# Electronic Supplementary Material (ESI) for Chemical Communications # 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_120601_lxj_24 _database_code_depnum_ccdc_archive 'CCDC 885330' #TrackingRef '120601_lxj_24.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H32 N4 O6' _chemical_formula_sum 'C34 H32 N4 O6' _chemical_formula_weight 592.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.5684(2) _cell_length_b 10.37340(15) _cell_length_c 13.8042(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.134(2) _cell_angle_gamma 90.00 _cell_volume 1523.34(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7742 _cell_measurement_theta_min 3.4788 _cell_measurement_theta_max 67.3700 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.734 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8320 _exptl_absorpt_correction_T_max 0.8670 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13194 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 67.48 _reflns_number_total 5419 _reflns_number_gt 4992 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0515P)^2^+0.1808P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0062(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_Flack 0.0(2) _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack (1983), 2523 Friedel pairs' _refine_ls_number_reflns 5419 _refine_ls_number_parameters 401 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.83193(14) 0.20916(16) 0.53255(11) 0.0612(4) Uani 1 1 d . . . O2 O 1.00313(13) 0.13041(12) 0.66397(10) 0.0493(3) Uani 1 1 d . . . O3 O 1.4062(2) 0.7408(3) 0.7238(2) 0.1290(11) Uani 1 1 d . . . O4 O 1.4719(3) 0.5675(4) 0.6787(3) 0.1435(12) Uani 1 1 d . . . O5 O 0.4472(3) 0.1862(3) 0.9709(3) 0.1465(13) Uani 1 1 d . . . O6 O 0.5322(3) 0.0218(3) 0.9417(3) 0.1505(14) Uani 1 1 d . . . N1 N 0.99873(13) 0.38931(15) 0.88266(11) 0.0412(3) Uani 1 1 d . . . N2 N 0.73038(14) 0.41956(15) 0.56943(11) 0.0441(3) Uani 1 1 d . . . H2 H 0.7164 0.3481 0.5351 0.053 Uiso 1 1 calc R . . N3 N 1.4031(2) 0.6248(4) 0.7112(2) 0.0956(9) Uani 1 1 d . . . N4 N 0.5236(2) 0.1365(2) 0.9456(2) 0.0780(6) Uani 1 1 d . . . C1 C 1.02987(16) 0.33468(16) 0.79848(13) 0.0371(4) Uani 1 1 d . . . H1 H 1.0630 0.2477 0.8203 0.045 Uiso 1 1 calc R . . C2 C 0.91652(16) 0.32259(17) 0.69455(13) 0.0373(4) Uani 1 1 d . . . C3 C 0.82523(15) 0.41595(16) 0.66578(13) 0.0364(3) Uani 1 1 d . . . C4 C 0.82846(17) 0.51146(16) 0.74789(13) 0.0403(4) Uani 1 1 d . . . H4A H 0.7442 0.5440 0.7311 0.048 Uiso 1 1 calc R . . H4B H 0.8810 0.5837 0.7465 0.048 Uiso 1 1 calc R . . C5 C 0.87896(17) 0.45366(16) 0.85913(13) 0.0388(4) Uani 1 1 d . . . H5 H 0.8956 0.5262 0.9083 0.047 Uiso 1 1 calc R . . C6 C 1.13272(16) 0.41315(19) 0.78114(12) 0.0406(4) Uani 1 1 d . . . C7 C 1.15137(19) 0.5430(2) 0.80556(17) 0.0527(5) Uani 1 1 d . . . H7 H 1.1041 0.5835 0.8378 0.063 Uiso 1 1 calc R . . C8 C 1.2397(2) 0.6140(2) 0.78273(19) 0.0635(6) Uani 1 1 d . . . H8 H 1.2504 0.7017 0.7975 0.076 Uiso 1 1 calc R . . C9 C 1.3108(2) 0.5507(3) 0.73764(17) 0.0637(6) Uani 1 1 d . . . C10 C 1.3001(2) 0.4216(3) 0.71848(19) 0.0711(7) Uani 1 1 d . . . H10 H 1.3522 0.3802 0.6914 0.085 Uiso 1 1 calc R . . C11 C 1.21086(19) 0.3534(2) 0.73992(17) 0.0568(5) Uani 1 1 d . . . H11 H 1.2027 0.2653 0.7265 0.068 Uiso 1 1 calc R . . C12 C 0.91178(16) 0.21814(18) 0.62196(13) 0.0413(4) Uani 1 1 d . . . C13 C 1.0187(2) 0.02312(19) 0.59964(17) 0.0580(5) Uani 1 1 d . . . C14 C 1.1324(4) -0.0451(3) 0.6764(3) 0.1116(13) Uani 1 1 d . . . H14A H 1.2035 0.0120 0.6978 0.167 Uiso 1 1 calc R . . H14B H 1.1496 -0.1200 0.6433 0.167 Uiso 1 1 calc R . . H14C H 1.1169 -0.0708 0.7370 0.167 Uiso 1 1 calc R . . C15 C 1.0421(3) 0.0745(3) 0.5070(2) 0.0743(7) Uani 1 1 d . . . H15A H 0.9679 0.1171 0.4594 0.111 Uiso 1 1 calc R . . H15B H 1.0628 0.0044 0.4713 0.111 Uiso 1 1 calc R . . H15C H 1.1106 0.1347 0.5313 0.111 Uiso 1 1 calc R . . C16 C 0.9043(4) -0.0637(3) 0.5632(2) 0.0896(9) Uani 1 1 d . . . H16A H 0.8899 -0.0939 0.6233 0.134 Uiso 1 1 calc R . . H16B H 0.9182 -0.1360 0.5258 0.134 Uiso 1 1 calc R . . H16C H 0.8322 -0.0163 0.5176 0.134 Uiso 1 1 calc R . . C17 C 0.65083(17) 0.52227(18) 0.51643(14) 0.0428(4) Uani 1 1 d . . . C18 C 0.5425(2) 0.4900(2) 0.43021(17) 0.0611(6) Uani 1 1 d . . . H18 H 0.5231 0.4038 0.4127 0.073 Uiso 1 1 calc R . . C19 C 0.4636(2) 0.5853(3) 0.3705(2) 0.0797(8) Uani 1 1 d . . . H19 H 0.3907 0.5630 0.3134 0.096 Uiso 1 1 calc