4) . . ? C1 C13 C14 118.3(4) . . ? C15 C14 C13 122.9(4) . . ? C14 C15 C16 120.7(4) . . ? C3 C16 C2 119.3(3) . . ? C3 C16 C15 123.2(4) . . ? C2 C16 C15 117.5(4) . . ? C22 C17 C18 116.8(4) . . ? C22 C17 C3 123.4(4) . . ? C18 C17 C3 119.8(4) . . ? C19 C18 C17 122.1(4) . . ? C18 C19 C20 120.2(4) . . ? C21 C20 C19 117.4(4) . . ? C21 C20 C23 120.4(4) . . ? C19 C20 C23 122.2(4) . . ? C22 C21 C20 122.3(4) . . ? C21 C22 C17 121.0(4) . . ? C24 C23 C28 117.3(4) . . ? C24 C23 C20 121.4(4) . . ? C28 C23 C20 121.1(4) . . ? C25 C24 C23 121.6(4) . . ? C26 C25 C24 120.2(4) . . ? C25 C26 C27 120.1(4) . . ? C25 C26 N3 119.0(4) . . ? C27 C26 N3 120.9(4) . . ? C26 C27 C28 119.1(4) . . ? C27 C28 C23 121.6(4) . . ? N1 C29 C30 124.2(4) . . ? N1 C29 N3 113.1(3) . . ? C30 C29 N3 122.7(4) . . ? C29 C30 C31 118.6(4) . . ? C30 C31 C32 118.7(4) . . ? C33 C32 C31 118.6(4) . . ? N1 C33 C32 124.1(4) . . ? C35 C34 N2 123.5(4) . . ? C35 C34 N3 119.3(4) . . ? N2 C34 N3 117.1(4) . . ? C34 C35 C36 118.2(5) . . ? C35 C36 C37 122.2(5) . . ? C36 C37 C38 118.4(5) . . ? C37 C38 N2 121.8(5) . . ? C29 N1 C33 115.8(3) . . ? C34 N2 C38 115.8(4) . . ? C34 N3 C29 121.2(3) . . ? C34 N3 C26 121.2(3) . . ? C29 N3 C26 117.5(3) . . ? 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 C13 C1 C2 C6 177.8(3) . . . . ? C9 C1 C2 C6 -1.9(5) . . . . ? C13 C1 C2 C16 -1.5(5) . . . . ? C9 C1 C2 C16 178.8(3) . . . . ? C16 C3 C4 C5 0.0(6) . . . . ? C17 C3 C4 C5 -178.1(4) . . . . ? C3 C4 C5 C6 2.8(6) . . . . ? C4 C5 C6 C2 -2.0(5) . . . . ? C4 C5 C6 C7 176.0(4) . . . . ? C16 C2 C6 C5 -1.7(5) . . . . ? C1 C2 C6 C5 179.0(3) . . . . ? C16 C2 C6 C7 -179.7(3) . . . . ? C1 C2 C6 C7 1.0(5) . . . . ? C5 C6 C7 C8 -177.0(4) . . . . ? C2 C6 C7 C8 1.0(6) . . . . ? C6 C7 C8 C9 -2.1(6) . . . . ? C13 C1 C9 C10 0.0(5) . . . . ? C2 C1 C9 C10 179.7(3) . . . . ? C13 C1 C9 C8 -178.8(4) . . . . ? C2 C1 C9 C8 0.8(5) . . . . ? C7 C8 C9 C10 -177.6(4) . . . . ? C7 C8 C9 C1 1.2(6) . . . . ? C1 C9 C10 C11 1.9(6) . . . . ? C8 C9 C10 C11 -179.3(4) . . . . ? C9 C10 C11 C12 -2.4(6) . . . . ? C10 C11 C12 C13 0.9(6) . . . . ? C11 C12 C13 C1 1.0(6) . . . . ? C11 C12 C13 C14 179.1(4) . . . . ? C9 C1 C13 C12 -1.5(5) . . . . ? C2 C1 C13 C12 178.9(3) . . . . ? C9 C1 C13 C14 -179.6(3) . . . . ? C2 C1 C13 C14 0.7(5) . . . . ? C12 C13 C14 C15 -177.8(4) . . . . ? C1 C13 C14 C15 0.3(6) . . . . ? C13 C14 C15 C16 -0.4(6) . . . . ? C4 C3 C16 C2 -3.6(5) . . . . ? C17 C3 C16 C2 174.5(3) . . . . ? C4 C3 C16 C15 179.0(3) . . . . ? C17 C3 C16 C15 -3.0(5) . . . . ? C6 C2 C16 C3 4.4(5) . . . . ? C1 C2 C16 C3 -176.3(3) . . . . ? C6 C2 C16 C15 -177.9(3) . . . . ? C1 C2 C16 C15 1.3(5) . . . . ? C14 C15 C16 C3 177.1(4) . . . . ? C14 C15 C16 C2 -0.4(5) . . . . ? C4 C3 C17 C22 -129.8(4) . . . . ? C16 C3 C17 C22 52.2(5) . . . . ? C4 C3 C17 C18 52.6(5) . . . . ? C16 C3 C17 C18 -125.5(4) . . . . ? C22 C17 C18 C19 -1.4(6) . . . . ? C3 C17 C18 C19 176.4(3) . . . . ? C17 C18 C19 C20 -1.0(6) . . . . ? C18 C19 C20 C21 3.6(5) . . . . ? C18 C19 C20 C23 -175.4(3) . . . . ? C19 C20 C21 C22 -3.9(6) . . . . ? C23 C20 C21 C22 175.2(4) . . . . ? C20 C21 C22 C17 1.5(6) . . . . ? C18 C17 C22 C21 1.1(6) . . . . ? C3 C17 C22 C21 -176.6(4) . . . . ? C21 C20 C23 C24 29.1(6) . . . . ? C19 C20 C23 C24 -151.9(4) . . . . ? C21 C20 C23 C28 -146.6(4) . . . . ? C19 C20 C23 C28 32.4(5) . . . . ? C28 C23 C24 C25 3.0(6) . . . . ? C20 C23 C24 C25 -172.9(4) . . . . ? C23 C24 C25 C26 -0.9(7) . . . . ? C24 C25 C26 C27 -2.2(6) . . . . ? C24 C25 C26 N3 -179.4(4) . . . . ? C25 C26 C27 C28 2.9(6) . . . . ? N3 C26 C27 C28 -179.9(3) . . . . ? C26 C27 C28 C23 -0.7(6) . . . . ? C24 C23 C28 C27 -2.2(6) . . . . ? C20 C23 C28 C27 173.7(4) . . . . ? N1 C29 C30 C31 -1.2(6) . . . . ? N3 C29 C30 C31 178.8(4) . . . . ? C29 C30 C31 C32 1.1(6) . . . . ? C30 C31 C32 C33 -1.7(6) . . . . ? C31 C32 C33 N1 2.4(6) . . . . ? N2 C34 C35 C36 2.0(8) . . . . ? N3 C34 C35 C36 -177.2(4) . . . . ? C34 C35 C36 C37 -2.4(8) . . . . ? C35 C36 C37 C38 1.0(8) . . . . ? C36 C37 C38 N2 0.8(7) . . . . ? C30 C29 N1 C33 1.8(5) . . . . ? N3 C29 N1 C33 -178.2(3) . . . . ? C32 C33 N1 C29 -2.4(6) . . . . ? C35 C34 N2 C38 -0.2(6) . . . . ? N3 C34 N2 C38 179.0(3) . . . . ? C37 C38 N2 C34 -1.2(6) . . . . ? C35 C34 N3 C29 -160.4(4) . . . . ? N2 C34 N3 C29 20.3(5) . . . . ? C35 C34 N3 C26 23.1(6) . . . . ? N2 C34 N3 C26 -156.1(3) . . . . ? N1 C29 N3 C34 -130.9(3) . . . . ? C30 C29 N3 C34 49.2(5) . . . . ? N1 C29 N3 C26 45.7(5) . . . . ? C30 C29 N3 C26 -134.3(4) . . . . ? C25 C26 N3 C34 -133.4(4) . . . . ? C27 C26 N3 C34 49.4(5) . . . . ? C25 C26 N3 C29 50.0(5) . . . . ? C27 C26 N3 C29 -127.