# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_shelxl _database_code_depnum_ccdc_archive 'CCDC 879852' #TrackingRef '11038_web_deposit_cif_file_0_KatherineChulvi_1335949995.KTCXCD.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H45 N5 O' _chemical_formula_weight 575.78 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 Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.1700(7) _cell_length_b 12.2955(5) _cell_length_c 20.5036(9) _cell_angle_alpha 90.00 _cell_angle_beta 103.669(5) _cell_angle_gamma 90.00 _cell_volume 3226.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9906 _exptl_absorpt_correction_T_max 0.9971 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15338 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0907 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5686 _reflns_number_gt 3202 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5686 _refine_ls_number_parameters 404 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1243 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1513 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 C1C C 0.4494(3) 0.1149(2) 0.26551(16) 0.0521(10) Uani 1 1 d . . . H1C1 H 0.4586 0.0685 0.2284 0.078 Uiso 1 1 calc R . . H1C2 H 0.4032 0.0785 0.2898 0.078 Uiso 1 1 calc R . . H1C3 H 0.5175 0.1282 0.2962 0.078 Uiso 1 1 calc R . . C2C C 0.3491(2) 0.2177(2) 0.16853(14) 0.0447(8) Uani 1 1 d . . . H2C1 H 0.3724 0.1559 0.1455 0.067 Uiso 1 1 calc R . . H2C2 H 0.3645 0.2857 0.1479 0.067 Uiso 1 1 calc R . . H2C3 H 0.2737 0.2121 0.1647 0.067 Uiso 1 1 calc R . . N3C N 0.40395(19) 0.21653(18) 0.23930(12) 0.0393(7) Uani 1 1 d . . . C4C C 0.3826(2) 0.2969(2) 0.28052(14) 0.0313(7) Uani 1 1 d . . . C5C C 0.3277(2) 0.3899(2) 0.25418(15) 0.0394(8) Uani 1 1 d . . . H5C H 0.3046 0.3974 0.2079 0.047 Uiso 1 1 d R . . C6C C 0.3072(2) 0.4710(2) 0.29551(14) 0.0395(8) Uani 1 1 d . . . H6C H 0.2705 0.5323 0.2765 0.047 Uiso 1 1 d R . . C7C C 0.3400(2) 0.4637(2) 0.36495(14) 0.0332(7) Uani 1 1 d . . . C8C C 0.3957(2) 0.3707(2) 0.39107(14) 0.0360(8) Uani 1 1 d . . . H8C H 0.4198 0.3642 0.4373 0.043 Uiso 1 1 d R . . C9C C 0.4161(2) 0.2894(2) 0.35079(14) 0.0352(7) Uani 1 1 d . . . H9C H 0.4525 0.2281 0.3700 0.042 Uiso 1 1 d R . . C10C C 0.3194(2) 0.5498(2) 0.40977(15) 0.0382(8) Uani 1 1 d . . . O O 0.35498(18) 0.54428(16) 0.47140(10) 0.0491(6) Uani 1 1 d . . . N1 N 0.17515(18) 0.8021(2) 0.36322(11) 0.0280(6) Uani 1 1 d . . . C11 C 0.2497(2) 0.6419(2) 0.38087(13) 0.0320(7) Uani 1 1 d . . . C12 C 0.1447(2) 0.6291(2) 0.34272(13) 0.0332(7) Uani 1 1 d . . . H12 H 0.1127 0.5636 0.3272 0.040 Uiso 1 1 d R . . C13 C 0.0996(2) 0.7292(2) 0.33290(13) 0.0280(7) Uani 1 1 d . . . C14 C 0.2669(2) 0.7517(2) 0.39302(13) 0.0295(7) Uani 1 1 d . . . C1 C -0.0099(2) 0.7660(2) 0.30204(13) 0.0293(7) Uani 1 1 d . . . C1A C -0.0771(2) 0.6695(2) 0.27020(13) 0.0382(8) Uani 1 1 d . . . H1A1 H -0.1482 0.6946 0.2500 0.057 Uiso 1 1 calc R . . H1A2 H -0.0792 0.6150 0.3048 0.057 Uiso 1 1 calc R . . H1A3 H -0.0469 0.6369 0.2354 0.057 Uiso 1 1 calc R . . C1B C -0.0108(2) 0.8516(2) 0.24699(13) 0.0381(8) Uani 1 1 d . . . H1B1 H -0.0828 0.8749 0.2278 0.057 Uiso 1 1 calc R . . H1B2 H 0.0185 0.8198 0.2116 0.057 Uiso 1 1 calc R . . H1B3 H 0.0313 0.9144 0.2665 0.057 Uiso 1 1 calc R . . N2 N -0.05714(19) 0.7552(2) 0.41356(11) 0.0310(6) Uani 1 1 d . . . C21 C -0.0527(2) 0.8155(2) 0.35767(13) 0.0290(7) Uani 1 1 d . . . C22 C -0.0886(2) 0.9164(2) 0.36749(14) 0.0384(8) Uani 1 1 d . . . H22 H -0.0949 0.9746 0.3379 0.046 Uiso 1 1 d R . . C23 C -0.1148(2) 0.9174(2) 0.43090(14) 0.0435(8) Uani 1 1 d . . . H23 H -0.1413 0.9763 0.4500 0.052 Uiso 1 1 d R . . C24 C -0.0941(2) 0.8168(2) 0.45857(13) 0.0343(7) Uani 1 1 d . . . C2 C -0.1125(2) 0.7674(3) 0.52229(13) 0.0399(8) Uani 1 1 d . . . C2A C -0.2103(3) 0.6950(3) 0.50497(16) 0.0593(10) Uani 1 1 d . . . H2A1 H -0.2710 0.7392 0.4836 0.089 Uiso 1 1 calc R . . H2A2 H -0.2221 0.6623 0.5461 0.089 Uiso 1 1 calc R . . H2A3 H -0.2001 0.6374 0.4741 0.089 Uiso 1 1 calc R . . C2B C -0.1304(3) 0.8586(3) 0.56942(15) 0.0626(11) Uani 1 1 d . . . H2B1 H -0.1910 0.9020 0.5471 0.094 Uiso 1 1 calc R . . H2B2 H -0.0684 0.9052 0.5807 0.094 Uiso 1 1 calc R . . H2B3 H -0.1431 0.8267 0.6106 0.094 Uiso 1 1 calc R . . N3 N 0.07652(19) 0.7439(2) 0.58148(11) 0.0315(6) Uani 1 1 d . . . C31 C -0.0201(2) 0.6986(2) 