R . . C20 C 0.4916(2) 0.7129(3) 0.3946(2) 0.0727(7) Uani 1 1 d . . . H20 H 0.4375 0.7768 0.3544 0.087 Uiso 1 1 calc R . . C21 C 0.5996(2) 0.7457(2) 0.47797(18) 0.0605(5) Uani 1 1 d . . . H21 H 0.6194 0.8322 0.4937 0.073 Uiso 1 1 calc R . . C22 C 0.67948(19) 0.6513(2) 0.53903(15) 0.0500(4) Uani 1 1 d . . . H22 H 0.7527 0.6745 0.5955 0.060 Uiso 1 1 calc R . . C23 C 0.78313(16) 0.36756(17) 0.87841(13) 0.0387(4) Uani 1 1 d . . . C24 C 0.79104(18) 0.23510(18) 0.87845(15) 0.0458(4) Uani 1 1 d . . . H24 H 0.8546 0.1963 0.8635 0.055 Uiso 1 1 calc R . . C25 C 0.70648(19) 0.15856(19) 0.90028(16) 0.0506(5) Uani 1 1 d . . . H25 H 0.7127 0.0692 0.9003 0.061 Uiso 1 1 calc R . . C26 C 0.61317(19) 0.2175(2) 0.92195(16) 0.0519(5) Uani 1 1 d . . . C27 C 0.6031(2) 0.3488(2) 0.9241(2) 0.0649(6) Uani 1 1 d . . . H27 H 0.5400 0.3869 0.9401 0.078 Uiso 1 1 calc R . . C28 C 0.6882(2) 0.4232(2) 0.90215(19) 0.0584(5) Uani 1 1 d . . . H28 H 0.6821 0.5125 0.9032 0.070 Uiso 1 1 calc R . . C29 C 1.08010(17) 0.36838(18) 0.98635(14) 0.0413(4) Uani 1 1 d . . . C30 C 1.0491(2) 0.4059(2) 1.07092(15) 0.0588(5) Uani 1 1 d . . . H30 H 0.9714 0.4435 1.0578 0.071 Uiso 1 1 calc R . . C31 C 1.1332(3) 0.3872(3) 1.17341(17) 0.0766(8) Uani 1 1 d . . . H31 H 1.1110 0.4135 1.2282 0.092 Uiso 1 1 calc R . . C32 C 1.2483(3) 0.3313(3) 1.19720(16) 0.0700(7) Uani 1 1 d . . . H32 H 1.3033 0.3187 1.2668 0.084 Uiso 1 1 calc R . . C33 C 1.2803(2) 0.2943(2) 1.11545(16) 0.0583(5) Uani 1 1 d . . . H33 H 1.3584 0.2568 1.1300 0.070 Uiso 1 1 calc R . . C34 C 1.19843(18) 0.31193(19) 1.01182(15) 0.0476(4) Uani 1 1 d . . . H34 H 1.2224 0.2858 0.9580 0.057 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 0.0613(8) 0.0664(9) 0.0460(8) -0.0203(7) 0.0106(6) 0.0086(7) O2 0.0576(8) 0.0417(7) 0.0475(7) -0.0081(6) 0.0196(6) 0.0077(6) O3 0.0934(17) 0.138(3) 0.150(2) 0.0335(19) 0.0426(15) -0.0504(17) O4 0.0970(17) 0.211(3) 0.160(2) 0.012(2) 0.0906(19) -0.035(2) O5 0.135(2) 0.1088(19) 0.275(4) 0.004(2) 0.165(3) -0.0066(16) O6 0.172(3) 0.0752(16) 0.287(4) 0.008(2) 0.179(3) -0.0196(16) N1 0.0423(8) 0.0508(9) 0.0333(7) -0.0032(6) 0.0178(6) 0.0016(6) N2 0.0451(8) 0.0417(8) 0.0413(7) -0.0031(6) 0.0125(6) 0.0014(7) N3 0.0615(14) 0.139(3) 0.0828(16) 0.0277(17) 0.0245(12) -0.0320(16) N4 0.0739(13) 0.0711(15) 0.1122(18) 0.0075(13) 0.0615(13) -0.0045(11) C1 0.0406(8) 0.0379(8) 0.0347(8) -0.0025(7) 0.0166(7) 0.0022(7) C2 0.0395(8) 0.0396(9) 0.0353(8) -0.0033(7) 0.0173(7) -0.0017(7) C3 0.0376(8) 0.0379(8) 0.0373(8) 0.0004(7) 0.0188(7) -0.0032(7) C4 0.0458(9) 0.0360(9) 0.0428(9) -0.0012(7) 0.0214(8) 0.0006(7) C5 0.0472(9) 0.0354(8) 0.0391(9) -0.0063(7) 0.0228(7) -0.0004(7) C6 0.0381(8) 0.0500(10) 0.0319(8) 0.0003(7) 0.0121(7) -0.0006(7) C7 0.0483(10) 0.0499(11) 0.0621(12) 0.0015(9) 0.0240(9) -0.0017(9) C8 0.0522(12) 0.0568(13) 0.0721(14) 0.0118(11) 0.0144(11) -0.0085(10) C9 0.0416(10) 0.0961(19) 0.0519(11) 0.0142(12) 0.0169(9) -0.0132(11) C10 0.0511(12) 0.106(2) 0.0671(13) -0.0166(14) 0.0352(11) -0.0152(13) C11 0.0494(11) 0.0684(14) 0.0602(12) -0.0153(10) 0.0297(10) -0.0058(9) C12 0.0443(9) 0.0423(9) 0.0402(9) -0.0053(8) 0.0199(8) -0.0005(8) C13 0.0863(15) 0.0395(10) 0.0574(11) -0.0065(9) 0.0383(11) 0.0083(10) C14 0.139(3) 0.080(2) 0.098(2) -0.0097(17) 0.027(2) 0.063(2) C15 0.0992(19) 0.0641(14) 0.0868(17) -0.0049(13) 0.0659(16) 0.0078(13) C16 0.149(3) 0.0583(15) 0.0778(16) -0.0208(13) 0.0618(18) -0.0349(17) C17 0.0388(9) 0.0507(10) 0.0408(9) 0.0024(8) 0.0178(7) 0.0024(8) C18 0.0514(11) 0.0623(14) 0.0551(12) 0.0030(10) 0.0053(10) -0.0026(10) C19 0.0614(14) 0.0811(18) 0.0705(15) 0.0143(14) -0.0023(12) 0.0011(13) C20 0.0602(14) 0.0761(17) 0.0726(15) 0.0214(13) 0.0161(11) 0.0187(13) C21 0.0716(14) 0.0525(12) 0.0638(13) 0.0091(10) 0.0333(11) 0.0101(10) C22 0.0525(11) 0.0521(11) 0.0455(10) 0.0027(9) 0.0195(8) 0.0031(9) C23 0.0424(9) 0.0386(9) 0.0386(8) -0.0003(7) 0.0197(7) 0.0046(7) C24 0.0505(10) 0.0406(10) 0.0557(11) -0.0010(8) 0.0311(9) 0.0055(8) C25 0.0580(11) 0.0387(10) 0.0630(12) 0.0026(9) 0.0323(10) 0.0018(8) C26 0.0519(11) 0.0556(11) 0.0574(11) 0.0067(9) 0.0312(9) -0.0009(9) C27 0.0589(12) 0.0589(13) 0.0966(17) -0.0003(12) 0.0516(13) 0.0098(10) C28 0.0665(13) 0.0412(10) 0.0861(15) 0.0013(10) 0.0500(12) 0.0101(9) C29 0.0471(10) 0.0412(9) 0.0361(8) -0.0022(7) 0.0167(7) -0.0102(7) C30 0.0607(12) 0.0801(15) 0.0398(9) -0.0054(10) 0.0242(9) -0.0113(11) C31 0.0914(19) 0.104(2) 