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 28.53 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.221 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.053 data_jia6a _database_code_depnum_ccdc_archive 'CCDC 244023' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H21 N3' _chemical_formula_weight 447.52 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 14.192(3) _cell_length_b 14.734(3) _cell_length_c 10.8767(19) _cell_angle_alpha 90.00 _cell_angle_beta 97.973(4) _cell_angle_gamma 90.00 _cell_volume 2252.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 301(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type 'Empirical (Buker SADABS)' _exptl_absorpt_correction_T_min 0.8221 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 301(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 15950 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 28.32 _reflns_number_total 5349 _reflns_number_gt 3000 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0489P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5349 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 0.873 _refine_ls_restrained_S_all 0.873 _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 0.47009(7) 0.16433(7) 0.12734(9) 0.0527(3) Uani 1 1 d . . . N2 N 0.32224(8) 0.09337(7) 0.11659(9) 0.0531(3) Uani 1 1 d . . . N3 N 0.45531(8) 0.32088(7) 0.12017(9) 0.0588(3) Uani 1 1 d . . . C1 C 0.84691(8) 0.19050(8) 0.39623(11) 0.0442(3) Uani 1 1 d . . . C2 C 0.90256(9) 0.26320(9) 0.36741(12) 0.0571(4) Uani 1 1 d . . . H2B H 0.8777 0.3035 0.3054 0.069 Uiso 1 1 calc R . . C3 C 0.99336(10) 0.27736(10) 0.42794(13) 0.0639(4) Uani 1 1 d . . . H3B H 1.0281 0.3269 0.4061 0.077 Uiso 1 1 calc R . . C4 C 1.03385(9) 0.21908(10) 0.52077(12) 0.0544(3) Uani 1 1 d . . . C5 C 1.12956(10) 0.23061(11) 0.58317(14) 0.0691(4) Uani 1 1 d . . . H5A H 1.1661 0.2789 0.5615 0.083 Uiso 1 1 calc R . . C6 C 1.16654(10) 0.17305(12) 0.67157(15) 0.0728(5) Uani 1 1 d . . . H6A H 1.2288 0.1820 0.7093 0.087 Uiso 1 1 calc R . . C7 C 1.11399(10) 0.09833(11) 0.71012(12) 0.0604(4) Uani 1 1 d . . . C8 C 1.15010(11) 0.03882(13) 0.80556(14) 0.0743(5) Uani 1 1 d . . . H8A H 1.2115 0.0476 0.8464 0.089 Uiso 1 1 calc R . . C9 C 1.09697(12) -0.03229(12) 0.84025(14) 0.0774(5) Uani 1 1 d . . . H9A H 1.1220 -0.0699 0.9054 0.093 Uiso 1 1 calc R . . C10 C 1.00684(11) -0.04819(10) 0.77910(12) 0.0668(4) Uani 1 1 d . . . H10A H 0.9719 -0.0971 0.8025 0.080 Uiso 1 1 calc R . . C11 C 0.96718(9) 0.00836(9) 0.68225(11) 0.0514(3) Uani 1 1 d . . . C12 C 0.87665(9) -0.00828(9) 0.61204(11) 0.0526(3) Uani 1 1 d . . . H12A H 0.8426 -0.0594 0.6299 0.063 Uiso 1 1 calc R . . C13 C 0.83870(8) 0.04770(8) 0.52044(11) 0.0463(3) Uani 1 1 d . . . H13A H 0.7799 0.0333 0.4759 0.056 Uiso 1 1 calc R . . C14 C 0.88598(8) 0.12866(8) 0.48949(10) 0.0415(3) Uani 1 1 d . . . C15 C 1.01957(8) 0.08362(9) 0.64886(11) 0.0486(3) Uani 1 1 d . . . C16 C 0.97950(8) 0.14433(8) 0.55293(11) 0.0457(3) Uani 1 1 d . . . C17 C 0.74887(8) 0.18102(8) 0.32804(10) 0.0421(3) Uani 1 1 d . . . C18 C 0.73099(9) 0.19713(8) 0.19983(11) 0.0514(3) Uani 1 1 d . . . H18A H 0.7813 0.2121 0.1573 0.062 Uiso 1 1 calc R . . C19 C 0.64026(9) 0.19117(9) 0.13556(12) 0.0520(3) Uani 1 1 d . . . H19A H 0.6305 0.2014 0.0504 0.062 Uiso 1 1 calc R . . C20 C 0.56401(9) 0.17027(8) 0.19605(11) 0.0450(3) Uani 1 1 d . . . C21 C 0.57992(8) 0.15562(8) 0.32224(11) 0.0459(3) Uani 1 1 d . . . H21A H 0.5289 0.1424 0.3645 0.055 Uiso 1 1 calc R . . C22 C 0.67068(8) 0.16032(8) 0.38680(11) 0.0436(3) Uani 1 1 d . . . H22A H 0.6797 0.1493 0.4718 0.052 Uiso 1 1 calc R . . C23 C 0.41657(9) 0.08436(8) 0.13234(10) 0.0472(3) Uani 1 1 d . . . C24 C 0.46195(10) 0.00112(9) 0.15334(11) 0.0579(4) Uani 1 1 d . . . H24A H 0.5279 -0.0031 0.1610 0.069 Uiso 1 1 calc R . . C25 C 0.40738(13) -0.07434(10) 0.16253(13) 0.0745(5) Uani 1 1 d . . . H25A H 0.4359 -0.1307 0.1786 0.089 Uiso 1 1 calc R . . C26 C 0.30953(13) -0.06615(11) 0.14781(13) 0.0772(5) Uani 1 1 d . . . H26A H 0.2709 -0.1165 0.1540 0.093 Uiso 1 1 calc R . . C27 C 0.27140(10) 0.01770(11) 0.12404(12) 0.0642(4) Uani 1 1 d . . . H27A H 0.2054 0.0228 0.1122 0.077 Uiso 1 1 calc R . . C28 C 0.43008(8) 0.24255(8) 0.06533(11) 0.0457(3) Uani 1 1 d . . . C29 C 0.37172(9) 0.23698(9) -0.04676(11) 0.0533(3) Uani 1 1 d . . . H29A H 0.3560 0.1809 -0.0833 0.064 Uiso 1 1 calc R . . C30 C 0.33729(9) 0.31554(10) -0.10320(12) 0.0567(4) Uani 1 1 d . . . H30A H 0.2971 0.3134 -0.1784 0.068 Uiso 1 1 calc R . . C31 C 0.36231(9) 0.39729(9) -0.04839(12) 0.0553(3) Uani 1 1 d . . . H31A H 0.3398 0.4515 -0.0851 0.066 Uiso 1 1 calc R . . C32 C 0.42106(10) 0.39662(9) 0.06112(12) 0.0617(4) Uani 1 1 d . . . H32A H 0.4388 0.4522 0.0978 0.074 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 0.0481(6) 0.0416(6) 0.0621(7) 0.0087(5) -0.0151(5) -0.0030(5) N2 0.0500(7) 0.0520(7) 0.0540(6) -0.0012(5) -0.0044(5) -0.0074(5) N3 