0.55548(13) 0.0344(7) Uani 1 1 d . . . C32 C -0.0087(2) 0.5897(2) 0.56550(14) 0.0395(8) Uani 1 1 d . . . H32 H -0.0613 0.5379 0.5534 0.047 Uiso 1 1 d R . . C33 C 0.0970(2) 0.5685(2) 0.59752(13) 0.0371(8) Uani 1 1 d . . . H33 H 0.1260 0.5005 0.6099 0.045 Uiso 1 1 d R . . C34 C 0.1488(2) 0.6652(2) 0.60690(12) 0.0301(7) Uani 1 1 d . . . C3 C 0.2603(2) 0.6939(2) 0.64039(13) 0.0334(7) Uani 1 1 d . . . C3A C 0.3269(2) 0.5904(2) 0.65005(16) 0.0513(9) Uani 1 1 d . . . H3A1 H 0.3994 0.6089 0.6718 0.077 Uiso 1 1 calc R . . H3A2 H 0.3243 0.5572 0.6063 0.077 Uiso 1 1 calc R . . H3A3 H 0.2997 0.5391 0.6783 0.077 Uiso 1 1 calc R . . C3B C 0.2638(3) 0.7447(3) 0.70938(14) 0.0543(10) Uani 1 1 d . . . H3B1 H 0.3361 0.7634 0.7314 0.081 Uiso 1 1 calc R . . H3B2 H 0.2368 0.6924 0.7372 0.081 Uiso 1 1 calc R . . H3B3 H 0.2207 0.8105 0.7036 0.081 Uiso 1 1 calc R . . N4 N 0.31798(18) 0.7430(2) 0.53632(11) 0.0309(6) Uani 1 1 d . . . C41 C 0.3004(2) 0.7744(2) 0.59700(13) 0.0307(7) Uani 1 1 d . . . C42 C 0.3147(2) 0.8842(2) 0.60174(14) 0.0370(8) Uani 1 1 d . . . H42 H 0.3076 0.9277 0.6375 0.044 Uiso 1 1 d R . . C43 C 0.3421(2) 0.9204(2) 0.54259(14) 0.0376(8) Uani 1 1 d . . . H43 H 0.3567 0.9918 0.5328 0.045 Uiso 1 1 d R . . C44 C 0.3434(2) 0.8322(2) 0.50277(14) 0.0315(7) Uani 1 1 d . . . C4 C 0.3585(2) 0.8181(2) 0.43231(14) 0.0352(7) Uani 1 1 d . . . C4A C 0.4624(2) 0.7611(3) 0.43289(15) 0.0494(9) Uani 1 1 d . . . H4A1 H 0.4704 0.7537 0.3868 0.074 Uiso 1 1 calc R . . H4A2 H 0.4629 0.6888 0.4531 0.074 Uiso 1 1 calc R . . H4A3 H 0.5204 0.8043 0.4591 0.074 Uiso 1 1 calc R . . C4B C 0.3617(2) 0.9303(2) 0.39993(15) 0.0483(9) Uani 1 1 d . . . H4B1 H 0.3721 0.9213 0.3545 0.072 Uiso 1 1 calc R . . H4B2 H 0.4195 0.9729 0.4269 0.072 Uiso 1 1 calc R . . H4B3 H 0.2957 0.9684 0.3978 0.072 Uiso 1 1 calc R . . H3 H 0.096(2) 0.812(2) 0.5792(14) 0.046(10) Uiso 1 1 d . . . H1 H 0.163(2) 0.872(2) 0.3632(13) 0.036(9) Uiso 1 1 d . . . H2 H -0.030(2) 0.692(2) 0.4212(13) 0.032(9) Uiso 1 1 d . . . H H 0.313(3) 0.667(2) 0.5187(16) 0.070(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1C 0.054(2) 0.0467(19) 0.047(2) -0.0070(16) -0.0065(18) 0.0071(17) C2C 0.043(2) 0.057(2) 0.0371(19) -0.0007(16) 0.0159(16) 0.0017(16) N3C 0.0374(17) 0.0422(15) 0.0365(15) -0.0005(12) 0.0054(13) 0.0062(12) C4C 0.0249(18) 0.0377(17) 0.0318(17) 0.0005(14) 0.0076(14) 0.0013(14) C5C 0.039(2) 0.0526(19) 0.0277(17) 0.0081(15) 0.0105(15) 0.0087(16) C6C 0.045(2) 0.0423(18) 0.0322(18) 0.0045(15) 0.0110(16) 0.0099(15) C7C 0.0327(19) 0.0394(17) 0.0298(17) 0.0046(14) 0.0122(14) 0.0038(14) C8C 0.0309(19) 0.0468(18) 0.0296(17) 0.0067(15) 0.0054(14) 0.0064(15) C9C 0.0317(19) 0.0387(17) 0.0351(18) 0.0035(15) 0.0076(15) 0.0041(14) C10C 0.039(2) 0.0494(19) 0.0293(18) 0.0046(15) 0.0140(15) 0.0055(15) O 0.0632(17) 0.0572(14) 0.0245(12) 0.0033(10) 0.0058(11) 0.0156(12) N1 0.0280(15) 0.0362(15) 0.0228(13) 0.0061(12) 0.0120(11) 0.0029(12) C11 0.0324(19) 0.0438(18) 0.0207(15) 0.0042(13) 0.0081(13) 0.0108(14) C12 0.039(2) 0.0409(17) 0.0205(15) -0.0001(13) 0.0085(14) 0.0022(15) C13 0.0299(18) 0.0408(17) 0.0165(14) 0.0043(13) 0.0117(13) 0.0015(14) C14 0.0281(18) 0.0440(18) 0.0196(15) 0.0061(13) 0.0118(13) 0.0041(14) C1 0.0323(18) 0.0406(16) 0.0160(14) 0.0052(13) 0.0077(13) 0.0020(14) C1A 0.042(2) 0.0509(18) 0.0231(16) -0.0042(14) 0.0113(14) 0.0012(15) C1B 0.038(2) 0.0548(19) 0.0221(16) 0.0096(14) 0.0093(14) 0.0065(15) N2 0.0352(16) 0.0421(15) 0.0187(13) 0.0028(12) 0.0120(11) 0.0072(13) C21 0.0277(18) 0.0408(17) 0.0198(15) 0.0015(13) 0.0081(13) 0.0025(14) C22 0.043(2) 0.0426(18) 0.0302(18) 0.0029(14) 0.0101(15) 0.0063(15) C23 0.051(2) 0.0495(19) 0.0302(18) -0.0113(16) 0.0092(16) 0.0125(17) C24 0.0241(18) 0.059(2) 0.0197(15) -0.0068(15) 0.0046(13) 0.0076(15) C2 0.0299(19) 0.072(2) 0.0180(15) -0.0015(15) 0.0065(14) 0.0030(16) C2A 0.035(2) 0.116(3) 0.0307(18) 0.0082(19) 0.0140(16) -0.008(2) C2B 0.054(3) 0.111(3) 0.0245(18) -0.0027(19) 0.0123(17) 0.036(2) N3 0.0288(16) 0.0431(16) 0.0217(13) 0.0018(12) 0.0043(11) -0.0039(13) C31 0.0302(19) 0.061(2) 0.0147(15) -0.0032(14) 0.0107(13) -0.0058(16) C32 0.041(2) 0.053(2) 0.0271(17) -0.0035(15) 0.0125(15) -0.0139(16) C33 0.047(2) 0.0424(18) 0.0246(16) 0.0030(14) 0.0132(15) -0.0002(16) C34 0.0326(19) 0.0419(17) 0.0174(15) 0.0026(13) 0.0092(13) 0.0007(15) C3 0.0297(19) 0.0511(18) 