# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_l _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H20 N2 O' _chemical_formula_weight 412.47 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.233(4) _cell_length_b 10.817(4) _cell_length_c 10.864(4) _cell_angle_alpha 62.661(4) _cell_angle_beta 78.149(4) _cell_angle_gamma 89.945(4) _cell_volume 1039.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4478 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 28.05 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9667 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 28.17 _reflns_number_total 4944 _reflns_number_gt 3919 _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, 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^)+(0.0711P)^2^+0.1944P] 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 4944 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1200 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 O1 O 0.16208(11) 0.31563(10) 0.38077(9) 0.0512(3) Uani 1 1 d . . . N1 N 0.34293(11) 0.21835(11) 0.07378(12) 0.0408(3) Uani 1 1 d . . . N2 N 0.23996(10) 0.38280(10) 0.14172(10) 0.0332(2) Uani 1 1 d . . . C1 C 0.28820(13) 0.11161(13) 0.20875(14) 0.0393(3) Uani 1 1 d . . . C2 C 0.30537(16) -0.02787(14) 0.23927(17) 0.0506(3) Uani 1 1 d . . . H2A H 0.3505 -0.0478 0.1681 0.061 Uiso 1 1 calc R . . C3 C 0.25535(17) -0.13428(15) 0.37433(18) 0.0554(4) Uani 1 1 d . . . H3A H 0.2661 -0.2263 0.3935 0.066 Uiso 1 1 calc R . . C4 C 0.18897(17) -0.10710(15) 0.48295(18) 0.0568(4) Uani 1 1 d . . . H4A H 0.1559 -0.1806 0.5740 0.068 Uiso 1 1 calc R . . C5 C 0.17219(15) 0.02815(15) 0.45588(16) 0.0490(3) Uani 1 1 d . . . H5A H 0.1291 0.0469 0.5287 0.059 Uiso 1 1 calc R . . C6 C 0.22048(13) 0.13813(13) 0.31766(13) 0.0386(3) Uani 1 1 d . . . C7 C 0.20316(12) 0.28130(13) 0.28960(13) 0.0367(3) Uani 1 1 d . . . C8 C 0.20606(12) 0.52236(12) 0.09869(12) 0.0336(2) Uani 1 1 d . . . C9 C 0.26601(12) 0.62728(12) -0.03122(12) 0.0346(3) Uani 1 1 d . . . C10 C 0.36086(12) 0.59852(13) -0.13213(12) 0.0349(3) Uani 1 1 d . . . C11 C 0.42235(13) 0.70407(14) -0.26971(13) 0.0410(3) Uani 1 1 d . . . H11A H 0.4077 0.7966 -0.2948 0.049 Uiso 1 1 calc R . . C12 C 0.50374(13) 0.67390(15) -0.36837(14) 0.0441(3) Uani 1 1 d . . . C13 C 0.52643(14) 0.53427(16) -0.32794(15) 0.0490(3) Uani 1 1 d . . . H13A H 0.5818 0.5124 -0.3929 0.059 Uiso 1 1 calc R . . C14 C 0.46859(14) 0.42903(15) -0.19428(14) 0.0449(3) Uani 1 1 d . . . H14A H 0.4857 0.3371 -0.1695 0.054 Uiso 1 1 calc R . . C15 C 0.38384(12) 0.45940(13) -0.09490(12) 0.0355(3) Uani 1 1 d . . . C16 C 0.32033(12) 0.34598(12) 0.04482(12) 0.0341(3) Uani 1 1 d . . . C17 C 0.56586(16) 0.78730(18) -0.51665(15) 0.0570(4) Uani 1 1 d . . . H17A H 0.5394 0.8759 -0.5264 0.086 Uiso 1 1 calc R . . H17B H 0.5359 0.7679 -0.5847 0.086 Uiso 1 1 calc R . . H17C H 0.6619 0.7903 -0.5332 0.086 Uiso 1 1 calc R . . C18 C 0.09310(12) 0.54542(12) 0.19406(12) 0.0335(3) Uani 1 1 d . . . C19 C -0.03595(13) 0.48791(14) 0.21645(14) 0.0419(3) Uani 1 1 d . . . H19A H -0.0508 0.4336 0.1736 0.050 Uiso 1 1 calc R . . C20 C -0.14278(13) 0.51066(15) 0.30207(15) 0.0459(3) Uani 1 1 d . . . H20A H -0.2291 0.4714 0.3170 0.055 Uiso 1 1 calc R . . C21 C -0.12128(14) 0.59151(14) 0.36534(14) 0.0454(3) Uani 1 1 d . . . H21A H -0.1928 0.6058 0.4240 0.055 Uiso 1 1 calc R . . C22 C 0.00632(14) 0.65110(14) 0.34151(14) 0.0440(3) Uani 1 1 d . . . H22A H 0.0205 0.7066 0.3833 0.053 Uiso 1 1 calc R . . C23 C 0.11307(13) 0.62898(13) 0.25603(13) 0.0391(3) Uani 1 1 d . . . H23A H 0.1988 0.6702 0.2398 0.047 Uiso 1 1 calc R . . C24 C 0.23103(13) 0.77363(13) -0.07443(13) 0.0389(3) Uani 1 1 d . . . C25 C 0.10818(16) 0.81345(16) -0.10671(16) 0.0527(4) Uani 1 1 d . . . H25A H 0.0464 0.7491 -0.1046 0.063 Uiso 1 1 calc R . . C26 C 0.0775(2) 0.94860(18) -0.14199(19) 0.0675(5) Uani 1 1 d . . . H26A H -0.0044 0.9751 -0.1646 0.081 Uiso 1 1 calc R . . C27 C 0.1673(2) 1.04348(17) -0.14368(18) 0.0699(5) Uani 1 1 d . . . H27A H 0.1453 1.1335 -0.1653 0.084 Uiso 1 1 calc R . . C28 C 0.2896(2) 1.00596(16) -0.11350(17) 0.0632(4) Uani 1 1 d . . . H28A H 0.3507 1.0709 -0.1157 0.076 Uiso 1 1 calc R . . C29 C 0.32235(16) 0.87127(14) -0.07971(15) 0.0491(3) Uani 1 1 d . . . H29A H 0.4058 0.8466 -0.0606 0.059 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 O1 0.0670(7) 0.0495(5) 0.0326(5) -0.0186(4) -0.0040(4) 0.0171(5) N1 0.0463(6) 0.0375(5) 0.0400(6) -0.0203(5) -0.0073(5) 0.0088(5) N2 0.0347(5) 0.0335(5) 0.0307(5) -0.0157(4) -0.0044(4) 0.0054(4) C1 0.0402(7) 0.0365(6) 0.0427(7) -0.0190(5) -0.0119(5) 0.0051(5) C2 0.0599(9) 0.0398(7) 0.0572(9) -0.0253(6) -0.0176(7) 0.0092(6) C3 0.0630(9) 0.0337(7) 0.0677(10) -0.0191(7) -0.0228(8) 0.0042(6) C4 0.0587(9) 0.0386(7) 0.0550(9) -0.0079(6) -0.0105(7) -0.0031(6) C5 0.0487(8) 0.0432(7) 0.0436(7) -0.0135(6) -0.0038(6) 0.0015(6) C6 0.0360(6) 0.0362(6) 0.0398(6) -0.0152(5) -0.0077(5) 0.0024(5) C7 0.0354(6) 0.0386(6) 0.0327(6) -0.0151(5) -0.0050(5) 0.0061(5) C8 0.0345(6) 0.0349(6) 0.0346(6) -0.0192(5) -0.0075(5) 0.0066(5) C9 0.0348(6) 0.0362(6) 0.0334(6) -0.0174(5) -0.0061(5) 0.0060(5) C10 0.0320(6) 0.0398(6) 0.0323(6) -0.0169(5) -0.0061(5) 0.0057(5) C11 0.0389(7) 0.0438(7) 0.0343(6) -0.0145(5) -0.0056(5) 0.0051(5) C12 0.0329(6) 0.0578(8) 0.0338(6) -0.0167(6) -0.0037(5) 0.0048(6) C13 0.0412(7) 0.0631(9) 0.0388(7) -0.0251(6) 0.0015(6) 0.0115(6) C14 0.0440(7) 0.0491(7) 0.0408(7) -0.0228(6) -0.0040(6) 0.0133(6) C15 0.0327(6) 0.0416(6) 0.0323(6) -0.0181(5) -0.0059(5) 0.0072(5) C16 0.0331(6) 0.0389(6) 0.0338(6) -0.0203(5) -0.0067(5) 0.0069(5) C17 0.0477(8) 0.0688(10) 0.0357(7) -0.0130(7) 0.0003(6) 0.0059(7) C18 0.0352(6) 0.0330(6) 0.0308(5) -0.0149(5) -0.0048(5) 0.0064(4) C19 0.0405(7) 0.0454(7) 0.0446(7) -0.0260(6) -0.0080(5) 0.0020(5) C20 0.0325(6) 0.0530(8) 0.0471(7) -0.0208(6) -0.0054(5) 0.0040(6) C21 0.0416(7) 0.0484(7) 0.0419(7) -0.0206(6) -0.0018(6) 0.0155(6) C22 0.0508(8) 0.0423(7) 0.0440(7) -0.0263(6) -0.0063(6) 0.0089(6) C23 0.0380(6) 0.0409(6) 0.0404(6) -0.0225(5) -0.0047(5) 0.0024(5) C24 0.0460(7) 0.0360(6) 0.0299(6) -0.0136(5) -0.0034(5) 0.0084(5) C25 0.0557(9) 0.0538(8) 0.0519(8) -0.0259(7) -0.0165(7) 0.0184(7) C26 0.0753(12) 0.0624(10) 0.0618(10) -0.0251(8) -0.0196(9) 0.0357(9) C27 0.1034(15) 0.0398(8) 0.0518(9) -0.0138(7) -0.0074(9) 0.0274(9) C28 0.0894(13) 0.0357(7) 0.0503(9) -0.0138(6) -0.0028(8) -0.0016(8) C29 0.0559(8) 0.0378(7) 0.0434(7) -0.0130(6) -0.0051(6) 0.0025(6) _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 O1 C7 1.2092(15) . ? N1 C16 1.2995(16) . ? N1 C1 1.3805(17) . ? N2 C16 1.4043(15) . ? N2 C8 1.4267(15) . ? N2 C7 1.4355(16) . ? C1 C6 1.3918(19) . ? C1 C2 1.4075(19) . ? C2 C3 1.372(2) . ? C2 H2A 0.9300 . ? C3 C4 1.389(2) . ? C3 H3A 0.9300 . ? C4 C5 1.372(2) . ? C4 H4A 0.9300 . ? C5 C6 1.4036(19) . ? C5 H5A 0.9300 . ? C6 C7 1.4529(18) . ? C8 C9 1.3531(17) . ? C8 C18 1.4889(16) . ? C9 C10 1.4547(16) . ? C9 