0.0713(8) 0.0436(7) 0.0559(7) -0.0009(5) -0.0112(6) 0.0039(6) C1 0.0372(7) 0.0463(8) 0.0485(7) -0.0011(5) 0.0043(6) 0.0009(6) C2 0.0500(8) 0.0566(9) 0.0644(8) 0.0086(7) 0.0063(7) -0.0055(7) C3 0.0516(9) 0.0615(10) 0.0795(10) 0.0014(8) 0.0119(8) -0.0174(7) C4 0.0405(7) 0.0592(9) 0.0628(8) -0.0099(7) 0.0050(6) -0.0073(7) C5 0.0430(8) 0.0785(11) 0.0850(11) -0.0188(9) 0.0054(8) -0.0152(8) C6 0.0408(8) 0.0923(13) 0.0804(11) -0.0277(9) -0.0091(8) -0.0039(8) C7 0.0441(8) 0.0751(10) 0.0587(8) -0.0217(7) -0.0046(7) 0.0096(8) C8 0.0549(9) 0.0962(13) 0.0636(9) -0.0206(9) -0.0201(8) 0.0234(9) C9 0.0782(12) 0.0835(13) 0.0638(10) -0.0030(9) -0.0137(9) 0.0278(10) C10 0.0688(10) 0.0688(10) 0.0603(9) 0.0046(7) -0.0001(8) 0.0172(8) C11 0.0494(8) 0.0548(9) 0.0488(7) -0.0037(6) 0.0028(6) 0.0111(7) C12 0.0457(8) 0.0525(8) 0.0590(8) 0.0040(6) 0.0050(6) 0.0023(6) C13 0.0359(7) 0.0496(8) 0.0521(7) -0.0008(6) 0.0016(6) 0.0000(6) C14 0.0338(6) 0.0456(7) 0.0448(6) -0.0062(5) 0.0042(5) 0.0011(5) C15 0.0394(7) 0.0596(9) 0.0453(7) -0.0133(6) -0.0002(6) 0.0092(6) C16 0.0361(7) 0.0530(8) 0.0475(7) -0.0107(6) 0.0044(6) 0.0011(6) C17 0.0395(7) 0.0379(7) 0.0479(7) 0.0006(5) 0.0027(6) 0.0033(5) C18 0.0476(8) 0.0551(9) 0.0516(7) 0.0074(6) 0.0075(6) 0.0014(6) C19 0.0562(9) 0.0536(9) 0.0435(7) 0.0074(6) -0.0029(6) 0.0003(6) C20 0.0439(7) 0.0368(7) 0.0508(7) 0.0035(5) -0.0061(6) 0.0021(6) C21 0.0382(7) 0.0463(8) 0.0522(7) 0.0028(6) 0.0024(6) 0.0025(6) C22 0.0421(7) 0.0460(8) 0.0419(6) 0.0013(5) 0.0026(6) 0.0042(6) C23 0.0544(8) 0.0415(8) 0.0418(7) 0.0003(5) -0.0072(6) -0.0024(6) C24 0.0650(9) 0.0463(9) 0.0568(8) 0.0010(6) -0.0114(7) 0.0022(7) C25 0.1038(13) 0.0417(9) 0.0682(10) 0.0044(7) -0.0226(9) -0.0033(9) C26 0.0950(13) 0.0574(11) 0.0726(10) 0.0093(8) -0.0118(9) -0.0285(9) C27 0.0627(9) 0.0697(11) 0.0573(8) 0.0007(7) -0.0013(7) -0.0191(8) C28 0.0419(7) 0.0427(8) 0.0496(7) 0.0041(6) -0.0041(6) 0.0010(6) C29 0.0534(8) 0.0474(8) 0.0539(8) 0.0029(6) -0.0114(6) -0.0060(6) C30 0.0474(8) 0.0624(9) 0.0559(8) 0.0122(7) -0.0087(6) -0.0020(7) C31 0.0482(8) 0.0518(9) 0.0645(9) 0.0125(7) 0.0033(7) 0.0139(7) C32 0.0775(10) 0.0421(8) 0.0629(9) -0.0037(6) 0.0000(8) 0.0082(7) _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 C23 1.4070(15) . ? N1 C28 1.4140(15) . ? N1 C20 1.4376(15) . ? N2 C23 1.3324(15) . ? N2 C27 1.3365(17) . ? N3 C28 1.3254(15) . ? N3 C32 1.3444(16) . ? C1 C2 1.3922(17) . ? C1 C14 1.4179(16) . ? C1 C17 1.4897(16) . ? C2 C3 1.3791(17) . ? C3 C4 1.3878(18) . ? C4 C16 1.4161(18) . ? C4 C5 1.4418(17) . ? C5 C6 1.334(2) . ? C6 C7 1.425(2) . ? C7 C8 1.400(2) . ? C7 C15 1.4280(17) . ? C8 C9 1.374(2) . ? C9 C10 1.3774(19) . ? C10 C11 1.3986(17) . ? C11 C15 1.4104(18) . ? C11 C12 1.4219(17) . ? C12 C13 1.3468(16) . ? C13 C14 1.4315(16) . ? C14 C16 1.4272(15) . ? C15 C16 1.4309(17) . ? C17 C22 1.3892(16) . ? C17 C18 1.4025(16) . ? C18 C19 1.3801(17) . ? C19 C20 1.3769(17) . ? C20 C21 1.3768(16) . ? C21 C22 1.3806(15) . ? C23 C24 1.3893(17) . ? C24 C25 1.3665(19) . ? C25 C26 1.381(2) . ? C26 C27 1.359(2) . ? C28 C29 1.3780(16) . ? C29 C30 1.3683(17) . ? C30 C31 1.3688(18) . ? C31 C32 1.3558(17) . ? 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 C23 N1 C28 121.19(10) . . ? C23 N1 C20 119.83(9) . . ? C28 N1 C20 118.71(10) . . ? C23 N2 C27 116.76(12) . . ? C28 N3 C32 116.78(11) . . ? C2 C1 C14 118.54(11) . . ? C2 C1 C17 118.67(11) . . ? C14 C1 C17 122.79(11) . . ? C3 C2 C1 122.04(13) . . ? C2 C3 C4 121.26(13) . . ? C3 C4 C16 118.43(12) . . ? C3 C4 C5 122.52(13) . . ? C16 C4 C5 119.03(13) . . ? C6 C5 C4 121.01(14) . . ? C5 C6 C7 122.25(14) . . ? C8 C7 C6 123.31(14) . . ? C8 C7 C15 118.30(15) . . ? C6 C7 C15 118.39(13) . . ? C9 C8 C7 121.51(14) . . ? C8 C9 C10 120.36(14) . . ? C9 C10 C11 120.80(15) . . ? C10 C11 C15 119.40(12) . . ? C10 C11 C12 122.75(13) . . ? C15 C11 C12 117.81(11) . . ? C13 C12 C11 122.04(13) . . ? C12 C13 C14 122.13(11) . . ? C1 C14 C16 119.15(11) . . ? C1 C14 C13 123.65(10) . . ? C16 C14 C13 117.12(11) . . ? C11 C15 C7 119.55(12) . . ? C11 C15 C16 120.59(11) . . ? C7 C15 C16 119.85(13) . . ? C4 C16 C14 120.55(11) . . ? C4 C16 C15 119.43(11) . . ? C14 C16 C15 120.02(12) . . ? C22 C17 C18 116.66(11) . . ? C22 C17 C1 122.82(11) . . ? C18 C17 C1 120.46(11) . . ? C19 C18 C17 121.35(12) . . ? C20 C19 C18 120.80(12) . . ? C21 C20 C19 118.71(11) . . ? C21 C20 N1 121.38(12) . . ? C19 C20 N1 119.91(11) . . ? C20 C21 C22 120.77(12) . . ? C21 C22 C17 121.70(11) . . ? N2 C23 C24 122.93(12) . . ? N2 C23 N1 116.72(11) . . ? C24 C23 N1 120.35(12) . . ? C25 C24 C23 118.41(14) . . ? C24 C25 C26 119.44(14) . . ? C27 C26 C25 117.96(14) . . ? N2 C27 C26 124.46(14) . . ? N3 C28 C29 122.80(11) . . ? N3 C28 N1 115.44(10) . . ? C29 C28 N1 121.72(11) . . ? C30 C29 C28 118.68(12) . . ? C29 C30 C31 119.61(12) . . ? C32 C31 C30 117.83(12) . . ? N3 C32 C31 124.28(13) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.136 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.026 data_jia7 _database_code_depnum_ccdc_archive 'CCDC 244024' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H17 N3' _chemical_formula_weight 371.43 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.697(2) _cell_length_b 7.5019(16) _cell_length_c 15.027(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.327(3) _cell_angle_gamma 90.00 _cell_volume 940.