0.0374(10) -0.0086(12) 0.0289(11) -0.0266(16) C32 0.0823(17) 0.0722(15) 0.0377(10) 0.0092(10) 0.0043(10) -0.0220(13) C33 0.0653(13) 0.0436(10) 0.0504(11) 0.0068(9) 0.0058(9) -0.0064(9) C34 0.0546(11) 0.0418(10) 0.0423(9) -0.0002(8) 0.0147(8) -0.0016(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.220(2) . ? O2 C12 1.342(2) . ? O2 C13 1.478(2) . ? O3 N3 1.215(4) . ? O4 N3 1.212(4) . ? O5 N4 1.189(3) . ? O6 N4 1.197(3) . ? N1 C29 1.387(2) . ? N1 C5 1.455(2) . ? N1 C1 1.459(2) . ? N2 C3 1.352(2) . ? N2 C17 1.410(2) . ? N2 H2 0.8600 . ? N3 C9 1.473(3) . ? N4 C26 1.466(3) . ? C1 C2 1.522(2) . ? C1 C6 1.536(2) . ? C1 H1 0.9800 . ? C2 C3 1.372(2) . ? C2 C12 1.462(2) . ? C3 C4 1.495(2) . ? C4 C5 1.534(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C23 1.526(2) . ? C5 H5 0.9800 . ? C6 C7 1.384(3) . ? C6 C11 1.389(3) . ? C7 C8 1.392(3) . ? C7 H7 0.9300 . ? C8 C9 1.377(4) . ? C8 H8 0.9300 . ? C9 C10 1.361(4) . ? C10 C11 1.377(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C13 C14 1.503(4) . ? C13 C15 1.504(3) . ? C13 C16 1.514(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C22 1.385(3) . ? C17 C18 1.389(3) . ? C18 C19 1.378(3) . ? C18 H18 0.9300 . ? C19 C20 1.372(4) . ? C19 H19 0.9300 . ? C20 C21 1.368(4) . ? C20 H20 0.9300 . ? C21 C22 1.383(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.377(2) . ? C23 C28 1.389(3) . ? C24 C25 1.382(3) . ? C24 H24 0.9300 . ? C25 C26 1.372(3) . ? C25 H25 0.9300 . ? C26 C27 1.368(3) . ? C27 C28 1.375(3) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C34 1.401(3) . ? C29 C30 1.404(3) . ? C30 C31 1.380(3) . ? C30 H30 0.9300 . ? C31 C32 1.369(4) . ? C31 H31 0.9300 . ? C32 C33 1.373(4) . ? C32 H32 0.9300 . ? C33 C34 1.383(3) . ? C33 H33 0.9300 . ? C34 H34 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 C12 O2 C13 120.81(15) . . ? C29 N1 C5 120.19(13) . . ? C29 N1 C1 118.77(14) . . ? C5 N1 C1 120.77(13) . . ? C3 N2 C17 130.04(15) . . ? C3 N2 H2 115.0 . . ? C17 N2 H2 115.0 . . ? O4 N3 O3 123.5(3) . . ? O4 N3 C9 118.8(3) . . ? O3 N3 C9 117.7(3) . . ? O5 N4 O6 121.9(2) . . ? O5 N4 C26 119.3(2) . . ? O6 N4 C26 118.8(2) . . ? N1 C1 C2 113.08(14) . . ? N1 C1 C6 111.53(14) . . ? C2 C1 C6 109.27(13) . . ? N1 C1 H1 107.6 . . ? C2 C1 H1 107.6 . . ? C6 C1 H1 107.6 . . ? C3 C2 C12 120.50(15) . . ? C3 C2 C1 119.67(15) . . ? C12 C2 C1 119.58(15) . . ? N2 C3 C2 122.64(15) . . ? N2 C3 C4 119.77(15) . . ? C2 C3 C4 117.48(15) . . ? C3 C4 C5 112.71(14) . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? N1 C5 C23 112.70(14) . . ? N1 C5 C4 110.95(13) . . ? C23 C5 C4 112.71(15) . . ? N1 C5 H5 106.7 . . ? C23 C5 H5 106.7 . . ? C4 C5 H5 106.7 . . ? C7 C6 C11 118.01(18) . . ? C7 C6 C1 122.25(16) . . ? C11 C6 C1 119.73(18) . . ? C6 C7 C8 121.2(2) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 118.2(2) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C10 C9 C8 122.1(2) . . ? C10 C9 N3 118.9(3) . . ? C8 C9 N3 118.9(3) . . ? C9 C10 C11 118.8(2) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C10 C11 C6 121.5(2) . . ? C10 C11 H11 119.2 . . ? C6 C11 H11 119.2 . . ? O1 C12 O2 122.69(16) . . ? O1 C12 C2 124.01(17) . . ? O2 C12 C2 113.29(14) . . ? O2 C13 C14 102.15(18) . . ? O2 C13 C15 110.43(17) . . ? C14 C13 C15 111.4(3) . . ? O2 C13 C16 110.50(19) . . ? C14 C13 C16 111.3(3) . . ? C15 C13 C16 110.8(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 118.80(18) . . ? C22 C17 N2 124.32(16) . . ? C18 C17 N2 116.61(18) . . ? C19 C18 C17 120.1(2) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 120.6(2) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C21 C20 C19 119.6(2) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 120.5(2) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C17 120.3(2) . . ? C21 C22 H22 119.9 . . ? C17 C22 H22 119.9 . . ? C24 C23 C28 118.23(17) . . ? C24 C23 C5 122.09(16) . . ? C28 C23 C5 119.59(16) . . ? C23 C24 C25 121.38(17) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C26 C25 C24 118.45(18) . . ? C26 C25 H25 120.8 . . ? C24 C25 H25 120.8 . . ? C27 C26 C25 121.95(19) . . ? C27 C26 N4 119.49(19) . . ? C25 C26 N4 118.6(2) . . ? C26 C27 C28 118.68(19) . . ? C26 C27 H27 120.7 . . ? C28 C27 H27 120.7 . . ? C27 C28 C23 121.30(19) . . ? C27 C28 H28 119.4 . . ? C23 C28 H28 119.4 . . ? N1 C29 C34 121.64(16) . . ? N1 C29 C30 121.54(18) . . ? C34 C29 C30 116.80(17) . . ? C31 C30 C29 120.4(2) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C32 C31 C30 122.2(2) . . ? C32 C31 H31 118.9 . . ? C30 C31 H31 118.9 . . ? C31 C32 C33 118.18(19) . . ? C31 C32 H32 120.9 . . ? C33 C32 H32 120.9 . . ? C32 C33 C34 121.1(2) . . ? C32 C33 H33 119.5 . . ? C34 C33 H33 119.5 . . ? C33 C34 C29 121.3(2) . . ? C33 C34 H34 119.3 . . ? C29 C34 H34 119.3 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 67.