C24 1.4967(17) . ? C10 C15 1.4011(17) . ? C10 C11 1.4075(17) . ? C11 C12 1.3795(19) . ? C11 H11A 0.9300 . ? C12 C13 1.400(2) . ? C12 C17 1.5066(19) . ? C13 C14 1.3729(19) . ? C13 H13A 0.9300 . ? C14 C15 1.4022(17) . ? C14 H14A 0.9300 . ? C15 C16 1.4552(17) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.3859(18) . ? C18 C23 1.3885(17) . ? C19 C20 1.3830(19) . ? C19 H19A 0.9300 . ? C20 C21 1.379(2) . ? C20 H20A 0.9300 . ? C21 C22 1.377(2) . ? C21 H21A 0.9300 . ? C22 C23 1.3783(18) . ? C22 H22A 0.9300 . ? C23 H23A 0.9300 . ? C24 C29 1.384(2) . ? C24 C25 1.389(2) . ? C25 C26 1.384(2) . ? C25 H25A 0.9300 . ? C26 C27 1.369(3) . ? C26 H26A 0.9300 . ? C27 C28 1.373(3) . ? C27 H27A 0.9300 . ? C28 C29 1.389(2) . ? C28 H28A 0.9300 . ? C29 H29A 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 C16 N1 C1 118.77(11) . . ? C16 N2 C8 121.32(10) . . ? C16 N2 C7 118.92(10) . . ? C8 N2 C7 119.45(9) . . ? N1 C1 C6 121.83(11) . . ? N1 C1 C2 119.39(12) . . ? C6 C1 C2 118.74(12) . . ? C3 C2 C1 119.82(14) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C2 C3 C4 121.20(13) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C5 C4 C3 119.95(14) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C4 C5 C6 119.61(14) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C1 C6 C5 120.66(12) . . ? C1 C6 C7 119.87(11) . . ? C5 C6 C7 119.44(12) . . ? O1 C7 N2 121.28(11) . . ? O1 C7 C6 124.29(11) . . ? N2 C7 C6 114.42(10) . . ? C9 C8 N2 120.52(10) . . ? C9 C8 C18 121.27(10) . . ? N2 C8 C18 117.88(10) . . ? C8 C9 C10 120.58(11) . . ? C8 C9 C24 120.04(10) . . ? C10 C9 C24 119.33(10) . . ? C15 C10 C11 118.81(11) . . ? C15 C10 C9 118.71(11) . . ? C11 C10 C9 122.30(11) . . ? C12 C11 C10 121.76(12) . . ? C12 C11 H11A 119.1 . . ? C10 C11 H11A 119.1 . . ? C11 C12 C13 118.31(12) . . ? C11 C12 C17 121.26(13) . . ? C13 C12 C17 120.42(13) . . ? C14 C13 C12 121.33(12) . . ? C14 C13 H13A 119.3 . . ? C12 C13 H13A 119.3 . . ? C13 C14 C15 120.34(13) . . ? C13 C14 H14A 119.8 . . ? C15 C14 H14A 119.8 . . ? C14 C15 C10 119.43(11) . . ? C14 C15 C16 119.56(11) . . ? C10 C15 C16 121.01(10) . . ? N1 C16 N2 124.01(11) . . ? N1 C16 C15 118.84(11) . . ? N2 C16 C15 117.14(10) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 119.02(11) . . ? C19 C18 C8 119.52(11) . . ? C23 C18 C8 121.39(11) . . ? C20 C19 C18 120.47(12) . . ? C20 C19 H19A 119.8 . . ? C18 C19 H19A 119.8 . . ? C21 C20 C19 119.96(13) . . ? C21 C20 H20A 120.0 . . ? C19 C20 H20A 120.0 . . ? C22 C21 C20 119.90(12) . . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C21 C22 C23 120.35(12) . . ? C21 C22 H22A 119.8 . . ? C23 C22 H22A 119.8 . . ? C22 C23 C18 120.28(12) . . ? C22 C23 H23A 119.9 . . ? C18 C23 H23A 119.9 . . ? C29 C24 C25 119.07(13) . . ? C29 C24 C9 119.18(12) . . ? C25 C24 C9 121.73(13) . . ? C26 C25 C24 120.19(16) . . ? C26 C25 H25A 119.9 . . ? C24 C25 H25A 119.9 . . ? C27 C26 C25 120.30(16) . . ? C27 C26 H26A 119.9 . . ? C25 C26 H26A 119.9 . . ? C26 C27 C28 120.11(15) . . ? C26 C27 H27A 119.9 . . ? C28 C27 H27A 119.9 . . ? C27 C28 C29 120.20(17) . . ? C27 C28 H28A 119.9 . . ? C29 C28 H28A 119.9 . . ? C24 C29 C28 120.11(15) . . ? C24 C29 H29A 119.9 . . ? C28 C29 H29A 119.9 . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 28.17 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.241 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 962573' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_031621c_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H22 N2 O2' _chemical_formula_weight 442.50 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.242(3) _cell_length_b 13.337(3) _cell_length_c 16.050(3) _cell_angle_alpha 67.201(3) _cell_angle_beta 81.584(4) _cell_angle_gamma 60.973(3) _cell_volume 2281.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9346 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.42 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32243 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0136 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8013 _reflns_number_gt 6840 _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, 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^)+(0.0554P)^2^+0.6041P] 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 8013 _refine_ls_number_parameters 617 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 N2 N 0.05878(9) 0.36340(9) 0.88732(7) 0.0347(2) Uani 1 1 d . . . N1 N -0.00782(10) 0.57794(10) 0.80176(7) 0.0377(3) Uani 1 1 d . . . C9 C 0.11533(11) 0.48472(11) 0.93271(8) 0.0332(3) Uani 1 1 d . . . C5 C -0.07958(12) 0.46607(12) 0.76084(9) 0.0385(3) Uani 1 1 d . . . C8 C 0.05203(11) 0.47825(11) 0.86975(8) 0.0334(3) Uani 1 1 d . . . C15 C 0.18155(11) 0.37989(12) 1.00676(8) 0.0340(3) Uani 1 1 d . . . C23 C 0.13550(11) 0.25473(11) 0.95745(9) 0.0350(3) Uani 1 1 d . . . O1 O -0.03439(10) 0.26658(9) 0.86604(8) 0.0544(3) Uani 1 1 d . . . C14 C 0.24368(12) 0.39023(13) 1.06386(9) 0.0385(3) Uani 1 1 d . . . H14 H 0.2875 0.3210 1.1132 0.046 Uiso 1 1 calc R . . C16 C 0.19109(11) 0.26247(12) 1.01706(9) 0.0353(3) Uani 1 1 d . . . C7 C -0.07084(12) 0.57238(12) 0.74427(9) 0.0380(3) Uani 1 1 d . . . C6 C -0.01988(12) 0.35702(12) 0.84008(9) 0.0385(3) Uani 1 1 d . . . C10 C 0.10970(12) 0.59718(12) 0.91953(9) 0.0396(3) Uani 1 1 d . . . H10 H 0.0636 0.6676 0.8718 0.047 Uiso 1 1 calc R . . C17 C 0.26974(11) 0.14782(12) 1.09111(9) 0.0372(3) Uani 1 1 d . . . C11 C 0.17137(12) 0.60482(13) 0.97628(10) 0.0427(3) Uani 1 1 d . . . H11 H 0.1665 0.6805 0.9665 0.051 Uiso 1 1 calc R . . C12 C 0.24170(12) 0.50026(13) 1.04884(9) 0.0405(3) Uani 1 1 d . . . C4 C -0.14696(13) 0.46461(14) 0.70233(10) 0.0471(3) Uani 1 1 d . . . H4 H -0.1536 0.3940 0.7146 0.056 Uiso 1 1 calc R . . C24 C 0.16815(11) 0.13332(12) 0.95281(9) 0.0372(3) Uani 1 1 d . . . C1 C -0.13042(14) 0.67698(14) 0.66737(10) 0.0490(4) Uani 1 1 d . . . H1 H -0.1266 0.7491 0.6553 0.059 Uiso 1 1 calc R . . O2 O 0.28898(11) -0.21596(10) 0.94931(9) 0.0677(3) Uani 1 1 d . . . C13 C 0.31377(14) 0.50918(15) 1.10730(11) 0.0526(4) Uani 1 1 d . . . H13A H 0.3356 0.4403 1.1637 0.079 Uiso 1 1 calc R . . H13B H 0.2697 0.5844 1.1186 0.079 Uiso 1 1 calc R . . H13C H 0.3820 0.5085 1.0769 0.079 Uiso 1 1 calc R . . C29 C 0.23869(13) 0.10094(13) 0.88584(10) 0.0468(3) Uani 1 1 d . . . H29 H 0.2578 0.1582 0.8417 0.056 Uiso 1 1 calc R . . C3 C -0.20300(15) 0.56646(16) 0.62731(10) 0.0560(4) Uani 1 1 d . . . H3 H -0.2468 0.5651 0.5878 0.067 Uiso 1 1 calc R . . C2 C -0.19409(15) 0.67246(15) 0.61035(11) 0.0574(4) Uani 1 1 d . . . H2 H -0.2323 0.7417 0.5591 0.069 Uiso 1 1 calc R . . C26 C 0.18030(14) -0.06789(13) 1.01370(11) 0.0508(4) Uani 1 1 d . . . H26 H 0.1593 -0.1245 1.0565 0.061 Uiso 1 1 calc R . . C27 C 0.25266(13) -0.09924(13) 0.94691(11) 0.0466(3) Uani 1 1 d . . . C25 C 0.13896(13) 0.04732(13) 1.01708(10) 0.0467(3) Uani 1 1 d . . . H25 H 0.0911 0.0675 1.0628 0.056 Uiso 1 1 calc R . . C28 C 