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type 'Empirical(Bruker SADABS)' _exptl_absorpt_correction_T_min 0.7374 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 6722 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 28.39 _reflns_number_total 3474 _reflns_number_gt 2154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0778P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(4) _refine_ls_number_reflns 3474 _refine_ls_number_parameters 262 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_restrained_S_all 0.910 _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 0.1114(3) 0.2474(4) 0.28762(18) 0.0522(7) Uani 1 1 d . . . C2 C 0.1639(3) 0.0774(4) 0.3152(2) 0.0613(8) Uani 1 1 d . . . H2A H 0.1509 0.0316 0.3702 0.074 Uiso 1 1 calc R . . C3 C 0.2356(3) -0.0253(4) 0.2618(2) 0.0625(8) Uani 1 1 d . . . H3A H 0.2712 -0.1393 0.2818 0.075 Uiso 1 1 calc R . . C4 C 0.2556(3) 0.0380(4) 0.1789(2) 0.0540(7) Uani 1 1 d . . . C5 C 0.3295(3) -0.0644(4) 0.1210(2) 0.0634(8) Uani 1 1 d . . . H5A H 0.3701 -0.1769 0.1407 0.076 Uiso 1 1 calc R . . C6 C 0.3414(4) -0.0025(4) 0.0400(2) 0.0661(8) Uani 1 1 d . . . H6A H 0.3861 -0.0747 0.0035 0.079 Uiso 1 1 calc R . . C7 C 0.2869(3) 0.1723(4) 0.0076(2) 0.0601(8) Uani 1 1 d . . . C8 C 0.2948(4) 0.2403(5) -0.0778(2) 0.0723(9) Uani 1 1 d . . . H8A H 0.3379 0.1704 -0.1159 0.087 Uiso 1 1 calc R . . C9 C 0.2401(4) 0.4076(6) -0.1060(2) 0.0776(10) Uani 1 1 d . . . H9A H 0.2447 0.4490 -0.1636 0.093 Uiso 1 1 calc R . . C10 C 0.1783(4) 0.5156(5) -0.0503(2) 0.0690(9) Uani 1 1 d . . . H10A H 0.1450 0.6305 -0.0698 0.083 Uiso 1 1 calc R . . C11 C 0.1650(3) 0.4547(4) 0.0349(2) 0.0558(7) Uani 1 1 d . . . C12 C 0.0986(3) 0.5596(4) 0.0938(2) 0.0599(8) Uani 1 1 d . . . H12A H 0.0660 0.6754 0.0759 0.072 Uiso 1 1 calc R . . C13 C 0.0813(3) 0.4979(4) 0.1740(2) 0.0546(7) Uani 1 1 d . . . H13A H 0.0369 0.5712 0.2102 0.066 Uiso 1 1 calc R . . C14 C 0.1302(3) 0.3209(3) 0.20489(18) 0.0473(6) Uani 1 1 d . . . C15 C 0.2020(3) 0.2122(3) 0.14961(18) 0.0481(6) Uani 1 1 d . . . C16 C 0.2196(3) 0.2804(4) 0.06439(19) 0.0498(6) Uani 1 1 d . . . C17 C 0.1506(3) 0.4228(4) 0.42898(19) 0.0597(7) Uani 1 1 d . . . C18 C 0.3059(3) 0.4627(5) 0.4296(2) 0.0783(10) Uani 1 1 d . . . H18A H 0.3402 0.4471 0.3769 0.094 Uiso 1 1 calc R . . C19 C 0.4083(4) 0.5260(6) 0.5105(3) 0.0947(13) Uani 1 1 d . . . H19A H 0.5142 0.5520 0.5135 0.114 Uiso 1 1 calc R . . C20 C 0.3539(4) 0.5504(5) 0.5864(2) 0.0877(12) Uani 1 1 d . . . H20A H 0.4209 0.5955 0.6414 0.105 Uiso 1 1 calc R . . C21 C 0.2000(4) 0.5074(5) 0.5797(2) 0.0751(9) Uani 1 1 d . . . H21A H 0.1634 0.5251 0.6316 0.090 Uiso 1 1 calc R . . C22 C -0.1203(3) 0.3969(4) 0.31699(19) 0.0537(7) Uani 1 1 d . . . C23 C -0.2091(2) 0.2958(3) 0.24955(15) 0.0373(5) Uani 1 1 d . . . H23A H -0.1635 0.2017 0.2256 0.045 Uiso 1 1 calc R . . C24 C -0.3634(3) 0.3313(4) 0.2171(2) 0.0616(7) Uani 1 1 d . . . H24A H -0.4242 0.2607 0.1692 0.074 Uiso 1 1 calc R . . C25 C -0.4402(3) 0.4662(4) 0.2498(2) 0.0645(8) Uani 1 1 d . . . H25A H -0.5500 0.4843 0.2262 0.077 Uiso 1 1 calc R . . C26 C -0.3491(4) 0.5722(5) 0.3181(2) 0.0699(9) Uani 1 1 d . . . H26A H -0.3969 0.6657 0.3411 0.084 Uiso 1 1 calc R . . N1 N 0.0967(3) 0.4408(4) 0.50310(16) 0.0687(7) Uani 1 1 d . . . N2 N -0.1845(4) 0.5421(4) 0.3541(2) 0.0931(10) Uani 1 1 d . . . N3 N 0.0430(3) 0.3554(3) 0.34657(15) 0.0593(6) 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 0.0375(14) 0.0609(16) 0.0545(16) -0.0092(14) 0.0069(12) 0.0028(13) C2 0.0532(17) 0.0664(19) 0.0592(18) 0.0033(16) 0.0075(14) 0.0056(16) C3 0.0518(17) 0.0519(17) 0.078(2) 0.0042(15) 0.0083(15) 0.0073(14) C4 0.0382(14) 0.0560(17) 0.0640(18) -0.0030(15) 0.0080(13) 0.0006(13) C5 0.0477(16) 0.0501(16) 0.090(2) -0.0138(16) 0.0156(15) 0.0026(13) C6 0.0552(18) 0.069(2) 0.077(2) -0.0215(17) 0.0232(16) -0.0033(16) C7 0.0391(15) 0.0725(19) 0.067(2) -0.0144(16) 0.0116(14) -0.0083(14) C8 0.0587(19) 0.094(3) 0.068(2) -0.018(2) 0.0238(17) -0.0180(19) C9 0.061(2) 0.103(3) 0.066(2) 0.007(2) 0.0132(16) -0.016(2) C10 0.0505(18) 0.082(2) 0.070(2) 0.0108(18) 0.0096(16) -0.0028(16) C11 0.0355(14) 0.0637(18) 0.0616(17) 0.0016(15) 0.0025(12) -0.0030(13) C12 