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.186 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.031 data_120827_lxf_lxj _database_code_depnum_ccdc_archive 'CCDC 898709' #TrackingRef '120827_lxf_lxj.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H30 N2 O' _chemical_formula_sum 'C30 H30 N2 O' _chemical_formula_weight 434.56 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' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.9799(5) _cell_length_b 8.7756(7) _cell_length_c 17.288(2) _cell_angle_alpha 87.612(10) _cell_angle_beta 85.963(9) _cell_angle_gamma 78.796(6) _cell_volume 1184.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1748 _cell_measurement_theta_min 2.9245 _cell_measurement_theta_max 29.4609 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9677 _exptl_absorpt_correction_T_max 0.9854 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7683 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5799 _reflns_number_gt 4145 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.078(16) _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 -2(4) _chemical_absolute_configuration unk _refine_ls_number_reflns 5799 _refine_ls_number_parameters 598 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1374 _refine_ls_R_factor_gt 0.1109 _refine_ls_wR_factor_ref 0.3099 _refine_ls_wR_factor_gt 0.2762 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _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 0.6246(8) 0.1847(8) 0.2438(3) 0.0729(17) Uani 1 1 d . . . H1 H 0.7197 0.1786 0.2214 0.109 Uiso 1 1 calc R . . O2 O 0.9876(9) 0.1328(8) 0.1550(4) 0.0828(19) Uani 1 1 d . . . H2 H 0.9531 0.2271 0.1519 0.124 Uiso 1 1 calc R . . N1 N 0.2048(7) 0.2859(6) 0.4087(3) 0.0487(15) Uani 1 1 d . . . N2 N 0.6672(9) 0.1655(8) 0.4898(4) 0.0635(17) Uani 1 1 d . . . H2A H 0.6834 0.2563 0.4745 0.076 Uiso 1 1 calc R . . N3 N 0.6289(7) 0.2465(6) -0.0146(3) 0.0482(14) Uani 1 1 d . . . N4 N 1.1152(10) 0.1412(9) -0.0952(5) 0.078(2) Uani 1 1 d . . . H4 H 1.1272 0.2306 -0.0803 0.094 Uiso 1 1 calc R . . C1 C 0.6398(10) 0.1047(10) 0.3155(5) 0.065(2) Uani 1 1 d . . . H1A H 0.7511 0.1067 0.3342 0.078 Uiso 1 1 calc R . . H1B H 0.6326 -0.0030 0.3088 0.078 Uiso 1 1 calc R . . C2 C 0.5025(8) 0.1748(8) 0.3746(4) 0.0482(17) Uani 1 1 d . . . H2B H 0.5186 0.2821 0.3783 0.058 Uiso 1 1 calc R . . C3 C 0.3171(8) 0.1909(8) 0.3510(4) 0.0436(15) Uani 1 1 d . . . H3 H 0.3105 0.2532 0.3025 0.052 Uiso 1 1 calc R . . C4 C 0.2577(9) 0.0430(8) 0.3338(5) 0.0495(17) Uani 1 1 d . . . C5 C 0.3259(11) -0.0336(10) 0.2660(5) 0.067(2) Uani 1 1 d . . . H5 H 0.4087 0.0034 0.2340 0.080 Uiso 1 1 calc R . . C6 C 0.2678(14) -0.1658(14) 0.2472(7) 0.089(3) Uani 1 1 d . . . H6 H 0.3158 -0.2185 0.2030 0.107 Uiso 1 1 calc R . . C7 C 0.1418(14) -0.2218(12) 0.2915(7) 0.087(3) Uani 1 1 d . . . H7 H 0.1031 -0.3093 0.2772 0.104 Uiso 1 1 calc R . . C8 C 0.0741(12) -0.1441(10) 0.3582(5) 0.068(2) Uani 1 1 d . . . H8 H -0.0096 -0.1805 0.3899 0.081 Uiso 1 1 calc R . . C9 C 0.1310(10) -0.0122(9) 0.3778(4) 0.0580(19) Uani 1 1 d . . . H9 H 0.0821 0.0405 0.4219 0.070 Uiso 1 1 calc R . . C10 C 0.0488(8) 0.3731(7) 0.3871(4) 0.0472(16) Uani 1 1 d . . . C11 C -0.0052(10) 0.3670(8) 0.3117(4) 0.0533(18) Uani 1 1 d . . . H11 H 0.0628 0.3024 0.2757 0.064 Uiso 1 1 calc R . . C12 C -0.1621(12) 0.4584(10) 0.2904(7) 0.076(3) Uani 1 1 d . . . H12 H -0.1964 0.4542 0.2404 0.091 Uiso 1 1 calc R . . C13 C -0.2645(12) 0.5538(11) 0.3434(7) 0.081(3) Uani 1 1 d . . . H13 H -0.3670 0.6155 0.3293 0.097 Uiso 1 1 calc R . . C14 C -0.2129(12) 0.5561(10) 0.4165(7) 0.076(3) Uani 1 1 d . . . H14 H -0.2834 0.6189 0.4525 0.091 Uiso 1 1 calc R . . C15 C -0.0593(11) 0.4686(9) 0.4399(6) 0.066(2) Uani 1 1 d . . . H15 H -0.0286 0.4736 0.4905 0.080 Uiso 1 1 calc R . . C16 C 0.2405(10) 0.2697(8) 0.4909(4) 0.0526(18) Uani 1 1 d . . . H16 H 0.1328 0.2604 0.5199 0.063 Uiso 1 1 calc R . . C17 C 0.2957(10) 0.4118(8) 0.5204(4) 0.0535(18) Uani 1 1 d . . . C18 C 0.3260(9) 0.5354(8) 0.4745(5) 0.0547(18) Uani 1 1 d . . . H18 H 0.3126 