0.28214(14) -0.01533(14) 0.88245(11) 0.0527(4) Uani 1 1 d . . . H28 H 0.3306 -0.0361 0.8371 0.063 Uiso 1 1 calc R . . C18 C 0.38013(14) 0.07165(17) 1.07583(12) 0.0640(5) Uani 1 1 d . . . H18 H 0.4087 0.0929 1.0187 0.077 Uiso 1 1 calc R . . C22 C 0.23177(14) 0.11734(17) 1.17720(11) 0.0595(4) Uani 1 1 d . . . H22 H 0.1584 0.1696 1.1897 0.071 Uiso 1 1 calc R . . C20 C 0.40991(18) -0.06848(16) 1.22753(14) 0.0719(6) Uani 1 1 d . . . H20 H 0.4557 -0.1430 1.2726 0.086 Uiso 1 1 calc R . . C21 C 0.30202(18) 0.0093(2) 1.24538(12) 0.0758(6) Uani 1 1 d . . . H21 H 0.2758 -0.0105 1.3036 0.091 Uiso 1 1 calc R . . C19 C 0.44938(17) -0.03616(19) 1.14398(15) 0.0804(6) Uani 1 1 d . . . H19 H 0.5239 -0.0871 1.1323 0.096 Uiso 1 1 calc R . . C30 C 0.3743(2) -0.2588(2) 0.8903(2) 0.0957(8) Uani 1 1 d . . . H30A H 0.3459 -0.2068 0.8288 0.144 Uiso 1 1 calc R . . H30B H 0.3928 -0.3417 0.9000 0.144 Uiso 1 1 calc R . . H30C H 0.4425 -0.2572 0.9019 0.144 Uiso 1 1 calc R . . N4 N 0.77614(10) 0.22604(10) 0.51596(7) 0.0387(3) Uani 1 1 d . . . C46 C 0.63714(12) 0.34489(12) 0.38935(9) 0.0389(3) Uani 1 1 d . . . O3 O 0.78277(10) 0.31792(10) 0.60867(7) 0.0563(3) Uani 1 1 d . . . C45 C 0.70618(12) 0.34022(12) 0.44620(9) 0.0380(3) Uani 1 1 d . . . C53 C 0.72292(12) 0.44787(12) 0.43218(9) 0.0398(3) Uani 1 1 d . . . O4 O 0.75814(12) 0.75913(11) 0.37889(9) 0.0717(4) Uani 1 1 d . . . C39 C 0.71341(13) 0.12064(13) 0.45796(10) 0.0449(3) Uani 1 1 d . . . C44 C 0.63099(12) 0.23439(12) 0.39989(9) 0.0411(3) Uani 1 1 d . . . C47 C 0.57587(12) 0.45931(12) 0.30830(9) 0.0401(3) Uani 1 1 d . . . C38 C 0.79540(13) 0.11372(12) 0.51394(9) 0.0415(3) Uani 1 1 d . . . N3 N 0.87553(11) 0.00694(11) 0.56290(9) 0.0487(3) Uani 1 1 d . . . C36 C 0.82016(12) 0.22481(13) 0.59242(9) 0.0419(3) Uani 1 1 d . . . C35 C 0.91173(13) 0.10498(14) 0.64590(10) 0.0452(3) Uani 1 1 d . . . C48 C 0.45882(13) 0.53808(14) 0.30569(10) 0.0481(3) Uani 1 1 d . . . H48 H 0.4161 0.5208 0.3555 0.058 Uiso 1 1 calc R . . C37 C 0.94072(13) 0.00175(13) 0.62547(10) 0.0467(3) Uani 1 1 d . . . C43 C 0.55002(14) 0.23652(14) 0.35118(10) 0.0484(4) Uani 1 1 d . . . H43 H 0.4955 0.3118 0.3120 0.058 Uiso 1 1 calc R . . C55 C 0.64501(14) 0.65997(13) 0.41544(10) 0.0476(4) Uani 1 1 d . . . H55 H 0.5826 0.7330 0.4171 0.057 Uiso 1 1 calc R . . C54 C 0.63020(13) 0.55850(13) 0.43336(10) 0.0438(3) Uani 1 1 d . . . H54 H 0.5574 0.5638 0.4464 0.053 Uiso 1 1 calc R . . C42 C 0.54893(15) 0.13009(15) 0.35973(11) 0.0544(4) Uani 1 1 d . . . C56 C 0.75254(15) 0.65342(14) 0.39495(10) 0.0500(4) Uani 1 1 d . . . C58 C 0.82995(14) 0.44248(14) 0.41311(11) 0.0524(4) Uani 1 1 d . . . H58 H 0.8928 0.3689 0.4128 0.063 Uiso 1 1 calc R . . C34 C 0.96942(15) 0.09316(16) 0.71812(11) 0.0584(4) Uani 1 1 d . . . H34 H 0.9476 0.1610 0.7337 0.070 Uiso 1 1 calc R . . C49 C 0.40487(15) 0.64234(15) 0.22961(12) 0.0575(4) Uani 1 1 d . . . H49 H 0.3263 0.6953 0.2287 0.069 Uiso 1 1 calc R . . C31 C 1.03262(15) -0.11209(15) 0.67509(12) 0.0596(4) Uani 1 1 d . . . H31 H 1.0536 -0.1814 0.6617 0.072 Uiso 1 1 calc R . . C52 C 0.63751(15) 0.48623(15) 0.23320(11) 0.0573(4) Uani 1 1 d . . . H52 H 0.7163 0.4342 0.2340 0.069 Uiso 1 1 calc R . . C40 C 0.71374(17) 0.01293(15) 0.46494(13) 0.0646(5) Uani 1 1 d . . . H40 H 0.7694 -0.0630 0.5024 0.077 Uiso 1 1 calc R . . C50 C 0.46700(17) 0.66791(16) 0.15535(12) 0.0643(5) Uani 1 1 d . . . H50 H 0.4307 0.7379 0.1041 0.077 Uiso 1 1 calc R . . C57 C 0.84593(15) 0.54441(16) 0.39429(12) 0.0577(4) Uani 1 1 d . . . H57 H 0.9187 0.5394 0.3814 0.069 Uiso 1 1 calc R . . C32 C 1.09104(16) -0.12076(17) 0.74292(13) 0.0691(5) Uani 1 1 d . . . H32 H 1.1535 -0.1956 0.7742 0.083 Uiso 1 1 calc R . . C41 C 0.63290(17) 0.01815(16) 0.41718(14) 0.0680(5) Uani 1 1 d . . . H41 H 0.6340 -0.0546 0.4231 0.082 Uiso 1 1 calc R . . C51 C 0.58303(18) 0.58967(18) 0.15716(12) 0.0712(5) Uani 1 1 d . . . H51 H 0.6252 0.6066 0.1068 0.085 Uiso 1 1 calc R . . C33 C 1.05834(17) -0.01902(18) 0.76594(13) 0.0709(5) Uani 1 1 d . . . H33 H 1.0970 -0.0272 0.8140 0.085 Uiso 1 1 calc R . . C59 C 0.8676(2) 0.7557(2) 0.36359(17) 0.0908(7) Uani 1 1 d . . . H59A H 0.9202 0.6926 0.4143 0.136 Uiso 1 1 calc R . . H59B H 0.8600 0.8341 0.3563 0.136 Uiso 1 1 calc R . . H59C H 0.8969 0.7382 0.3098 0.136 Uiso 1 1 calc R . . C60 C 0.46083(18) 0.13272(18) 0.30848(14) 0.0723(5) Uani 1 1 d . . . H60A H 0.4084 0.2166 0.2736 0.108 Uiso 1 1 calc R . . H60B H 0.4185 0.0949 0.3504 0.108 Uiso 1 1 calc R . . H60C H 0.4993 0.0884 0.2687 0.108 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 N2 0.0389(6) 0.0306(5) 0.0349(6) -0.0104(4) -0.0031(5) -0.0165(5) N1 0.0424(6) 0.0334(6) 0.0355(6) -0.0108(5) -0.0027(5) -0.0168(5) C9 0.0331(6) 0.0337(7) 0.0341(6) -0.0137(5) 0.0028(5) -0.0160(5) C5 0.0404(7) 0.0401(7) 0.0347(7) -0.0144(6) -0.0007(6) -0.0173(6) C8 0.0350(7) 0.0305(6) 0.0340(6) -0.0123(5) 0.0026(5) -0.0148(5) C15 0.0342(7) 0.0352(7) 0.0331(6) -0.0136(5) 0.0031(5) -0.0161(6) C23 0.0371(7) 0.0305(6) 0.0350(7) -0.0094(5) -0.0003(5) -0.0154(6) O1 0.0610(7) 0.0402(6) 0.0648(7) -0.0085(5) -0.0190(5) -0.0281(5) C14 0.0399(7) 0.0391(7) 0.0347(7) -0.0126(6) -0.0025(5) -0.0167(6) C16 0.0366(7) 0.0330(7) 0.0347(7) -0.0110(5) -0.0001(5) -0.0156(6) C7 0.0398(7) 0.0388(7) 0.0340(7) -0.0144(6) 0.0007(5) -0.0162(6) C6 0.0409(7) 0.0371(7) 0.0410(7) -0.0158(6) -0.0027(6) -0.0185(6) C10 0.0429(7) 0.0329(7) 0.0408(7) -0.0104(6) -0.0028(6) -0.0173(6) C17 0.0402(7) 0.0338(7) 0.0379(7) -0.0109(6) -0.0046(6) -0.0176(6) C11 0.0480(8) 0.0385(7) 0.0490(8) -0.0186(6) 0.0003(6) -0.0232(6) C12 0.0405(7) 0.0452(8) 0.0421(7) -0.0208(6) 0.0027(6) -0.0213(6) C4 0.0544(9) 0.0499(8) 0.0430(8) -0.0175(7) -0.0044(6) -0.0267(7) C24 0.0397(7) 0.0314(7) 0.0392(7) -0.0099(5) -0.0063(6) -0.0159(6) C1 0.0578(9) 0.0413(8) 0.0418(8) -0.0087(6) -0.0074(7) -0.0211(7) O2 0.0746(8) 0.0403(6) 0.0938(9) -0.0307(6) 0.0017(7) -0.0256(6) C13 0.0538(9) 0.0552(9) 0.0577(9) -0.0238(8) -0.0071(7) -0.0270(8) C29 0.0548(9) 0.0411(8) 0.0499(8) -0.0166(7) 0.0069(7) -0.0277(7) C3 0.0655(10) 0.0635(10) 0.0407(8) -0.0150(7) -0.0133(7) -0.0304(9) C2 0.0688(11) 0.0521(9) 0.0401(8) -0.0048(7) -0.0166(7) -0.0241(8) C26 0.0608(10) 0.0375(8) 0.0526(9) -0.0068(7) -0.0036(7) -0.0275(7) C27 0.0461(8) 0.0338(7) 0.0613(9) -0.0174(7) -0.0102(7) -0.0163(6) C25 0.0551(9) 0.0396(8) 0.0437(8) -0.0119(6) 0.0029(6) -0.0237(7) C28 0.0559(9) 0.0485(9) 0.0626(10) -0.0299(8) 0.0108(7) -0.0259(8) C18 0.0468(9) 0.0704(11) 0.0479(9) -0.0189(8) -0.0022(7) -0.0087(8) C22 0.0464(9) 0.0682(11) 0.0445(9) -0.0064(8) -0.0009(7) -0.0225(8) C20 0.0782(13) 0.0473(10) 0.0709(13) 0.0034(9) -0.0388(10) -0.0229(10) C21 0.0753(13) 0.0867(14) 0.0475(10) 0.0111(9) -0.0130(9) -0.0478(12) C19 0.0552(11) 0.0693(12) 0.0768(14) -0.0275(11) -0.0202(10) 0.0070(9) C30 0.0832(15) 0.0665(13) 0.154(2) -0.0707(15) 0.0288(15) -0.0300(11) N4 0.0440(6) 0.0338(6) 0.0389(6) -0.0113(5) -0.0019(5) -0.0192(5) C46 0.0428(7) 