0.0413(15) 0.0582(17) 0.074(2) 0.0052(16) 0.0062(14) 0.0085(13) C13 0.0379(14) 0.0544(16) 0.0673(19) -0.0080(14) 0.0080(13) 0.0042(12) C14 0.0331(12) 0.0504(14) 0.0539(15) -0.0086(12) 0.0046(11) 0.0011(11) C15 0.0319(13) 0.0506(14) 0.0569(17) -0.0081(12) 0.0042(12) -0.0020(11) C16 0.0299(12) 0.0598(16) 0.0563(15) -0.0064(14) 0.0068(11) -0.0044(12) C17 0.0487(16) 0.0716(18) 0.0549(17) -0.0121(15) 0.0082(14) -0.0013(15) C18 0.0496(17) 0.119(3) 0.0668(19) -0.025(2) 0.0163(15) -0.0132(19) C19 0.059(2) 0.123(3) 0.094(3) -0.031(2) 0.008(2) -0.012(2) C20 0.072(2) 0.106(3) 0.070(2) -0.033(2) -0.0050(19) 0.003(2) C21 0.074(2) 0.086(2) 0.0583(18) -0.0161(17) 0.0080(17) 0.0039(19) C22 0.0422(14) 0.0603(16) 0.0601(16) -0.0014(14) 0.0169(12) 0.0037(13) C23 0.0287(11) 0.0440(12) 0.0377(12) -0.0084(11) 0.0070(9) -0.0024(11) C24 0.0529(17) 0.0673(18) 0.0597(17) 0.0011(14) 0.0079(14) -0.0105(15) C25 0.0398(14) 0.075(2) 0.075(2) 0.0052(17) 0.0104(14) 0.0013(16) C26 0.0534(18) 0.073(2) 0.085(2) -0.0080(18) 0.0221(17) 0.0094(17) N1 0.0588(14) 0.0887(19) 0.0560(15) -0.0136(14) 0.0118(12) -0.0002(14) N2 0.0704(19) 0.097(2) 0.110(2) -0.0144(19) 0.0226(17) 0.0095(17) N3 0.0424(12) 0.0773(16) 0.0543(13) -0.0144(12) 0.0070(10) 0.0018(12) _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 1.378(4) . ? C1 C14 1.411(4) . ? C1 N3 1.446(3) . ? C2 C3 1.382(4) . ? C3 C4 1.389(4) . ? C4 C15 1.416(4) . ? C4 C5 1.440(4) . ? C5 C6 1.335(4) . ? C6 C7 1.432(4) . ? C7 C8 1.400(4) . ? C7 C16 1.418(4) . ? C8 C9 1.367(5) . ? C9 C10 1.378(5) . ? C10 C11 1.395(4) . ? C11 C16 1.419(4) . ? C11 C12 1.422(4) . ? C12 C13 1.339(4) . ? C13 C14 1.431(4) . ? C14 C15 1.427(3) . ? C15 C16 1.427(4) . ? C17 N1 1.331(3) . ? C17 C18 1.381(4) . ? C17 N3 1.419(3) . ? C18 C19 1.374(4) . ? C19 C20 1.365(5) . ? C20 C21 1.353(4) . ? C21 N1 1.342(4) . ? C22 C23 1.326(3) . ? C22 N3 1.398(3) . ? C22 N2 1.409(4) . ? C23 C24 1.320(3) . ? C24 C25 1.377(4) . ? C25 C26 1.362(4) . ? C26 N2 1.400(4) . ? 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 C14 121.1(3) . . ? C2 C1 N3 119.5(3) . . ? C14 C1 N3 119.4(2) . . ? C1 C2 C3 120.4(3) . . ? C2 C3 C4 121.4(3) . . ? C3 C4 C15 118.8(3) . . ? C3 C4 C5 123.3(3) . . ? C15 C4 C5 117.9(3) . . ? C6 C5 C4 121.9(3) . . ? C5 C6 C7 121.7(3) . . ? C8 C7 C16 118.5(3) . . ? C8 C7 C6 123.3(3) . . ? C16 C7 C6 118.2(3) . . ? C9 C8 C7 121.2(3) . . ? C8 C9 C10 120.8(3) . . ? C9 C10 C11 120.8(3) . . ? C10 C11 C16 118.8(3) . . ? C10 C11 C12 122.9(3) . . ? C16 C11 C12 118.3(3) . . ? C13 C12 C11 122.5(3) . . ? C12 C13 C14 121.0(3) . . ? C1 C14 C15 117.9(2) . . ? C1 C14 C13 123.4(2) . . ? C15 C14 C13 118.7(2) . . ? C4 C15 C16 120.1(2) . . ? C4 C15 C14 120.4(3) . . ? C16 C15 C14 119.5(2) . . ? C7 C16 C11 119.9(3) . . ? C7 C16 C15 120.1(3) . . ? C11 C16 C15 120.0(2) . . ? N1 C17 C18 123.1(2) . . ? N1 C17 N3 117.7(2) . . ? C18 C17 N3 119.2(3) . . ? C19 C18 C17 118.1(3) . . ? C20 C19 C18 119.6(3) . . ? C21 C20 C19 118.3(3) . . ? N1 C21 C20 124.2(3) . . ? C23 C22 N3 115.9(2) . . ? C23 C22 N2 122.3(2) . . ? N3 C22 N2 121.8(2) . . ? C24 C23 C22 118.7(2) . . ? C23 C24 C25 124.1(3) . . ? C26 C25 C24 117.4(3) . . ? C25 C26 N2 120.8(3) . . ? C17 N1 C21 116.6(3) . . ? C26 N2 C22 116.6(3) . . ? C22 N3 C17 124.0(2) . . ? C22 N3 C1 119.1(2) . . ? C17 N3 C1 116.8(2) . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.246 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.034 data_p21n _database_code_depnum_ccdc_archive 'CCDC 244025' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H21 F6 N3 O4 Zn' _chemical_formula_weight 738.93 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 8.147(2) _cell_length_b 19.807(6) _cell_length_c 18.873(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.531(5) _cell_angle_gamma 90.00 _cell_volume 3011.8(15) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 0.901 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 21529 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 28.27 _reflns_number_total 7180 _reflns_number_gt 5471 _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^)+(0.0517P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7180 _refine_ls_number_parameters 559 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0904 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 Zn1 Zn 0.56203(3) 0.094061(10) 0.545886(11) 0.02409(7) Uani 1 1 d . . . O1 O 0.68817(17) 0.01337(6) 0.58744(7) 0.0315(3) Uani 1 1 d . . . O2 O 0.68060(17) -0.06601(7) 0.50182(7) 0.0350(3) Uani 1 1 d . . . O3 O 0.62811(18) 0.09607(6) 0.44766(7) 0.0322(3) Uani 1 1 d . . . O4 O 0.5054(2) 0.19621(9) 0.44192(9) 0.0605(5) Uani 1 1 d . . . N1 N 0.74654(19) 0.16360(7) 0.58877(8) 0.0254(3) Uani 1 1 d . . . N2 N 0.44610(19) 0.12069(7) 0.63074(8) 0.0253(3) Uani 