0.5354 0.4215 0.066 Uiso 1 1 calc R . . C19 C 0.3764(12) 0.6606(10) 0.5059(7) 0.079(3) Uani 1 1 d . . . H19 H 0.3999 0.7418 0.4733 0.095 Uiso 1 1 calc R . . C20 C 0.3924(15) 0.6674(13) 0.5836(9) 0.099(4) Uani 1 1 d . . . H20 H 0.4217 0.7541 0.6043 0.118 Uiso 1 1 calc R . . C21 C 0.365(2) 0.5456(18) 0.6301(8) 0.116(5) Uani 1 1 d . . . H21 H 0.3817 0.5461 0.6827 0.139 Uiso 1 1 calc R . . C22 C 0.3121(17) 0.4198(11) 0.5999(6) 0.092(4) Uani 1 1 d . . . H22 H 0.2872 0.3400 0.6332 0.111 Uiso 1 1 calc R . . C23 C 0.3690(10) 0.1158(9) 0.5057(4) 0.0556(18) Uani 1 1 d . . . H23A H 0.3951 0.1085 0.5598 0.067 Uiso 1 1 calc R . . H23B H 0.3154 0.0289 0.4958 0.067 Uiso 1 1 calc R . . C24 C 0.5330(10) 0.1031(8) 0.4559(4) 0.0518(17) Uani 1 1 d . . . H24 H 0.5775 -0.0081 0.4493 0.062 Uiso 1 1 calc R . . C25 C 0.7697(9) 0.0849(9) 0.5454(4) 0.0509(17) Uani 1 1 d . . . C26 C 0.8415(11) 0.1739(12) 0.5947(5) 0.068(2) Uani 1 1 d . . . H26 H 0.8107 0.2817 0.5938 0.082 Uiso 1 1 calc R . . C27 C 0.9610(13) 0.0957(15) 0.6455(5) 0.080(3) Uani 1 1 d . . . H27 H 1.0084 0.1531 0.6792 0.096 Uiso 1 1 calc R . . C28 C 1.0089(13) -0.0595(17) 0.6469(7) 0.093(4) Uani 1 1 d . . . H28 H 1.0938 -0.1082 0.6787 0.111 Uiso 1 1 calc R . . C29 C 0.9322(14) -0.1460(13) 0.6012(6) 0.085(3) Uani 1 1 d . . . H29 H 0.9598 -0.2539 0.6046 0.102 Uiso 1 1 calc R . . C30 C 0.8149(12) -0.0747(10) 0.5504(5) 0.068(2) Uani 1 1 d . . . H30 H 0.7653 -0.1348 0.5190 0.082 Uiso 1 1 calc R . . C31 C 1.0393(12) 0.0757(14) 0.0803(5) 0.082(3) Uani 1 1 d . . . H31A H 1.0508 -0.0365 0.0824 0.098 Uiso 1 1 calc R . . H31B H 1.1509 0.0993 0.0649 0.098 Uiso 1 1 calc R . . C32 C 0.9200(9) 0.1406(10) 0.0211(5) 0.059(2) Uani 1 1 d . . . H32 H 0.9306 0.2500 0.0154 0.071 Uiso 1 1 calc R . . C33 C 0.9746(9) 0.0750(8) -0.0595(4) 0.0524(18) Uani 1 1 d . . . H33 H 1.0198 -0.0361 -0.0513 0.063 Uiso 1 1 calc R . . C34 C 1.2329(10) 0.0677(11) -0.1527(4) 0.064(2) Uani 1 1 d . . . C35 C 1.2774(14) -0.0929(12) -0.1571(6) 0.079(3) Uani 1 1 d . . . H35 H 1.2204 -0.1570 -0.1252 0.095 Uiso 1 1 calc R . . C36 C 1.4085(16) -0.1553(15) -0.2100(7) 0.097(4) Uani 1 1 d . . . H36 H 1.4376 -0.2628 -0.2134 0.116 Uiso 1 1 calc R . . C37 C 1.4962(13) -0.0668(19) -0.2570(6) 0.096(4) Uani 1 1 d . . . H37 H 1.5877 -0.1123 -0.2900 0.116 Uiso 1 1 calc R . . C38 C 1.4471(13) 0.0907(17) -0.2547(5) 0.087(3) Uani 1 1 d . . . H38 H 1.5031 0.1530 -0.2881 0.105 Uiso 1 1 calc R . . C39 C 1.3160(13) 0.1594(12) -0.2038(6) 0.080(3) Uani 1 1 d . . . H39 H 1.2832 0.2670 -0.2037 0.096 Uiso 1 1 calc R . . C40 C 0.8254(9) 0.0862(9) -0.1100(4) 0.0540(18) Uani 1 1 d . . . H40A H 0.7718 -0.0031 -0.0990 0.065 Uiso 1 1 calc R . . H40B H 0.8675 0.0835 -0.1640 0.065 Uiso 1 1 calc R . . C41 C 0.6905(9) 0.2359(8) -0.0969(4) 0.0506(17) Uani 1 1 d . . . H41 H 0.5922 0.2252 -0.1257 0.061 Uiso 1 1 calc R . . C42 C 0.7497(10) 0.3819(9) -0.1298(4) 0.0552(19) Uani 1 1 d . . . C43 C 0.7799(17) 0.4002(12) -0.2087(6) 0.092(3) Uani 1 1 d . . . H43 H 0.7647 0.3219 -0.2407 0.110 Uiso 1 1 calc R . . C44 C 0.8311(18) 0.5281(16) -0.2417(8) 0.114(5) Uani 1 1 d . . . H44 H 0.8472 0.5378 -0.2954 0.137 Uiso 1 1 calc R . . C45 C 0.8598(18) 0.6470(13) -0.1939(9) 0.106(4) Uani 1 1 d . . . H45 H 0.8994 0.7337 -0.2149 0.127 Uiso 1 1 calc R . . C46 C 0.8274(12) 0.6290(10) -0.1174(7) 0.078(3) Uani 1 1 d . . . H46 H 0.8421 0.7064 -0.0849 0.093 Uiso 1 1 calc R . . C47 C 0.7731(10) 0.4998(9) -0.0856(5) 0.061(2) Uani 1 1 d . . . H47 H 0.7516 0.4926 -0.0321 0.074 Uiso 1 1 calc R . . C48 C 0.4677(9) 0.3316(8) 0.0072(5) 0.0533(18) Uani 1 1 d . . . C49 C 0.3747(11) 0.4314(10) -0.0473(6) 0.069(2) Uani 1 1 d . . . H49 H 0.4196 0.4394 -0.0982 0.083 Uiso 1 1 calc R . . C50 C 0.2163(13) 0.5173(11) -0.0245(7) 0.083(3) Uani 1 1 d . . . H50 H 0.1543 0.5781 -0.0621 0.099 Uiso 1 1 calc R . . C51 C 0.1469(13) 0.5188(12) 0.0474(9) 0.096(4) Uani 1 1 d . . . H51 H 0.0414 0.5809 0.0609 0.115 Uiso 1 1 calc R . . C52 C 0.2402(13) 0.4223(11) 0.1019(7) 0.092(3) Uani 1 1 d . . . H52 H 0.1955 0.4214 0.1530 0.111 Uiso 1 1 calc R . . C53 C 0.3974(10) 0.3273(10) 0.0829(5) 0.063(2) Uani 1 1 d . . . H53 H 0.4546 0.2619 0.1203 0.076 Uiso 1 1 calc R . . C54 C 0.7252(9) 0.1468(8) 0.0413(4) 0.0483(17) Uani 1 1 d . . . H54 H 0.6997 0.2013 0.0904 0.058 Uiso 1 1 calc R . . C55 C 0.6707(10) -0.0101(8) 0.0572(5) 0.0555(18) Uani 1 1 d . . . C56 C 0.5492(12) -0.0566(10) 0.0147(6) 0.068(2) Uani 1 1 d . . . H56 H 0.5011 0.0089 -0.0249 0.082 Uiso 1 1 calc R . . C57 C 0.4982(16) -0.1942(14) 0.0288(8) 0.101(4) Uani 1 1 d . . . H57 H 0.4163 -0.2219 -0.0007 0.121 Uiso 1 1 calc R . . C58 C 0.568(2) -0.2934(13) 0.0874(10) 0.117(5) Uani 1 1 d . . . H58 H 0.5358 -0.3890 0.0967 0.140 Uiso 1 1 calc R . . C59 C 0.686(2) -0.2499(14) 0.1316(9) 0.108(5) Uani 1 1 d . . . H59 H 0.7345 -0.3167 0.1707 0.130 Uiso 1 1 calc R . . C60 C 0.7342(14) -0.1065(10) 0.1182(5) 0.075(3) Uani 1 1 d . . . H60 H 0.8092 -0.0752 0.1503 0.090 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 0.066(3) 0.111(5) 0.049(3) -0.003(3) 0.005(3) -0.038(3) O2 0.073(4) 0.102(5) 0.076(4) -0.016(3) -0.028(3) -0.010(4) N1 0.048(3) 0.050(3) 0.046(3) 0.003(2) -0.005(3) -0.003(3) N2 0.059(4) 0.067(4) 0.069(4) 0.017(3) -0.025(3) -0.020(3) N3 0.035(3) 0.052(3) 0.057(3) -0.002(3) 0.001(2) -0.006(2) N4 0.077(5) 0.077(5) 0.084(5) -0.032(4) 0.027(4) -0.029(4) C1 0.041(4) 0.075(5) 0.081(6) -0.002(4) -0.012(4) -0.016(4) C2 0.038(4) 0.045(4) 0.063(4) 0.006(3) -0.013(3) -0.011(3) C3 0.037(3) 0.051(4) 0.043(3) 0.002(3) -0.006(3) -0.009(3) C4 0.043(4) 0.044(4) 0.066(4) 0.011(3) -0.015(3) -0.019(3) C5 0.062(5) 0.079(6) 0.061(5) -0.021(4) 0.001(4) -0.016(4) C6 0.079(7) 0.101(7) 0.094(7) -0.044(6) -0.001(5) -0.030(6) C7 0.086(7) 0.073(6) 0.112(8) -0.026(6) 0.001(6) -0.041(5) C8 0.073(6) 0.062(5) 0.077(5) -0.003(4) -0.005(4) -0.035(4) C9 0.053(4) 0.066(5) 0.055(4) 0.000(3) -0.003(3) -0.014(4) C10 0.038(3) 0.030(3) 0.074(5) 0.003(3) 0.001(3) -0.010(3) C11 0.050(4) 0.054(4) 0.057(4) 0.001(3) -0.012(3) -0.011(3) C12 0.056(5) 0.056(5) 0.115(7) 0.021(5) -0.025(5) -0.012(4) C13 0.047(5) 0.066(6) 0.124(9) -0.005(5) -0.013(5) 0.006(4) C14 0.054(5) 0.063(5) 0.110(8) -0.007(5) 0.006(5) -0.012(4) C15 0.056(5) 0.061(5) 0.086(6) 0.000(4) -0.008(4) -0.018(4) C16 0.059(4) 0.051(4) 0.048(4) 0.007(3) 0.004(3) -0.015(3) C17 0.054(4) 0.051(4) 0.052(4) -0.006(3) -0.003(3) -0.002(3) C18 0.048(4) 0.048(4) 0.068(5) -0.013(3) -0.001(3) -0.008(3) C19 0.059(5) 0.053(5) 0.126(9) -0.019(5) 0.003(5) -0.013(4) C20 0.084(7) 0.070(7) 0.146(11) -0.060(7) -0.043(7) 0.000(5) C21 0.157(13) 0.106(9) 0.085(8) -0.037(7) -0.050(8) -0.003(9) C22 0.135(10) 0.064(5) 0.076(6) -0.017(5) -0.039(6) 0.002(6) C23 0.063(4) 0.060(4) 0.049(4) 0.017(3) -0.017(3) -0.024(4) C24 0.061(5) 0.046(4) 0.052(4) 0.007(3) -0.018(3) -0.017(3) C25 0.044(4) 0.066(4) 0.045(4) -0.001(3) -0.005(3) -0.013(3) C26 0.058(5) 0.092(6) 0.058(5) -0.002(4) -0.001(4) -0.023(4) C27 0.073(6) 0.123(9) 0.055(5) -0.004(5) -0.010(4) -0.041(6) C28 0.056(5) 0.136(11) 0.079(6) 0.032(7) -0.013(5) -0.005(6) C29 0.078(6) 0.084(7) 0.085(7) 0.018(5) -0.016(5) 0.001(5) C30 0.072(5) 0.066(5) 0.061(5) 0.014(4) -0.011(4) -0.002(4) C31 0.059(5) 0.117(8) 0.072(6) -0.009(5) -0.001(4) -0.025(5) C32 0.037(4) 0.070(5) 0.076(5) -0.021(4) -0.003(4) -0.018(3) C33 0.043(4) 0.047(4) 0.061(4) 0.002(3) 0.016(3) -0.001(3) C34 0.041(4) 0.105(7) 0.051(4) -0.022(4) 0.005(3) -0.023(4) C35 0.087(7) 0.078(6) 0.074(6) -0.010(5) 0.009(5) -0.023(5) C36 0.086(7) 0.099(8) 0.093(7) -0.015(6) -0.002(6) 0.013(6) C37 0.054(5) 0.158(13) 0.075(7) -0.031(7) 0.008(5) -0.013(7) C38 0.071(6) 0.148(11) 0.048(5) 0.010(6) -0.006(4) -0.037(7) C39 0.071(6) 0.087(6) 0.085(6) -0.001(5) -0.017(5) -0.017(5) C40 0.057(4) 0.060(4) 0.047(4) -0.021(3) 0.012(3) -0.018(3) C41 0.050(4) 0.051(4) 0.051(4) -0.008(3) -0.006(3) -0.008(3) C42 0.058(4) 0.050(4) 0.055(4) 0.004(3) -0.004(3) -0.003(3) C43 0.135(10) 0.083(7) 0.053(5) 0.006(5) 0.018(5) -0.020(6) C44 0.135(11) 0.103(9) 0.085(7) 0.052(7) 0.027(7) 0.004(8) C45 0.118(9) 0.060(6) 0.129(11) 0.042(7) 0.015(8) -0.006(6) C46 0.066(5) 0.053(5) 0.113(8) 0.019(5) -0.008(5) -0.010(4) C47 0.057(4) 0.060(5) 0.065(5) 0.013(4) -0.009(4) -0.006(4) C48 0.042(4) 0.045(4) 0.075(5) 0.001(3) 0.001(3) -0.018(3) C49 0.050(4) 0.066(5) 0.088(6) -0.002(4) -0.002(4) -0.007(4) C50 0.061(5) 0.060(5) 0.126(9) 0.003(5) -0.015(6) -0.004(4) C51 0.050(5) 0.064(6) 0.163(11) -0.003(7) 0.010(6) 0.009(4) C52 0.065(6) 0.072(6) 0.132(9) 0.004(6) 0.040(6) -0.009(5) C53 0.048(4) 0.065(5) 0.076(5) 0.002(4) 0.012(4) -0.013(4) C54 0.049(4) 0.046(4) 0.049(4) -0.007(3) 0.005(3) -0.006(3) C55 0.054(4) 0.048(4) 0.066(5) -0.014(3) 0.009(3) -0.015(3) C56 0.069(5) 0.054(5) 0.083(6) -0.016(4) 0.013(4) -0.019(4) C57 0.093(8) 0.079(7) 0.139(11) -0.037(7) 0.036(7) -0.043(6) C58 0.156(14) 0.056(6) 0.140(12) 