0.0338(7) 0.0397(7) -0.0130(6) 0.0005(6) -0.0176(6) O3 0.0686(7) 0.0510(6) 0.0522(6) -0.0243(5) -0.0066(5) -0.0236(6) C45 0.0414(7) 0.0329(7) 0.0390(7) -0.0129(6) 0.0019(6) -0.0171(6) C53 0.0478(8) 0.0360(7) 0.0375(7) -0.0127(6) -0.0001(6) -0.0210(6) O4 0.0985(10) 0.0557(7) 0.0852(9) -0.0340(6) 0.0225(7) -0.0527(7) C39 0.0540(9) 0.0366(7) 0.0461(8) -0.0144(6) -0.0034(6) -0.0218(7) C44 0.0475(8) 0.0376(7) 0.0416(7) -0.0161(6) 0.0015(6) -0.0211(6) C47 0.0468(8) 0.0357(7) 0.0409(7) -0.0141(6) -0.0030(6) -0.0202(6) C38 0.0484(8) 0.0347(7) 0.0415(7) -0.0119(6) 0.0004(6) -0.0207(6) N3 0.0542(8) 0.0356(6) 0.0504(7) -0.0102(5) -0.0067(6) -0.0183(6) C36 0.0459(8) 0.0450(8) 0.0401(7) -0.0148(6) 0.0006(6) -0.0253(7) C35 0.0448(8) 0.0470(8) 0.0441(8) -0.0078(6) -0.0012(6) -0.0276(7) C48 0.0474(8) 0.0479(8) 0.0464(8) -0.0137(7) -0.0012(6) -0.0223(7) C37 0.0467(8) 0.0434(8) 0.0457(8) -0.0061(6) -0.0033(6) -0.0241(7) C43 0.0531(9) 0.0432(8) 0.0505(8) -0.0167(7) -0.0063(7) -0.0219(7) C55 0.0561(9) 0.0341(7) 0.0468(8) -0.0136(6) -0.0081(7) -0.0149(7) C54 0.0451(8) 0.0392(8) 0.0461(8) -0.0147(6) -0.0050(6) -0.0179(6) C42 0.0625(10) 0.0533(9) 0.0605(10) -0.0263(8) -0.0014(8) -0.0315(8) C56 0.0767(11) 0.0433(8) 0.0414(8) -0.0168(6) 0.0066(7) -0.0365(8) C58 0.0537(9) 0.0450(8) 0.0671(10) -0.0298(8) 0.0153(8) -0.0255(7) C34 0.0645(10) 0.0621(10) 0.0535(9) -0.0084(8) -0.0124(8) -0.0388(9) C49 0.0497(9) 0.0500(9) 0.0607(10) -0.0144(8) -0.0118(8) -0.0151(8) C31 0.0564(10) 0.0434(9) 0.0647(10) -0.0036(8) -0.0099(8) -0.0216(8) C52 0.0529(9) 0.0534(9) 0.0490(9) -0.0138(7) 0.0057(7) -0.0174(8) C40 0.0794(12) 0.0372(8) 0.0753(12) -0.0132(8) -0.0232(9) -0.0245(8) C50 0.0744(12) 0.0525(10) 0.0480(9) -0.0009(8) -0.0162(8) -0.0247(9) C57 0.0644(10) 0.0620(10) 0.0689(11) -0.0353(9) 0.0254(8) -0.0432(9) C32 0.0601(11) 0.0565(11) 0.0711(12) 0.0091(9) -0.0236(9) -0.0304(9) C41 0.0848(13) 0.0448(9) 0.0855(13) -0.0225(9) -0.0179(10) -0.0337(9) C51 0.0750(13) 0.0723(12) 0.0447(9) -0.0058(8) 0.0066(8) -0.0315(10) C33 0.0749(12) 0.0717(12) 0.0629(11) 0.0031(9) -0.0261(9) -0.0452(11) C59 0.1218(19) 0.0920(15) 0.1129(18) -0.0615(14) 0.0525(15) -0.0842(15) C60 0.0793(13) 0.0718(12) 0.0863(13) -0.0347(11) -0.0116(10) -0.0420(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 N2 C8 1.4048(16) . ? N2 C6 1.4262(17) . ? N2 C23 1.4286(16) . ? N1 C8 1.3011(17) . ? N1 C7 1.3754(17) . ? C9 C10 1.3965(18) . ? C9 C15 1.4013(18) . ? C9 C8 1.4548(18) . ? C5 C7 1.3973(19) . ? C5 C4 1.3981(19) . ? C5 C6 1.4502(19) . ? C15 C14 1.4017(18) . ? C15 C16 1.4523(18) . ? C23 C16 1.3507(18) . ? C23 C24 1.4897(18) . ? O1 C6 1.2156(16) . ? C14 C12 1.3793(19) . ? C16 C17 1.4980(18) . ? C7 C1 1.4052(19) . ? C10 C11 1.3701(19) . ? C17 C18 1.370(2) . ? C17 C22 1.374(2) . ? C11 C12 1.402(2) . ? C12 C13 1.5048(19) . ? C4 C3 1.364(2) . ? C24 C29 1.374(2) . ? C24 C25 1.3877(19) . ? C1 C2 1.367(2) . ? O2 C27 1.3742(17) . ? O2 C30 1.407(3) . ? C29 C28 1.389(2) . ? C3 C2 1.393(2) . ? C26 C27 1.378(2) . ? C26 C25 1.380(2) . ? C27 C28 1.372(2) . ? C18 C19 1.378(3) . ? C22 C21 1.383(2) . ? C20 C19 1.350(3) . ? C20 C21 1.368(3) . ? N4 C38 1.4053(17) . ? N4 C36 1.4250(18) . ? N4 C45 1.4297(17) . ? C46 C45 1.3480(19) . ? C46 C44 1.4583(18) . ? C46 C47 1.4994(19) . ? O3 C36 1.2131(17) . ? C45 C53 1.4849(18) . ? C53 C58 1.378(2) . ? C53 C54 1.394(2) . ? O4 C56 1.3689(17) . ? O4 C59 1.416(3) . ? C39 C40 1.395(2) . ? C39 C44 1.399(2) . ? C39 C38 1.455(2) . ? C44 C43 1.400(2) . ? C47 C52 1.382(2) . ? C47 C48 1.383(2) . ? C38 N3 1.2969(18) . ? N3 C37 1.3785(19) . ? C36 C35 1.457(2) . ? C35 C37 1.397(2) . ? C35 C34 1.397(2) . ? C48 C49 1.382(2) . ? C37 C31 1.405(2) . ? C43 C42 1.379(2) . ? C55 C54 1.376(2) . ? C55 C56 1.381(2) . ? C42 C41 1.392(2) . ? C42 C60 1.503(2) . ? C56 C57 1.381(2) . ? C58 C57 1.388(2) . ? C34 C33 1.371(2) . ? C49 C50 1.373(3) . ? C31 C32 1.364(3) . ? C52 C51 1.379(2) . ? C40 C41 1.366(2) . ? C50 C51 1.373(3) . ? C32 C33 1.392(3) . ? 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 C8 N2 C6 119.34(10) . . ? C8 N2 C23 121.23(10) . . ? C6 N2 C23 119.17(10) . . ? C8 N1 C7 118.59(11) . . ? C10 C9 C15 119.37(12) . . ? C10 C9 C8 119.59(11) . . ? C15 C9 C8 121.04(11) . . ? C7 C5 C4 120.49(12) . . ? C7 C5 C6 119.80(12) . . ? C4 C5 C6 119.70(13) . . ? N1 C8 N2 124.01(11) . . ? N1 C8 C9 118.80(11) . . ? N2 C8 C9 117.19(11) . . ? C9 C15 C14 118.79(12) . . ? C9 C15 C16 118.70(11) . . ? C14 C15 C16 122.30(11) . . ? C16 C23 N2 120.50(11) . . ? C16 C23 C24 120.71(11) . . ? N2 C23 C24 117.90(11) . . ? C12 C14 C15 121.84(12) . . ? C23 C16 C15 120.72(11) . . ? C23 C16 C17 119.84(12) . . ? C15 C16 C17 119.32(11) . . ? N1 C7 C5 121.95(12) . . ? N1 C7 C1 119.49(12) . . ? C5 C7 C1 118.55(12) . . ? O1 C6 N2 121.39(12) . . ? O1 C6 C5 124.10(12) . . ? N2 C6 C5 114.51(11) . . ? C11 C10 C9 120.66(12) . . ? C18 C17 C22 118.34(14) . . ? C18 C17 C16 121.78(13) . . ? C22 C17 C16 119.88(13) . . ? C10 C11 C12 121.01(12) . . ? C14 C12 C11 118.25(12) . . ? C14 C12 C13 121.57(13) . . ? C11 C12 C13 120.18(13) . . ? C3 C4 C5 120.19(14) . . ? C29 C24 C25 118.38(13) . . ? C29 C24 C23 118.20(12) . . ? C25 C24 C23 123.19(13) . . ? C2 C1 C7 119.81(14) . . ? C27 O2 C30 118.16(14) . . ? C24 C29 C28 121.57(14) . . ? C4 C3 C2 119.48(14) . . ? C1 C2 C3 121.47(14) . . ? C27 C26 C25 120.09(14) . . ? C28 C27 O2 124.11(15) . . ? C28 C27 C26 120.24(13) . . ? O2 C27 C26 115.64(14) . . ? C26 C25 C24 120.58(14) . . ? C27 C28 C29 119.13(15) . . ? C17 C18 C19 120.85(17) . . ? C17 C22 C21 120.40(17) . . ? C19 C20 C21 119.45(16) . . ? C20 C21 C22 120.23(18) . . ? C20 C19 C18 120.58(18) . . ? C38 N4 C36 118.70(11) . . ? C38 N4 C45 120.70(11) . . ? C36 N4 C45 120.42(11) . . ? C45 C46 C44 120.34(12) . . ? C45 C46 C47 120.76(12) . . ? C44 C46 C47 118.54(12) . . ? C46 C45 N4 120.15(12) . . ? C46 C45 C53 121.66(12) . . ? N4 C45 C53 117.79(11) . . ? C58 C53 C54 118.33(13) . . ? C58 C53 C45 120.51(13) . . ? C54 C53 C45 121.08(13) . . ? C56 O4 C59 118.01(15) . . ? C40 C39 C44 119.42(14) . . ? C40 C39 C38 119.66(13) . . ? C44 C39 C38 120.87(12) . . ? C39 C44 C43 118.66(13) . . ? C39 C44 C46 118.34(12) . . ? C43 C44 C46 122.93(13) . . ? C52 C47 C48 118.77(14) . . ? C52 C47 C46 119.20(13) . . ? C48 C47 C46 122.02(13) . . ? N3 C38 N4 123.91(13) . . ? N3 C38 C39 119.60(12) . . ? N4 C38 C39 116.31(12) . . ? C38 N3 C37 118.45(13) . . ? O3 C36 N4 120.92(13) . . ? O3 C36 C35 124.90(13) . . ? N4 C36 C35 114.17(12) . . ? C37 C35 C34 120.12(14) . . ? C37 C35 C36 119.83(13) . . ? C34 C35 C36 120.05(14) . . ? C49 C48 C47 120.53(15) . . ? N3 C37 C35 121.43(13) . . ? N3 C37 C31 119.24(14) . . ? C35 C37 C31 119.12(14) . . ? C42 C43 C44 121.81(14) . . ? C54 C55 C56 120.01(14) . . ? C55 C54 C53 120.83(14) . . ? C43 C42 C41 118.23(14) . . ? C43 C42 C60 121.73(15) . . ? C41 C42 C60 120.04(15) . . ? O4 C56 C57 124.44(15) . . ? O4 C56 C55 115.36(14) . . ? C57 C56 C55 120.17(13) . . ? C53 C58 C57 121.43(14) . . ? C33 C34 C35 119.64(17) . . ? C50 C49 C48 120.15(16) . . ? C32 C31 C37 119.86(17) . . ? C51 C52 C47 120.46(16) . . ? C41 C40 C39 120.52(15) . . ? C51 C50 C49 119.67(15) . . ? C56 C57 C58 119.22(15) . . ? C31 C32 C33 120.84(16) . . ? C40 C41 C42 121.35(15) . . ? C50 C51 C52 120.42(17) . . ? C34 C33 C32 120.30(17) . . ? 