0.0205(15) 0.0034(14) 0.0084(13) -0.0032(15) C3A 0.043(2) 0.060(2) 0.052(2) 0.0285(17) 0.0133(17) 0.0052(17) C3B 0.043(2) 0.096(3) 0.0236(17) -0.0060(18) 0.0076(16) -0.021(2) N4 0.0296(15) 0.0432(15) 0.0196(13) 0.0001(12) 0.0054(11) -0.0049(12) C41 0.0257(17) 0.0484(19) 0.0184(15) 0.0029(14) 0.0062(13) 0.0003(14) C42 0.036(2) 0.0467(19) 0.0260(17) -0.0049(14) 0.0019(14) 0.0058(15) C43 0.037(2) 0.0409(17) 0.0314(17) 0.0037(15) 0.0008(15) -0.0053(15) C44 0.0252(17) 0.0409(17) 0.0279(16) 0.0061(15) 0.0056(13) -0.0038(14) C4 0.0278(18) 0.0472(18) 0.0329(17) 0.0114(15) 0.0119(14) -0.0001(14) C4A 0.030(2) 0.081(2) 0.041(2) 0.0125(17) 0.0147(16) 0.0095(18) C4B 0.039(2) 0.067(2) 0.0402(19) 0.0164(17) 0.0117(16) -0.0075(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1C N3C 1.434(3) . ? C1C H1C1 0.9800 . ? C1C H1C2 0.9800 . ? C1C H1C3 0.9800 . ? C2C N3C 1.460(3) . ? C2C H2C1 0.9800 . ? C2C H2C2 0.9800 . ? C2C H2C3 0.9800 . ? N3C C4C 1.372(3) . ? C4C C5C 1.392(4) . ? C4C C9C 1.407(4) . ? C5C C6C 1.376(4) . ? C5C H5C 0.9300 . ? C6C C7C 1.390(4) . ? C6C H6C 0.9300 . ? C7C C8C 1.396(3) . ? C7C C10C 1.468(4) . ? C8C C9C 1.363(4) . ? C8C H8C 0.9300 . ? C9C H9C 0.9300 . ? C10C O 1.241(3) . ? C10C C11 1.490(4) . ? N1 C14 1.367(3) . ? N1 C13 1.373(3) . ? N1 H1 0.87(2) . ? C11 C14 1.382(4) . ? C11 C12 1.428(4) . ? C12 C13 1.361(4) . ? C12 H12 0.9300 . ? C13 C1 1.502(4) . ? C14 C4 1.520(4) . ? C1 C21 1.514(4) . ? C1 C1A 1.531(3) . ? C1 C1B 1.541(3) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C1B H1B1 0.9800 . ? C1B H1B2 0.9800 . ? C1B H1B3 0.9800 . ? N2 C24 1.369(3) . ? N2 C21 1.377(3) . ? N2 H2 0.86(2) . ? C21 C22 1.360(4) . ? C22 C23 1.422(4) . ? C22 H22 0.9300 . ? C23 C24 1.362(4) . ? C23 H23 0.9300 . ? C24 C2 1.511(4) . ? C2 C31 1.505(4) . ? C2 C2B 1.535(4) . ? C2 C2A 1.536(4) . ? C2A H2A1 0.9800 . ? C2A H2A2 0.9800 . ? C2A H2A3 0.9800 . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? N3 C34 1.371(3) . ? N3 C31 1.376(3) . ? N3 H3 0.88(3) . ? C31 C32 1.358(4) . ? C32 C33 1.416(4) . ? C32 H32 0.9300 . ? C33 C34 1.361(4) . ? C33 H33 0.9300 . ? C34 C3 1.509(4) . ? C3 C41 1.506(4) . ? C3 C3A 1.531(4) . ? C3 C3B 1.537(4) . ? C3A H3A1 0.9800 . ? C3A H3A2 0.9800 . ? C3A H3A3 0.9800 . ? C3B H3B1 0.9800 . ? C3B H3B2 0.9800 . ? C3B H3B3 0.9800 . ? N4 C41 1.373(3) . ? N4 C44 1.378(3) . ? N4 H 1.00(3) . ? C41 C42 1.364(4) . ? C42 C43 1.417(4) . ? C42 H42 0.9300 . ? C43 C44 1.360(4) . ? C43 H43 0.9300 . ? C44 C4 1.514(4) . ? C4 C4A 1.535(4) . ? C4 C4B 1.536(4) . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C4A H4A3 0.9800 . ? C4B H4B1 0.9800 . ? C4B H4B2 0.9800 . ? C4B H4B3 0.9800 . ? 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 N3C C1C H1C1 109.5 . . ? N3C C1C H1C2 109.5 . . ? H1C1 C1C H1C2 109.5 . . ? N3C C1C H1C3 109.5 . . ? H1C1 C1C H1C3 109.5 . . ? H1C2 C1C H1C3 109.5 . . ? N3C C2C H2C1 109.5 . . ? N3C C2C H2C2 109.5 . . ? H2C1 C2C H2C2 109.5 . . ? N3C C2C H2C3 109.5 . . ? H2C1 C2C H2C3 109.5 . . ? H2C2 C2C H2C3 109.5 . . ? C4C N3C C1C 121.7(2) . . ? C4C N3C C2C 118.7(2) . . ? C1C N3C C2C 116.4(2) . . ? N3C C4C C5C 121.1(3) . . ? N3C C4C C9C 121.6(2) . . ? C5C C4C C9C 117.4(3) . . ? C6C C5C C4C 121.1(3) . . ? C6C C5C H5C 119.5 . . ? C4C C5C H5C 119.5 . . ? C5C C6C C7C 121.7(3) . . ? C5C C6C H6C 119.2 . . ? C7C C6C H6C 119.1 . . ? C6C C7C C8C 117.0(3) . . ? C6C C7C C10C 122.5(3) . . ? C8C C7C C10C 120.6(3) . . ? C9C C8C C7C 122.0(3) . . ? C9C C8C H8C 119.1 . . ? C7C C8C H8C 118.9 . . ? C8C C9C C4C 120.9(3) . . ? C8C C9C H9C 119.6 . . ? C4C C9C H9C 119.6 . . ? O C10C C7C 121.1(3) . . ? O C10C C11 119.7(3) . . ? C7C C10C C11 119.1(2) . . ? C14 N1 C13 112.1(2) . . ? C14 N1 H1 126.2(18) . . ? C13 N1 H1 121.7(18) . . ? C14 C11 C12 107.6(2) . . ? C14 C11 C10C 127.7(3) . . ? C12 C11 C10C 124.0(3) . . ? C13 C12 C11 108.2(2) . . ? C13 C12 H12 125.9 . . ? C11 C12 H12 125.9 . . ? C12 C13 N1 106.2(3) . . ? C12 C13 C1 132.6(3) . . ? N1 C13 C1 121.0(2) . . ? N1 C14 C11 105.8(2) . . ? N1 C14 C4 120.1(2) . . ? C11 C14 C4 134.1(3) . . ? C13 C1 C21 107.2(2) . . ? C13 C1 C1A 110.3(2) . . ? C21 C1 C1A 110.6(2) . . ? C13 C1 C1B 110.8(2) . . ? C21 C1 C1B 109.7(2) . . ? C1A C1 C1B 108.3(2) . . ? C1 C1A H1A1 109.5 . . ? C1 C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C1 C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? C1 