# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 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_2tbu _database_code_depnum_ccdc_archive 'CCDC 882411' #TrackingRef '- Compound 1.cif' _audit_creation_date 2012-03-26 _audit_creation_method ; Olex2 1.2-alpha (compiled 2012.03.09 svn.r2242, GUI svn.r4116) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C25 H24 N2' _chemical_formula_sum 'C25 H24 N2' _chemical_formula_weight 352.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0032 0.0015 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 9.692(2) _cell_length_b 19.705(5) _cell_length_c 21.494(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.178(3) _cell_angle_gamma 90.00 _cell_volume 4040.3(16) _cell_formula_units_Z 8 _cell_measurement_reflns_used 5965 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 24.80 _cell_measurement_theta_min 2.34 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.8280 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1504 _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0859 _diffrn_reflns_av_unetI/netI 0.0801 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 31649 _diffrn_reflns_theta_full 24.21 _diffrn_reflns_theta_max 24.21 _diffrn_reflns_theta_min 1.37 _diffrn_ambient_temperature 120.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.68890 _diffrn_source 'I19 at Diamond' _diffrn_source_current 90.0 _diffrn_source_power 4.5 _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _reflns_number_gt 4663 _reflns_number_total 6990 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker APEX2' _computing_data_collection 'Bruker SAINT' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.232 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 501 _refine_ls_number_reflns 6990 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0559 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+1.4200P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1293 _refine_ls_wR_factor_ref 0.1471 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 N1B N 0.3648(2) 0.26213(9) 0.46134(9) 0.0304(5) Uani 1 1 d . . . N1A N 0.8651(2) 0.24252(9) 0.46040(9) 0.0297(5) Uani 1 1 d . . . N3A N 0.65490(19) 0.20863(9) 0.47472(9) 0.0309(4) Uani 1 1 d . . . N3B N 0.15340(19) 0.29842(9) 0.47124(9) 0.0307(4) Uani 1 1 d . . . C5A C 0.8350(2) 0.18483(11) 0.42407(11) 0.0317(5) Uani 1 1 d . . . C4A C 0.7032(2) 0.16483(11) 0.43230(11) 0.0316(5) Uani 1 1 d . . . C4B C 0.1963(2) 0.33213(11) 0.42090(11) 0.0308(5) Uani 1 1 d . . . C2B C 0.2588(2) 0.25798(10) 0.49505(11) 0.0290(5) Uani 1 1 d . . . C5B C 0.3287(2) 0.31043(11) 0.41513(11) 0.0309(5) Uani 1 1 d . . . C11B C 0.2515(2) 0.14477(11) 0.54128(12) 0.0369(6) Uani 1 1 d . . . H11B H 0.2349 0.1281 0.4992 0.044 Uiso 1 1 calc R . . C22B C 0.6013(3) 0.29985(14) 0.31064(12) 0.0451(7) Uani 1 1 d . . . H22B H 0.6503 0.2658 0.2921 0.054 Uiso 1 1 calc R . . C6A C 0.7589(2) 0.31010(11) 0.53688(11) 0.0305(5) Uani 1 1 d . . . C19A C 0.9725(3) 0.08829(12) 0.39078(13) 0.0431(6) Uani 1 1 d . . . H19A H 0.9238 0.0577 0.4134 0.052 Uiso 1 1 calc R . . C26B C 0.1602(3) 0.34779(12) 0.62255(13) 0.0436(7) Uani 1 1 d . . . H26D H 0.1669 0.3960 0.6339 0.065 Uiso 1 1 calc R . . H26E H 0.1073 0.3238 0.6506 0.065 Uiso 1 1 calc R . . H26F H 0.1122 0.3429 0.5787 0.065 Uiso 1 1 calc R . . C17B C 0.1081(3) 0.39304(12) 0.31946(12) 0.0382(6) Uani 1 1 d . . . H17B H 0.1713 0.3676 0.2995 0.046 Uiso 1 1 calc R . . C27A C 0.8763(3) 0.23586(15) 0.70435(12) 0.0495(7) Uani 1 1 d . . . H27A H 0.8159 0.2630 0.7268 0.074 Uiso 1 1 calc R . . H27B H 0.9679 0.2579 0.7077 0.074 Uiso 1 1 calc R . . H27C H 0.8885 0.1905 0.7231 0.074 Uiso 1 1 calc R . . C23B C 0.4995(2) 0.28130(12) 0.34568(11) 0.0373(6) Uani 1 1 d . . . H23B H 0.4785 0.2347 0.3504 0.045 Uiso 1 1 calc R . . C27B C 0.3831(3) 0.32906(13) 0.69801(12) 0.0468(7) Uani 1 1 d . . . H27D H 0.3912 0.3779 0.7064 0.070 Uiso 1 1 calc R . . H27E H 0.4769 0.3088 0.7041 0.070 Uiso 1 1 calc R . . H27F H 0.3286 0.3080 0.7271 0.070 Uiso 1 1 calc R . . C19B C 0.4586(3) 0.39896(12) 0.36536(12) 0.0392(6) Uani 1 1 d . . . H19B H 0.4101 0.4333 0.3839 0.047 Uiso 1 1 calc R . . C13B C 0.0076(2) 0.41832(11) 0.41089(12) 0.0374(6) Uani 1 1 d . . . H13B H 0.0022 0.4108 0.4541 0.045 Uiso 1 1 calc R . . C8B C 0.2997(2) 0.19314(12) 0.66275(12) 0.0358(6) Uani 1 1 d . . . H8B H 0.3166 0.2088 0.7052 0.043 Uiso 1 1 calc R . . C6B C 0.2678(2) 0.21452(11) 0.55171(11) 0.0297(5) Uani 1 1 d . . . C10A C 0.7408(3) 0.43178(12) 0.54864(14) 0.0453(7) Uani 1 1 d . . . H10A H 0.7255 0.4757 0.5304 0.054 Uiso 1 1 calc R . . C13A C 0.5228(3) 0.07506(12) 0.43534(13) 0.0419(6) Uani 1 1 d . . . H13A H 0.5147 0.0892 0.4768 0.050 Uiso 1 1 calc R . . C22A C 1.1190(3) 0.17633(15) 0.32513(13) 0.0482(7) Uani 1 1 d . . . H22A H 1.1695 0.2068 0.3032 0.058 Uiso 1 1 calc R . . C9B C 0.2823(3) 0.12469(12) 0.65180(13) 0.0410(6) Uani 1 1 d . . . H9B H 0.2864 0.0944 0.6865 0.049 Uiso 1 1 calc R . . C18B C 0.4285(2) 0.33057(11) 0.37383(11) 0.0314(5) Uani 1 1 d . . . C12A C 0.6160(2) 0.10860(11) 0.40260(12) 0.0345(6) Uani 1 1 d . . . C11A C 0.7356(2) 0.37484(11) 0.51086(12) 0.0365(6) Uani 1 1 d . . . H11A H 0.7157 0.3799 0.4662 0.044 Uiso 1 1 calc R . . C25B C 0.3941(3) 0.35682(12) 0.58737(12) 0.0394(6) Uani 1 1 d . . . H25D H 0.4139 0.4026 0.6045 0.059 Uiso 1 1 calc R . . H25E H 0.3400 0.3599 0.5444 0.059 Uiso 1 1 calc R . . H25F H 0.4825 0.3331 0.5864 0.059 Uiso 1 1 calc R . . C12B C 0.1038(2) 0.38167(11) 0.38294(11) 0.0325(6) Uani 1 1 d . . . C10B C 0.2590(3) 0.09948(12) 0.59093(13) 0.0411(6) Uani 1 1 d . . . H10B H 0.2483 0.0521 0.5833 0.049 Uiso 1 1 calc R . . C25A C 0.6653(3) 0.19548(13) 0.63135(12) 0.0425(6) Uani 1 1 d . . . H25A H 0.6782 0.1509 0.6517 0.064 Uiso 1 1 calc R . . H25B H 0.6208 0.1899 0.5870 0.064 Uiso 1 1 calc R . . H25C H 0.6056 0.2237 0.6532 0.064 Uiso 1 1 calc R . . C17A C 0.6229(3) 0.08759(12) 0.34130(12) 0.0411(6) Uani 1 1 d . . . H17A H 0.6840 0.1103 0.3182 0.049 Uiso 1 1 calc R . . C2A C 0.7558(2) 0.25369(11) 0.49095(11) 0.0290(5) Uani 1 1 d . . . C15B C -0.0723(3) 0.47745(12) 0.31360(14) 0.0469(7) Uani 1 1 d . . . H15B H -0.1311 0.5106 0.2902 0.056 Uiso 1 1 calc R . . C18A C 0.9396(2) 0.15712(12) 0.38846(11) 0.0345(6) Uani 1 1 d . . . C9A C 0.7686(3) 0.42355(13) 0.61338(14) 0.0471(7) Uani 1 1 d . . . H9A H 0.7720 0.4621 0.6402 0.057 Uiso 1 1 calc R . . C24B C 0.3088(2) 0.31732(11) 0.62961(11) 0.0334(6) Uani 1 1 d . . . C24A C 0.8085(2) 0.22995(12) 0.63462(11) 0.0353(6) Uani 1 1 d . . . C14A C 0.4426(3) 0.02140(13) 0.40732(16) 0.0534(8) Uani 1 1 d . . . H14A H 0.3803 -0.0014 0.4298 0.064 Uiso 1 1 calc R . . C7A C 0.7872(2) 0.30041(12) 0.60309(11) 0.0332(6) Uani 1 1 d . . . C20A C 1.0783(3) 0.06442(14) 0.35943(13) 0.0515(7) Uani 1 1 d . . . H20A H 1.1000 0.0174 0.3603 0.062 Uiso 1 1 calc R . . C14B C -0.0802(3) 0.46562(12) 0.37619(13) 0.0445(7) Uani 1 1 d . . . H14B H -0.1459 0.4899 0.3956 0.053 Uiso 1 1 calc R . . C8A C 0.7916(2) 0.35949(13) 0.63941(13) 0.0411(6) Uani 1 1 d . . . H8A H 0.8114 0.3554 0.6841 0.049 Uiso 1 1 calc R . . C23A C 1.0126(2) 0.20065(13) 0.35491(11) 0.0369(6) Uani 1 1 d . . . H23A H 0.9895 0.2475 0.3523 0.044 Uiso 1 1 calc R . . C16B C 0.0218(3) 0.44083(12) 0.28494(12) 0.0415(6) Uani 1 1 d . . . H16B H 0.0270 0.4486 0.2418 0.050 Uiso 1 1 calc R . . C26A C 0.9047(3) 0.18280(12) 0.60368(12) 0.0399(6) Uani 1 1 d . . . H26A H 0.9909 0.2071 0.5996 0.060 Uiso 1 1 calc R . . H26B H 0.8559 0.1689 0.5617 0.060 Uiso 1 1 calc R . . H26C H 0.9283 0.1425 0.6301 0.060 Uiso 1 1 calc R . . C20B C 0.5597(3) 0.41670(13) 0.32969(12) 0.0456(7) Uani 1 1 d . . . H20B H 0.5797 0.4632 0.3238 0.055 Uiso 1 1 calc R . . C21A C 1.1510(3) 0.10851(15) 0.32739(13) 0.0519(7) Uani 1 1 d . . . H21A H 1.2233 0.0919 0.3068 0.062 Uiso 1 1 calc R . . C7B C 0.2935(2) 0.24087(11) 0.61390(11) 0.0302(5) Uani 1 1 d . . . C15A C 0.4527(3) 0.00074(13) 0.34654(16) 0.0563(8) Uani 1 1 d . . . H15A H 0.3981 -0.0363 0.3277 0.068 Uiso 1 1 calc R . . C21B C 0.6312(3) 0.36711(15) 0.30272(12) 0.0495(7) Uani 1 1 d . . . H21B H 0.7008 0.3795 0.2788 0.059 Uiso 1 1 calc R . . C16A C 0.5420(3) 0.03407(13) 0.31360(14) 0.0495(7) Uani 1 1 d . . . H16A H 0.5481 0.0203 0.2718 0.059 Uiso 1 1 calc R . . H1A H 0.946(3) 0.2655(12) 0.4680(12) 0.045(7) Uiso 1 1 d . . . H1B H 0.446(3) 0.2425(13) 0.4711(12) 0.049(8) 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 N1B 0.0253(11) 0.0342(10) 0.0330(12) 0.0023(9) 0.0090(9) 0.0022(9) N1A 0.0241(10) 0.0334(10) 0.0328(12) -0.0027(8) 0.0083(9) -0.0002(8) N3A 0.0282(10) 0.0331(10) 0.0315(12) -0.0019(8) 0.0060(9) -0.0010(8) N3B 0.0283(10) 0.0336(10) 0.0311(12) 0.0023(8) 0.0076(9) 0.0012(8) C5A 