1 1 d . . . N3 N 0.55043(19) 0.23247(7) 0.63425(8) 0.0270(3) Uani 1 1 d . . . C1 C 0.7109(2) 0.22281(9) 0.61640(9) 0.0246(4) Uani 1 1 d . . . C2 C 0.8287(3) 0.27423(10) 0.62870(11) 0.0340(5) Uani 1 1 d . . . H2 H 0.800(3) 0.3146(12) 0.6476(12) 0.043(6) Uiso 1 1 d . . . C3 C 0.9854(3) 0.26300(11) 0.61318(12) 0.0381(5) Uani 1 1 d . . . H3 H 1.065(3) 0.2965(11) 0.6200(12) 0.039(6) Uiso 1 1 d . . . C4 C 1.0244(2) 0.20096(10) 0.58627(11) 0.0318(4) Uani 1 1 d . . . H4 H 1.129(3) 0.1923(9) 0.5743(10) 0.026(5) Uiso 1 1 d . . . C5 C 0.9032(2) 0.15337(10) 0.57524(11) 0.0292(4) Uani 1 1 d . . . H5 H 0.923(2) 0.1101(10) 0.5538(11) 0.025(5) Uiso 1 1 d . . . C6 C 0.4555(2) 0.18154(9) 0.66153(10) 0.0258(4) Uani 1 1 d . . . C7 C 0.3709(2) 0.19593(11) 0.71872(11) 0.0324(4) Uani 1 1 d . . . H7 H 0.376(3) 0.2395(11) 0.7393(11) 0.038(6) Uiso 1 1 d . . . C8 C 0.2766(3) 0.14621(11) 0.74393(11) 0.0362(5) Uani 1 1 d . . . H8 H 0.226(3) 0.1548(10) 0.7822(12) 0.036(6) Uiso 1 1 d . . . C9 C 0.2670(3) 0.08370(11) 0.71272(11) 0.0354(5) Uani 1 1 d . . . H9 H 0.202(3) 0.0506(10) 0.7298(12) 0.035(6) Uiso 1 1 d . . . C10 C 0.3547(3) 0.07210(11) 0.65687(11) 0.0314(4) Uani 1 1 d . . . H10 H 0.355(2) 0.0302(10) 0.6352(11) 0.027(5) Uiso 1 1 d . . . C11 C 0.4796(2) 0.29929(9) 0.62511(10) 0.0277(4) Uani 1 1 d . . . C12 C 0.4849(3) 0.34447(10) 0.68159(12) 0.0395(5) Uani 1 1 d . . . H12 H 0.546(3) 0.3337(10) 0.7241(12) 0.029(5) Uiso 1 1 d . . . C13 C 0.4076(3) 0.40668(11) 0.67018(12) 0.0441(6) Uani 1 1 d . . . H13 H 0.413(3) 0.4371(12) 0.7071(13) 0.042(6) Uiso 1 1 d . . . C14 C 0.3280(3) 0.42539(10) 0.60320(11) 0.0341(5) Uani 1 1 d . . . C15 C 0.3278(3) 0.38035(10) 0.54661(11) 0.0323(4) Uani 1 1 d . . . H15 H 0.272(3) 0.3963(11) 0.4990(13) 0.042(6) Uiso 1 1 d . . . C16 C 0.4021(2) 0.31747(10) 0.55799(11) 0.0299(4) Uani 1 1 d . . . H16 H 0.405(3) 0.2889(11) 0.5228(12) 0.035(6) Uiso 1 1 d . . . C17 C 0.2466(3) 0.49308(10) 0.59098(11) 0.0365(5) Uani 1 1 d . . . C18 C 0.3170(4) 0.54146(12) 0.55158(15) 0.0552(7) Uani 1 1 d . . . H18 H 0.415(3) 0.5304(13) 0.5315(14) 0.060(8) Uiso 1 1 d . . . C19 C 0.2523(4) 0.60563(12) 0.54178(15) 0.0554(7) Uani 1 1 d . . . H19 H 0.302(3) 0.6374(13) 0.5162(14) 0.061(8) Uiso 1 1 d . . . C20 C 0.0474(3) 0.69201(11) 0.56629(13) 0.0429(5) Uani 1 1 d . . . H20 H 0.101(3) 0.7206(11) 0.5454(11) 0.034(6) Uiso 1 1 d . . . C21 C -0.0818(3) 0.70966(11) 0.59729(12) 0.0427(5) Uani 1 1 d . . . H21 H -0.129(3) 0.7551(13) 0.5903(13) 0.058(7) Uiso 1 1 d . . . C22 C -0.2884(3) 0.68202(13) 0.67690(14) 0.0484(6) Uani 1 1 d . . . H22 H -0.329(3) 0.7274(13) 0.6710(13) 0.057(7) Uiso 1 1 d . . . C23 C -0.3533(3) 0.63679(14) 0.72088(15) 0.0539(7) Uani 1 1 d . . . H23 H -0.436(3) 0.6527(13) 0.7506(14) 0.064(8) Uiso 1 1 d . . . C24 C -0.2976(3) 0.57102(14) 0.72680(14) 0.0495(6) Uani 1 1 d . . . H24 H -0.348(3) 0.5390(13) 0.7600(14) 0.060(8) Uiso 1 1 d . . . C25 C -0.1093(3) 0.48169(11) 0.69394(14) 0.0434(5) Uani 1 1 d . . . H25 H -0.162(3) 0.4512(12) 0.7197(13) 0.053(7) Uiso 1 1 d . . . C26 C 0.0206(3) 0.46297(10) 0.66180(12) 0.0373(5) Uani 1 1 d . . . H26 H 0.071(3) 0.4161(11) 0.6673(12) 0.035(6) Uiso 1 1 d . . . C27 C 0.1136(3) 0.62442(10) 0.57166(11) 0.0374(5) Uani 1 1 d . . . C28 C 0.0370(3) 0.57596(9) 0.61103(10) 0.0295(4) Uani 1 1 d . . . C29 C 0.1029(2) 0.50962(9) 0.62055(10) 0.0296(4) Uani 1 1 d . . . C30 C -0.1607(3) 0.66282(10) 0.63886(11) 0.0370(5) Uani 1 1 d . . . C31 C -0.1009(2) 0.59549(9) 0.64499(11) 0.0309(4) Uani 1 1 d . . . C32 C -0.1730(3) 0.54901(11) 0.68864(12) 0.0375(5) Uani 1 1 d . . . C33 C 0.7378(2) -0.03724(9) 0.55775(10) 0.0258(4) Uani 1 1 d . . . C34 C 0.8973(3) -0.06725(11) 0.59902(13) 0.0434(6) Uani 1 1 d . . . C35 C 0.5787(3) 0.15051(10) 0.41764(11) 0.0345(5) Uani 1 1 d . . . C36 C 0.6141(3) 0.15838(11) 0.34046(12) 0.0411(5) Uani 1 1 d . . . F1 F 0.9531(2) -0.12050(9) 0.56983(10) 0.0512(4) Uani 0.90 1 d P . . F1A F 0.8398(17) -0.1125(6) 0.6462(8) 0.025(3) Uiso 0.10 1 d P . . F2 F 1.0167(3) -0.02278(11) 0.6059(3) 0.1598(17) Uani 0.90 1 d P . . F2A F 0.9692(13) -0.0369(5) 0.6430(5) 0.011(2) Uiso 0.10 1 d P . . F3 F 0.8771(5) -0.0850(2) 0.66371(12) 0.1476(18) Uani 0.90 1 d P . . F3A F 0.986(3) -0.0935(9) 0.5631(11) 0.056(6) Uiso 0.10 1 d P . . F4 F 0.7021(3) 0.10842(11) 0.31838(9) 0.0703(6) Uani 0.90 1 d P . . F4A F 0.497(3) 0.1348(10) 0.2991(13) 0.053(6) Uiso 0.10 1 d P . . F5 F 0.4735(3) 0.15945(13) 0.29480(11) 0.0681(7) Uani 0.90 1 d P . . F5A F 0.6175(18) 0.2147(8) 0.3139(9) 0.034(3) Uiso 0.10 1 d P . . F6 F 0.6868(5) 0.21617(15) 0.33231(14) 0.1273(14) Uani 0.90 1 d P . . F6A F 0.7619(19) 0.1488(8) 0.3316(8) 0.048(4) Uiso 0.10 1 d P . . 