0.005(7) 0.037(11) -0.043(8) C59 0.117(10) 0.068(7) 0.119(10) 0.029(7) 0.039(9) 0.009(7) C60 0.089(6) 0.063(5) 0.070(5) 0.018(4) -0.005(5) -0.010(5) _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 C1 1.400(10) . ? O1 H1 0.8200 . ? O2 C31 1.410(11) . ? O2 H2 0.8200 . ? N1 C10 1.395(8) . ? N1 C3 1.465(8) . ? N1 C16 1.465(10) . ? N2 C25 1.387(9) . ? N2 C24 1.460(11) . ? N2 H2A 0.8600 . ? N3 C48 1.391(9) . ? N3 C54 1.437(9) . ? N3 C41 1.472(9) . ? N4 C34 1.404(10) . ? N4 C33 1.450(11) . ? N4 H4 0.8600 . ? C1 C2 1.502(11) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C24 1.533(10) . ? C2 C3 1.541(9) . ? C2 H2B 0.9800 . ? C3 C4 1.512(10) . ? C3 H3 0.9800 . ? C4 C9 1.373(11) . ? C4 C5 1.400(11) . ? C5 C6 1.389(14) . ? C5 H5 0.9300 . ? C6 C7 1.376(16) . ? C6 H6 0.9300 . ? C7 C8 1.386(14) . ? C7 H7 0.9300 . ? C8 C9 1.385(12) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.397(11) . ? C10 C11 1.407(11) . ? C11 C12 1.413(11) . ? C11 H11 0.9300 . ? C12 C13 1.379(14) . ? C12 H12 0.9300 . ? C13 C14 1.359(15) . ? C13 H13 0.9300 . ? C14 C15 1.391(13) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.519(11) . ? C16 C23 1.553(10) . ? C16 H16 0.9800 . ? C17 C18 1.367(11) . ? C17 C22 1.396(12) . ? C18 C19 1.384(13) . ? C18 H18 0.9300 . ? C19 C20 1.362(17) . ? C19 H19 0.9300 . ? C20 C21 1.35(2) . ? C20 H20 0.9300 . ? C21 C22 1.388(19) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.503(11) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24 0.9800 . ? C25 C30 1.378(12) . ? C25 C26 1.401(12) . ? C26 C27 1.402(13) . ? C26 H26 0.9300 . ? C27 C28 1.341(16) . ? C27 H27 0.9300 . ? C28 C29 1.369(17) . ? C28 H28 0.9300 . ? C29 C30 1.371(13) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C32 1.468(12) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.533(10) . ? C32 C54 1.559(10) . ? C32 H32 0.9800 . ? C33 C40 1.510(11) . ? C33 H33 0.9800 . ? C34 C35 1.389(14) . ? C34 C39 1.391(14) . ? C35 C36 1.384(15) . ? C35 H35 0.9300 . ? C36 C37 1.354(19) . ? C36 H36 0.9300 . ? C37 C38 1.363(17) . ? C37 H37 0.9300 . ? C38 C39 1.378(15) . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 C41 1.542(10) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 C42 1.525(11) . ? C41 H41 0.9800 . ? C42 C47 1.361(12) . ? C42 C43 1.377(12) . ? C43 C44 1.358(17) . ? C43 H43 0.9300 . ? C44 C45 1.42(2) . ? C44 H44 0.9300 . ? C45 C46 1.339(17) . ? C45 H45 0.9300 . ? C46 C47 1.371(13) . ? C46 H46 0.9300 . ? C47 H47 0.9300 . ? C48 C53 1.389(11) . ? C48 C49 1.409(11) . ? C49 C50 1.381(12) . ? C49 H49 0.9300 . ? C50 C51 1.324(17) . ? C50 H50 0.9300 . ? C51 C52 1.395(17) . ? C51 H51 0.9300 . ? C52 C53 1.390(12) . ? C52 H52 0.9300 . ? C53 H53 0.9300 . ? C54 C55 1.531(11) . ? C54 H54 0.9800 . ? C55 C60 1.385(12) . ? C55 C56 1.388(13) . ? C56 C57 1.355(15) . ? C56 H56 0.9300 . ? C57 C58 1.38(2) . ? C57 H57 0.9300 . ? C58 C59 1.37(2) . ? C58 H58 0.9300 . ? C59 C60 1.391(18) . ? C59 H59 0.9300 . ? C60 H60 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 C1 O1 H1 109.5 . . ? C31 O2 H2 109.5 . . ? C10 N1 C3 119.4(6) . . ? C10 N1 C16 119.3(6) . . ? C3 N1 C16 120.5(5) . . ? C25 N2 C24 123.0(7) . . ? C25 N2 H2A 118.5 . . ? C24 N2 H2A 118.5 . . ? C48 N3 C54 119.9(5) . . ? C48 N3 C41 120.8(6) . . ? C54 N3 C41 118.5(5) . . ? C34 N4 C33 123.7(7) . . ? C34 N4 H4 118.1 . . ? C33 N4 H4 118.1 . . ? O1 C1 C2 111.8(6) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? C1 C2 C24 112.0(5) . . ? C1 C2 C3 115.7(6) . . ? C24 C2 C3 114.2(6) . . ? C1 C2 H2B 104.4 . . ? C24 C2 H2B 104.4 . . ? C3 C2 H2B 104.4 . . ? N1 C3 C4 113.4(6) . . ? N1 C3 C2 107.7(6) . . ? C4 C3 C2 117.2(6) . . ? N1 C3 H3 105.9 . . ? C4 C3 H3 105.9 . . ? C2 C3 H3 105.9 . . ? C9 C4 C5 118.6(7) . . ? C9 C4 C3 123.4(7) . . ? C5 C4 C3 117.8(7) . . ? C6 C5 C4 118.9(9) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C7 C6 C5 122.5(9) . . ? C7 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? C6 C7 C8 118.1(9) . . ? C6 C7 H7 121.0 . . ? C8 C7 H7 121.0 . . ? C9 C8 C7 120.1(9) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C4 C9 C8 121.9(8) . . ? C4 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? N1 C10 C15 121.0(7) . . ? N1 C10 C11 121.1(6) . . ? C15 C10 C11 117.9(6) . . ? C10 C11 C12 120.4(8) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 120.4(10) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 118.7(8) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C15 