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 C7 N1 C8 N2 1.56(19) . . . . ? C7 N1 C8 C9 -177.70(11) . . . . ? C6 N2 C8 N1 -12.57(19) . . . . ? C23 N2 C8 N1 173.33(12) . . . . ? C6 N2 C8 C9 166.70(11) . . . . ? C23 N2 C8 C9 -7.40(17) . . . . ? C10 C9 C8 N1 0.63(18) . . . . ? C15 C9 C8 N1 -179.67(11) . . . . ? C10 C9 C8 N2 -178.68(11) . . . . ? C15 C9 C8 N2 1.01(17) . . . . ? C10 C9 C15 C14 -2.20(18) . . . . ? C8 C9 C15 C14 178.10(11) . . . . ? C10 C9 C15 C16 -177.04(12) . . . . ? C8 C9 C15 C16 3.27(18) . . . . ? C8 N2 C23 C16 9.66(18) . . . . ? C6 N2 C23 C16 -164.46(12) . . . . ? C8 N2 C23 C24 -159.65(11) . . . . ? C6 N2 C23 C24 26.24(17) . . . . ? C9 C15 C14 C12 -0.29(19) . . . . ? C16 C15 C14 C12 174.34(12) . . . . ? N2 C23 C16 C15 -5.09(19) . . . . ? C24 C23 C16 C15 163.92(12) . . . . ? N2 C23 C16 C17 179.00(11) . . . . ? C24 C23 C16 C17 -12.00(19) . . . . ? C9 C15 C16 C23 -1.24(18) . . . . ? C14 C15 C16 C23 -175.88(12) . . . . ? C9 C15 C16 C17 174.70(11) . . . . ? C14 C15 C16 C17 0.06(19) . . . . ? C8 N1 C7 C5 5.16(19) . . . . ? C8 N1 C7 C1 -176.16(13) . . . . ? C4 C5 C7 N1 178.23(13) . . . . ? C6 C5 C7 N1 -0.8(2) . . . . ? C4 C5 C7 C1 -0.5(2) . . . . ? C6 C5 C7 C1 -179.47(13) . . . . ? C8 N2 C6 O1 -163.94(13) . . . . ? C23 N2 C6 O1 10.29(19) . . . . ? C8 N2 C6 C5 15.66(17) . . . . ? C23 N2 C6 C5 -170.11(11) . . . . ? C7 C5 C6 O1 170.10(14) . . . . ? C4 C5 C6 O1 -8.9(2) . . . . ? C7 C5 C6 N2 -9.49(18) . . . . ? C4 C5 C6 N2 171.50(12) . . . . ? C15 C9 C10 C11 2.3(2) . . . . ? C8 C9 C10 C11 -177.98(12) . . . . ? C23 C16 C17 C18 79.60(19) . . . . ? C15 C16 C17 C18 -96.37(17) . . . . ? C23 C16 C17 C22 -100.85(17) . . . . ? C15 C16 C17 C22 83.17(17) . . . . ? C9 C10 C11 C12 0.1(2) . . . . ? C15 C14 C12 C11 2.6(2) . . . . ? C15 C14 C12 C13 -176.53(13) . . . . ? C10 C11 C12 C14 -2.5(2) . . . . ? C10 C11 C12 C13 176.65(13) . . . . ? C7 C5 C4 C3 1.4(2) . . . . ? C6 C5 C4 C3 -179.64(14) . . . . ? C16 C23 C24 C29 -99.53(16) . . . . ? N2 C23 C24 C29 69.75(17) . . . . ? C16 C23 C24 C25 74.86(18) . . . . ? N2 C23 C24 C25 -115.85(15) . . . . ? N1 C7 C1 C2 -179.41(14) . . . . ? C5 C7 C1 C2 -0.7(2) . . . . ? C25 C24 C29 C28 -1.1(2) . . . . ? C23 C24 C29 C28 173.55(13) . . . . ? C5 C4 C3 C2 -1.1(2) . . . . ? C7 C1 C2 C3 1.0(3) . . . . ? C4 C3 C2 C1 -0.1(3) . . . . ? C30 O2 C27 C28 9.4(2) . . . . ? C30 O2 C27 C26 -171.99(17) . . . . ? C25 C26 C27 C28 -1.3(2) . . . . ? C25 C26 C27 O2 -179.93(13) . . . . ? C27 C26 C25 C24 1.0(2) . . . . ? C29 C24 C25 C26 0.2(2) . . . . ? C23 C24 C25 C26 -174.17(13) . . . . ? O2 C27 C28 C29 178.92(14) . . . . ? C26 C27 C28 C29 0.4(2) . . . . ? C24 C29 C28 C27 0.8(2) . . . . ? C22 C17 C18 C19 3.3(3) . . . . ? C16 C17 C18 C19 -177.17(17) . . . . ? C18 C17 C22 C21 -2.9(3) . . . . ? C16 C17 C22 C21 177.54(15) . . . . ? C19 C20 C21 C22 3.2(3) . . . . ? C17 C22 C21 C20 -0.3(3) . . . . ? C21 C20 C19 C18 -2.8(3) . . . . ? C17 C18 C19 C20 -0.4(3) . . . . ? C44 C46 C45 N4 1.5(2) . . . . ? C47 C46 C45 N4 -171.53(12) . . . . ? C44 C46 C45 C53 174.15(12) . . . . ? C47 C46 C45 C53 1.1(2) . . . . ? C38 N4 C45 C46 15.00(19) . . . . ? C36 N4 C45 C46 -160.11(13) . . . . ? C38 N4 C45 C53 -157.89(12) . . . . ? C36 N4 C45 C53 27.00(18) . . . . ? C46 C45 C53 C58 -115.27(16) . . . . ? N4 C45 C53 C58 57.51(18) . . . . ? C46 C45 C53 C54 61.43(19) . . . . ? N4 C45 C53 C54 -125.79(14) . . . . ? C40 C39 C44 C43 0.8(2) . . . . ? C38 C39 C44 C43 -176.54(14) . . . . ? C40 C39 C44 C46 -176.09(15) . . . . ? C38 C39 C44 C46 6.6(2) . . . . ? C45 C46 C44 C39 -12.1(2) . . . . ? C47 C46 C44 C39 161.15(13) . . . . ? C45 C46 C44 C43 171.18(14) . . . . ? C47 C46 C44 C43 -15.6(2) . . . . ? C45 C46 C47 C52 76.45(18) . . . . ? C44 C46 C47 C52 -96.73(17) . . . . ? C45 C46 C47 C48 -104.60(17) . . . . ? C44 C46 C47 C48 82.22(17) . . . . ? C36 N4 C38 N3 -19.8(2) . . . . ? C45 N4 C38 N3 165.01(13) . . . . ? C36 N4 C38 C39 155.40(13) . . . . ? C45 N4 C38 C39 -19.79(18) . . . . ? C40 C39 C38 N3 7.0(2) . . . . ? C44 C39 C38 N3 -175.68(14) . . . . ? C40 C39 C38 N4 -168.43(15) . . . . ? C44 C39 C38 N4 8.9(2) . . . . ? N4 C38 N3 C37 4.8(2) . . . . ? C39 C38 N3 C37 -170.23(13) . . . . ? C38 N4 C36 O3 -161.38(14) . . . . ? C45 N4 C36 O3 13.8(2) . . . . ? C38 N4 C36 C35 19.19(18) . . . . ? C45 N4 C36 C35 -165.60(12) . . . . ? O3 C36 C35 C37 174.28(14) . . . . ? N4 C36 C35 C37 -6.31(19) . . . . ? O3 C36 C35 C34 -4.9(2) . . . . ? N4 C36 C35 C34 174.46(13) . . . . ? C52 C47 C48 C49 -0.6(2) . . . . ? C46 C47 C48 C49 -179.52(14) . . . . ? C38 N3 C37 C35 9.2(2) . . . . ? C38 N3 C37 C31 -176.03(14) . . . . ? C34 C35 C37 N3 171.17(14) . . . . ? C36 C35 C37 N3 -8.1(2) . . . . ? C34 C35 C37 C31 -3.6(2) . . . . ? C36 C35 C37 C31 177.21(14) . . . . ? C39 C44 C43 C42 0.6(2) . . . . ? C46 C44 C43 C42 177.39(14) . . . . ? C56 C55 C54 C53 0.7(2) . . . . ? C58 C53 C54 C55 0.4(2) . . . . ? C45 C53 C54 C55 -176.42(13) . . . . ? C44 C43 C42 C41 -1.4(3) . . . . ? C44 C43 C42 C60 179.05(16) . . . . ? C59 O4 C56 C57 -2.3(2) . . . . ? C59 O4 C56 C55 175.79(16) . . . . ? C54 C55 C56 O4 -179.54(13) . . . . ? C54 C55 C56 C57 -1.4(2) . . . . ? C54 C53 C58 C57 -0.8(2) . . . . ? C45 C53 C58 C57 175.98(14) . . . . ? C37 C35 C34 C33 3.2(2) . . . . ? C36 C35 C34 C33 -177.58(15) . . . . ? C47 C48 C49 C50 0.7(2) . . . . ? N3 C37 C31 C32 -173.99(15) . . . . ? C35 C37 C31 C32 0.9(2) . . . . ? C48 C47 C52 C51 -0.1(2) . . . . ? C46 C47 C52 C51 178.89(16) . . . . ? C44 C39 C40 C41 -1.4(3) . . . . ? C38 C39 C40 C41 175.92(17) . . . . ? C48 C49 C50 C51 -0.2(3) . . . . ? O4 C56 C57 C58 178.91(15) . . . . ? C55 C56 C57 C58 0.9(2) . . . . ? C53 C58 C57 C56 0.2(3) . . . . ? C37 C31 C32 C33 2.2(3) . . . . ? C39 C40 C41 C42 0.6(3) . . . . ? C43 C42 C41 C40 0.8(3) . . . . ? C60 C42 C41 C40 -179.69(19) . . . . ? C49 C50 C51 C52 -0.4(3) . . . . ? C47 C52 C51 C50 0.6(3) . . . . ? C35 C34 C33 C32 -0.1(3) . . . . ? C31 C32 C33 C34 -2.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.216 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 962574' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_l _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 N2 O' _chemical_formula_weight 350.40 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 13.5728(5) _cell_length_b 18.3397(7) _cell_length_c 14.2808(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3554.