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 Zn1 0.02686(12) 0.02239(11) 0.02279(12) -0.00265(8) 0.00288(8) 0.00286(8) O1 0.0382(8) 0.0257(7) 0.0293(7) -0.0005(5) 0.0013(6) 0.0081(6) O2 0.0296(8) 0.0442(8) 0.0300(8) -0.0088(6) 0.0006(6) -0.0016(6) O3 0.0373(8) 0.0331(7) 0.0260(7) 0.0019(6) 0.0040(6) 0.0008(6) O4 0.0854(14) 0.0538(10) 0.0446(10) -0.0001(8) 0.0170(9) 0.0307(10) N1 0.0261(8) 0.0253(7) 0.0250(8) -0.0006(6) 0.0042(6) 0.0030(6) N2 0.0243(8) 0.0273(8) 0.0236(8) -0.0024(6) 0.0019(6) -0.0003(6) N3 0.0267(8) 0.0237(8) 0.0307(9) -0.0049(6) 0.0047(7) 0.0032(6) C1 0.0254(9) 0.0256(9) 0.0218(9) -0.0007(7) -0.0002(7) 0.0035(7) C2 0.0346(11) 0.0269(10) 0.0393(12) -0.0075(9) 0.0021(9) -0.0015(8) C3 0.0310(11) 0.0358(11) 0.0466(13) -0.0013(10) 0.0028(10) -0.0066(9) C4 0.0241(10) 0.0377(11) 0.0333(11) 0.0037(9) 0.0030(8) 0.0032(8) C5 0.0269(10) 0.0314(10) 0.0296(11) 0.0001(8) 0.0047(8) 0.0055(8) C6 0.0231(9) 0.0284(9) 0.0245(10) -0.0033(7) -0.0012(7) 0.0034(7) C7 0.0314(11) 0.0395(11) 0.0254(10) -0.0072(9) 0.0017(8) 0.0063(9) C8 0.0288(11) 0.0561(14) 0.0241(11) -0.0007(9) 0.0052(8) 0.0059(10) C9 0.0303(11) 0.0466(13) 0.0291(11) 0.0077(9) 0.0037(9) -0.0029(9) C10 0.0331(11) 0.0304(10) 0.0301(11) 0.0002(8) 0.0028(8) -0.0009(8) C11 0.0267(10) 0.0242(9) 0.0319(10) -0.0053(8) 0.0035(8) 0.0042(7) C12 0.0545(14) 0.0332(11) 0.0272(11) -0.0069(9) -0.0057(10) 0.0120(10) C13 0.0648(16) 0.0345(11) 0.0311(12) -0.0109(9) 0.0009(11) 0.0146(11) C14 0.0388(12) 0.0305(10) 0.0343(11) -0.0032(8) 0.0096(9) 0.0076(9) C15 0.0356(11) 0.0315(10) 0.0292(11) -0.0013(8) 0.0024(9) 0.0039(8) C16 0.0336(11) 0.0292(10) 0.0274(11) -0.0072(8) 0.0063(8) 0.0018(8) C17 0.0497(13) 0.0300(10) 0.0312(11) 0.0003(8) 0.0107(9) 0.0097(9) C18 0.0682(18) 0.0506(14) 0.0551(16) 0.0120(12) 0.0365(14) 0.0209(13) C19 0.0753(19) 0.0434(13) 0.0554(17) 0.0186(12) 0.0361(15) 0.0103(12) C20 0.0623(16) 0.0264(10) 0.0384(13) 0.0083(9) 0.0017(11) 0.0011(10) C21 0.0552(15) 0.0262(10) 0.0419(13) -0.0014(9) -0.0092(11) 0.0107(10) C22 0.0411(13) 0.0475(13) 0.0527(15) -0.0091(12) -0.0058(11) 0.0219(11) C23 0.0341(13) 0.0690(17) 0.0583(17) -0.0110(14) 0.0061(12) 0.0146(12) C24 0.0329(12) 0.0630(15) 0.0536(16) 0.0010(12) 0.0090(11) 0.0059(11) C25 0.0361(12) 0.0385(12) 0.0565(15) 0.0109(11) 0.0097(11) -0.0020(10) C26 0.0400(12) 0.0236(10) 0.0474(14) 0.0036(9) 0.0035(10) 0.0016(9) C27 0.0539(14) 0.0291(10) 0.0297(11) 0.0051(9) 0.0077(10) 0.0063(9) C28 0.0358(11) 0.0262(9) 0.0247(10) -0.0011(7) -0.0013(8) 0.0034(8) C29 0.0367(11) 0.0230(9) 0.0281(10) -0.0026(8) 0.0008(8) 0.0037(8) C30 0.0379(12) 0.0333(10) 0.0358(12) -0.0044(9) -0.0080(9) 0.0098(9) C31 0.0305(10) 0.0291(9) 0.0304(10) -0.0037(8) -0.0046(8) 0.0051(8) C32 0.0292(11) 0.0397(11) 0.0421(13) 0.0011(9) 0.0005(9) 0.0025(9) C33 0.0278(10) 0.0250(9) 0.0243(10) 0.0020(7) 0.0035(7) -0.0008(7) C34 0.0438(13) 0.0377(11) 0.0440(14) -0.0131(10) -0.0092(11) 0.0143(10) C35 0.0364(11) 0.0395(11) 0.0267(11) 0.0000(9) 0.0021(9) -0.0006(9) C36 0.0466(14) 0.0445(12) 0.0316(12) 0.0050(10) 0.0043(10) -0.0023(10) F1 0.0532(11) 0.0375(10) 0.0610(11) -0.0104(9) 0.0017(8) 0.0205(9) F2 0.0410(13) 0.0506(13) 0.357(5) -0.008(2) -0.073(2) -0.0022(10) F3 0.182(3) 0.227(4) 0.0302(13) 0.0205(17) 0.0042(16) 0.154(3) F4 0.0794(14) 0.1015(15) 0.0343(9) 0.0073(9) 0.0229(9) 0.0429(12) F5 0.0825(15) 0.0834(17) 0.0321(10) -0.0050(10) -0.0120(8) 0.0357(13) F6 0.202(3) 0.124(2) 0.0625(17) -0.0072(14) 0.0434(19) -0.119(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9966(13) . ? Zn1 O3 2.0060(14) . ? Zn1 N2 2.0453(15) . ? Zn1 N1 2.1097(16) . ? Zn1 O2 2.1210(15) 3_656 ? O1 C33 1.245(2) . ? O2 C33 1.229(2) . ? O2 Zn1 2.1210(15) 3_656 ? O3 C35 1.256(2) . ? O4 C35 1.211(2) . ? N1 C1 1.333(2) . ? N1 C5 1.354(2) . ? N2 C6 1.335(2) . ? N2 C10 1.354(2) . ? N3 C1 1.411(2) . ? N3 C6 1.414(2) . ? N3 C11 1.444(2) . ? C1 C2 1.395(3) . ? C2 C3 1.369(3) . ? C3 C4 1.384(3) . ? C4 C5 1.359(3) . ? C6 C7 1.394(3) . ? C7 C8 1.377(3) . ? C8 C9 1.368(3) . ? C9 C10 1.377(3) . ? C11 C16 1.377(3) . ? C11 C12 1.388(3) . ? C12 C13 1.386(3) . ? C13 C14 1.383(3) . ? C14 C15 1.391(3) . ? C14 C17 1.498(3) . ? C15 C16 1.388(3) . ? C17 C18 1.388(3) . ? C17 C29 1.408(3) . ? C18 C19 1.378(3) . ? C19 C27 1.387(3) . ? C20 C21 1.325(3) . ? C20 C27 1.441(3) . ? C21 C30 1.428(3) . ? C22 C23 1.379(4) . ? C22 C30 1.402(3) . ? C23 C24 1.379(4) . ? C24 C32 1.398(3) . ? C25 C26 1.348(3) . ? C25 C32 1.429(3) . ? C26 C29 1.436(3) . ? C27 C28 1.414(3) . ? C28 C29 1.421(3) . ? C28 C31 1.427(3) . ? C30 C31 1.419(3) . ? C31 C32 1.419(3) . ? C33 C34 1.532(3) . ? C34 F2A 1.117(11) . ? C34 F3A 1.18(2) . ? C34 F1 1.303(3) . ? C34 F3 1.304(4) . ? C34 F2 1.304(3) . ? C34 F1A 1.393(14) . ? C35 C36 1.534(3) . ? C36 F5A 1.225(17) . ? C36 F4A 1.23(2) . ? C36 F6A 1.254(15) . ? C36 F6 1.308(3) . ? C36 F4 1.325(3) . ? C36 F5 1.328(3) . ? F1 F3A 0.621(17) . ? F1A F3 0.685(12) . ? F2 F2A 0.894(9) . ? F2 F3A 1.617(19) . ? F2A F3 1.306(10) . ? F4 F6A 0.951(16) . ? F4 F4A 1.74(2) . ? F4A F5 0.526(18) . ? F5 F5A 1.606(16) . ? F5A F6 0.618(14) . ? F5A F6A 1.76(2) . ? F6 F6A 1.469(16) . ? 