C1B H1B1 109.5 . . ? C1 C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? C1 C1B H1B3 109.5 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? C24 N2 C21 110.8(2) . . ? C24 N2 H2 125.4(18) . . ? C21 N2 H2 123.0(19) . . ? C22 C21 N2 106.4(2) . . ? C22 C21 C1 133.0(3) . . ? N2 C21 C1 120.5(2) . . ? C21 C22 C23 108.2(3) . . ? C21 C22 H22 125.9 . . ? C23 C22 H22 125.9 . . ? C24 C23 C22 107.7(3) . . ? C24 C23 H23 126.2 . . ? C22 C23 H23 126.1 . . ? C23 C24 N2 106.8(3) . . ? C23 C24 C2 131.9(3) . . ? N2 C24 C2 121.0(3) . . ? C31 C2 C24 109.8(2) . . ? C31 C2 C2B 110.7(2) . . ? C24 C2 C2B 109.3(3) . . ? C31 C2 C2A 108.8(3) . . ? C24 C2 C2A 109.3(2) . . ? C2B C2 C2A 108.9(3) . . ? C2 C2A H2A1 109.5 . . ? C2 C2A H2A2 109.5 . . ? H2A1 C2A H2A2 109.5 . . ? C2 C2A H2A3 109.5 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? C2 C2B H2B1 109.5 . . ? C2 C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? C2 C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? C34 N3 C31 111.0(2) . . ? C34 N3 H3 121(2) . . ? C31 N3 H3 128(2) . . ? C32 C31 N3 106.3(3) . . ? C32 C31 C2 132.1(3) . . ? N3 C31 C2 121.5(3) . . ? C31 C32 C33 108.2(3) . . ? C31 C32 H32 125.9 . . ? C33 C32 H32 125.9 . . ? C34 C33 C32 108.1(3) . . ? C34 C33 H33 125.9 . . ? C32 C33 H33 126.0 . . ? C33 C34 N3 106.4(3) . . ? C33 C34 C3 132.1(3) . . ? N3 C34 C3 121.4(2) . . ? C41 C3 C34 108.9(2) . . ? C41 C3 C3A 110.6(2) . . ? C34 C3 C3A 109.3(2) . . ? C41 C3 C3B 109.8(2) . . ? C34 C3 C3B 109.1(2) . . ? C3A C3 C3B 109.1(2) . . ? C3 C3A H3A1 109.5 . . ? C3 C3A H3A2 109.5 . . ? H3A1 C3A H3A2 109.5 . . ? C3 C3A H3A3 109.5 . . ? H3A1 C3A H3A3 109.5 . . ? H3A2 C3A H3A3 109.5 . . ? C3 C3B H3B1 109.5 . . ? C3 C3B H3B2 109.5 . . ? H3B1 C3B H3B2 109.5 . . ? C3 C3B H3B3 109.5 . . ? H3B1 C3B H3B3 109.5 . . ? H3B2 C3B H3B3 109.5 . . ? C41 N4 C44 110.0(2) . . ? C41 N4 H 125.6(19) . . ? C44 N4 H 124.4(19) . . ? C42 C41 N4 107.0(2) . . ? C42 C41 C3 132.1(3) . . ? N4 C41 C3 120.6(2) . . ? C41 C42 C43 108.0(3) . . ? C41 C42 H42 126.0 . . ? C43 C42 H42 126.0 . . ? C44 C43 C42 107.8(3) . . ? C44 C43 H43 126.1 . . ? C42 C43 H43 126.1 . . ? C43 C44 N4 107.2(3) . . ? C43 C44 C4 133.4(3) . . ? N4 C44 C4 119.2(2) . . ? C44 C4 C14 107.5(2) . . ? C44 C4 C4A 111.3(2) . . ? C14 C4 C4A 110.7(2) . . ? C44 C4 C4B 109.4(2) . . ? C14 C4 C4B 110.6(2) . . ? C4A C4 C4B 107.3(2) . . ? C4 C4A H4A1 109.5 . . ? C4 C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? C4 C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 109.5 . . ? C4 C4B H4B1 109.5 . . ? C4 C4B H4B2 109.5 . . ? H4B1 C4B H4B2 109.5 . . ? C4 C4B H4B3 109.5 . . ? H4B1 C4B H4B3 109.5 . . ? H4B2 C4B H4B3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.201 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.048 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 879855' #TrackingRef 'KTCXDII.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H54 N6 O2' _chemical_formula_weight 722.95 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.051(3) _cell_length_b 10.220(5) _cell_length_c 20.088(7) _cell_angle_alpha 76.98(4) _cell_angle_beta 76.86(3) _cell_angle_gamma 86.88(3) _cell_volume 1957.7(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9954 _exptl_absorpt_correction_T_max 0.9985 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8850 _diffrn_reflns_av_R_equivalents 0.0957 _diffrn_reflns_av_sigmaI/netI 0.2883 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5810 _reflns_number_gt 2048 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0097P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5810 _refine_ls_number_parameters 508 _refine_ls_number_restraints 84 _refine_ls_R_factor_all 0.2362 _refine_ls_R_factor_gt 0.1000 _refine_ls_wR_factor_ref 0.1997 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.966 _refine_ls_shift/su_max 0.056 _refine_ls_shift/su_mean 0.004 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 C4 C -0.0455(6) 1.2052(7) 0.3632(3) 0.0216(16) Uani 1 1 d U . . C4A C -0.1350(6) 1.2971(6) 0.3179(3) 0.0257(16) Uani 1 1 d U . . H4A1 H -0.0888 1.3832 0.2960 0.039 Uiso 1 1 calc R . . H4A2 H -0.2236 1.3126 0.3477 0.039 Uiso 1 1 calc R . . H4A3 H -0.1493 1.2534 0.2813 0.039 Uiso 1 1 calc R . . C4B C -0.0458(6) 1.2657(7) 0.4263(3) 0.0338(18) Uani 1 1 d . . . H4B1 H 0.0012 1.3525 0.4103 0.051 Uiso 1 