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8545 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.46 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9684 _exptl_absorpt_correction_T_max 0.9762 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18095 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.66 _reflns_number_total 7820 _reflns_number_gt 6148 _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, 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^)+(0.0911P)^2^+0.5226P] 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 0.0043(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(16) _refine_ls_number_reflns 7820 _refine_ls_number_parameters 488 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1551 _refine_ls_wR_factor_gt 0.1384 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.008 _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 0.57248(13) 0.22865(10) 0.20656(13) 0.0442(4) Uani 1 1 d . . . C8 C 0.47922(16) 0.19578(12) 0.20731(15) 0.0438(5) Uani 1 1 d . . . C9 C 0.39493(16) 0.24423(13) 0.21113(15) 0.0443(5) Uani 1 1 d . . . C16 C 0.50524(17) 0.34759(13) 0.24057(17) 0.0465(5) Uani 1 1 d . . . C15 C 0.40691(16) 0.31900(13) 0.22547(15) 0.0444(5) Uani 1 1 d . . . C2 C 0.6390(2) 0.11001(14) 0.17281(17) 0.0532(6) Uani 1 1 d . . . N2 N 0.46452(15) 0.12606(11) 0.20097(15) 0.0532(5) Uani 1 1 d . . . C1 C 0.65408(18) 0.18831(14) 0.17163(18) 0.0512(6) Uani 1 1 d . . . C14 C 0.32341(18) 0.36388(15) 0.22470(17) 0.0538(6) Uani 1 1 d . . . H14A H 0.3308 0.4136 0.2354 0.065 Uiso 1 1 calc R . . C7 C 0.5459(2) 0.08155(14) 0.18924(17) 0.0538(6) Uani 1 1 d . . . C19 C 0.68565(17) 0.32872(13) 0.25525(18) 0.0479(5) Uani 1 1 d . . . O1 O 0.72832(14) 0.21820(11) 0.14430(16) 0.0703(6) Uani 1 1 d . . . C18 C 0.58420(15) 0.30373(13) 0.23021(16) 0.0444(5) Uani 1 1 d . . . C10 C 0.30060(18) 0.21629(15) 0.19548(19) 0.0559(6) Uani 1 1 d . . . H10A H 0.2920 0.1665 0.1864 0.067 Uiso 1 1 calc R . . C11 C 0.22087(18) 0.26171(17) 0.19338(19) 0.0600(7) Uani 1 1 d . . . H11A H 0.1588 0.2424 0.1816 0.072 Uiso 1 1 calc R . . C12 C 0.23056(17) 0.33615(17) 0.20844(19) 0.0577(6) Uani 1 1 d . . . C17 C 0.5151(2) 0.42528(15) 0.2723(2) 0.0647(7) Uani 1 1 d . . . H17A H 0.5836 0.4371 0.2795 0.097 Uiso 1 1 calc R . . H17B H 0.4819 0.4314 0.3311 0.097 Uiso 1 1 calc R . . H17C H 0.4861 0.4570 0.2264 0.097 Uiso 1 1 calc R . . C3 C 0.7183(2) 0.06344(16) 0.1541(2) 0.0656(7) Uani 1 1 d . . . H3A H 0.7805 0.0828 0.1425 0.079 Uiso 1 1 calc R . . C24 C 0.73015(17) 0.30235(14) 0.33579(19) 0.0533(6) Uani 1 1 d . . . H24A H 0.6990 0.2664 0.3709 0.064 Uiso 1 1 calc R . . C6 C 0.5326(3) 0.00546(17) 0.1881(2) 0.0712(9) Uani 1 1 d . . . H6A H 0.4708 -0.0144 0.2001 0.085 Uiso 1 1 calc R . . C4 C 0.7046(3) -0.01062(18) 0.1527(2) 0.0769(9) Uani 1 1 d . . . H4A H 0.7574 -0.0416 0.1408 0.092 Uiso 1 1 calc R . . C23 C 0.8206(2) 0.32926(17) 0.3644(2) 0.0666(8) Uani 1 1 d . . . H23A H 0.8500 0.3116 0.4186 0.080 Uiso 1 1 calc R . . C22 C 0.8666(2) 0.38193(19) 0.3126(3) 0.0726(8) Uani 1 1 d . . . H22A H 0.9274 0.4000 0.3317 0.087 Uiso 1 1 calc R . . C20 C 0.7333(2) 0.38131(16) 0.2043(2) 0.0697(8) Uani 1 1 d . . . H20A H 0.7044 0.3992 0.1499 0.084 Uiso 1 1 calc R . . C5 C 0.6111(3) -0.03924(17) 0.1691(3) 0.0823(10) Uani 1 1 d . . . H5A H 0.6017 -0.0895 0.1672 0.099 Uiso 1 1 calc R . . C13 C 0.1426(2) 0.38669(19) 0.2086(3) 0.0797(9) Uani 1 1 d . . . H13A H 0.1642 0.4357 0.2201 0.119 Uiso 1 1 calc R . . H13B H 0.0975 0.3721 0.2569 0.119 Uiso 1 1 calc R . . H13C H 0.1102 0.3844 0.1489 0.119 Uiso 1 1 calc R . . C21 C 0.8236(2) 0.4081(2) 0.2327(3) 0.0781(9) Uani 1 1 d . . . H21A H 0.8551 0.4439 0.1976 0.094 Uiso 1 1 calc R . . N3 N 0.17130(14) 0.26977(10) 0.45909(13) 0.0414(4) Uani 1 1 d . . . C40 C 0.24150(17) 0.15146(12) 0.42563(16) 0.0442(5) Uani 1 1 d . . . C32 C 0.26392(17) 0.30316(12) 0.46126(15) 0.0449(5) Uani 1 1 d . . . C39 C 0.33824(16) 0.18068(13) 0.44486(15) 0.0443(5) Uani 1 1 d . . . O2 O 0.01217(12) 0.27936(9) 0.51255(13) 0.0531(4) Uani 1 1 d . . . C26 C 0.10228(19) 0.38804(13) 0.49257(16) 0.0490(5) Uani 1 1 d . . . C33 C 0.34925(17) 0.25563(13) 0.46096(17) 0.0472(5) Uani 1 1 d . . . C25 C 0.08790(16) 0.30947(13) 0.49024(15) 0.0447(5) Uani 1 1 d . . . N4 N 0.27705(16) 0.37310(11) 0.46840(15) 0.0547(5) Uani 1 1 d . . . C42 C 0.16136(16) 0.19437(12) 0.43350(14) 0.0412(5) Uani 1 1 d . . . C31 C 0.1955(2) 0.41682(13) 0.47831(17) 0.0523(6) Uani 1 1 d . . . C38 C 0.42331(18) 0.13711(15) 0.44609(19) 0.0540(6) Uani 1 1 d . . . H38A H 0.4175 0.0875 0.4337 0.065 Uiso 1 1 calc R . . C43 C 0.06110(16) 0.16804(12) 0.40794(16) 0.0427(5) Uani 1 1 d . . . C36 C 0.51521(19) 0.16553(18) 0.4650(2) 0.0623(7) Uani 1 1 d . . . C35 C 0.5224(2) 0.23898(19) 0.4848(2) 0.0681(8) Uani 1 1 d . . . H35A H 0.5834 0.2584 0.5012 0.082 Uiso 1 1 calc R . . C48 C 0.01247(17) 0.19577(14) 0.33058(18) 0.0513(6) Uani 1 1 d . . . H48A H 0.0409 0.2333 0.2961 0.062 Uiso 1 1 calc R . . C41 C 0.2351(2) 0.07383(13) 0.3922(2) 0.0586(6) Uani 1 1 d . . . H41A H 0.1673 0.0611 0.3820 0.088 Uiso 1 1 calc R . . H41B H 0.2628 0.0420 0.4386 0.088 Uiso 1 1 calc R . . H41C H 0.2709 0.0688 0.3346 0.088 Uiso 1 1 calc R . . C34 C 0.44250(18) 0.28364(16) 0.4810(2) 0.0632(7) Uani 1 1 d . . . H34A H 0.4501 0.3333 0.4919 0.076 Uiso 1 1 calc R . . C27 C 0.0223(2) 0.43365(15) 0.51072(19) 0.0606(7) Uani 1 1 d . . . H27A H -0.0396 0.4139 0.5223 0.073 Uiso 1 1 calc R . . C46 C -0.1209(2) 0.11238(17) 0.3560(2) 0.0666(8) Uani 1 1 d . . . H46A H -0.1819 0.0937 0.3386 0.080 Uiso 1 1 calc R . . C47 C -0.07808(19) 0.16814(17) 0.3042(2) 0.0625(7) Uani 1 1 d . . . H47A H -0.1103 0.1868 0.2520 0.075 Uiso 1 1 calc R . . C30 C 0.2074(3) 0.49369(16) 0.4789(2) 0.0687(8) Uani 1 1 d . . . H30A H 0.2692 0.5141 0.4686 0.082 Uiso 1 1 calc R . . C28 C 0.0356(3) 0.50792(17) 0.5114(3) 0.0753(9) Uani 1 1 d . . . H28A H -0.0174 0.5387 0.5231 0.090 Uiso 1 1 calc R . . C44 C 0.01786(19) 0.11198(14) 0.4587(2) 0.0545(6) Uani 1 1 d . . . H44A H 0.0501 0.0925 0.5104 0.065 Uiso 1 1 calc R . . C29 C 0.1288(3) 0.53708(16) 0.4943(2) 0.0805(10) Uani 1 1 d . . . H29A H 0.1369 0.5874 0.4935 0.097 Uiso 1 1 calc R . . C37 C 0.6043(2) 0.1165(2) 0.4631(3) 0.0907(11) Uani 1 1 d . . . H37A H 0.5843 0.0677 0.4481 0.136 Uiso 1 1 calc R . . H37B H 0.6356 0.1170 0.5234 0.136 Uiso 1 1 calc R . . H37C H 0.6498 0.1337 0.4166 0.136 Uiso 1 1 calc R . . C45 C -0.0734(2) 0.08515(16) 0.4322(2) 0.0646(7) Uani 1 1 d . . . H45A H -0.1025 0.0481 0.4670 0.078 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 0.0436(9) 0.0463(10) 0.0427(10) 0.0024(8) -0.0028(8) -0.0026(8) C8 0.0476(12) 0.0466(12) 0.0371(10) 0.0054(10) -0.0029(9) -0.0064(9) C9 0.0446(11) 0.0537(13) 0.0345(10) 0.0060(10) 0.0029(8) -0.0043(9) C16 0.0517(12) 0.0469(13) 0.0408(11) 0.0017(10) -0.0045(9) -0.0029(10) C15 0.0445(11) 0.0548(14) 0.0339(10) 0.0033(9) 0.0009(9) 0.0008(10) C2 0.0642(15) 0.0524(14) 0.0430(12) 0.0039(11) -0.0069(11) 0.0065(12) N2 0.0602(12) 0.0494(11) 0.0501(11) 0.0062(10) -0.0056(9) -0.0081(9) C1 0.0503(13) 0.0559(14) 0.0475(12) -0.0029(12) 0.0003(10) 0.0020(11) C14 0.0551(13) 