0.0280(12) 0.0349(12) 0.0329(14) -0.0024(10) 0.0074(11) 0.0009(10) C4A 0.0296(13) 0.0337(12) 0.0318(14) 0.0006(10) 0.0062(11) 0.0024(10) C4B 0.0295(13) 0.0324(11) 0.0310(14) 0.0014(10) 0.0073(11) 0.0003(9) C2B 0.0244(12) 0.0320(11) 0.0310(14) -0.0015(10) 0.0061(11) -0.0007(9) C5B 0.0281(12) 0.0344(12) 0.0306(14) 0.0015(10) 0.0061(11) 0.0001(10) C11B 0.0288(13) 0.0377(13) 0.0454(16) -0.0004(11) 0.0098(12) 0.0022(10) C22B 0.0390(15) 0.0631(17) 0.0363(16) -0.0067(13) 0.0151(13) -0.0040(13) C6A 0.0219(12) 0.0348(12) 0.0364(15) -0.0041(10) 0.0093(11) -0.0014(9) C19A 0.0381(14) 0.0416(14) 0.0487(17) -0.0068(12) 0.0057(13) 0.0026(11) C26B 0.0402(15) 0.0377(13) 0.0574(18) -0.0014(12) 0.0210(14) 0.0047(11) C17B 0.0346(14) 0.0394(13) 0.0400(17) 0.0016(11) 0.0049(12) 0.0005(11) C27A 0.0381(15) 0.0709(18) 0.0394(18) 0.0036(13) 0.0062(13) -0.0090(13) C23B 0.0329(13) 0.0460(14) 0.0340(15) -0.0017(11) 0.0085(12) -0.0014(11) C27B 0.0524(17) 0.0495(15) 0.0394(17) -0.0062(12) 0.0108(14) -0.0026(13) C19B 0.0353(14) 0.0441(14) 0.0382(16) 0.0050(11) 0.0064(12) -0.0005(11) C13B 0.0331(13) 0.0370(12) 0.0438(16) 0.0035(11) 0.0113(12) 0.0014(10) C8B 0.0302(13) 0.0439(13) 0.0355(15) 0.0039(11) 0.0112(11) 0.0064(10) C6B 0.0180(11) 0.0369(12) 0.0347(15) 0.0015(10) 0.0063(10) 0.0005(9) C10A 0.0392(15) 0.0365(13) 0.062(2) -0.0019(12) 0.0132(14) 0.0000(11) C13A 0.0345(14) 0.0384(13) 0.0508(18) 0.0047(12) 0.0018(13) -0.0004(11) C22A 0.0390(15) 0.0686(18) 0.0389(17) -0.0013(13) 0.0122(13) 0.0062(13) C9B 0.0367(14) 0.0436(14) 0.0454(17) 0.0135(12) 0.0147(13) 0.0061(11) C18B 0.0277(12) 0.0398(12) 0.0265(14) 0.0040(10) 0.0040(11) 0.0015(10) C12A 0.0288(13) 0.0324(12) 0.0397(16) 0.0005(10) -0.0012(11) 0.0021(10) C11A 0.0316(13) 0.0381(13) 0.0415(16) 0.0004(11) 0.0111(12) -0.0006(10) C25B 0.0365(14) 0.0368(13) 0.0462(17) -0.0046(11) 0.0109(13) -0.0055(11) C12B 0.0285(13) 0.0323(12) 0.0360(15) 0.0005(10) 0.0035(11) -0.0038(9) C10B 0.0392(15) 0.0321(12) 0.0535(19) 0.0063(12) 0.0121(13) 0.0029(11) C25A 0.0343(14) 0.0527(15) 0.0420(16) 0.0030(12) 0.0104(12) -0.0052(12) C17A 0.0406(15) 0.0363(13) 0.0429(17) -0.0045(11) -0.0022(13) 0.0041(11) C2A 0.0243(12) 0.0331(11) 0.0297(14) 0.0001(9) 0.0049(10) 0.0001(9) C15B 0.0410(15) 0.0371(13) 0.060(2) 0.0094(12) 0.0007(14) 0.0053(11) C18A 0.0269(13) 0.0429(13) 0.0332(15) -0.0081(10) 0.0043(11) 0.0020(10) C9A 0.0352(15) 0.0427(14) 0.066(2) -0.0179(13) 0.0148(14) -0.0022(11) C24B 0.0292(13) 0.0377(12) 0.0353(15) -0.0003(10) 0.0113(11) 0.0012(10) C24A 0.0264(12) 0.0490(14) 0.0318(15) 0.0005(11) 0.0085(11) -0.0013(10) C14A 0.0381(16) 0.0410(15) 0.077(2) 0.0114(14) -0.0022(15) -0.0055(12) C7A 0.0201(11) 0.0448(13) 0.0364(15) -0.0064(11) 0.0092(11) -0.0035(10) C20A 0.0471(16) 0.0497(15) 0.0556(19) -0.0143(13) 0.0035(15) 0.0169(13) C14B 0.0413(15) 0.0370(13) 0.0560(19) 0.0046(12) 0.0111(14) 0.0054(11) C8A 0.0284(13) 0.0541(15) 0.0416(16) -0.0119(12) 0.0087(12) -0.0029(11) C23A 0.0312(13) 0.0497(14) 0.0305(14) -0.0038(11) 0.0068(11) 0.0041(11) C16B 0.0422(15) 0.0427(14) 0.0371(16) 0.0051(11) 0.0002(13) -0.0017(12) C26A 0.0315(13) 0.0453(14) 0.0445(16) 0.0056(11) 0.0109(12) 0.0048(11) C20B 0.0437(16) 0.0499(15) 0.0433(17) 0.0096(12) 0.0080(14) -0.0099(12) C21A 0.0437(16) 0.0719(19) 0.0422(18) -0.0104(14) 0.0131(14) 0.0109(14) C7B 0.0207(12) 0.0366(12) 0.0342(15) 0.0020(10) 0.0075(11) 0.0021(9) C15A 0.0497(18) 0.0331(14) 0.076(2) -0.0052(14) -0.0165(17) -0.0005(12) C21B 0.0422(16) 0.0745(19) 0.0345(16) 0.0035(14) 0.0141(13) -0.0106(14) C16A 0.0510(17) 0.0392(14) 0.0518(19) -0.0086(13) -0.0085(15) 0.0067(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 N1B C2B 1.360(3) . ? N1B C5B 1.375(3) . ? N1A C5A 1.381(3) . ? N1A C2A 1.359(3) . ? N3A C4A 1.395(3) . ? N3A C2A 1.321(3) . ? N3B C4B 1.394(3) . ? N3B C2B 1.325(3) . ? C5A C4A 1.378(3) . ? C5A C18A 1.478(3) . ? C4A C12A 1.469(3) . ? C4B C5B 1.378(3) . ? C4B C12B 1.471(3) . ? C2B C6B 1.479(3) . ? C5B C18B 1.478(3) . ? C11B C6B 1.397(3) . ? C11B C10B 1.383(3) . ? C22B C23B 1.392(3) . ? C22B C21B 1.374(4) . ? C6A C11A 1.395(3) . ? C6A C2A 1.483(3) . ? C6A C7A 1.414(3) . ? C19A C18A 1.392(3) . ? C19A C20A 1.404(4) . ? C26B C24B 1.542(3) . ? C17B C12B 1.391(3) . ? C17B C16B 1.385(3) . ? C27A C24A 1.531(4) . ? C23B C18B 1.389(3) . ? C27B C24B 1.536(4) . ? C19B C18B 1.397(3) . ? C19B C20B 1.391(3) . ? C13B C12B 1.396(3) . ? C13B C14B 1.387(3) . ? C8B C9B 1.374(3) . ? C8B C7B 1.403(3) . ? C6B C7B 1.415(3) . ? C10A C11A 1.381(3) . ? C10A C9A 1.379(4) . ? C13A C12A 1.405(3) . ? C13A C14A 1.385(4) . ? C22A C23A 1.391(3) . ? C22A C21A 1.371(4) . ? C9B C10B 1.380(4) . ? C12A C17A 1.394(3) . ? C25B C24B 1.542(3) . ? C25A C24A 1.535(3) . ? C17A C16A 1.384(3) . ? C15B C14B 1.381(4) . ? C15B C16B 1.390(4) . ? C18A C23A 1.391(3) . ? C9A C8A 1.383(4) . ? C24B C7B 1.545(3) . ? C24A C7A 1.543(3) . ? C24A C26A 1.547(3) . ? C14A C15A 1.388(4) . ? C7A C8A 1.398(3) . ? C20A C21A 1.377(4) . ? C20B C21B 1.383(4) . ? C15A C16A 1.378(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2B N1B C5B 107.87(19) . . ? C2A N1A C5A 107.59(18) . . ? C2A N3A C4A 105.67(18) . . ? C2B N3B C4B 105.71(18) . . ? N1A C5A C18A 120.10(19) . . ? C4A C5A N1A 105.69(19) . . ? C4A C5A C18A 134.2(2) . . ? N3A C4A C12A 121.14(19) . . ? C5A C4A N3A 109.44(19) . . ? C5A C4A C12A 129.4(2) . . ? N3B C4B C12B 120.69(19) . . ? C5B C4B N3B 109.39(19) . . ? C5B C4B C12B 129.9(2) . . ? N1B C2B C6B 122.24(19) . . ? N3B C2B N1B 111.17(19) . . ? N3B C2B C6B 126.56(19) . . ? N1B C5B C4B 105.76(19) . . ? N1B C5B C18B 120.65(19) . . ? C4B C5B C18B 133.5(2) . . ? C10B C11B C6B 121.5(2) . . ? C21B C22B C23B 120.4(2) . . ? C11A C6A C2A 115.8(2) . . ? C11A C6A C7A 121.1(2) . . ? C7A C6A C2A 123.1(2) . . ? C18A C19A C20A 119.4(2) . . ? C16B C17B C12B 121.0(2) . . ? C18B C23B C22B 120.3(2) . . ? C20B C19B C18B 119.8(2) . . ? C14B C13B C12B 120.6(2) . . ? C9B C8B C7B 122.8(2) . . ? C11B C6B C2B 116.7(2) . . ? C11B C6B C7B 120.6(2) . . ? C7B C6B C2B 122.72(19) . . ? C9A C10A C11A 118.6(2) . . ? C14A C13A C12A 120.2(3) . . ? C21A C22A C23A 120.0(3) . . ? C8B C9B C10B 120.7(2) . . ? C23B C18B C5B 120.1(2) . . ? C23B C18B C19B 119.1(2) . . ? C19B C18B C5B 120.7(2) . . ? C13A C12A C4A 120.6(2) . . ? C17A C12A C4A 121.0(2) . . ? C17A C12A C13A 118.4(2) . . ? C10A C11A C6A 121.4(2) . . ? C17B C12B C4B 122.0(2) . . ? C17B C12B C13B 118.5(2) . . ? C13B C12B C4B 119.5(2) . . ? C9B C10B C11B 118.5(2) . . ? C16A C17A C12A 121.0(3) . . ? N1A C2A C6A 121.13(19) . . ? N3A C2A N1A 111.54(19) . . ? N3A C2A C6A 127.32(19) . . ? C14B C15B C16B 119.9(2) . . ? C19A C18A C5A 121.0(2) . . ? C23A C18A C5A 119.9(2) . . ? C23A C18A C19A 119.0(2) . . ? C10A C9A C8A 120.3(2) . . ? C26B C24B C7B 107.83(19) . . ? C27B C24B C26B 107.9(2) . . ? C27B C24B C25B 106.1(2) . . ? C27B C24B C7B 111.5(2) . . ? C25B C24B C26B 109.5(2) . . ? C25B C24B C7B 113.84(18) . . ? C27A C24A C25A 107.85(19) . . ? C27A C24A C7A 111.3(2) . . ? C27A C24A C26A 106.2(2) . . ? C25A C24A C7A 109.2(2) . . ? C25A C24A C26A 108.9(2) . . ? C7A C24A C26A 113.30(19) . . ? C13A C14A C15A 120.4(3) . . ? C6A C7A C24A 123.4(2) . . ? C8A C7A C6A 115.5(2) . . ? C8A C7A C24A 121.0(2) . . ? C21A C20A C19A 120.7(2) . . ? C15B C14B C13B 120.2(2) . . ? C9A C8A C7A 123.2(3) . . ? C18A C23A C22A 120.8(2) . . ? C17B C16B C15B 119.8(2) . . ? C21B C20B C19B 120.5(2) . . ? C22A C21A C20A 120.0(2) . . ? C8B C7B C6B 116.0(2) . . ? C8B C7B C24B 120.0(2) . . ? C6B C7B C24B 124.0(2) . . ? C16A C15A C14A 119.9(3) . . ? C22B C21B C20B 119.8(2) . . ? C15A C16A C17A 120.1(3) . . ? data_4-tbu _database_code_depnum_ccdc_archive 'CCDC 882412' #TrackingRef '- Compound 3.cif' _audit_creation_date 2012-04-25 _audit_creation_method ; Olex2 1.1 (compiled Nov 1 2011 20:42:30, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C25 H24 N2' _chemical_formula_sum 'C25 H24 N2' _chemical_formula_weight 352.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0032 0.0015 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 36.809(6) _cell_length_b 12.205(2) _cell_length_c 8.9185(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.551(2) _cell_angle_gamma 90.00 _cell_volume 3987.9(11) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9818 _cell_measurement_temperature 120 _cell_measurement_theta_max 27.37 _cell_measurement_theta_min 2.69 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9207 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.1133 before and 0.0721 after correction. The Ratio of minimum to maximum transmission is 0.9207. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description lath _exptl_crystal_F_000 1504 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_unetI/netI 0.0483 _diffrn_reflns_limit_h_max 49 _diffrn_reflns_limit_h_min -49 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 39090 _diffrn_reflns_theta_full 27.37 _diffrn_reflns_theta_max 27.37 _diffrn_reflns_theta_min 1.62 _diffrn_ambient_temperature 393(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.971 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.68890 _diffrn_source 'I19 at Diamond Light source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _reflns_number_gt 8181 _reflns_number_total 9628 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker APEX2' _computing_data_collection 'Bruker SAINT' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 1.281 _refine_diff_density_min -1.092 _refine_diff_density_rms 0.071 _refine_ls_extinction_coef 0.103(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 494 _refine_ls_number_reflns 9628 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0834 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0999P)^2^+4.5082P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2142 _refine_ls_wR_factor_ref 0.2205 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 N1A N 0.36453(4) 0.26400(14) 0.59315(19) 0.0239(4) Uani 1 1 d . . . H1A H 0.3650 0.2130 0.6630 0.029 Uiso 1 1 calc R . . N3A N 0.37570(4) 0.35009(14) 0.38435(19) 0.0245(4) Uani 1 1 d . . . C2A C 0.38320(5) 0.26210(16) 0.4704(2) 0.0234(4) Uani 1 1 d . . . C7A C 0.43043(5) 0.18553(18) 0.3212(2) 0.0284(4) Uani 1 1 d . . . H7A H 0.4343 0.2567 0.2826 0.034 Uiso 1 1 calc R . . C23A C 0.30500(5) 0.30893(19) 0.7902(2) 0.0288(4) Uani 1 1 d . . . H23A H 0.3041 0.2359 0.7532 0.035 Uiso 1 1 calc R . . C5A C 0.34456(5) 0.35934(16) 0.5905(2) 0.0247(4) Uani 1 1 d . . . C10A C 0.42203(6) -0.02071(18) 0.4399(3) 0.0312(5) Uani 1 1 d . . . H10A H 0.4195 -0.0910 0.4837 0.037 Uiso 1 1 calc R . . C8A C 0.44889(6) 0.09669(19) 0.2681(3) 0.0314(5) Uani 1 1 d . . . H8A H 0.4646 0.1077 0.1910 0.038 Uiso 1 1 calc R . . C6A C 0.40630(5) 0.17113(16) 0.4309(2) 0.0243(4) Uani 1 1 d . . . C18A C 0.32364(5) 0.38917(17) 0.7166(2) 0.0260(4) Uani 1 1 d . . . C11A C 0.40282(6) 0.06711(17) 0.4922(2) 0.0283(4) Uani 1 1 d . . . H11A H 0.3873 0.0562 0.5699 0.034 Uiso 1 1 calc R . . C9A C 0.44481(6) -0.00866(18) 0.3254(2) 0.0301(4) Uani 1 1 d . A . C19A C 0.32407(6) 0.49633(18) 0.7713(3) 0.0320(5) Uani 1 1 d . . . H19A H 0.3364 0.5519 0.7215 0.038 Uiso 1 1 calc R . . C12A C 0.33486(6) 0.51180(16) 0.3899(2) 0.0270(4) Uani 1 1 d . . . C20A C 0.30672(7) 0.5222(2) 0.8973(3) 0.0382(5) Uani 1 1 d . . . H20A H 0.3070 0.5956 0.9328 0.046 Uiso 1 1 calc R . . C4A C 0.35132(5) 0.41138(16) 0.4586(2) 0.0255(4) Uani 1 1 d . . . C17A C 0.29804(6) 0.53651(19) 0.4012(3) 0.0330(5) Uani 1 1 d . . . H17A H 0.2837 0.4893 0.4561 0.040 Uiso 1 1 calc R . . C22A C 0.28777(6) 0.3353(2) 0.9174(3) 0.0356(5) Uani 1 1 d . . . H22A H 0.2752 0.2803 0.9671 0.043 Uiso 1 1 calc R . . C16A C 0.28247(7) 0.6295(2) 0.3327(3) 0.0387(5) Uani 1 1 d . . . H16A H 0.2575 0.6457 0.3417 0.046 Uiso 1 1 calc R . . C13A C 0.35525(6) 0.58246(18) 0.3081(3) 0.0326(5) Uani 1 1 d . . . H13A H 0.3803 0.5670 0.2995 0.039 Uiso 1 1 calc R . . C21A C 0.28898(7) 0.4420(2) 0.9720(3) 0.0403(6) Uani 1 1 d . . . H21A H 0.2777 0.4598 1.0602 0.048 Uiso 1 1 calc R . . C15A C 0.30290(7) 0.6989(2) 0.2515(3) 0.0410(6) Uani 1 1 d . . . H15A H 0.2921 0.7624 0.2044 0.049 Uiso 1 1 calc R . . C14A C 0.33948(7) 0.67497(19) 0.2392(3) 0.0400(6) Uani 1 1 d . . . H14A H 0.3537 0.7222 0.1834 0.048 Uiso 1 1 calc R . . N1B N 0.13650(4) 0.26277(14) 0.19638(19) 0.0243(4) Uani 1 1 d . . . H1B H 0.1367 0.2116 0.2659 0.029 Uiso 1 1 calc R . . N3B N 0.12368(4) 0.34893(14) -0.02103(19) 0.0254(4) Uani 1 1 d . . . C6B C 0.09452(5) 0.16851(16) 0.0009(2) 0.0248(4) Uani 1 1 d . . . C7B C 0.06997(5) 0.18341(17) -0.1266(2) 0.0285(4) Uani 1 1 d . . . H7B H 0.0662 0.2547 -0.1678 0.034 Uiso 1 1 calc R . . C12B C 0.16177(6) 0.51459(16) 0.0118(2) 0.0263(4) Uani 1 1 d . . . C2B C 0.11742(5) 0.26008(16) 0.0585(2) 0.0244(4) Uani 1 1 d . . . C11B C 0.09825(6) 0.06389(17) 0.0633(2) 0.0282(4) Uani 1 1 d . . . H11B H 0.1143 0.0523 0.1517 0.034 Uiso 1 1 calc R . . C18B C 0.17737(5) 0.39011(17) 0.3490(2) 0.0262(4) Uani 1 1 d . . . C5B C 0.15564(5) 0.36026(16) 0.2082(2) 0.0249(4) Uani 1 1 d . . . C10B C 0.07861(6) -0.02360(18) -0.0031(2) 0.0313(5) Uani 1 1 d . . . H10B H 0.0812 -0.0940 0.0420 0.038 Uiso 1 1 calc R . . C17B C 0.13930(6) 0.57744(18) -0.0900(3) 0.0309(5) Uani 1 1 d . . . H17B H 0.1145 0.5567 -0.1139 0.037 Uiso 1 1 calc R . . C8B C 0.05106(6) 0.09555(18) -0.1936(2) 0.0315(5) Uani 1 1 d . . . H8B H 0.0349 0.1074 -0.2819 0.038 Uiso 1 1 calc R . . C19B C 0.19657(5) 0.31054(18) 0.4366(2) 0.0282(4) Uani 1 1 d . . . H19B H 0.1967 0.2369 0.4022 0.034 Uiso 1 1 calc R . . C9B C 0.05507(6) -0.01055(18) -0.1346(2) 0.0298(4) Uani 1 1 d . B . C14B C 0.21128(6) 0.64055(19) -0.0198(3) 0.0344(5) Uani 1 1 d . . . H14B H 0.2359 0.6624 0.0052 0.041 Uiso 1 1 calc R . . C20B C 0.21554(6) 0.33815(19) 0.5740(2) 0.0321(5) Uani 1 1 d . . . H20B H 0.2282 0.2831 0.6336 0.038 Uiso 1 1 calc R . . C13B C 0.19794(6) 0.54777(18) 0.0465(3) 0.0299(4) Uani 1 1 d . . . H13B H 0.2136 0.5064 0.1162 0.036 Uiso 1 1 calc R . . C4B C 0.14755(5) 0.41222(16) 0.0714(2) 0.0246(4) Uani 1 1 d . . . C21B C 0.21605(6) 0.4458(2) 0.6243(3) 0.0348(5) Uani 1 1 d . . . H21B H 0.2292 0.4647 0.7177 0.042 Uiso 1 1 calc R . . C23B C 0.17788(6) 0.49830(18) 0.4011(2) 0.0305(4) Uani 1 1 d . . . H23B H 0.1649 0.5534 0.3429 0.037 Uiso 1 1 calc R . . C16B C 0.15275(7) 0.67001(19) -0.1569(3) 0.0358(5) Uani 1 1 d . . . H16B H 0.1372 0.7119 -0.2263 0.043 Uiso 1 1 calc R . . C22B C 0.19727(7) 0.5257(2) 0.5376(3) 0.0351(5) Uani 1 1 d . . . H22B H 0.1977 0.5995 0.5716 0.042 Uiso 1 1 calc R . . C15B C 0.18895(7) 0.70129(18) -0.1220(3) 0.0348(5) Uani 1 1 d . . . H15B H 0.1983 0.7641 -0.1682 0.042 Uiso 1 1 calc R . . C24A C 0.46404(8) -0.1073(2) 0.2632(3) 0.0456(6) Uani 1 1 d . . . C24B C 0.03482(8) -0.1076(2) -0.2107(3) 0.0458(6) Uani 1 1 d . . . C27A C 0.49328(16) -0.1508(5) 0.4017(7) 0.0474(5) Uani 0.50 1 d P A 4 H27D H 0.5043 -0.2197 0.3722 0.071 Uiso 0.50 1 calc PR A 4 H27E H 0.4805 -0.1630 0.4917 0.071 Uiso 0.50 1 calc PR A 4 H27F H 0.5124 -0.0958 0.4236 0.071 Uiso 0.50 1 calc PR A 4 C25A C 0.48648(16) -0.0848(5) 0.1367(7) 0.0474(5) Uani 0.50 1 d P A 4 H25D H 0.5052 -0.0303 0.1683 0.071 Uiso 0.50 1 calc PR A 4 H25E H 0.4708 -0.0568 0.0502 0.071 Uiso 0.50 1 calc PR A 4 H25F H 0.4983 -0.1527 0.1082 0.071 Uiso 0.50 1 calc PR A 4 C27B C 0.00495(15) -0.1474(4) -0.0916(6) 0.0437(5) Uani 0.50 1 d P B 2 H27A H -0.0136 -0.0904 -0.0855 0.066 Uiso 0.50 1 calc PR B 2 H27B H 0.0178 -0.1595 0.0085 0.066 Uiso 0.50 1 calc PR B 2 H27C H -0.0068 -0.2156 -0.1281 0.066 Uiso 0.50 1 calc PR B 2 C26B C 0.01127(15) -0.0843(4) -0.3522(6) 0.0437(5) Uani 0.50 1 d P B 2 H26A H -0.0005 -0.1522 -0.3901 0.066 Uiso 0.50 1 calc PR B 2 H26B H 0.0263 -0.0548 -0.4278 0.066 Uiso 0.50 1 calc PR B 2 H26C H -0.0074 -0.0306 -0.3319 0.066 Uiso 0.50 1 calc PR B 2 C26A C 0.43752(16) -0.2006(5) 0.2253(7) 0.0474(5) Uani 0.50 1 d P A 4 H26D H 0.4196 -0.1785 0.1423 0.071 Uiso 0.50 1 calc PR A 4 H26E H 0.4249 -0.2185 0.3140 0.071 Uiso 0.50 1 calc PR A 4 H26F H 0.4509 -0.2650 0.1953 0.071 Uiso 0.50 1 calc PR A 4 C25B C 0.05924(15) -0.2036(4) -0.2257(6) 0.0437(5) Uani 0.50 1 d P B 2 H25A H 0.0449 -0.2651 -0.2702 0.066 Uiso 0.50 1 calc PR B 2 H25B H 0.0706 -0.2246 -0.1260 0.066 Uiso 0.50 1 calc PR B 2 H25C H 0.0782 -0.1841 -0.2908 0.066 Uiso 0.50 1 calc PR B 2 C30B C -0.00212(15) -0.0832(4) -0.2606(6) 0.0437(5) Uani 0.50 1 d P B 1 H30A H -0.0122 -0.1415 -0.3278 0.066 Uiso 0.50 1 calc PR B 1 H30B H -0.0033 -0.0133 -0.3150 0.066 Uiso 0.50 1 calc PR B 1 H30C H -0.0163 -0.0779 -0.1734 0.066 Uiso 0.50 1 calc PR B 1 C29B C 0.05618(15) -0.1092(4) -0.3785(6) 0.0437(5) Uani 0.50 1 d P B 1 H29A H 0.0456 -0.1677 -0.4442 0.066 Uiso 0.50 1 calc PR B 1 H29B H 0.0824 -0.1224 -0.3551 0.066 Uiso 0.50 1 calc PR B 1 H29C H 0.0525 -0.0385 -0.4296 0.066 Uiso 0.50 1 calc PR B 1 C28B C 0.04490(16) -0.2138(4) -0.1489(6) 0.0437(5) Uani 0.50 1 d P B 1 H28A H 0.0380 -0.2188 -0.0458 0.066 Uiso 0.50 1 calc PR B 1 H28B H 0.0713 -0.2238 -0.1480 0.066 Uiso 0.50 1 calc PR B 1 H28C H 0.0323 -0.2710 -0.2110 0.066 Uiso 0.50 1 calc PR B 1 C28A C 0.44232(16) -0.1055(5) 0.0788(6) 0.0474(5) Uani 0.50 1 d P A 3 H28D H 0.4446 -0.0324 0.0353 0.071 Uiso 0.50 1 calc PR A 3 H28E H 0.4164 -0.1234 0.0811 0.071 Uiso 0.50 1 calc PR A 3 H28F H 0.4538 -0.1596 0.0174 0.071 Uiso 0.50 1 calc PR A 3 C29A C 0.45193(17) -0.2125(5) 0.3073(7) 0.0474(5) Uani 0.50 1 d P A 3 H29D H 0.4607 -0.2687 0.2409 0.071 Uiso 0.50 1 calc