1 calc R . . H4B2 H 0.0015 1.2047 0.4585 0.051 Uiso 1 1 calc R . . H4B3 H -0.1402 1.2787 0.4504 0.051 Uiso 1 1 calc R . . C41 C -0.1486(6) 0.8556(7) 0.3734(3) 0.0256(17) Uani 1 1 d U . . C42 C -0.1903(6) 0.8588(6) 0.4436(3) 0.0265(17) Uani 1 1 d . . . H42 H -0.2310 0.7863 0.4800 0.032 Uiso 1 1 calc R . . C43 C -0.1627(6) 0.9866(7) 0.4525(3) 0.0300(18) Uani 1 1 d U . . H43 H -0.1807 1.0145 0.4957 0.036 Uiso 1 1 calc R . . C44 C -0.1044(6) 1.0656(7) 0.3867(3) 0.0223(16) Uani 1 1 d . . . N4 N -0.0970(5) 0.9823(6) 0.3404(3) 0.0275(15) Uani 1 1 d . . . C1 C 0.4531(6) 1.0922(7) 0.3330(3) 0.0227(16) Uani 1 1 d . . . C1A C 0.5760(6) 1.1088(7) 0.2703(3) 0.0302(18) Uani 1 1 d . . . H1A1 H 0.6592 1.0782 0.2869 0.045 Uiso 1 1 calc R . . H1A2 H 0.5856 1.2036 0.2462 0.045 Uiso 1 1 calc R . . H1A3 H 0.5617 1.0552 0.2378 0.045 Uiso 1 1 calc R . . C1B C 0.4829(6) 1.1698(7) 0.3849(3) 0.0284(18) Uani 1 1 d . . . H1B1 H 0.5666 1.1347 0.3999 0.043 Uiso 1 1 calc R . . H1B2 H 0.4064 1.1590 0.4259 0.043 Uiso 1 1 calc R . . H1B3 H 0.4946 1.2652 0.3623 0.043 Uiso 1 1 calc R . . C10C C 0.0821(7) 1.2128(7) 0.1910(3) 0.0291(18) Uani 1 1 d . . . C2 C 0.3298(6) 0.6101(7) 0.3526(3) 0.0279(17) Uani 1 1 d U . . C2A C 0.4553(6) 0.5643(7) 0.3022(3) 0.0335(19) Uani 1 1 d U . . H2A1 H 0.5278 0.5335 0.3275 0.050 Uiso 1 1 calc R . . H2A2 H 0.4887 0.6398 0.2630 0.050 Uiso 1 1 calc R . . H2A3 H 0.4286 0.4906 0.2841 0.050 Uiso 1 1 calc R . . C2B C 0.2835(6) 0.4906(6) 0.4162(3) 0.0350(19) Uani 1 1 d . . . H2B1 H 0.3580 0.4654 0.4408 0.052 Uiso 1 1 calc R . . H2B2 H 0.2601 0.4137 0.3995 0.052 Uiso 1 1 calc R . . H2B3 H 0.2034 0.5175 0.4483 0.052 Uiso 1 1 calc R . . C3 C -0.1495(6) 0.7487(6) 0.3338(3) 0.0225(16) Uani 1 1 d . . . C3A C -0.2283(6) 0.7957(7) 0.2754(3) 0.0303(18) Uani 1 1 d . . . H3A1 H -0.2361 0.7211 0.2533 0.045 Uiso 1 1 calc R . . H3A2 H -0.1792 0.8701 0.2403 0.045 Uiso 1 1 calc R . . H3A3 H -0.3198 0.8259 0.2955 0.045 Uiso 1 1 calc R . . C3B C -0.2203(6) 0.6212(6) 0.3831(3) 0.038(2) Uani 1 1 d U . . H3B1 H -0.2179 0.5510 0.3567 0.057 Uiso 1 1 calc R . . H3B2 H -0.3154 0.6421 0.4028 0.057 Uiso 1 1 calc R . . H3B3 H -0.1724 0.5894 0.4212 0.057 Uiso 1 1 calc R . . C9C C 0.1301(6) 1.3080(6) 0.1245(3) 0.0209(16) Uani 1 1 d . . . C8C C 0.2143(6) 1.4162(7) 0.1182(3) 0.0337(19) Uani 1 1 d . . . H4C H 0.2422 1.4301 0.1582 0.040 Uiso 1 1 calc R . . C7C C 0.0868(6) 1.2919(7) 0.0653(3) 0.0286(18) Uani 1 1 d U . . H5C H 0.0273 1.2199 0.0695 0.034 Uiso 1 1 calc R . . C6C C 0.2574(6) 1.5034(7) 0.0538(3) 0.0299(18) Uani 1 1 d . . . H6C H 0.3166 1.5754 0.0498 0.036 Uiso 1 1 calc R . . C5C C 0.1280(6) 1.3768(7) 0.0023(3) 0.0288(17) Uani 1 1 d . . . H7C H 0.0983 1.3625 -0.0372 0.035 Uiso 1 1 calc R . . C4C C 0.2148(7) 1.4869(7) -0.0057(3) 0.0330(19) Uani 1 1 d . . . C1C C 0.2198(7) 1.5500(8) -0.1325(3) 0.050(2) Uani 1 1 d . . . H10A H 0.2239 1.6355 -0.1668 0.075 Uiso 1 1 calc R . . H10B H 0.1264 1.5150 -0.1195 0.075 Uiso 1 1 calc R . . H10C H 0.2823 1.4853 -0.1530 0.075 Uiso 1 1 calc R . . C11 C 0.0986(6) 1.1934(6) 0.3195(3) 0.0218(16) Uani 1 1 d U . . C2C C 0.3680(7) 1.6657(8) -0.0803(4) 0.066(3) Uani 1 1 d . . . H11A H 0.3842 1.7197 -0.1283 0.099 Uiso 1 1 calc R . . H11B H 0.4517 1.6170 -0.0724 0.099 Uiso 1 1 calc R . . H11C H 0.3415 1.7248 -0.0472 0.099 Uiso 1 1 calc R . . C12 C 0.1534(6) 1.2050(7) 0.2502(3) 0.0258(18) Uani 1 1 d . . . C21C C 0.0456(7) 0.7449(7) 0.1669(4) 0.0301(18) Uani 1 1 d . . . C13 C 0.2985(6) 1.1750(6) 0.2419(3) 0.0247(17) Uani 1 1 d . . . H13 H 0.3622 1.1753 0.1989 0.030 Uiso 1 1 calc R . . C14 C 0.3270(6) 1.1460(6) 0.3079(3) 0.0226(17) Uani 1 1 d U . . C20C C 0.1315(7) 0.8480(7) 0.1106(4) 0.036(2) Uani 1 1 d . . . C18C C 0.1200(7) 0.8642(8) 0.0423(4) 0.043(2) Uani 1 1 d . . . H15C H 0.0583 0.8088 0.0317 0.051 Uiso 1 1 calc R . . C19C C 0.2224(6) 0.9314(7) 0.1253(4) 0.038(2) Uani 1 1 d . . . H16C H 0.2304 0.9230 0.1723 0.046 Uiso 1 1 calc R . . C16C C 0.1947(7) 0.9575(7) -0.0106(4) 0.041(2) Uani 1 1 d . . . H17C H 0.1832 0.9665 -0.0571 0.050 Uiso 1 1 calc R . . C17C C 0.3005(7) 1.0254(7) 0.0724(3) 0.0332(19) Uani 1 1 d U . . H18C H 0.3625 1.0801 0.0832 0.040 Uiso 1 1 calc R . . C15C C 0.2884(7) 1.0405(8) 0.0025(4) 0.038(2) Uani 1 1 d . . . C21 C 0.4290(6) 0.9454(7) 0.3687(3) 0.0201(15) Uani 1 1 d . . . C13C C 0.4554(6) 1.2270(7) -0.0367(3) 