0.0583(15) 0.0479(13) 0.0018(11) 0.0040(10) 0.0066(11) C7 0.0717(16) 0.0451(13) 0.0446(13) 0.0040(11) -0.0084(11) -0.0013(12) C19 0.0445(12) 0.0459(13) 0.0533(13) -0.0037(10) -0.0006(10) -0.0032(10) O1 0.0582(12) 0.0697(12) 0.0830(14) -0.0095(11) 0.0148(10) -0.0050(9) C18 0.0461(12) 0.0477(13) 0.0392(11) 0.0016(10) -0.0045(9) -0.0058(9) C10 0.0553(13) 0.0616(15) 0.0507(14) 0.0035(12) 0.0080(11) -0.0099(12) C11 0.0449(12) 0.0829(19) 0.0521(14) 0.0051(14) 0.0076(10) -0.0105(12) C12 0.0445(13) 0.0851(19) 0.0435(12) 0.0036(13) 0.0062(10) 0.0094(12) C17 0.0656(16) 0.0577(16) 0.0709(18) -0.0095(14) -0.0105(13) 0.0011(13) C3 0.0793(19) 0.0640(18) 0.0534(15) 0.0002(13) -0.0063(13) 0.0150(14) C24 0.0498(13) 0.0534(14) 0.0566(14) 0.0019(12) -0.0039(11) 0.0039(10) C6 0.098(2) 0.0505(16) 0.065(2) 0.0076(13) -0.0047(18) -0.0049(15) C4 0.103(3) 0.0622(18) 0.066(2) 0.0028(16) -0.0070(19) 0.0292(18) C23 0.0529(14) 0.0785(19) 0.0684(18) -0.0105(15) -0.0170(13) 0.0147(14) C22 0.0462(14) 0.087(2) 0.085(2) -0.0211(18) -0.0020(14) -0.0113(14) C20 0.0671(17) 0.0776(19) 0.0645(16) 0.0139(16) -0.0081(14) -0.0190(14) C5 0.126(3) 0.0477(17) 0.073(2) 0.0046(15) -0.0159(19) 0.0153(19) C13 0.0530(15) 0.101(3) 0.085(2) 0.0005(19) 0.0095(15) 0.0157(15) C21 0.0703(18) 0.081(2) 0.083(2) -0.0020(18) 0.0019(16) -0.0296(16) N3 0.0490(10) 0.0392(9) 0.0360(9) 0.0005(8) 0.0010(7) -0.0033(8) C40 0.0483(11) 0.0460(12) 0.0384(11) 0.0009(10) -0.0057(9) -0.0017(10) C32 0.0535(13) 0.0459(12) 0.0353(10) 0.0011(10) 0.0022(9) -0.0081(10) C39 0.0476(11) 0.0496(13) 0.0358(10) 0.0050(9) -0.0010(9) -0.0021(10) O2 0.0537(9) 0.0543(10) 0.0511(9) -0.0041(8) 0.0062(8) 0.0009(8) C26 0.0671(14) 0.0450(12) 0.0349(10) 0.0011(10) -0.0027(10) 0.0009(11) C33 0.0492(12) 0.0519(13) 0.0406(11) -0.0019(10) 0.0057(9) -0.0072(10) C25 0.0521(13) 0.0477(12) 0.0343(10) 0.0016(10) -0.0008(9) 0.0008(10) N4 0.0646(13) 0.0479(11) 0.0516(12) 0.0005(10) 0.0014(10) -0.0119(9) C42 0.0466(11) 0.0406(12) 0.0365(11) 0.0032(9) -0.0005(8) -0.0040(9) C31 0.0735(16) 0.0416(12) 0.0418(12) 0.0008(11) -0.0029(11) -0.0033(12) C38 0.0509(12) 0.0569(15) 0.0541(14) 0.0074(12) -0.0019(10) 0.0012(11) C43 0.0438(11) 0.0427(12) 0.0417(11) -0.0047(9) 0.0015(9) -0.0009(9) C36 0.0459(13) 0.082(2) 0.0594(16) 0.0114(16) 0.0009(12) 0.0028(13) C35 0.0453(13) 0.086(2) 0.0729(19) -0.0023(16) 0.0074(12) -0.0129(13) C48 0.0472(12) 0.0564(14) 0.0501(13) -0.0018(12) 0.0009(10) 0.0029(10) C41 0.0583(14) 0.0491(14) 0.0685(17) -0.0076(12) -0.0114(12) 0.0034(12) C34 0.0506(14) 0.0672(17) 0.0719(19) -0.0062(14) 0.0120(12) -0.0172(12) C27 0.0784(17) 0.0541(15) 0.0492(14) -0.0012(12) -0.0023(13) 0.0118(13) C46 0.0466(13) 0.0755(19) 0.0777(19) -0.0235(16) 0.0047(13) -0.0103(13) C47 0.0496(14) 0.0762(18) 0.0618(16) -0.0103(14) -0.0075(12) 0.0083(13) C30 0.093(2) 0.0468(15) 0.066(2) 0.0033(13) -0.0108(17) -0.0111(14) C28 0.108(3) 0.0544(17) 0.0634(19) 0.0012(15) -0.0032(19) 0.0202(17) C44 0.0608(14) 0.0499(14) 0.0528(13) 0.0006(12) 0.0030(11) -0.0072(11) C29 0.125(3) 0.0407(15) 0.075(2) 0.0042(14) -0.0123(19) 0.0034(17) C37 0.0525(16) 0.104(3) 0.115(3) 0.009(2) -0.0094(18) 0.0138(16) C45 0.0631(15) 0.0621(17) 0.0686(18) -0.0093(14) 0.0153(13) -0.0213(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 N1 C8 1.402(3) . ? N1 C1 1.422(3) . ? N1 C18 1.427(3) . ? C8 N2 1.297(3) . ? C8 C9 1.450(3) . ? C9 C15 1.396(3) . ? C9 C10 1.397(3) . ? C16 C18 1.348(3) . ? C16 C15 1.450(3) . ? C16 C17 1.501(4) . ? C15 C14 1.401(3) . ? C2 C7 1.387(4) . ? C2 C3 1.400(4) . ? C2 C1 1.451(3) . ? N2 C7 1.384(3) . ? C1 O1 1.212(3) . ? C14 C12 1.379(4) . ? C14 H14A 0.9300 . ? C7 C6 1.407(4) . ? C19 C20 1.370(4) . ? C19 C24 1.386(4) . ? C19 C18 1.495(3) . ? C10 C11 1.366(4) . ? C10 H10A 0.9300 . ? C11 C12 1.388(4) . ? C11 H11A 0.9300 . ? C12 C13 1.512(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C3 C4 1.371(4) . ? C3 H3A 0.9300 . ? C24 C23 1.385(4) . ? C24 H24A 0.9300 . ? C6 C5 1.371(5) . ? C6 H6A 0.9300 . ? C4 C5 1.394(5) . ? C4 H4A 0.9300 . ? C23 C22 1.367(5) . ? C23 H23A 0.9300 . ? C22 C21 1.368(5) . ? C22 H22A 0.9300 . ? C20 C21 1.381(4) . ? C20 H20A 0.9300 . ? C5 H5A 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C21 H21A 0.9300 . ? N3 C32 1.399(3) . ? N3 C25 1.418(3) . ? N3 C42 1.437(3) . ? C40 C42 1.347(3) . ? C40 C39 1.445(3) . ? C40 C41 1.504(3) . ? C32 N4 1.299(3) . ? C32 C33 1.450(3) . ? C39 C33 1.402(3) . ? C39 C38 1.404(3) . ? O2 C25 1.209(3) . ? C26 C31 1.387(3) . ? C26 C27 1.395(4) . ? C26 C25 1.455(3) . ? C33 C34 1.396(3) . ? N4 C31 1.373(3) . ? C42 C43 1.489(3) . ? C31 C30 1.419(4) . ? C38 C36 1.379(4) . ? C38 H38A 0.9300 . ? C43 C48 1.384(3) . ? C43 C44 1.388(3) . ? C36 C35 1.380(4) . ? C36 C37 1.507(4) . ? C35 C34 1.361(4) . ? C35 H35A 0.9300 . ? C48 C47 1.382(4) . ? C48 H48A 0.9300 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C34 H34A 0.9300 . ? C27 C28 1.374(4) . ? C27 H27A 0.9300 . ? C46 C45 1.361(5) . ? C46 C47 1.389(4) . ? C46 H46A 0.9300 . ? C47 H47A 0.9300 . ? C30 C29 1.349(5) . ? C30 H30A 0.9300 . ? C28 C29 1.395(5) . ? C28 H28A 0.9300 . ? C44 C45 1.385(4) . ? C44 H44A 0.9300 . ? C29 H29A 0.9300 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C45 H45A 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 C8 N1 C1 118.82(19) . . ? C8 N1 C18 120.92(18) . . ? C1 N1 C18 119.88(18) . . ? N2 C8 N1 124.2(2) . . ? N2 C8 C9 119.0(2) . . ? N1 C8 C9 116.70(19) . . ? C15 C9 C10 119.4(2) . . ? C15 C9 C8 121.04(19) . . ? C10 C9 C8 119.5(2) . . ? C18 C16 C15 120.0(2) . . ? C18 C16 C17 121.9(2) . . ? C15 C16 C17 118.0(2) . . ? C9 C15 C14 118.8(2) . . ? C9 C15 C16 119.0(2) . . ? C14 C15 C16 122.2(2) . . ? C7 C2 C3 120.2(3) . . ? C7 C2 C1 120.2(2) . . ? C3 C2 C1 119.6(2) . . ? C8 N2 C7 117.8(2) . . ? O1 C1 N1 121.7(2) . . ? O1 C1 C2 124.7(2) . . ? N1 C1 C2 113.6(2) . . ? C12 C14 C15 121.6(2) . . ? C12 C14 H14A 119.2 . . ? C15 C14 H14A 119.2 . . ? N2 C7 C2 121.7(2) . . ? N2 C7 C6 118.9(3) . . ? C2 C7 C6 119.2(3) . . ? C20 C19 C24 118.7(2) . . ? C20 C19 C18 121.6(2) . . ? C24 C19 C18 119.5(2) . . ? C16 C18 N1 120.87(19) . . ? C16 C18 C19 121.5(2) . . ? N1 C18 C19 117.09(19) . . ? C11 C10 C9 120.4(2) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C10 C11 C12 121.4(2) . . ? C10 C11 H11A 119.3 . . ? C12 C11 H11A 119.3 . . ? C14 C12 C11 118.4(2) . . ? C14 C12 C13 119.7(3) . . ? C11 C12 C13 121.9(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C4 C3 C2 120.2(3) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C23 C24 C19 120.4(3) . . ? C23 C24 H24A 119.8 . . ? C19 C24 H24A 119.8 . . ? C5 C6 C7 119.7(3) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C3 C4 C5 119.6(3) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C22 C23 C24 119.8(3) . . ? C22 C23 H23A 120.1 . . ? C24 C23 H23A 120.1 . . ? C23 C22 C21 120.3(3) . . ? C23 C22 H22A 119.9 . . ? C21 C22 H22A 119.9 . . ? C19 C20 C21 120.9(3) . . ? C19 C20 H20A 119.6 . . ? C21 C20 H20A 119.6 . . ? C6 C5 C4 121.0(3) . . ? C6 C5 H5A 119.5 . . ? C4 C5 H5A 119.