PR A 3 H29E H 0.4252 -0.2138 0.2996 0.071 Uiso 0.50 1 calc PR A 3 H29F H 0.4616 -0.2274 0.4115 0.071 Uiso 0.50 1 calc PR A 3 C30A C 0.50060(16) -0.0838(5) 0.2366(7) 0.0474(5) Uani 0.50 1 d P A 3 H30D H 0.5154 -0.0745 0.3331 0.071 Uiso 0.50 1 calc PR A 3 H30E H 0.5013 -0.0163 0.1776 0.071 Uiso 0.50 1 calc PR A 3 H30F H 0.5104 -0.1445 0.1809 0.071 Uiso 0.50 1 calc PR A 3 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 N1A 0.0243(8) 0.0260(8) 0.0213(8) 0.0010(6) 0.0024(6) -0.0002(6) N3A 0.0240(8) 0.0259(8) 0.0238(8) -0.0001(6) 0.0026(6) 0.0001(6) C2A 0.0216(8) 0.0284(9) 0.0200(9) -0.0005(7) 0.0017(7) -0.0010(7) C7A 0.0251(9) 0.0311(10) 0.0292(11) 0.0056(8) 0.0042(8) 0.0013(7) C23A 0.0244(9) 0.0377(11) 0.0240(10) 0.0039(8) 0.0008(7) 0.0035(8) C5A 0.0233(8) 0.0263(9) 0.0244(10) -0.0029(7) 0.0018(7) 0.0004(7) C10A 0.0363(11) 0.0285(10) 0.0299(11) 0.0031(8) 0.0084(9) 0.0030(8) C8A 0.0290(10) 0.0381(11) 0.0282(11) 0.0045(9) 0.0088(8) 0.0043(8) C6A 0.0216(8) 0.0291(9) 0.0222(9) 0.0006(7) 0.0016(7) 0.0010(7) C18A 0.0233(9) 0.0333(10) 0.0212(9) -0.0010(8) 0.0007(7) 0.0039(7) C11A 0.0296(9) 0.0314(10) 0.0249(10) 0.0008(8) 0.0082(8) 0.0014(8) C9A 0.0316(10) 0.0315(10) 0.0281(11) -0.0014(8) 0.0066(8) 0.0043(8) C19A 0.0357(11) 0.0333(11) 0.0266(11) -0.0034(8) 0.0005(8) 0.0040(8) C12A 0.0323(10) 0.0256(9) 0.0229(10) -0.0021(7) 0.0011(8) 0.0027(7) C20A 0.0443(12) 0.0422(12) 0.0277(12) -0.0065(9) 0.0011(9) 0.0138(10) C4A 0.0247(9) 0.0274(9) 0.0243(10) -0.0024(7) 0.0009(7) 0.0000(7) C17A 0.0335(11) 0.0352(11) 0.0301(11) -0.0008(9) 0.0018(8) 0.0041(9) C22A 0.0274(10) 0.0520(14) 0.0280(11) 0.0092(10) 0.0058(8) 0.0083(9) C16A 0.0384(12) 0.0389(12) 0.0376(13) -0.0045(10) -0.0029(10) 0.0114(10) C13A 0.0354(11) 0.0297(10) 0.0327(12) 0.0004(8) 0.0035(9) -0.0004(8) C21A 0.0377(12) 0.0599(15) 0.0240(11) 0.0009(10) 0.0064(9) 0.0195(11) C15A 0.0535(14) 0.0293(11) 0.0377(13) -0.0002(9) -0.0085(11) 0.0087(10) C14A 0.0518(14) 0.0302(11) 0.0371(13) 0.0048(9) -0.0006(11) -0.0040(10) N1B 0.0266(8) 0.0253(8) 0.0208(8) 0.0004(6) 0.0013(6) -0.0005(6) N3B 0.0252(8) 0.0257(8) 0.0249(9) -0.0009(6) 0.0011(6) -0.0010(6) C6B 0.0235(9) 0.0283(9) 0.0225(10) 0.0002(7) 0.0017(7) -0.0015(7) C7B 0.0264(9) 0.0303(10) 0.0280(10) 0.0062(8) -0.0020(8) -0.0015(8) C12B 0.0296(9) 0.0257(9) 0.0238(10) -0.0019(7) 0.0033(7) 0.0002(7) C2B 0.0234(8) 0.0272(9) 0.0224(10) 0.0001(7) 0.0021(7) 0.0006(7) C11B 0.0311(10) 0.0302(10) 0.0220(10) 0.0017(8) -0.0040(8) -0.0014(8) C18B 0.0247(9) 0.0302(10) 0.0240(10) -0.0022(8) 0.0036(7) -0.0023(7) C5B 0.0237(8) 0.0258(9) 0.0252(10) -0.0023(7) 0.0022(7) -0.0007(7) C10B 0.0376(11) 0.0277(10) 0.0274(11) 0.0040(8) -0.0034(8) -0.0028(8) C17B 0.0302(10) 0.0308(10) 0.0312(11) 0.0010(8) 0.0002(8) -0.0014(8) C8B 0.0301(10) 0.0362(11) 0.0269(11) 0.0056(8) -0.0042(8) -0.0033(8) C19B 0.0269(9) 0.0324(10) 0.0252(10) -0.0003(8) 0.0018(8) -0.0013(8) C9B 0.0317(10) 0.0313(10) 0.0253(10) 0.0000(8) -0.0027(8) -0.0050(8) C14B 0.0309(10) 0.0332(11) 0.0391(12) -0.0010(9) 0.0038(9) -0.0060(8) C20B 0.0282(10) 0.0418(12) 0.0258(11) 0.0027(9) 0.0001(8) -0.0020(8) C13B 0.0284(10) 0.0310(10) 0.0302(11) 0.0004(8) 0.0014(8) -0.0003(8) C4B 0.0237(8) 0.0260(9) 0.0242(10) -0.0019(7) 0.0020(7) 0.0001(7) C21B 0.0343(11) 0.0457(13) 0.0238(11) -0.0037(9) -0.0008(8) -0.0067(9) C23B 0.0336(10) 0.0316(10) 0.0262(11) -0.0031(8) 0.0014(8) -0.0010(8) C16B 0.0402(12) 0.0303(11) 0.0363(12) 0.0042(9) 0.0014(9) 0.0016(9) C22B 0.0419(12) 0.0343(11) 0.0288(11) -0.0068(9) 0.0027(9) -0.0060(9) C15B 0.0412(12) 0.0273(10) 0.0364(12) 0.0012(9) 0.0072(9) -0.0050(9) C24A 0.0488(14) 0.0361(12) 0.0557(17) -0.0116(11) 0.0244(12) 0.0025(10) C24B 0.0522(15) 0.0340(12) 0.0464(15) -0.0093(10) -0.0191(12) -0.0017(11) C27A 0.0538(14) 0.0442(11) 0.0459(13) -0.0030(10) 0.0136(10) 0.0130(10) C25A 0.0538(14) 0.0442(11) 0.0459(13) -0.0030(10) 0.0136(10) 0.0130(10) C27B 0.0486(12) 0.0412(10) 0.0399(12) -0.0049(9) -0.0025(9) -0.0107(9) C26B 0.0486(12) 0.0412(10) 0.0399(12) -0.0049(9) -0.0025(9) -0.0107(9) C26A 0.0538(14) 0.0442(11) 0.0459(13) -0.0030(10) 0.0136(10) 0.0130(10) C25B 0.0486(12) 0.0412(10) 0.0399(12) -0.0049(9) -0.0025(9) -0.0107(9) C30B 0.0486(12) 0.0412(10) 0.0399(12) -0.0049(9) -0.0025(9) -0.0107(9) C29B 0.0486(12) 0.0412(10) 0.0399(12) -0.0049(9) -0.0025(9) -0.0107(9) C28B 0.0486(12) 0.0412(10) 0.0399(12) -0.0049(9) -0.0025(9) -0.0107(9) C28A 0.0538(14) 0.0442(11) 0.0459(13) -0.0030(10) 0.0136(10) 0.0130(10) C29A 0.0538(14) 0.0442(11) 0.0459(13) -0.0030(10) 0.0136(10) 0.0130(10) C30A 0.0538(14) 0.0442(11) 0.0459(13) -0.0030(10) 0.0136(10) 0.0130(10) _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 N1A H1A 0.8800 . ? N1A C2A 1.348(3) . ? N1A C5A 1.375(2) . ? N3A C2A 1.333(3) . ? N3A C4A 1.385(3) . ? C2A C6A 1.462(3) . ? C7A H7A 0.9500 . ? C7A C8A 1.387(3) . ? C7A C6A 1.395(3) . ? C23A H23A 0.9500 . ? C23A C18A 1.396(3) . ? C23A C22A 1.389(3) . ? C5A C18A 1.469(3) . ? C5A C4A 1.380(3) . ? C10A H10A 0.9500 . ? C10A C11A 1.389(3) . ? C10A C9A 1.390(3) . ? C8A H8A 0.9500 . ? C8A C9A 1.397(3) . ? C6A C11A 1.393(3) . ? C18A C19A 1.395(3) . ? C11A H11A 0.9500 . ? C9A C24A 1.527(3) . ? C19A H19A 0.9500 . ? C19A C20A 1.381(3) . ? C12A C4A 1.474(3) . ? C12A C17A 1.401(3) . ? C12A C13A 1.395(3) . ? C20A H20A 0.9500 . ? C20A C21A 1.382(4) . ? C17A H17A 0.9500 . ? C17A C16A 1.386(3) . ? C22A H22A 0.9500 . ? C22A C21A 1.390(4) . ? C16A H16A 0.9500 . ? C16A C15A 1.383(4) . ? C13A H13A 0.9500 . ? C13A C14A 1.386(3) . ? C21A H21A 0.9500 . ? C15A H15A 0.9500 . ? C15A C14A 1.392(4) . ? C14A H14A 0.9500 . ? N1B H1B 0.8800 . ? N1B C2B 1.356(3) . ? N1B C5B 1.382(2) . ? N3B C2B 1.328(3) . ? N3B C4B 1.381(2) . ? C6B C7B 1.394(3) . ? C6B C2B 1.463(3) . ? C6B C11B 1.394(3) . ? C7B H7B 0.9500 . ? C7B C8B 1.383(3) . ? C12B C17B 1.397(3) . ? C12B C13B 1.397(3) . ? C12B C4B 1.474(3) . ? C11B H11B 0.9500 . ? C11B C10B 1.389(3) . ? C18B C5B 1.468(3) . ? C18B C19B 1.395(3) . ? C18B C23B 1.399(3) . ? C5B C4B 1.382(3) . ? C10B H10B 0.9500 . ? C10B C9B 1.398(3) . ? C17B H17B 0.9500 . ? C17B C16B 1.391(3) . ? C8B H8B 0.9500 . ? C8B C9B 1.400(3) . ? C19B H19B 0.9500 . ? C19B C20B 1.392(3) . ? C9B C24B 1.524(3) . ? C14B H14B 0.9500 . ? C14B C13B 1.389(3) . ? C14B C15B 1.382(3) . ? C20B H20B 0.9500 . ? C20B C21B 1.388(3) . ? C13B H13B 0.9500 . ? C21B H21B 0.9500 . ? C21B C22B 1.387(3) . ? C23B H23B 0.9500 . ? C23B C22B 1.391(3) . ? C16B H16B 0.9500 . ? C16B C15B 1.392(3) . ? C22B H22B 0.9500 . ? C15B H15B 0.9500 . ? C24A C27A 1.646(7) . ? C24A C25A 1.487(6) . ? C24A C26A 1.517(7) . ? C24A C28A 1.758(7) . ? C24A C29A 1.428(6) . ? C24A C30A 1.418(6) . ? C24B C27B 1.673(6) . ? C24B C26B 1.488(6) . ? C24B C25B 1.490(6) . ? C24B C30B 1.421(6) . ? C24B C29B 1.756(6) . ? C24B C28B 1.443(6) . ? C27A H27D 0.9800 . ? C27A H27E 0.9800 . ? C27A H27F 0.9800 . ? C25A H25D 0.9800 . ? C25A H25E 0.9800 . ? C25A H25F 0.9800 . ? C27B H27A 0.9800 . ? C27B H27B 0.9800 . ? C27B H27C 0.9800 . ? C26B H26A 0.9800 . ? C26B H26B 0.9800 . ? C26B H26C 0.9800 . ? C26A H26D 0.9800 . ? C26A H26E 0.9800 . ? C26A H26F 0.9800 . ? C25B H25A 0.9800 . ? C25B H25B 0.9800 . ? C25B H25C 0.9800 . ? C30B H30A 0.9800 . ? C30B H30B 0.9800 . ? C30B H30C 0.9800 . ? C29B H29A 0.9800 . ? C29B H29B 0.9800 . ? C29B H29C 0.9800 . ? C28B H28A 0.9800 . ? C28B H28B 0.9800 . ? C28B H28C 0.9800 . ? C28A H28D 0.9800 . ? C28A H28E 0.9800 . ? C28A H28F 0.9800 . ? C29A H29D 0.9800 . ? C29A H29E 0.9800 . ? C29A H29F 0.9800 . ? C30A H30D 0.9800 . ? C30A H30E 0.9800 . ? C30A H30F 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 C2A N1A H1A 125.8 . . ? C2A N1A C5A 108.31(16) . . ? C5A N1A H1A 125.8 . . ? C2A N3A C4A 105.52(16) . . ? N1A C2A C6A 124.23(18) . . ? N3A C2A N1A 111.10(17) . . ? N3A C2A C6A 124.50(18) . . ? C8A C7A H7A 119.8 . . ? C8A C7A C6A 120.48(19) . . ? C6A C7A H7A 119.8 . . ? C18A C23A H23A 119.8 . . ? C22A C23A H23A 119.8 . . ? C22A C23A C18A 120.4(2) . . ? N1A C5A C18A 121.02(18) . . ? N1A C5A C4A 105.30(17) . . ? C4A C5A C18A 133.59(19) . . ? C11A C10A H10A 119.1 . . ? C11A C10A C9A 121.8(2) . . ? C9A C10A H10A 119.1 . . ? C7A C8A H8A 119.3 . . ? C7A C8A C9A 121.4(2) . . ? C9A C8A H8A 119.3 . . ? C7A C6A C2A 119.85(18) . . ? C11A C6A C2A 121.36(18) . . ? C11A C6A C7A 118.61(18) . . ? C23A C18A C5A 120.28(19) . . ? C23A C18A C19A 118.9(2) . . ? C19A C18A C5A 120.69(19) . . ? C10A C11A C6A 120.18(19) . . ? C10A C11A H11A 119.9 . . ? C6A C11A H11A 119.9 . . ? C10A C9A C8A 117.38(19) . . ? C10A C9A C24A 121.1(2) . . ? C8A C9A C24A 121.5(2) . . ? C18A C19A H19A 119.8 . . ? C20A C19A C18A 120.5(2) . . ? C20A C19A H19A 119.8 . . ? C17A C12A C4A 120.68(19) . . ? C13A C12A C4A 120.75(19) . . ? C13A