0.040(2) Uani 1 1 d . . . H21A H 0.4915 1.2927 -0.0801 0.061 Uiso 1 1 calc R . . H21B H 0.5313 1.1781 -0.0190 0.061 Uiso 1 1 calc R . . H21C H 0.4026 1.2737 -0.0016 0.061 Uiso 1 1 calc R . . C22 C 0.4485(6) 0.8709(7) 0.4308(3) 0.0299(18) Uani 1 1 d . . . H22 H 0.4816 0.9041 0.4646 0.036 Uiso 1 1 calc R . . C12C C 0.3538(7) 1.1451(8) -0.1226(3) 0.055(3) Uani 1 1 d . . . H22A H 0.4070 1.2224 -0.1527 0.083 Uiso 1 1 calc R . . H22B H 0.2575 1.1583 -0.1248 0.083 Uiso 1 1 calc R . . H22C H 0.3882 1.0633 -0.1386 0.083 Uiso 1 1 calc R . . C23 C 0.4114(6) 0.7348(7) 0.4376(3) 0.0321(19) Uani 1 1 d U . . H23 H 0.4149 0.6629 0.4765 0.039 Uiso 1 1 calc R . . C24 C 0.3708(6) 0.7259(7) 0.3798(3) 0.0261(17) Uani 1 1 d . . . C31 C 0.2179(7) 0.6501(6) 0.3151(3) 0.0250(17) Uani 1 1 d . . . C32 C 0.2140(7) 0.6718(7) 0.2454(4) 0.0352(19) Uani 1 1 d . . . H32 H 0.2891 0.6616 0.2085 0.042 Uiso 1 1 calc R . . C33 C 0.0787(6) 0.7123(7) 0.2372(3) 0.0277(17) Uani 1 1 d . . . C34 C -0.0014(6) 0.7127(6) 0.3028(3) 0.0204(16) Uani 1 1 d U . . N1 N 0.2040(5) 1.1596(5) 0.3538(3) 0.0226(14) Uani 1 1 d U . . H1 H 0.1944 1.1482 0.3994 0.027 Uiso 1 1 calc R . . N2 N 0.3823(5) 0.8557(5) 0.3365(2) 0.0249(14) Uani 1 1 d . . . H2 H 0.3627 0.8771 0.2949 0.030 Uiso 1 1 calc R . . N3 N 0.0858(5) 0.6766(5) 0.3501(3) 0.0236(14) Uani 1 1 d . . . N3C N 0.2599(6) 1.5710(6) -0.0699(3) 0.0391(17) Uani 1 1 d . . . N14C N 0.3668(6) 1.1322(6) -0.0508(3) 0.0409(17) Uani 1 1 d . . . O11C O -0.0162(4) 1.1362(5) 0.2001(2) 0.0378(14) Uani 1 1 d . . . O22C O -0.0504(4) 0.6887(5) 0.1554(2) 0.0474(16) Uani 1 1 d . . . H4 H -0.061(6) 1.008(7) 0.293(3) 0.06(3) Uiso 1 1 d . . . H3 H 0.038(8) 0.683(9) 0.405(4) 0.12(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C4 0.004(3) 0.031(4) 0.030(4) -0.009(3) -0.001(3) -0.002(3) C4A 0.016(4) 0.022(4) 0.035(4) -0.008(3) 0.002(3) 0.009(3) C4B 0.032(5) 0.031(4) 0.050(5) -0.025(4) -0.019(4) 0.012(3) C41 0.018(4) 0.023(4) 0.034(4) 0.002(3) -0.011(3) 0.002(3) C42 0.026(4) 0.022(4) 0.028(4) -0.001(3) -0.004(3) -0.001(3) C43 0.031(4) 0.040(4) 0.018(4) -0.009(3) 0.000(3) -0.007(3) C44 0.009(4) 0.034(4) 0.026(4) -0.011(3) -0.007(3) 0.010(3) N4 0.025(4) 0.023(3) 0.039(4) -0.013(3) -0.010(3) 0.003(3) C1 0.018(4) 0.027(4) 0.029(4) -0.010(3) -0.013(3) 0.001(3) C1A 0.019(4) 0.033(4) 0.037(4) -0.009(4) -0.003(3) 0.000(3) C1B 0.021(4) 0.029(4) 0.037(4) -0.004(4) -0.013(3) -0.007(3) C10C 0.022(4) 0.029(4) 0.043(5) -0.013(4) -0.019(3) 0.010(3) C2 0.024(4) 0.025(4) 0.037(4) -0.006(3) -0.013(3) -0.001(3) C2A 0.017(4) 0.047(5) 0.041(5) -0.015(4) -0.012(3) 0.011(4) C2B 0.024(4) 0.015(4) 0.062(5) 0.006(4) -0.017(4) 0.007(3) C3 0.016(4) 0.016(4) 0.032(4) 0.003(3) -0.005(3) -0.006(3) C3A 0.020(4) 0.037(5) 0.039(4) -0.014(4) -0.012(3) 0.007(3) C3B 0.028(5) 0.031(5) 0.048(5) -0.002(4) 0.002(4) -0.011(3) C9C 0.031(4) 0.014(4) 0.014(3) -0.004(3) 0.002(3) 0.005(3) C8C 0.034(5) 0.031(5) 0.038(5) 0.000(4) -0.019(3) -0.003(4) C7C 0.021(4) 0.038(4) 0.028(4) -0.006(3) -0.008(3) 0.001(3) C6C 0.031(5) 0.030(4) 0.031(4) -0.002(3) -0.014(3) -0.005(3) C5C 0.023(4) 0.035(5) 0.029(4) -0.009(4) -0.009(3) 0.005(3) C4C 0.038(5) 0.036(5) 0.028(4) -0.013(4) -0.008(4) 0.009(4) C1C 0.062(6) 0.063(6) 0.028(4) -0.002(4) -0.023(4) 0.001(5) C11 0.019(4) 0.016(3) 0.031(4) -0.002(3) -0.008(3) 0.002(3) C2C 0.075(7) 0.066(7) 0.059(6) 0.011(5) -0.035(5) -0.037(5) C12 0.017(4) 0.033(4) 0.025(4) 0.005(3) -0.009(3) -0.008(3) C21C 0.020(4) 0.033(5) 0.042(5) -0.016(4) -0.009(3) 0.006(3) C13 0.026(4) 0.025(4) 0.020(4) 0.005(3) -0.007(3) -0.008(3) C14 0.016(4) 0.023(4) 0.026(4) -0.006(3) 0.003(3) -0.008(3) C20C 0.033(5) 0.041(5) 0.039(5) -0.013(4) -0.015(4) -0.004(4) C18C 0.035(5) 0.058(6) 0.046(5) -0.021(5) -0.022(4) 0.009(4) C19C 0.033(5) 0.042(5) 0.040(5) -0.011(4) -0.012(4) 0.023(4) C16C 0.053(6) 0.039(5) 0.028(4) 0.000(4) -0.004(4) -0.016(4) C17C 0.041(5) 0.030(4) 0.031(4) -0.001(3) -0.019(3) -0.001(3) C15C 0.038(5) 0.038(5) 0.037(5) -0.006(4) -0.010(4) 0.001(4) C21 0.011(4) 0.027(4) 0.024(4) -0.009(3) -0.004(3) 0.006(3) C13C 0.041(5) 0.030(5) 0.049(5) -0.004(4) -0.012(4) -0.003(4) C22 0.037(5) 0.026(4) 0.032(4) -0.013(4) -0.014(3) 0.011(3) C12C 0.068(6) 0.072(7) 0.026(4) -0.010(5) -0.010(4) -0.009(5) C23 0.031(4) 0.039(5) 0.030(4) -0.012(4) -0.009(3) 0.000(3) C24 0.028(5) 0.025(4) 