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C22 C21 C20 119.9(3) . . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C32 N3 C25 119.07(18) . . ? C32 N3 C42 120.77(18) . . ? C25 N3 C42 119.95(17) . . ? C42 C40 C39 120.1(2) . . ? C42 C40 C41 122.2(2) . . ? C39 C40 C41 117.7(2) . . ? N4 C32 N3 123.9(2) . . ? N4 C32 C33 119.0(2) . . ? N3 C32 C33 117.04(19) . . ? C33 C39 C38 117.9(2) . . ? C33 C39 C40 119.5(2) . . ? C38 C39 C40 122.6(2) . . ? C31 C26 C27 120.6(2) . . ? C31 C26 C25 119.8(2) . . ? C27 C26 C25 119.6(2) . . ? C34 C33 C39 119.4(2) . . ? C34 C33 C32 120.2(2) . . ? C39 C33 C32 120.3(2) . . ? O2 C25 N3 121.8(2) . . ? O2 C25 C26 124.1(2) . . ? N3 C25 C26 114.13(19) . . ? C32 N4 C31 118.3(2) . . ? C40 C42 N3 120.50(19) . . ? C40 C42 C43 121.9(2) . . ? N3 C42 C43 117.40(18) . . ? N4 C31 C26 121.9(2) . . ? N4 C31 C30 119.3(2) . . ? C26 C31 C30 118.7(3) . . ? C36 C38 C39 122.1(3) . . ? C36 C38 H38A 119.0 . . ? C39 C38 H38A 119.0 . . ? C48 C43 C44 119.2(2) . . ? C48 C43 C42 120.8(2) . . ? C44 C43 C42 119.9(2) . . ? C38 C36 C35 118.3(3) . . ? C38 C36 C37 119.8(3) . . ? C35 C36 C37 121.9(3) . . ? C34 C35 C36 121.5(3) . . ? C34 C35 H35A 119.2 . . ? C36 C35 H35A 119.2 . . ? C47 C48 C43 120.5(3) . . ? C47 C48 H48A 119.8 . . ? C43 C48 H48A 119.8 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C35 C34 C33 120.7(3) . . ? C35 C34 H34A 119.7 . . ? C33 C34 H34A 119.7 . . ? C28 C27 C26 119.6(3) . . ? C28 C27 H27A 120.2 . . ? C26 C27 H27A 120.2 . . ? C45 C46 C47 119.8(3) . . ? C45 C46 H46A 120.1 . . ? C47 C46 H46A 120.1 . . ? C48 C47 C46 119.8(3) . . ? C48 C47 H47A 120.1 . . ? C46 C47 H47A 120.1 . . ? C29 C30 C31 119.8(3) . . ? C29 C30 H30A 120.1 . . ? C31 C30 H30A 120.1 . . ? C27 C28 C29 119.9(3) . . ? C27 C28 H28A 120.1 . . ? C29 C28 H28A 120.1 . . ? C45 C44 C43 119.9(3) . . ? C45 C44 H44A 120.0 . . ? C43 C44 H44A 120.0 . . ? C30 C29 C28 121.3(3) . . ? C30 C29 H29A 119.3 . . ? C28 C29 H29A 119.3 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C46 C45 C44 120.8(3) . . ? C46 C45 H45A 119.6 . . ? C44 C45 H45A 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C8 N2 18.2(3) . . . . ? C18 N1 C8 N2 -168.8(2) . . . . ? C1 N1 C8 C9 -158.9(2) . . . . ? C18 N1 C8 C9 14.1(3) . . . . ? N2 C8 C9 C15 174.8(2) . . . . ? N1 C8 C9 C15 -8.0(3) . . . . ? N2 C8 C9 C10 -8.5(3) . . . . ? N1 C8 C9 C10 168.8(2) . . . . ? C10 C9 C15 C14 0.7(3) . . . . ? C8 C9 C15 C14 177.4(2) . . . . ? C10 C9 C15 C16 -179.3(2) . . . . ? C8 C9 C15 C16 -2.6(3) . . . . ? C18 C16 C15 C9 7.5(3) . . . . ? C17 C16 C15 C9 -169.6(2) . . . . ? C18 C16 C15 C14 -172.5(2) . . . . ? C17 C16 C15 C14 10.5(3) . . . . ? N1 C8 N2 C7 -2.5(3) . . . . ? C9 C8 N2 C7 174.5(2) . . . . ? C8 N1 C1 O1 158.7(2) . . . . ? C18 N1 C1 O1 -14.3(4) . . . . ? C8 N1 C1 C2 -21.6(3) . . . . ? C18 N1 C1 C2 165.4(2) . . . . ? C7 C2 C1 O1 -168.3(3) . . . . ? C3 C2 C1 O1 9.5(4) . . . . ? C7 C2 C1 N1 11.9(3) . . . . ? C3 C2 C1 N1 -170.3(2) . . . . ? C9 C15 C14 C12 -1.2(3) . . . . ? C16 C15 C14 C12 178.7(2) . . . . ? C8 N2 C7 C2 -8.0(3) . . . . ? C8 N2 C7 C6 176.1(2) . . . . ? C3 C2 C7 N2 -175.0(2) . . . . ? C1 C2 C7 N2 2.8(4) . . . . ? C3 C2 C7 C6 0.9(4) . . . . ? C1 C2 C7 C6 178.6(3) . . . . ? C15 C16 C18 N1 -1.5(3) . . . . ? C17 C16 C18 N1 175.4(2) . . . . ? C15 C16 C18 C19 -173.2(2) . . . . ? C17 C16 C18 C19 3.7(4) . . . . ? C8 N1 C18 C16 -9.7(3) . . . . ? C1 N1 C18 C16 163.2(2) . . . . ? C8 N1 C18 C19 162.3(2) . . . . ? C1 N1 C18 C19 -24.8(3) . . . . ? C20 C19 C18 C16 -69.0(4) . . . . ? C24 C19 C18 C16 106.1(3) . . . . ? C20 C19 C18 N1 119.0(3) . . . . ? C24 C19 C18 N1 -65.9(3) . . . . ? C15 C9 C10 C11 0.6(4) . . . . ? C8 C9 C10 C11 -176.2(2) . . . . ? C9 C10 C11 C12 -1.3(4) . . . . ? C15 C14 C12 C11 0.5(4) . . . . ? C15 C14 C12 C13 179.8(2) . . . . ? C10 C11 C12 C14 0.7(4) . . . . ? C10 C11 C12 C13 -178.5(3) . . . . ? C7 C2 C3 C4 -0.6(4) . . . . ? C1 C2 C3 C4 -178.4(3) . . . . ? C20 C19 C24 C23 0.5(4) . . . . ? C18 C19 C24 C23 -174.7(2) . . . . ? N2 C7 C6 C5 174.8(3) . . . . ? C2 C7 C6 C5 -1.2(4) . . . . ? C2 C3 C4 C5 0.6(5) . . . . ? C19 C24 C23 C22 -0.3(4) . . . . ? C24 C23 C22 C21 0.0(5) . . . . ? C24 C19 C20 C21 -0.4(5) . . . . ? C18 C19 C20 C21 174.7(3) . . . . ? C7 C6 C5 C4 1.2(5) . . . . ? C3 C4 C5 C6 -1.0(6) . . . . ? C23 C22 C21 C20 0.1(5) . . . . ? C19 C20 C21 C22 0.1(5) . . . . ? C25 N3 C32 N4 -17.2(3) . . . . ? C42 N3 C32 N4 168.1(2) . . . . ? C25 N3 C32 C33 159.03(19) . . . . ? C42 N3 C32 C33 -15.6(3) . . . . ? C42 C40 C39 C33 -7.4(3) . . . . ? C41 C40 C39 C33 169.4(2) . . . . ? C42 C40 C39 C38 174.1(2) . . . . ? C41 C40 C39 C38 -9.0(3) . . . . ? C38 C39 C33 C34 -2.5(3) . . . . ? C40 C39 C33 C34 179.0(2) . . . . ? C38 C39 C33 C32 -179.5(2) . . . . ? C40 C39 C33 C32 1.9(3) . . . . ? N4 C32 C33 C34 8.8(3) . . . . ? N3 C32 C33 C34 -167.7(2) . . . . ? N4 C32 C33 C39 -174.2(2) . . . . ? N3 C32 C33 C39 9.3(3) . . . . ? C32 N3 C25 O2 -160.9(2) . . . . ? C42 N3 C25 O2 13.8(3) . . . . ? C32 N3 C25 C26 19.1(3) . . . . ? C42 N3 C25 C26 -166.19(18) . . . . ? C31 C26 C25 O2 171.0(2) . . . . ? C27 C26 C25 O2 -7.9(3) . . . . ? C31 C26 C25 N3 -9.0(3) . . . . ? C27 C26 C25 N3 172.1(2) . . . . ? N3 C32 N4 C31 2.8(3) . . . . ? C33 C32 N4 C31 -173.4(2) . . . . ? C39 C40 C42 N3 1.3(3) . . . . ? C41 C40 C42 N3 -175.4(2) . . . . ? C39 C40 C42 C43 175.6(2) . . . . ? C41 C40 C42 C43 -1.1(3) . . . . ? C32 N3 C42 C40 10.6(3) . . . . ? C25 N3 C42 C40 -164.0(2) . . . . ? C32 N3 C42 C43 -163.96(19) . . . . ? C25 N3 C42 C43 21.5(3) . . . . ? C32 N4 C31 C26 8.2(3) . . . . ? C32 N4 C31 C30 -175.1(3) . . . . ? C27 C26 C31 N4 174.2(2) . . . . ? C25 C26 C31 N4 -4.7(3) . . . . ? C27 C26 C31 C30 -2.4(4) . . . . ? C25 C26 C31 C30 178.6(2) . . . . ? C33 C39 C38 C36 1.8(4) . . . . ? C40 C39 C38 C36 -179.6(2) . . . . ? C40 C42 C43 C48 -111.1(3) . . . . ? N3 C42 C43 C48 63.4(3) . . . . ? C40 C42 C43 C44 65.0(3) . . . . ? N3 C42 C43 C44 -120.5(2) . . . . ? C39 C38 C36 C35 1.1(4) . . . . ? C39 C38 C36 C37 -178.5(3) . . . . ? C38 C36 C35 C34 -3.6(5) . . . . ? C37 C36 C35 C34 176.1(3) . . . . ? C44 C43 C48 C47 0.1(4) . . . . ? C42 C43 C48 C47 176.3(2) . . . . ? C36 C35 C34 C33 2.9(5) . . . . ? C39 C33 C34 C35 0.2(4) . . . . ? C32 C33 C34 C35 177.2(2) . . . . ? C31 C26 C27 C28 2.2(4) . . . . ? C25 C26 C27 C28 -178.9(3) . . . . ? C43 C48 C47 C46 0.3(4) . . . . ? C45 C46 C47 C48 -0.2(4) . . . . ? N4 C31 C30 C29 -176.0(3) . . . . ? C26 C31 C30 C29 0.8(4) . . . . ? C26 C27 C28 C29 -0.3(5) . . . . ? C48 C43 C44 C45 -0.8(4) . . . . ? C42 C43 C44 C45 -176.9(2) . . . . ? C31 C30 C29 C28 1.1(5) . . . . ? C27 C28 C29 C30 -1.4(5) . . . . ? C47 C46 C45 C44 -0.5(4) . . . . ? C43 C44 C45 C46 0.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.66 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.263 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 962575'