C12A C17A 118.5(2) . . ? C19A C20A H20A 119.8 . . ? C19A C20A C21A 120.5(2) . . ? C21A C20A H20A 119.8 . . ? N3A C4A C12A 120.61(18) . . ? C5A C4A N3A 109.73(17) . . ? C5A C4A C12A 129.52(18) . . ? C12A C17A H17A 119.8 . . ? C16A C17A C12A 120.4(2) . . ? C16A C17A H17A 119.8 . . ? C23A C22A H22A 120.0 . . ? C23A C22A C21A 120.0(2) . . ? C21A C22A H22A 120.0 . . ? C17A C16A H16A 119.7 . . ? C15A C16A C17A 120.6(2) . . ? C15A C16A H16A 119.7 . . ? C12A C13A H13A 119.6 . . ? C14A C13A C12A 120.8(2) . . ? C14A C13A H13A 119.6 . . ? C20A C21A C22A 119.7(2) . . ? C20A C21A H21A 120.2 . . ? C22A C21A H21A 120.2 . . ? C16A C15A H15A 120.3 . . ? C16A C15A C14A 119.5(2) . . ? C14A C15A H15A 120.3 . . ? C13A C14A C15A 120.2(2) . . ? C13A C14A H14A 119.9 . . ? C15A C14A H14A 119.9 . . ? C2B N1B H1B 126.1 . . ? C2B N1B C5B 107.79(16) . . ? C5B N1B H1B 126.1 . . ? C2B N3B C4B 105.73(17) . . ? C7B C6B C2B 119.53(18) . . ? C7B C6B C11B 118.42(18) . . ? C11B C6B C2B 121.90(18) . . ? C6B C7B H7B 119.6 . . ? C8B C7B C6B 120.73(19) . . ? C8B C7B H7B 119.6 . . ? C17B C12B C4B 119.41(18) . . ? C13B C12B C17B 118.45(19) . . ? C13B C12B C4B 122.01(19) . . ? N1B C2B C6B 124.55(18) . . ? N3B C2B N1B 111.30(17) . . ? N3B C2B C6B 124.06(18) . . ? C6B C11B H11B 119.8 . . ? C10B C11B C6B 120.45(19) . . ? C10B C11B H11B 119.8 . . ? C19B C18B C5B 120.73(19) . . ? C19B C18B C23B 118.75(19) . . ? C23B C18B C5B 120.46(19) . . ? N1B C5B C18B 120.72(18) . . ? N1B C5B C4B 105.24(17) . . ? C4B C5B C18B 133.98(19) . . ? C11B C10B H10B 119.2 . . ? C11B C10B C9B 121.6(2) . . ? C9B C10B H10B 119.2 . . ? C12B C17B H17B 119.6 . . ? C16B C17B C12B 120.8(2) . . ? C16B C17B H17B 119.6 . . ? C7B C8B H8B 119.2 . . ? C7B C8B C9B 121.63(19) . . ? C9B C8B H8B 119.2 . . ? C18B C19B H19B 119.7 . . ? C20B C19B C18B 120.6(2) . . ? C20B C19B H19B 119.7 . . ? C10B C9B C8B 117.06(19) . . ? C10B C9B C24B 121.5(2) . . ? C8B C9B C24B 121.47(19) . . ? C13B C14B H14B 119.8 . . ? C15B C14B H14B 119.8 . . ? C15B C14B C13B 120.4(2) . . ? C19B C20B H20B 119.9 . . ? C21B C20B C19B 120.2(2) . . ? C21B C20B H20B 119.9 . . ? C12B C13B H13B 119.7 . . ? C14B C13B C12B 120.7(2) . . ? C14B C13B H13B 119.7 . . ? N3B C4B C12B 119.13(18) . . ? N3B C4B C5B 109.92(17) . . ? C5B C4B C12B 130.82(18) . . ? C20B C21B H21B 120.2 . . ? C22B C21B C20B 119.7(2) . . ? C22B C21B H21B 120.2 . . ? C18B C23B H23B 119.8 . . ? C22B C23B C18B 120.5(2) . . ? C22B C23B H23B 119.8 . . ? C17B C16B H16B 120.0 . . ? C17B C16B C15B 120.0(2) . . ? C15B C16B H16B 120.0 . . ? C21B C22B C23B 120.3(2) . . ? C21B C22B H22B 119.9 . . ? C23B C22B H22B 119.9 . . ? C14B C15B C16B 119.7(2) . . ? C14B C15B H15B 120.1 . . ? C16B C15B H15B 120.1 . . ? C9A C24A C27A 105.9(3) . . ? C9A C24A C28A 98.3(2) . . ? C27A C24A C28A 155.7(3) . . ? C25A C24A C9A 116.2(3) . . ? C25A C24A C27A 104.9(3) . . ? C25A C24A C26A 111.2(4) . . ? C25A C24A C28A 61.5(3) . . ? C26A C24A C9A 111.2(3) . . ? C26A C24A C27A 106.5(4) . . ? C26A C24A C28A 64.9(3) . . ? C29A C24A C9A 116.2(3) . . ? C29A C24A C27A 72.6(4) . . ? C29A C24A C25A 125.8(4) . . ? C29A C24A C26A 34.3(3) . . ? C29A C24A C28A 98.2(4) . . ? C30A C24A C9A 112.5(3) . . ? C30A C24A C27A 68.2(4) . . ? C30A C24A C25A 39.7(3) . . ? C30A C24A C26A 135.6(3) . . ? C30A C24A C28A 101.2(4) . . ? C30A C24A C29A 123.7(4) . . ? C9B C24B C27B 105.4(3) . . ? C9B C24B C29B 98.5(2) . . ? C27B C24B C29B 156.0(3) . . ? C26B C24B C9B 116.7(3) . . ? C26B C24B C27B 103.2(3) . . ? C26B C24B C25B 112.4(4) . . ? C26B C24B C29B 63.4(3) . . ? C25B C24B C9B 112.2(3) . . ? C25B C24B C27B 105.5(3) . . ? C25B C24B C29B 65.9(3) . . ? C30B C24B C9B 112.9(3) . . ? C30B C24B C27B 65.9(3) . . ? C30B C24B C26B 39.9(3) . . ? C30B C24B C25B 134.7(3) . . ? C30B C24B C29B 103.3(3) . . ? C30B C24B C28B 120.7(4) . . ? C28B C24B C9B 115.6(3) . . ? C28B C24B C27B 70.0(3) . . ? C28B C24B C26B 127.1(3) . . ? C28B C24B C25B 36.2(3) . . ? C28B C24B C29B 101.3(3) . . ? C24A C27A H27D 109.5 . . ? C24A C27A H27E 109.5 . . ? C24A C27A H27F 109.5 . . ? C24A C25A H25D 109.5 . . ? C24A C25A H25E 109.5 . . ? C24A C25A H25F 109.5 . . ? C24B C27B H27A 109.5 . . ? C24B C27B H27B 109.5 . . ? C24B C27B H27C 109.5 . . ? H27A C27B H27B 109.5 . . ? H27A C27B H27C 109.5 . . ? H27B C27B H27C 109.5 . . ? C24B C26B H26A 109.5 . . ? C24B C26B H26B 109.5 . . ? C24B C26B H26C 109.5 . . ? H26A C26B H26B 109.5 . . ? H26A C26B H26C 109.5 . . ? H26B C26B H26C 109.5 . . ? C24A C26A H26D 109.5 . . ? C24A C26A H26E 109.5 . . ? C24A C26A H26F 109.5 . . ? C24B C25B H25A 109.5 . . ? C24B C25B H25B 109.5 . . ? C24B C25B H25C 109.5 . . ? H25A C25B H25B 109.5 . . ? H25A C25B H25C 109.5 . . ? H25B C25B H25C 109.5 . . ? C24B C30B H30A 109.5 . . ? C24B C30B H30B 109.5 . . ? C24B C30B H30C 109.5 . . ? C24B C29B H29A 109.5 . . ? C24B C29B H29B 109.5 . . ? C24B C29B H29C 109.5 . . ? C24B C28B H28A 109.5 . . ? C24B C28B H28B 109.5 . . ? C24B C28B H28C 109.5 . . ? C24A C28A H28D 109.5 . . ? C24A C28A H28E 109.5 . . ? C24A C28A H28F 109.5 . . ? C24A C29A H29D 109.5 . . ? C24A C29A H29E 109.5 . . ? C24A C29A H29F 109.5 . . ? C24A C30A H30D 109.5 . . ? C24A C30A H30E 109.5 . . ? C24A C30A H30F 109.5 . . ? _vrf_DIFMN02_ALERT_2_B ; PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00 _refine_diff_density_min given = -1.092 RESPONSE: This is a synchrotron dataset of a very weak crystal. It is possible that the data collection is not as complete as would be wished for. ; _vrf_DIFMX01_ALERT_2_B ; PROBLEM:The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 1.281 RESPONSE: This is a synchrotron dataset of a very weak crystal. It is possible that the data collection is not as complete as would be wished for. ; _vrf_PLAT230_Global ; PROBLEM: Hirshfeld Test Diff for several atoms RESPONSE: The affected atoms belong to the dynamically disordered t-butyl groups and have only been modelled for two positions. More positions might be possible. ; data_cn_4tbu _database_code_depnum_ccdc_archive 'CCDC 882413' #TrackingRef '- Compound 4.cif' _audit_creation_date 2011-11-09 _audit_creation_method ; Olex2 1.1-alpha (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C50 H46 N4' _chemical_formula_sum 'C50 H46 N4' _chemical_formula_weight 702.91 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.6166(2) _cell_length_b 12.1515(2) _cell_length_c 26.5190(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.3060(4) _cell_angle_gamma 90.00 _cell_volume 4023.00(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9908 _cell_measurement_temperature 99.98 _cell_measurement_theta_max 68.227 _cell_measurement_theta_min 3.695 _exptl_absorpt_coefficient_mu 0.519 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.6199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0840 before and 0.0411 after correction. The Ratio of minimum to maximum transmission is 0.8231. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1496 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.11 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of \w scans, each set at different \f and/or 2\q angles, with additional \f scans, each set at different \w and/or 2\q angles, to aid absorption correction parameters. Each image (1.0 s exposure) covering -0.50\ degrees in \w or \f. The crystal to detector distance was 5.00 cm ; _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_unetI/netI 0.0170 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 43177 _diffrn_reflns_theta_full 68.66 _diffrn_reflns_theta_max 68.66 _diffrn_reflns_theta_min 3.37 _diffrn_ambient_temperature 99.98 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'Bruker Pt 135 CCD area detector' _diffrn_measured_fraction_theta_full 0.952 _diffrn_measured_fraction_theta_max 0.952 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Pt 135 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_collimation 'focused optics' _diffrn_radiation_monochromator 'Bruker Helios multilayer optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54188 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'Microstar rotating anode' _diffrn_source_target Cu _diffrn_source_type 'rotating anode' _reflns_number_gt 6530 _reflns_number_total 7083 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_collection 'Proteum2 (Bruker, 2010)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.216 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.033 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 493 _refine_ls_number_reflns 7083 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0353 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+1.3850P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0882 _refine_ls_wR_factor_ref 0.0903 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 N3 N 0.48641(7) 0.18615(7) 0.23296(3) 0.0228(2) Uani 1 1 d . . . N4 N 0.62203(7) 0.05451(8) 0.22345(3) 0.0226(2) Uani 1 1 d . . . N1 N 0.31133(7) -0.10440(8) 0.15672(3) 0.0232(2) Uani 1 1 d . . . N2 N 0.43701(7) 0.00788(7) 0.19555(3) 0.0216(2) Uani 1 1 d . . . C42 C 0.53638(8) 0.14019(9) 0.14805(4) 0.0226(2) Uani 1 1 d . . . C15 C 0.35161(9) -0.00460(9) 0.15686(4) 0.0220(2) Uani 1 1 d . . . C35 C 0.65295(9) 0.11626(9) 0.26218(4) 0.0226(2) Uani 1 1 d . . . C27 C 0.51724(9) 0.09762(9) 0.20031(4) 0.0226(2) Uani 1 1 d . . . C9 C 0.52240(9) -0.11201(9) 0.26931(4) 0.0231(2) Uani 1 1 d . . . C8 C 0.44711(9) -0.09187(9) 0.22209(4) 0.0217(2) Uani 1 1 d . . . C36 C 0.75743(9) 0.09791(9) 0.29398(4) 0.0232(2) Uani 1 1 d . . . C44 C 0.59047(9) 0.10117(10) 0.06642(4) 0.0258(2) Uani 1 1 d . . . H44 H 0.6105 0.0488 0.0429 0.031 Uiso 1 1 calc R . . C14 C 0.51012(9) -0.05716(10) 0.31431(4) 0.0270(3) Uani 1 1 d . . . H14 H 0.4547 -0.0043 0.3145 0.032 Uiso 1 1 calc R . . C21 C 0.23456(9) 0.26361(10) 0.10262(4) 0.0269(3) Uani 1 1 d . . . H21 H 0.2251 0.3368 0.1137 0.032 Uiso 1 1 calc R . . C6 C 0.34120(9) -0.27412(9) 0.20777(4) 0.0241(2) Uani 1 1 d . . . C22 C 0.28742(9) 0.18856(9) 0.13679(4) 0.0258(2) Uani 1 1 d . . . H22 H 0.3135 0.2109 0.1706 0.031 Uiso 1 1 calc R . . C28 C 0.56623(9) 0.19897(9) 0.26851(4) 0.0227(2) Uani 1 1 d . . . C45 C 0.58580(9) 0.21275(10) 0.05304(4) 0.0245(2) Uani 1 1 d . . . C37 C 0.77523(9) 0.12218(10) 0.34577(4) 0.0279(3) Uani 1 1 d . . . H37 H 0.7199 0.1546 0.3616 0.033 Uiso 1 1 calc R . . C10 C 0.60339(9) -0.18997(10) 0.26995(5) 0.0290(3) Uani 1 1 d . . . H10 H 0.6120 -0.2282 0.2396 0.035 Uiso 1 1 calc R . . C1 C 0.29120(9) -0.33828(10) 0.16761(5) 0.0275(3) Uani 1 1 d . . . H1 H 0.2764 -0.3075 0.1344 0.033 Uiso 1 1 calc R . . C46 C 0.55641(9) 0.28608(10) 0.08885(4) 0.0267(3) Uani 1 1 d . . . H46 H 0.5525 0.3624 0.0810 0.032 Uiso 1 1 calc R . . C7 C 0.36950(9) -0.15955(9) 0.19715(4) 0.0223(2) Uani 1 1 d . . . C13 C 0.57899(10) -0.07981(12) 0.35883(5) 0.0346(3) Uani 1 1 d . . . H13 H 0.5707 -0.0422 0.3894 0.041 Uiso 1 1 calc R . . C29 C 0.56495(9) 0.28443(9) 0.30830(4) 0.0235(2) Uani 1 1 d . . . C2 C 0.26280(10) -0.44644(10) 0.17555(5) 0.0327(3) Uani 1 1 d . . . H2 H 0.2288 -0.4890 0.1478 0.039 Uiso 1 1 calc R . . C34 C 0.65355(9) 0.35100(10) 0.32393(4) 0.0275(3) Uani 1 1 d . . . H34 H 0.7182 0.3399 0.3102 0.033 Uiso 1 1 calc R . . C5 C 0.36031(9) -0.32106(10) 0.25634(5) 0.0277(3) Uani 1 1 d . . . H5 H 0.3931 -0.2784 0.2843 0.033 Uiso 1 1 calc R . . C38 C 0.87372(10) 0.09907(11) 0.37435(5) 0.0321(3) Uani 1 1 d . . . H38 H 0.8856 0.1156 0.4097 0.038 Uiso 1 1 calc R . . C41 C 0.83936(9) 0.04933(9) 0.27155(5) 0.0266(3) Uani 1 1 d . . . H41 H 0.8276 0.0316 0.2363 0.032 Uiso 1 1 calc R . . C17 C 0.26095(10) 0.05026(10) 0.07234(5) 0.0293(3) Uani 1 1 d . . . H17 H 0.2687 -0.0236 0.0617 0.035 Uiso 1 1 calc R . . C16 C 0.30239(9) 0.08104(9) 0.12179(4) 0.0232(2) Uani 1 1 d . . . C40 C 0.93739(9) 0.02670(10) 0.30017(5) 0.0302(3) Uani 1 1 d . . . H40 H 0.9928 -0.0062 0.2846 0.036 Uiso 1 1 calc R . . C43 C 0.56658(9) 0.06531(9) 0.11299(4) 0.0251(2) Uani 1 1 d . . . H43 H 0.5708 -0.0109 0.1211 0.030 Uiso 1 1 calc R . . C48 C 0.61312(10) 0.24914(10) 0.00105(4) 0.0285(3) Uani 1 1 d . . . C30 C 0.47059(9) 0.30153(10) 0.32900(4) 0.0267(3) Uani 1 1 d . . . H30 H 0.4095 0.2572 0.3182 0.032 Uiso 1 1 calc R . . C19 C 0.20865(10) 0.12580(10) 0.03850(5) 0.0314(3) Uani 1 1 d . . . H19 H 0.1814 0.1029 0.0049 0.038 Uiso 1 1 calc R . . C20 C 0.19508(9) 0.23499(10) 0.05273(4) 0.0264(3) Uani 1 1 d . . . C31 C 0.46553(10) 0.38293(11) 0.36524(5) 0.0310(3) Uani 1 1 d . . . H31 H 0.4016 0.3933 0.3796 0.037 Uiso 1 1 calc R . . C49 C 0.54260(10) 0.18604(11) -0.04151(5) 0.0325(3) Uani 1 1 d . . . H49A H 0.5568 0.1070 -0.0376 0.049 Uiso 1 1 calc R . . H49B H 0.5591 0.2105 -0.0747 0.049 Uiso 1 1 calc R . . H49C H 0.4670 0.2005 -0.0394 0.049 Uiso 1 1 calc R . . C47 C 0.53261(9) 0.25109(10) 0.13581(4) 0.0254(2) Uani 1 1 d . . . H47 H 0.5137 0.3034 0.1596 0.030 Uiso 1 1 calc R . . C50 C 0.59504(12) 0.37272(11) -0.00806(5) 0.0371(3) Uani 1 1 d . . . H50A H 0.5201 0.3908 -0.0060 0.056 Uiso 1 1 calc R . . H50B H 0.6117 0.3921 -0.0419 0.056 Uiso 1 1 calc R . . H50C H 0.6418 0.4143 0.0179 0.056 Uiso 1 1 calc R . . C26 C 0.13889(11) 0.43377(11) 0.03506(5) 0.0375(3) Uani 1 1 d . . . H26A H 0.1002 0.4356 0.0645 0.056 Uiso 1 1 calc R . . H26B H 0.1041 0.4834 0.0086 0.056 Uiso 1 1 calc R . . H26C H 0.2131 0.4574 0.0455 0.056 Uiso 1 1 calc R . . C39 C 0.95465(10) 0.05208(10) 0.35157(5) 0.0315(3) Uani 1 1 d . . . H39 H 1.0222 0.0372 0.3712 0.038 Uiso 1 1 calc R . . C51 C 0.73171(10) 0.22390(12) -0.00136(5) 0.0360(3) Uani 1 1 d . . . H51A H 0.7769 0.2701 0.0233 0.054 Uiso 1 1 calc R . . H51B H 0.7477 0.2393 -0.0357 0.054 Uiso 1 1 calc R . . H51C H 0.7461 0.1462 0.0068 0.054 Uiso 1 1 calc R . . C3 C 0.28376(10) -0.49287(10) 0.22380(5) 0.0348(3) Uani 1 1 d . . . H3 H 0.2653 -0.5673 0.2291 0.042 Uiso 1 1 calc R . . C33 C 0.64755(10) 0.43354(10) 0.35958(5) 0.0320(3) Uani 1 1 d . . . H33 H 0.7077 0.4796 0.3697 0.038 Uiso 1 1 calc R . . C11 C 0.67153(10) -0.21216(11) 0.31450(5) 0.0373(3) Uani 1 1 d . . . H11 H 0.7266 -0.2655 0.3146 0.045 Uiso 1 1 calc R . . C4 C 0.33183(10) -0.42952(10) 0.26403(5) 0.0322(3) Uani 1 1 d . . . H4 H 0.3455 -0.4605 0.2972 0.039 Uiso 1 1 calc R . . C32 C 0.55381(10) 0.44898(10) 0.38040(5) 0.0325(3) Uani 1 1 d . . . H32 H 0.5502 0.5050 0.4051 0.039 Uiso 1 1 calc R . . C12 C 0.65961(11) -0.15689(12) 0.35879(5) 0.0396(3) Uani 1 1 d . . . H12 H 0.7068 -0.1718 0.3893 0.047 Uiso 1 1 calc R . . C23 C 0.13788(11) 0.31640(11) 0.01402(5) 0.0344(3) Uani 1 1 d . . . C24 C 0.02101(13) 0.28002(14) -0.00045(7) 0.0579(5) Uani 1 1 d . . . H24A H 0.0190 0.2051 -0.0142 0.087 Uiso 1 1 calc R . . H24B H -0.0155 0.3301 -0.0263 0.087 Uiso 1 1 calc R . . H24C H -0.0151 0.2816 0.0299 0.087 Uiso 1 1 calc R . . C25 C 0.19412(18) 0.31792(16) -0.03331(6) 0.0717(6) Uani 1 1 d . . . H25A H 0.2692 0.3394 -0.0236 0.107 Uiso 1 1 calc R . . H25B H 0.1584 0.3709 -0.0580 0.107 Uiso 1 1 calc R . . H25C H 0.1908 0.2444 -0.0487 0.107 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 N3 0.0250(5) 0.0209(5) 0.0225(5) 0.0000(4) 0.0037(4) -0.0012(4) N4 0.0225(5) 0.0228(5) 0.0224(5) 0.0010(4) 0.0029(4) -0.0014(4) N1 0.0227(5) 0.0231(5) 0.0237(5) -0.0007(4) 0.0027(4) 0.0007(4) N2 0.0225(4) 0.0196(5) 0.0221(5) 0.0000(4) 0.0015(4) -0.0003(4) C42 0.0196(5) 0.0241(6) 0.0234(6) -0.0009(4) 0.0005(4) -0.0017(4) C15 0.0211(5) 0.0227(6) 0.0220(6) -0.0018(4) 0.0029(4) 0.0002(4) C35 0.0239(5) 0.0221(6) 0.0223(6) 0.0020(4) 0.0055(4) -0.0029(5) C27 0.0226(5) 0.0209(5) 0.0238(6) -0.0019(4) 0.0017(4) -0.0012(4) C9 0.0222(5) 0.0221(6) 0.0248(6) 0.0029(4) 0.0028(4) -0.0032(5) C8 0.0232(5) 0.0202(5) 0.0223(6) 0.0003(4) 0.0046(4) 0.0021(4) C36 0.0228(5) 0.0207(5) 0.0258(6) 0.0028(4) 0.0026(4) -0.0029(5) C44 0.0264(6) 0.0262(6) 0.0248(6) -0.0040(4) 0.0040(5) 0.0006(5) C14 0.0242(6) 0.0305(6) 0.0267(6) 0.0001(5) 0.0052(5) -0.0019(5) C21 0.0272(6) 0.0241(6) 0.0292(6) 0.0002(5) 0.0034(5) 0.0024(5) C6 0.0194(5) 0.0236(6) 0.0301(6) 0.0001(5) 0.0067(5) 0.0017(5) C22 0.0268(6) 0.0263(6) 0.0238(6) -0.0012(4) 0.0018(5) 0.0000(5) C28 0.0229(5) 0.0221(6) 0.0235(6) 0.0026(4) 0.0047(4) -0.0023(5) C45 0.0216(5) 0.0271(6) 0.0241(6) -0.0015(4) 0.0007(4) -0.0031(5) C37 0.0267(6) 0.0295(6) 0.0274(6) -0.0001(5) 0.0034(5) -0.0003(5) C10 0.0282(6) 0.0270(6) 0.0315(7) 0.0018(5) 0.0031(5) 0.0025(5) C1 0.0247(6) 0.0268(6) 0.0315(6) -0.0007(5) 0.0058(5) -0.0008(5) C46 0.0295(6) 0.0214(6) 0.0290(6) -0.0001(5) 0.0032(5) -0.0019(5) C7 0.0219(5) 0.0231(6) 0.0224(6) -0.0004(4) 0.0049(4) 0.0022(4) C13 0.0343(7) 0.0461(8) 0.0231(6) 0.0006(5) 0.0036(5) -0.0082(6) C29 0.0263(6) 0.0230(6) 0.0205(6) 0.0020(4) 0.0016(4) 0.0012(5) C2 0.0277(6) 0.0272(6) 0.0441(8) -0.0058(5) 0.0079(5) -0.0047(5) C34 0.0266(6) 0.0277(6) 0.0282(6) -0.0006(5) 0.0045(5) -0.0015(5) C5 0.0246(6) 0.0286(6) 0.0305(6) 0.0020(5) 0.0065(5) 0.0010(5) C38 0.0320(6) 0.0348(7) 0.0274(6) 0.0008(5) -0.0022(5) -0.0023(5) C41 0.0278(6) 0.0246(6) 0.0279(6) 0.0018(5) 0.0055(5) -0.0017(5) C17 0.0328(6) 0.0264(6) 0.0277(6) -0.0030(5) 0.0010(5) 0.0042(5) C16 0.0197(5) 0.0255(6) 0.0240(6) 0.0011(4) 0.0025(4) -0.0001(4) C40 0.0245(6) 0.0294(6) 0.0377(7) 0.0066(5) 0.0077(5) 0.0012(5) C43 0.0255(6) 0.0219(6) 0.0275(6) -0.0011(4) 0.0019(5) 0.0002(5) C48 0.0320(6) 0.0298(6) 0.0236(6) -0.0013(5) 0.0038(5) -0.0049(5) C30 0.0250(6) 0.0288(6) 0.0259(6) 0.0003(5) 0.0020(5) -0.0003(5) C19 0.0359(7) 0.0342(7) 0.0223(6) -0.0032(5) -0.0019(5) 