0.027(4) -0.004(3) -0.007(3) -0.005(3) C31 0.029(5) 0.016(4) 0.031(4) -0.004(3) -0.008(3) -0.003(3) C32 0.026(5) 0.031(5) 0.051(5) -0.013(4) -0.010(4) 0.000(4) C33 0.018(4) 0.027(4) 0.044(5) -0.006(4) -0.023(3) 0.011(3) C34 0.015(4) 0.016(3) 0.033(4) -0.005(3) -0.011(3) 0.002(3) N1 0.022(3) 0.025(3) 0.022(3) -0.003(3) -0.010(2) -0.002(3) N2 0.033(4) 0.024(3) 0.021(3) -0.003(3) -0.012(3) -0.007(3) N3 0.006(3) 0.027(3) 0.037(4) -0.005(3) -0.007(3) 0.007(3) N3C 0.043(4) 0.047(4) 0.026(4) 0.005(3) -0.014(3) -0.016(3) N14C 0.047(4) 0.042(4) 0.036(4) -0.013(3) -0.005(3) -0.013(3) O11C 0.034(3) 0.045(3) 0.035(3) -0.005(3) -0.011(2) -0.011(3) O22C 0.032(3) 0.069(4) 0.043(3) -0.013(3) -0.008(3) -0.019(3) _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 C4 C44 1.507(8) . ? C4 C4B 1.530(8) . ? C4 C11 1.527(8) . ? C4 C4A 1.554(8) . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C4A H4A3 0.9800 . ? C4B H4B1 0.9800 . ? C4B H4B2 0.9800 . ? C4B H4B3 0.9800 . ? C41 N4 1.384(8) . ? C41 C42 1.384(8) . ? C41 C3 1.491(9) . ? C42 C43 1.408(9) . ? C42 H42 0.9500 . ? C43 C44 1.400(8) . ? C43 H43 0.9500 . ? C44 N4 1.383(8) . ? N4 H4 0.93(6) . ? C1 C14 1.500(8) . ? C1 C21 1.517(8) . ? C1 C1B 1.532(8) . ? C1 C1A 1.537(7) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C1B H1B1 0.9800 . ? C1B H1B2 0.9800 . ? C1B H1B3 0.9800 . ? C10C O11C 1.249(7) . ? C10C C9C 1.462(8) . ? C10C C12 1.505(8) . ? C2 C31 1.482(8) . ? C2 C24 1.520(9) . ? C2 C2A 1.551(8) . ? C2 C2B 1.559(8) . ? C2A H2A1 0.9800 . ? C2A H2A2 0.9800 . ? C2A H2A3 0.9800 . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? C3 C3A 1.536(8) . ? C3 C34 1.537(8) . ? C3 C3B 1.544(7) . ? C3A H3A1 0.9800 . ? C3A H3A2 0.9800 . ? C3A H3A3 0.9800 . ? C3B H3B1 0.9800 . ? C3B H3B2 0.9800 . ? C3B H3B3 0.9800 . ? C9C C8C 1.395(8) . ? C9C C7C 1.400(8) . ? C8C C6C 1.388(8) . ? C8C H4C 0.9500 . ? C7C C5C 1.355(8) . ? C7C H5C 0.9500 . ? C6C C4C 1.405(8) . ? C6C H6C 0.9500 . ? C5C C4C 1.419(8) . ? C5C H7C 0.9500 . ? C4C N3C 1.373(7) . ? C1C N3C 1.466(7) . ? C1C H10A 0.9800 . ? C1C H10B 0.9800 . ? C1C H10C 0.9800 . ? C11 C12 1.357(8) . ? C11 N1 1.379(7) . ? C2C N3C 1.443(8) . ? C2C H11A 0.9800 . ? C2C H11B 0.9800 . ? C2C H11C 0.9800 . ? C12 C13 1.453(8) . ? C21C O22C 1.240(7) . ? C21C C33 1.485(8) . ? C21C C20C 1.500(8) . ? C13 C14 1.384(8) . ? C13 H13 0.9500 . ? C14 N1 1.385(7) . ? C20C C18C 1.374(8) . ? C20C C19C 1.404(9) . ? C18C C16C 1.364(8) . ? C18C H15C 0.9500 . ? C19C C17C 1.383(8) . ? C19C H16C 0.9500 . ? C16C C15C 1.406(9) . ? C16C H17C 0.9500 . ? C17C C15C 1.411(8) . ? C17C H18C 0.9500 . ? C15C N14C 1.375(8) . ? C21 C22 1.357(8) . ? C21 N2 1.390(7) . ? C13C N14C 1.464(7) . ? C13C H21A 0.9800 . ? C13C H21B 0.9800 . ? C13C H21C 0.9800 . ? C22 C23 1.429(9) . ? C22 H22 0.9500 . ? C12C N14C 1.453(7) . ? C12C H22A 0.9800 . ? C12C H22B 0.9800 . ? C12C H22C 0.9800 . ? C23 C24 1.340(8) . ? C23 H23 0.9500 . ? C24 N2 1.406(7) . ? C31 C32 1.376(8) . ? C31 N3 1.397(7) . ? C32 C33 1.435(8) . ? C32 H32 0.9500 . ? C33 C34 1.380(8) . ? C34 N3 1.412(7) . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? N3 H3 1.11(8) . ? 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 C44 C4 C4B 110.7(5) . . ? C44 C4 C11 106.8(5) . . ? C4B C4 C11 112.1(5) . . ? C44 C4 C4A 109.5(5) . . ? C4B C4 C4A 107.6(5) . . ? C11 C4 C4A 110.2(5) . . ? C4 C4A H4A1 109.5 . . ? C4 C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? C4 C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 109.5 . . ? C4 C4B H4B1 109.5 . . ? C4 C4B H4B2 109.5 . . ? H4B1 C4B H4B2 109.5 . . ? C4 C4B H4B3 109.5 . . ? H4B1 C4B H4B3 109.5 . . ? H4B2 C4B H4B3 109.5 . . ? N4 C41 C42 105.2(6) . . ? N4 C41 C3 121.7(6) . . ? C42 C41 C3 133.1(6) . . ? C41 C42 C43 109.1(6) . . ? C41 C42 H42 125.5 . . ? C43 C42 H42 125.5 . . ? C44 C43 C42 108.3(6) . . ? C44 C43 H43 125.9 . . ? C42 C43 H43 125.8 . . ? N4 C44 C43 104.9(6) . . ? N4 C44 C4 121.7(5) . . ? C43 C44 C4 133.2(6) . . ? C41 N4 C44 112.5(6) . . ? C41 N4 H4 124(5) . . ? C44 N4 H4 124(5) . . ? C14 C1 C21 108.0(5) . . ? C14 C1 C1B 110.7(5) . . ? C21 C1 C1B 109.6(5) . . ? C14 C1 C1A 109.4(5) . . ? C21 C1 C1A 111.0(5) . . ? C1B C1 C1A 108.1(5) . . ? C1 C1A H1A1 109.5 . . ? C1 C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C1 C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? C1 C1B H1B1 109.5 . . ? C1 