122.8(9) . . ? C13 C14 H14 118.6 . . ? C15 C14 H14 118.6 . . ? C14 C15 C10 119.8(9) . . ? C14 C15 H15 120.1 . . ? C10 C15 H15 120.1 . . ? N1 C16 C17 112.6(6) . . ? N1 C16 C23 109.8(6) . . ? C17 C16 C23 113.5(6) . . ? N1 C16 H16 106.8 . . ? C17 C16 H16 106.8 . . ? C23 C16 H16 106.8 . . ? C18 C17 C22 117.3(8) . . ? C18 C17 C16 124.4(6) . . ? C22 C17 C16 118.3(8) . . ? C17 C18 C19 120.9(8) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C20 C19 C18 121.4(10) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C21 C20 C19 118.8(10) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? C20 C21 C22 120.7(11) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C21 C22 C17 120.8(12) . . ? C21 C22 H22 119.6 . . ? C17 C22 H22 119.6 . . ? C24 C23 C16 113.1(6) . . ? C24 C23 H23A 109.0 . . ? C16 C23 H23A 109.0 . . ? C24 C23 H23B 109.0 . . ? C16 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? N2 C24 C23 114.8(6) . . ? N2 C24 C2 110.0(6) . . ? C23 C24 C2 111.8(6) . . ? N2 C24 H24 106.6 . . ? C23 C24 H24 106.6 . . ? C2 C24 H24 106.6 . . ? C30 C25 N2 124.0(7) . . ? C30 C25 C26 119.0(7) . . ? N2 C25 C26 116.8(7) . . ? C25 C26 C27 118.1(9) . . ? C25 C26 H26 121.0 . . ? C27 C26 H26 121.0 . . ? C28 C27 C26 121.8(10) . . ? C28 C27 H27 119.1 . . ? C26 C27 H27 119.1 . . ? C27 C28 C29 119.6(9) . . ? C27 C28 H28 120.2 . . ? C29 C28 H28 120.2 . . ? C28 C29 C30 120.5(10) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C29 C30 C25 120.7(10) . . ? C29 C30 H30 119.6 . . ? C25 C30 H30 119.6 . . ? O2 C31 C32 113.6(7) . . ? O2 C31 H31A 108.8 . . ? C32 C31 H31A 108.8 . . ? O2 C31 H31B 108.8 . . ? C32 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? C31 C32 C33 113.4(6) . . ? C31 C32 C54 117.7(7) . . ? C33 C32 C54 111.2(6) . . ? C31 C32 H32 104.3 . . ? C33 C32 H32 104.3 . . ? C54 C32 H32 104.3 . . ? N4 C33 C40 114.1(6) . . ? N4 C33 C32 110.8(7) . . ? C40 C33 C32 112.5(5) . . ? N4 C33 H33 106.2 . . ? C40 C33 H33 106.2 . . ? C32 C33 H33 106.2 . . ? C35 C34 C39 118.9(8) . . ? C35 C34 N4 122.5(9) . . ? C39 C34 N4 118.5(9) . . ? C36 C35 C34 118.5(10) . . ? C36 C35 H35 120.8 . . ? C34 C35 H35 120.8 . . ? C37 C36 C35 122.9(11) . . ? C37 C36 H36 118.6 . . ? C35 C36 H36 118.6 . . ? C36 C37 C38 118.3(9) . . ? C36 C37 H37 120.9 . . ? C38 C37 H37 120.9 . . ? C37 C38 C39 121.3(11) . . ? C37 C38 H38 119.3 . . ? C39 C38 H38 119.3 . . ? C38 C39 C34 120.0(10) . . ? C38 C39 H39 120.0 . . ? C34 C39 H39 120.0 . . ? C33 C40 C41 112.5(6) . . ? C33 C40 H40A 109.1 . . ? C41 C40 H40A 109.1 . . ? C33 C40 H40B 109.1 . . ? C41 C40 H40B 109.1 . . ? H40A C40 H40B 107.8 . . ? N3 C41 C42 113.5(6) . . ? N3 C41 C40 110.4(6) . . ? C42 C41 C40 113.3(6) . . ? N3 C41 H41 106.3 . . ? C42 C41 H41 106.3 . . ? C40 C41 H41 106.3 . . ? C47 C42 C43 116.5(8) . . ? C47 C42 C41 123.8(7) . . ? C43 C42 C41 119.7(8) . . ? C44 C43 C42 122.5(12) . . ? C44 C43 H43 118.7 . . ? C42 C43 H43 118.7 . . ? C43 C44 C45 119.7(11) . . ? C43 C44 H44 120.2 . . ? C45 C44 H44 120.2 . . ? C46 C45 C44 117.2(10) . . ? C46 C45 H45 121.4 . . ? C44 C45 H45 121.4 . . ? C45 C46 C47 122.0(11) . . ? C45 C46 H46 119.0 . . ? C47 C46 H46 119.0 . . ? C42 C47 C46 122.1(9) . . ? C42 C47 H47 119.0 . . ? C46 C47 H47 119.0 . . ? C53 C48 N3 122.0(7) . . ? C53 C48 C49 118.1(7) . . ? N3 C48 C49 119.8(7) . . ? C50 C49 C48 119.2(9) . . ? C50 C49 H49 120.4 . . ? C48 C49 H49 120.4 . . ? C51 C50 C49 124.3(10) . . ? C51 C50 H50 117.9 . . ? C49 C50 H50 117.9 . . ? C50 C51 C52 116.5(9) . . ? C50 C51 H51 121.7 . . ? C52 C51 H51 121.7 . . ? C53 C52 C51 122.7(10) . . ? C53 C52 H52 118.7 . . ? C51 C52 H52 118.7 . . ? C48 C53 C52 119.0(8) . . ? C48 C53 H53 120.5 . . ? C52 C53 H53 120.5 . . ? N3 C54 C55 114.8(6) . . ? N3 C54 C32 109.0(6) . . ? C55 C54 C32 116.1(6) . . ? N3 C54 H54 105.3 . . ? C55 C54 H54 105.3 . . ? C32 C54 H54 105.3 . . ? C60 C55 C56 117.7(8) . . ? C60 C55 C54 120.5(8) . . ? C56 C55 C54 121.7(7) . . ? C57 C56 C55 122.3(11) . . ? C57 C56 H56 118.9 . . ? C55 C56 H56 118.9 . . ? C56 C57 C58 119.7(14) . . ? C56 C57 H57 120.1 . . ? C58 C57 H57 120.1 . . ? C59 C58 C57 119.6(11) . . ? C59 C58 H58 120.2 . . ? C57 C58 H58 120.2 . . ? C58 C59 C60 120.3(11) . . ? C58 C59 H59 119.8 . . ? C60 C59 H59 119.8 . . ? C55 C60 C59 120.2(12) . . ? C55 C60 H60 119.9 . . ? C59 C60 H60 119.9 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.560 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.106