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 O1 Zn1 O3 100.71(5) . . ? O1 Zn1 N2 99.75(6) . . ? O3 Zn1 N2 159.52(6) . . ? O1 Zn1 N1 94.36(6) . . ? O3 Zn1 N1 93.90(6) . . ? N2 Zn1 N1 85.23(6) . . ? O1 Zn1 O2 110.48(6) . 3_656 ? O3 Zn1 O2 88.50(6) . 3_656 ? N2 Zn1 O2 83.70(6) . 3_656 ? N1 Zn1 O2 154.16(6) . 3_656 ? C33 O1 Zn1 130.59(13) . . ? C33 O2 Zn1 134.19(12) . 3_656 ? C35 O3 Zn1 108.77(12) . . ? C1 N1 C5 118.15(16) . . ? C1 N1 Zn1 122.72(12) . . ? C5 N1 Zn1 117.90(12) . . ? C6 N2 C10 118.82(17) . . ? C6 N2 Zn1 124.76(13) . . ? C10 N2 Zn1 116.41(13) . . ? C1 N3 C6 124.51(14) . . ? C1 N3 C11 117.66(14) . . ? C6 N3 C11 117.83(14) . . ? N1 C1 C2 121.54(17) . . ? N1 C1 N3 118.43(16) . . ? C2 C1 N3 120.02(16) . . ? C3 C2 C1 119.07(19) . . ? C2 C3 C4 119.7(2) . . ? C5 C4 C3 118.08(19) . . ? N1 C5 C4 123.46(18) . . ? N2 C6 C7 121.24(17) . . ? N2 C6 N3 118.99(16) . . ? C7 C6 N3 119.76(17) . . ? C8 C7 C6 119.14(19) . . ? C9 C8 C7 119.84(19) . . ? C8 C9 C10 118.5(2) . . ? N2 C10 C9 122.41(19) . . ? C16 C11 C12 119.74(18) . . ? C16 C11 N3 118.05(16) . . ? C12 C11 N3 122.20(18) . . ? C13 C12 C11 119.5(2) . . ? C14 C13 C12 121.4(2) . . ? C13 C14 C15 118.49(19) . . ? C13 C14 C17 121.14(18) . . ? C15 C14 C17 120.36(19) . . ? C16 C15 C14 120.4(2) . . ? C11 C16 C15 120.48(18) . . ? C18 C17 C29 119.04(19) . . ? C18 C17 C14 119.44(19) . . ? C29 C17 C14 121.49(18) . . ? C19 C18 C17 121.9(2) . . ? C18 C19 C27 120.8(2) . . ? C21 C20 C27 121.8(2) . . ? C20 C21 C30 121.5(2) . . ? C23 C22 C30 120.8(2) . . ? C24 C23 C22 120.8(2) . . ? C23 C24 C32 120.6(2) . . ? C26 C25 C32 121.8(2) . . ? C25 C26 C29 121.83(19) . . ? C19 C27 C28 118.75(19) . . ? C19 C27 C20 122.7(2) . . ? C28 C27 C20 118.5(2) . . ? C27 C28 C29 120.43(18) . . ? C27 C28 C31 119.34(17) . . ? C29 C28 C31 120.11(18) . . ? C17 C29 C28 119.07(18) . . ? C17 C29 C26 123.16(18) . . ? C28 C29 C26 117.76(18) . . ? C22 C30 C31 119.0(2) . . ? C22 C30 C21 122.3(2) . . ? C31 C30 C21 118.6(2) . . ? C30 C31 C32 119.38(19) . . ? C30 C31 C28 120.11(19) . . ? C32 C31 C28 120.40(17) . . ? C24 C32 C31 119.4(2) . . ? C24 C32 C25 122.6(2) . . ? C31 C32 C25 117.93(19) . . ? O2 C33 O1 130.74(18) . . ? O2 C33 C34 116.23(17) . . ? O1 C33 C34 113.03(17) . . ? F2A C34 F3A 111.2(12) . . ? F2A C34 F1 124.9(6) . . ? F3A C34 F1 28.4(8) . . ? F2A C34 F3 64.8(5) . . ? F3A C34 F3 126.2(10) . . ? F1 C34 F3 106.2(2) . . ? F2A C34 F2 42.4(5) . . ? F3A C34 F2 80.9(9) . . ? F1 C34 F2 106.7(3) . . ? F3 C34 F2 106.5(3) . . ? F2A C34 F1A 93.4(7) . . ? F3A C34 F1A 112.1(10) . . ? F1 C34 F1A 85.4(6) . . ? F3 C34 F1A 29.2(5) . . ? F2 C34 F1A 133.4(6) . . ? F2A C34 C33 118.7(6) . . ? F3A C34 C33 115.2(11) . . ? F1 C34 C33 114.96(18) . . ? F3 C34 C33 111.4(2) . . ? F2 C34 C33 110.6(2) . . ? F1A C34 C33 103.6(6) . . ? O4 C35 O3 127.9(2) . . ? O4 C35 C36 117.13(19) . . ? O3 C35 C36 114.99(18) . . ? F5A C36 F4A 98.5(11) . . ? F5A C36 F6A 90.2(10) . . ? F4A C36 F6A 121.9(12) . . ? F5A C36 F6 28.0(7) . . ? F4A C36 F6 125.4(10) . . ? F6A C36 F6 69.9(8) . . ? F5A C36 F4 120.4(7) . . ? F4A C36 F4 85.5(9) . . ? F6A C36 F4 43.2(7) . . ? F6 C36 F4 110.0(3) . . ? F5A C36 F5 77.9(7) . . ? F4A C36 F5 23.3(9) . . ? F6A C36 F5 132.0(7) . . ? F6 C36 F5 105.8(3) . . ? F4 C36 F5 105.2(2) . . ? F5A C36 C35 119.9(8) . . ? F4A C36 C35 109.0(10) . . ? F6A C36 C35 115.5(7) . . ? F6 C36 C35 110.7(2) . . ? F4 C36 C35 114.18(18) . . ? F5 C36 C35 110.6(2) . . ? F3A F1 C34 65(2) . . ? F3 F1A C34 68.2(12) . . ? F2A F2 C34 57.5(7) . . ? F2A F2 F3A 93.9(10) . . ? C34 F2 F3A 46.3(7) . . ? F2 F2A C34 80.0(8) . . ? F2 F2A F3 142.9(11) . . ? C34 F2A F3 64.5(6) . . ? F1A F3 C34 82.6(13) . . ? F1A F3 F2A 132.0(14) . . ? C34 F3 F2A 50.7(5) . . ? F1 F3A C34 86(2) . . ? F1 F3A F2 133(3) . . ? C34 F3A F2 52.8(8) . . ? F6A F4 C36 64.5(9) . . ? F6A F4 F4A 104.0(12) . . ? C36 F4 F4A 44.9(7) . . ? F5 F4A C36 89(3) . . ? F5 F4A F4 129(3) . . ? C36 F4A F4 49.5(8) . . ? F4A F5 C36 68(3) . . ? F4A F5 F5A 111(3) . . ? C36 F5 F5A 48.2(6) . . ? F6 F5A C36 83.5(17) . . ? F6 F5A F5 137(2) . . ? C36 F5A F5 53.9(6) . . ? F6 F5A F6A 52.9(14) . . ? C36 F5A F6A 45.6(7) . . ? F5 F5A F6A 89.0(9) . . ? F5A F6 C36 68.5(16) . . ? F5A F6 F6A 107.4(17) . . ? C36 F6 F6A 53.3(6) . . ? F4 F6A C36 72.3(10) . . ? F4 F6A F6 124.6(14) . . ? C36 F6A F6 56.8(7) . . ? F4 F6A F5A 105.8(13) . . ? C36 F6A F5A 44.2(7) . . ? F6 F6A F5A 19.6(5) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.504 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.057