C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? C1 C1B H1B3 109.5 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? O11C C10C C9C 121.6(6) . . ? O11C C10C C12 118.8(6) . . ? C9C C10C C12 119.6(5) . . ? C31 C2 C24 111.2(6) . . ? C31 C2 C2A 109.3(6) . . ? C24 C2 C2A 109.4(5) . . ? C31 C2 C2B 110.1(5) . . ? C24 C2 C2B 108.3(5) . . ? C2A C2 C2B 108.4(6) . . ? C2 C2A H2A1 109.5 . . ? C2 C2A H2A2 109.5 . . ? H2A1 C2A H2A2 109.5 . . ? C2 C2A H2A3 109.5 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? C2 C2B H2B1 109.5 . . ? C2 C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? C2 C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? C41 C3 C3A 110.7(5) . . ? C41 C3 C34 109.0(5) . . ? C3A C3 C34 110.4(6) . . ? C41 C3 C3B 110.4(5) . . ? C3A C3 C3B 107.8(5) . . ? C34 C3 C3B 108.5(5) . . ? C3 C3A H3A1 109.5 . . ? C3 C3A H3A2 109.5 . . ? H3A1 C3A H3A2 109.5 . . ? C3 C3A H3A3 109.5 . . ? H3A1 C3A H3A3 109.5 . . ? H3A2 C3A H3A3 109.5 . . ? C3 C3B H3B1 109.5 . . ? C3 C3B H3B2 109.5 . . ? H3B1 C3B H3B2 109.5 . . ? C3 C3B H3B3 109.5 . . ? H3B1 C3B H3B3 109.5 . . ? H3B2 C3B H3B3 109.5 . . ? C8C C9C C7C 118.9(6) . . ? C8C C9C C10C 122.4(6) . . ? C7C C9C C10C 118.7(6) . . ? C6C C8C C9C 120.2(6) . . ? C6C C8C H4C 119.9 . . ? C9C C8C H4C 119.9 . . ? C5C C7C C9C 121.3(6) . . ? C5C C7C H5C 119.3 . . ? C9C C7C H5C 119.3 . . ? C8C C6C C4C 121.0(6) . . ? C8C C6C H6C 119.5 . . ? C4C C6C H6C 119.5 . . ? C7C C5C C4C 121.0(6) . . ? C7C C5C H7C 119.5 . . ? C4C C5C H7C 119.5 . . ? N3C C4C C6C 121.2(6) . . ? N3C C4C C5C 121.2(6) . . ? C6C C4C C5C 117.6(6) . . ? N3C C1C H10A 109.5 . . ? N3C C1C H10B 109.5 . . ? H10A C1C H10B 109.5 . . ? N3C C1C H10C 109.5 . . ? H10A C1C H10C 109.5 . . ? H10B C1C H10C 109.5 . . ? C12 C11 N1 106.9(5) . . ? C12 C11 C4 134.7(6) . . ? N1 C11 C4 118.4(6) . . ? N3C C2C H11A 109.5 . . ? N3C C2C H11B 109.5 . . ? H11A C2C H11B 109.5 . . ? N3C C2C H11C 109.5 . . ? H11A C2C H11C 109.5 . . ? H11B C2C H11C 109.5 . . ? C11 C12 C13 107.9(6) . . ? C11 C12 C10C 129.1(6) . . ? C13 C12 C10C 121.4(6) . . ? O22C C21C C33 120.7(6) . . ? O22C C21C C20C 121.2(6) . . ? C33 C21C C20C 118.0(6) . . ? C14 C13 C12 107.6(6) . . ? C14 C13 H13 126.2 . . ? C12 C13 H13 126.2 . . ? C13 C14 N1 105.6(6) . . ? C13 C14 C1 131.8(6) . . ? N1 C14 C1 122.1(5) . . ? C18C C20C C19C 118.2(6) . . ? C18C C20C C21C 119.6(6) . . ? C19C C20C C21C 122.1(6) . . ? C16C C18C C20C 121.8(7) . . ? C16C C18C H15C 119.1 . . ? C20C C18C H15C 119.1 . . ? C17C C19C C20C 121.0(7) . . ? C17C C19C H16C 119.5 . . ? C20C C19C H16C 119.5 . . ? C18C C16C C15C 121.1(7) . . ? C18C C16C H17C 119.5 . . ? C15C C16C H17C 119.5 . . ? C19C C17C C15C 120.2(6) . . ? C19C C17C H18C 119.9 . . ? C15C C17C H18C 119.9 . . ? N14C C15C C16C 121.4(6) . . ? N14C C15C C17C 120.9(6) . . ? C16C C15C C17C 117.6(6) . . ? C22 C21 N2 105.4(6) . . ? C22 C21 C1 133.0(6) . . ? N2 C21 C1 121.6(5) . . ? N14C C13C H21A 109.5 . . ? N14C C13C H21B 109.5 . . ? H21A C13C H21B 109.5 . . ? N14C C13C H21C 109.5 . . ? H21A C13C H21C 109.5 . . ? H21B C13C H21C 109.5 . . ? C21 C22 C23 109.4(6) . . ? C21 C22 H22 125.3 . . ? C23 C22 H22 125.3 . . ? N14C C12C H22A 109.5 . . ? N14C C12C H22B 109.5 . . ? H22A C12C H22B 109.5 . . ? N14C C12C H22C 109.5 . . ? H22A C12C H22C 109.5 . . ? H22B C12C H22C 109.5 . . ? C24 C23 C22 108.3(6) . . ? C24 C23 H23 125.9 . . ? C22 C23 H23 125.9 . . ? C23 C24 N2 106.4(6) . . ? C23 C24 C2 134.1(6) . . ? N2 C24 C2 119.3(5) . . ? C32 C31 N3 105.7(6) . . ? C32 C31 C2 132.3(6) . . ? N3 C31 C2 122.0(6) . . ? C31 C32 C33 109.4(6) . . ? C31 C32 H32 125.3 . . ? C33 C32 H32 125.3 . . ? C34 C33 C32 107.8(6) . . ? C34 C33 C21C 131.2(6) . . ? C32 C33 C21C 121.0(6) . . ? C33 C34 N3 106.1(5) . . ? C33 C34 C3 137.2(6) . . ? N3 C34 C3 116.6(6) . . ? C11 N1 C14 111.9(5) . . ? C11 N1 H1 124.0 . . ? C14 N1 H1 124.1 . . ? C21 N2 C24 110.6(5) . . ? C21 N2 H2 124.7 . . ? C24 N2 H2 124.7 . . ? C31 N3 C34 110.9(6) . . ? C31 N3 H3 135(4) . . ? C34 N3 H3 114(4) . . ? C4C N3C C2C 120.5(6) . . ? C4C N3C C1C 121.0(6) . . ? C2C N3C C1C 117.4(5) . . ? C15C N14C C12C 120.1(6) . . ? C15C N14C C13C 121.5(6) . . ? C12C N14C C13C 118.1(5) . . ? _diffrn_measured_fraction_theta_max 0.842 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.842 _refine_diff_density_max 0.271 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.064