0.0063(5) C20 0.0234(5) 0.0303(6) 0.0257(6) 0.0026(5) 0.0046(5) 0.0040(5) C31 0.0302(6) 0.0361(7) 0.0272(6) -0.0015(5) 0.0056(5) 0.0066(5) C49 0.0358(7) 0.0355(7) 0.0253(6) -0.0010(5) 0.0017(5) -0.0035(6) C47 0.0276(6) 0.0234(6) 0.0252(6) -0.0038(4) 0.0041(5) -0.0007(5) C50 0.0523(8) 0.0321(7) 0.0273(6) 0.0032(5) 0.0072(6) -0.0064(6) C26 0.0408(7) 0.0331(7) 0.0377(7) 0.0084(6) 0.0029(6) 0.0099(6) C39 0.0233(6) 0.0309(7) 0.0385(7) 0.0071(5) -0.0015(5) -0.0026(5) C51 0.0343(7) 0.0457(8) 0.0292(7) -0.0063(5) 0.0091(5) -0.0091(6) C3 0.0287(6) 0.0245(6) 0.0537(8) 0.0036(6) 0.0147(6) -0.0027(5) C33 0.0337(6) 0.0293(6) 0.0315(7) -0.0041(5) -0.0005(5) -0.0048(5) C11 0.0307(6) 0.0381(7) 0.0414(8) 0.0094(6) -0.0007(6) 0.0072(6) C4 0.0281(6) 0.0315(7) 0.0390(7) 0.0094(5) 0.0114(5) 0.0018(5) C32 0.0408(7) 0.0298(6) 0.0260(6) -0.0057(5) 0.0013(5) 0.0049(6) C12 0.0320(7) 0.0523(8) 0.0315(7) 0.0131(6) -0.0050(5) -0.0015(6) C23 0.0403(7) 0.0356(7) 0.0265(6) 0.0036(5) 0.0025(5) 0.0138(6) C24 0.0517(9) 0.0453(9) 0.0660(11) -0.0063(8) -0.0274(8) 0.0155(8) C25 0.1193(17) 0.0621(11) 0.0406(9) 0.0255(8) 0.0355(10) 0.0489(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 N3 C27 1.4682(14) . ? N3 C28 1.2857(15) . ? N4 C35 1.2861(14) . ? N4 C27 1.4712(14) . ? N1 C15 1.3147(15) . ? N1 C7 1.3819(14) . ? N2 C15 1.3846(14) . ? N2 C27 1.4808(14) . ? N2 C8 1.3981(14) . ? C42 C27 1.5309(15) . ? C42 C43 1.3928(16) . ? C42 C47 1.3852(16) . ? C15 C16 1.4720(15) . ? C35 C36 1.4756(15) . ? C35 C28 1.5127(16) . ? C9 C8 1.4788(16) . ? C9 C14 1.3949(16) . ? C9 C10 1.3917(17) . ? C8 C7 1.3731(16) . ? C36 C37 1.3910(16) . ? C36 C41 1.3959(16) . ? C44 H44 0.9500 . ? C44 C45 1.4006(17) . ? C44 C43 1.3832(16) . ? C14 H14 0.9500 . ? C14 C13 1.3887(17) . ? C21 H21 0.9500 . ? C21 C22 1.3867(16) . ? C21 C20 1.3888(17) . ? C6 C1 1.3949(17) . ? C6 C7 1.4745(16) . ? C6 C5 1.3974(17) . ? C22 H22 0.9500 . ? C22 C16 1.3865(16) . ? C28 C29 1.4822(15) . ? C45 C46 1.3911(16) . ? C45 C48 1.5335(16) . ? C37 H37 0.9500 . ? C37 C38 1.3875(17) . ? C10 H10 0.9500 . ? C10 C11 1.3834(18) . ? C1 H1 0.9500 . ? C1 C2 1.3863(17) . ? C46 H46 0.9500 . ? C46 C47 1.3894(16) . ? C13 H13 0.9500 . ? C13 C12 1.383(2) . ? C29 C34 1.3936(17) . ? C29 C30 1.3966(16) . ? C2 H2 0.9500 . ? C2 C3 1.3884(19) . ? C34 H34 0.9500 . ? C34 C33 1.3878(17) . ? C5 H5 0.9500 . ? C5 C4 1.3888(17) . ? C38 H38 0.9500 . ? C38 C39 1.3827(18) . ? C41 H41 0.9500 . ? C41 C40 1.3821(17) . ? C17 H17 0.9500 . ? C17 C16 1.3911(16) . ? C17 C19 1.3828(17) . ? C40 H40 0.9500 . ? C40 C39 1.3837(18) . ? C43 H43 0.9500 . ? C48 C49 1.5373(17) . ? C48 C50 1.5329(18) . ? C48 C51 1.5377(17) . ? C30 H30 0.9500 . ? C30 C31 1.3871(17) . ? C19 H19 0.9500 . ? C19 C20 1.3967(17) . ? C20 C23 1.5295(16) . ? C31 H31 0.9500 . ? C31 C32 1.3846(18) . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C47 H47 0.9500 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C26 C23 1.5310(18) . ? C39 H39 0.9500 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C3 H3 0.9500 . ? C3 C4 1.3825(19) . ? C33 H33 0.9500 . ? C33 C32 1.3883(18) . ? C11 H11 0.9500 . ? C11 C12 1.380(2) . ? C4 H4 0.9500 . ? C32 H32 0.9500 . ? C12 H12 0.9500 . ? C23 C24 1.534(2) . ? C23 C25 1.529(2) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 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 C28 N3 C27 105.96(9) . . ? C35 N4 C27 106.02(9) . . ? C15 N1 C7 106.46(9) . . ? C15 N2 C27 126.37(9) . . ? C15 N2 C8 106.41(9) . . ? C8 N2 C27 125.74(9) . . ? C43 C42 C27 118.53(10) . . ? C47 C42 C27 122.42(10) . . ? C47 C42 C43 118.86(10) . . ? N1 C15 N2 111.24(10) . . ? N1 C15 C16 121.51(10) . . ? N2 C15 C16 127.07(10) . . ? N4 C35 C36 120.73(10) . . ? N4 C35 C28 109.60(10) . . ? C36 C35 C28 129.62(10) . . ? N3 C27 N4 108.28(9) . . ? N3 C27 N2 110.71(9) . . ? N3 C27 C42 112.10(9) . . ? N4 C27 N2 109.60(9) . . ? N4 C27 C42 104.37(9) . . ? N2 C27 C42 111.53(9) . . ? C14 C9 C8 120.54(10) . . ? C10 C9 C8 120.25(10) . . ? C10 C9 C14 119.14(11) . . ? N2 C8 C9 124.77(10) . . ? C7 C8 N2 105.67(9) . . ? C7 C8 C9 129.41(10) . . ? C37 C36 C35 122.40(10) . . ? C37 C36 C41 119.11(11) . . ? C41 C36 C35 118.41(10) . . ? C45 C44 H44 119.2 . . ? C43 C44 H44 119.2 . . ? C43 C44 C45 121.64(11) . . ? C9 C14 H14 120.0 . . ? C13 C14 C9 119.96(11) . . ? C13 C14 H14 120.0 . . ? C22 C21 H21 119.0 . . ? C22 C21 C20 122.03(11) . . ? C20 C21 H21 119.0 . . ? C1 C6 C7 118.50(10) . . ? C1 C6 C5 118.31(11) . . ? C5 C6 C7 123.18(11) . . ? C21 C22 H22 119.8 . . ? C16 C22 C21 120.32(11) . . ? C16 C22 H22 119.8 . . ? N3 C28 C35 109.91(10) . . ? N3 C28 C29 121.26(10) . . ? C29 C28 C35 128.83(10) . . ? C44 C45 C48 120.02(10) . . ? C46 C45 C44 116.91(11) . . ? C46 C45 C48 123.07(11) . . ? C36 C37 H37 120.0 . . ? C38 C37 C36 120.04(11) . . ? C38 C37 H37 120.0 . . ? C9 C10 H10 119.7 . . ? C11 C10 C9 120.51(12) . . ? C11 C10 H10 119.7 . . ? C6 C1 H1 119.6 . . ? C2 C1 C6 120.81(12) . . ? C2 C1 H1 119.6 . . ? C45 C46 H46 119.0 . . ? C47 C46 C45 121.97(11) . . ? C47 C46 H46 119.0 . . ? N1 C7 C6 119.34(10) . . ? C8 C7 N1 110.18(10) . . ? C8 C7 C6 130.46(10) . . ? C14 C13 H13 119.9 . . ? C12 C13 C14 120.23(12) . . ? C12 C13 H13 119.9 . . ? C34 C29 C28 121.84(10) . . ? C34 C29 C30 119.31(11) . . ? C30 C29 C28 118.79(10) . . ? C1 C2 H2 119.8 . . ? C1 C2 C3 120.41(12) . . ? C3 C2 H2 119.8 . . ? C29 C34 H34 119.9 . . ? C33 C34 C29 120.11(11) . . ? C33 C34 H34 119.9 . . ? C6 C5 H5 119.7 . . ? C4 C5 C6 120.59(12) . . ? C4 C5 H5 119.7 . . ? C37 C38 H38 119.8 . . ? C39 C38 C37 120.30(12) . . ? C39 C38 H38 119.8 . . ? C36 C41 H41 119.7 . . ? C40 C41 C36 120.61(11) . . ? C40 C41 H41 119.7 . . ? C16 C17 H17 119.6 . . ? C19 C17 H17 119.6 . . ? C19 C17 C16 120.82(11) . . ? C22 C16 C15 123.19(10) . . ? C22 C16 C17 118.40(11) . . ? C17 C16 C15 118.19(10) . . ? C41 C40 H40 120.1 . . ? C41 C40 C39 119.84(11) . . ? C39 C40 H40 120.1 . . ? C42 C43 H43 119.8 . . ? C44 C43 C42 120.40(11) . . ? C44 C43 H43 119.8 . . ? C45 C48 C49 109.56(10) . . ? C45 C48 C51 109.04(10) . . ? C49 C48 C51 109.47(10) . . ? C50 C48 C45 112.12(10) . . ? C50 C48 C49 108.40(10) . . ? C50 C48 C51 108.20(11) . . ? C29 C30 H30 119.8 . . ? C31 C30 C29 120.37(11) . . ? C31 C30 H30 119.8 . . ? C17 C19 H19 119.3 . . ? C17 C19 C20 121.40(11) . . ? C20 C19 H19 119.3 . . ? C21 C20 C19 117.00(11) . . ? C21 C20 C23 123.16(11) . . ? C19 C20 C23 119.83(11) . . ? C30 C31 H31 120.0 . . ? C32 C31 C30 119.93(11) . . ? C32 C31 H31 120.0 . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49B 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C42 C47 C46 120.21(11) . . ? C42 C47 H47 119.9 . . ? C46 C47 H47 119.9 . . ? C48 C50 H50A 109.5 . . ? C48 C50 H50B 109.5 . . ? C48 C50 H50C 109.5 . . ? H50A C50 H50B 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? C38 C39 C40 120.09(11) . . ? C38 C39 H39 120.0 . . ? C40 C39 H39 120.0 . . ? C48 C51 H51A 109.5 . . ? C48 C51 H51B 109.5 . . ? C48 C51 H51C 109.5 . . ? H51A C51 H51B 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C2 C3 H3 120.4 . . ? C4 C3 C2 119.26(12) . . ? C4 C3 H3 120.4 . . ? C34 C33 H33 119.9 . . ? C34 C33 C32 120.14(11) . . ? C32 C33 H33 119.9 . . ? C10 C11 H11 120.0 . . ? C12 C11 C10 120.08(12) . . ? C12 C11 H11 120.0 . . ? C5 C4 H4 119.7 . . ? C3 C4 C5 120.60(12) . . ? C3 C4 H4 119.7 . . ? C31 C32 C33 120.13(11) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? C13 C12 H12 120.0 . . ? C11 C12 C13 120.06(12) . . ? C11 C12 H12 120.0 . . ? C20 C23 C26 112.31(10) . . ? C20 C23 C24 108.95(11) . . ? C26 C23 C24 108.46(11) . . ? C25 C23 C20 109.21(11) . . ? C25 C23 C26 107.92(12) . . ? C25 C23 C24 109.97(14) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? data_oo_2tbu _database_code_depnum_ccdc_archive 'CCDC 882414' #TrackingRef '- Compound 5 Form I.cif' _audit_creation_date 2011-11-09 _audit_creation_method ; Olex2 1.1-alpha (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C50 H46 N4 O2' _chemical_formula_sum 'C50 H46 N4 O2' _chemical_formula_weight 734.91 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.88770(10) _cell_length_b 23.4338(4) _cell_length_c 10.4997(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.4170(3) _cell_angle_gamma 90.00 _cell_volume 1991.21(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9990 _cell_measurement_temperature 100.01 _cell_measurement_theta_max 68.407 _cell_measurement_theta_min 3.772 _exptl_absorpt_coefficient_mu 0.585 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.6792 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0550 before and 0.0354 after correction. The Ratio of minimum to maximum transmission is 0.9019. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 780 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of \w scans, each set at different \f and/or 2\q angles, with additional \f scans, each set at different \w and/or 2\q angles, to aid absorption correction parameters. Each image (1.0 s exposure) covering -0.50\ degrees in \w or \f. The crystal to detector distance was 5.00 cm ; _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_unetI/netI 0.0185 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 15174 _diffrn_reflns_theta_full 68.94 _diffrn_reflns_theta_max 68.94 _diffrn_reflns_theta_min 3.77 _diffrn_ambient_temperature 100.01 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'Bruker Pt 135 CCD area detector' _diffrn_measured_fraction_theta_full 0.953 _diffrn_measured_fraction_theta_max 0.953 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Pt 135 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_collimation 'focused optics' _diffrn_radiation_monochromator 'Bruker Helios multilayer optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54188 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'Microstar rotating anode' _diffrn_source_target Cu _diffrn_source_type 'rotating anode' _diffrn_special_details ? _reflns_number_gt 3365 _reflns_number_total 3528 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_collection 'Proteum2 (Bruker, 2010)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.245 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.035 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 256 _refine_ls_number_reflns 3528 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0350 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.7102P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0897 _refine_ls_wR_factor_ref 0.0907 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.90968(8) 0.00424(3) 0.47313(8) 0.01975(18) Uani 1 1 d . . . N2 N 0.97014(11) -0.13941(4) 0.48008(10) 0.0208(2) Uani 1 1 d . . . N1 N 0.88845(11) -0.07564(4) 0.60956(9) 0.0197(2) Uani 1 1 d . . . C7 C 0.91295(12) -0.09585(4) 0.39921(11) 0.0189(2) Uani 1 1 d . . . C6 C 0.90568(13) -0.09134(5) 0.25832(12) 0.0207(2) Uani 1 1 d . . . C5 C 0.83635(14) -0.04337(5) 0.17570(12) 0.0250(3) Uani 1 1 d . . . H5 H 0.7907 -0.0137 0.2105 0.030 Uiso 1 1 calc R . . C8 C 0.84531(13) -0.05115(4) 0.46933(11) 0.0187(2) Uani 1 1 d . . . C9 C 0.65803(13) -0.04475(5) 0.39516(11) 0.0201(2) Uani 1 1 d . . . C20 C 1.11706(15) -0.24140(5) 0.88290(12) 0.0263(3) Uani 1 1 d . . . H20 H 1.2161 -0.2602 0.9420 0.032 Uiso 1 1 calc R . . C15 C 0.95008(13) -0.12469(5) 0.60615(11) 0.0194(2) Uani 1 1 d . . . C16 C 0.97618(14) -0.17006(5) 0.71317(12) 0.0207(2) Uani 1 1 d . . . C1 C 0.97069(14) -0.13476(5) 0.20466(12) 0.0243(3) Uani 1 1 d . . . H1 H 1.0168 -0.1678 0.2592 0.029 Uiso 1 1 calc R . . C10 C 0.58345(14) 0.00854(5) 0.37827(11) 0.0220(2) Uani 1 1 d . . . H10 H 0.6493 0.0420 0.4083 0.026 Uiso 1 1 calc R . . C2 C 0.96816(15) -0.12975(5) 0.07258(13) 0.0282(3) Uani 1 1 d . . . H2 H 1.0131 -0.1593 0.0369 0.034 Uiso 1 1 calc R . . C18 C 0.82256(15) -0.23386(5) 0.79833(13) 0.0271(3) Uani 1 1 d . . . H18 H 0.7206 -0.2461 0.7982 0.033 Uiso 1 1 calc R . . C19 C 0.96851(16) -0.26066(5) 0.88124(13) 0.0277(3) Uani 1 1 d . . . H19 H 0.9674 -0.2923 0.9373 0.033 Uiso 1 1 calc R . . C11 C 0.41247(14) 0.01269(5) 0.31739(12) 0.0251(3) Uani 1 1 d . . . H11 H 0.3614 0.0491 0.3050 0.030 Uiso 1 1 calc R . . C12 C 0.31593(14) -0.03582(5) 0.27458(12) 0.0274(3) Uani 1 1 d . . . H12 H 0.1989 -0.0328 0.2353 0.033 Uiso 1 1 calc R . . C3 C 0.90021(15) -0.08164(6) -0.00830(13) 0.0296(3) Uani 1 1 d . . . H3 H 0.8993 -0.0782 -0.0988 0.036 Uiso 1 1 calc R . . C21 C 1.12771(14) -0.19564(5) 0.80167(12) 0.0224(2) Uani 1 1 d . . . C22 C 1.29810(14) -0.17417(5) 0.81645(13) 0.0273(3) Uani 1 1 d . . . C17 C 0.82800(14) -0.18877(5) 0.71536(12) 0.0237(2) Uani 1 1 d . . . H17 H 0.7281 -0.1700 0.6582 0.028 Uiso 1 1 calc R . . C14 C 0.56121(15) -0.09327(5) 0.34897(13) 0.0278(3) Uani 1 1 d . . . H14 H 0.6119 -0.1296 0.3583 0.033 Uiso 1 1 calc R . . C4 C 0.83385(15) -0.03884(5) 0.04360(13) 0.0296(3) Uani 1 1 d . . . H4 H 0.7863 -0.0061 -0.0120 0.036 Uiso 1 1 calc R . . C13 C 0.39024(15) -0.08869(6) 0.28917(14) 0.0313(3) Uani 1 1 d . . . H13 H 0.3241 -0.1220 0.2582 0.038 Uiso 1 1 calc R . . C25 C 1.30770(16) -0.10909(6) 0.83575(17) 0.0401(3) Uani 1 1 d . . . H25A H 1.2264 -0.0909 0.7513 0.060 Uiso 1 1 calc R . . H25B H 1.4188 -0.0959 0.8520 0.060 Uiso 1 1 calc R . . H25C H 1.2840 -0.0990 0.9162 0.060 Uiso 1 1 calc R . . C23 C 1.43978(15) -0.19955(6) 0.94623(14) 0.0339(3) Uani 1 1 d . . . H23A H 1.4200 -0.1916 1.0296 0.051 Uiso 1 1 calc R . . H23B H 1.5448 -0.1823 0.9569 0.051 Uiso 1 1 calc R . . H23C H 1.4446 -0.2409 0.9346 0.051 Uiso 1 1 calc R . . C24 C 1.32876(17) -0.19112(8) 0.68815(15) 0.0457(4) Uani 1 1 d . . . H24A H 1.3238 -0.2328 0.6784 0.069 Uiso 1 1 calc R . . H24B H 1.4381 -0.1776 0.6999 0.069 Uiso 1 1 calc R . . H24C H 1.2440 -0.1738 0.6042 0.069 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 0.0146(4) 0.0164(4) 0.0251(4) 0.0008(3) 0.0051(3) 0.0014(3) N2 0.0211(5) 0.0187(5) 0.0213(5) 0.0005(4) 0.0075(4) 0.0004(4) N1 0.0188(4) 0.0186(5) 0.0197(5) 0.0012(4) 0.0062(4) 0.0003(4) C7 0.0149(5) 0.0170(5) 0.0222(6) -0.0011(4) 0.0053(4) -0.0016(4) C6 0.0183(5) 0.0207(5) 0.0215(6) -0.0017(4) 0.0066(4) -0.0022(4) C5 0.0269(6) 0.0239(6) 0.0240(6) 0.0011(5) 0.0103(5) 0.0039(5) C8 0.0200(5) 0.0160(5) 0.0191(5) 0.0006(4) 0.0071(4) -0.0002(4) C9 0.0200(5) 0.0222(5) 0.0177(5) 0.0017(4) 0.0075(4) 0.0008(4) C20 0.0322(6) 0.0203(6) 0.0254(6) 0.0035(5) 0.0109(5) 0.0058(5) C15 0.0168(5) 0.0191(5) 0.0199(5) -0.0005(4) 0.0052(4) -0.0011(4) C16 0.0264(6) 0.0157(5) 0.0198(5) -0.0016(4) 0.0092(4) 0.0004(4) C1 0.0233(6) 0.0216(6) 0.0260(6) -0.0011(5) 0.0082(5) 0.0001(4) C10 0.0241(6) 0.0227(6) 0.0194(6) 0.0021(4) 0.0092(4) 0.0015(4) C2 0.0280(6) 0.0301(6) 0.0263(6) -0.0076(5) 0.0110(5) -0.0006(5) C18 0.0304(6) 0.0235(6) 0.0284(6) -0.0011(5) 0.0130(5) -0.0051(5) C19 0.0387(7) 0.0184(5) 0.0274(6) 0.0027(5) 0.0151(5) -0.0011(5) C11 0.0248(6) 0.0288(6) 0.0218(6) 0.0058(5) 0.0097(5) 0.0067(5) C12 0.0187(5) 0.0379(7) 0.0234(6) 0.0065(5) 0.0065(4) 0.0021(5) C3 0.0298(6) 0.0373(7) 0.0207(6) -0.0016(5) 0.0093(5) -0.0006(5) C21 0.0273(6) 0.0186(5) 0.0213(6) -0.0004(4) 0.0100(5) 0.0027(4) C22 0.0238(6) 0.0273(6) 0.0289(6) 0.0082(5) 0.0090(5) 0.0053(5) C17 0.0248(6) 0.0209(5) 0.0228(6) -0.0010(5) 0.0073(5) -0.0005(5) C14 0.0242(6) 0.0221(6) 0.0340(7) 0.0011(5) 0.0091(5) -0.0005(5) C4 0.0334(7) 0.0306(6) 0.0233(6) 0.0047(5) 0.0102(5) 0.0048(5) C13 0.0236(6) 0.0300(6) 0.0360(7) 0.0011(5) 0.0080(5) -0.0051(5) C25 0.0243(6) 0.0289(7) 0.0574(9) 0.0136(6) 0.0072(6) -0.0009(5) C23 0.0272(6) 0.0330(7) 0.0353(7) 0.0103(6) 0.0067(5) 0.0048(5) C24 0.0282(7) 0.0746(11) 0.0359(8) 0.0101(7) 0.0150(6) 0.0126(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 O1 1.4787(14) 3_756 ? O1 C8 1.4124(12) . ? N2 C7 1.2901(14) . ? N2 C15 1.4485(14) . ? N1 C8 1.4756(14) . ? N1 C15 1.2802(14) . ? C7 C6 1.4577(16) . ? C7 C8 1.5384(15) . ? C6 C5 1.3977(16) . ? C6 C1 1.3985(16) . ? C5 H5 0.9500 . ? C5 C4 1.3820(17) . ? C8 C9 1.5258(15) . ? C9 C10 1.3904(16) . ? C9 C14 1.3868(16) . ? C20 H20 0.9500 . ? C20 C19 1.3885(18) . ? C20 C21 1.3974(16) . ? C15 C16 1.4937(15) . ? C16 C21 1.4149(16) . ? C16 C17 1.3972(16) . ? C1 H1 0.9500 . ? C1 C2 1.3826(17) . ? C10 H10 0.9500 . ? C10 C11 1.3872(16) . ? C2 H2 0.9500 . ? C2 C3 1.3902(18) . ? C18 H18 0.9500 . ? C18 C19 1.3789(18) . ? C18 C17 1.3830(17) . ? C19 H19 0.9500 . ? C11 H11 0.9500 . ? C11 C12 1.3827(18) . ? C12 H12 0.9500 . ? C12 C13 1.3823(18) . ? C3 H3 0.9500 . ? C3 C4 1.3844(18) . ? C21 C22 1.5415(16) . ? C22 C25 1.5363(18) . ? C22 C23 1.5419(16) . ? C22 C24 1.5330(19) . ? C17 H17 0.9500 . ? C14 H14 0.9500 . ? C14 C13 1.3877(17) . ? C4 H4 0.9500 . ? C13 H13 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 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 C8 O1 O1 104.51(8) . 3_756 ? C7 N2 C15 104.43(9) . . ? C15 N1 C8 105.01(9) . . ? N2 C7 C6 124.44(10) . . ? N2 C7 C8 110.45(9) . . ? C6 C7 C8 125.04(9) . . ? C5 C6 C7 120.76(10) . . ? C5 C6 C1 118.99(11) . . ? C1 C6 C7 120.24(10) . . ? C6 C5 H5 119.8 . . ? C4 C5 C6 120.31(11) . . ? C4 C5 H5 119.8 . . ? O1 C8 N1 113.21(8) . . ? O1 C8 C7 113.92(9) . . ? O1 C8 C9 105.53(8) . . ? N1 C8 C7 102.77(8) . . ? N1 C8 C9 109.04(8) . . ? C9 C8 C7 112.48(9) . . ? C10 C9 C8 121.02(10) . . ? C14 C9 C8 119.09(10) . . ? C14 C9 C10 119.84(10) . . ? C19 C20 H20 118.5 . . ? C19 C20 C21 123.07(11) . . ? C21 C20 H20 118.5 . . ? N2 C15 C16 118.58(9) . . ? N1 C15 N2 117.07(10) . . ? N1 C15 C16 123.59(10) . . ? C21 C16 C15 127.25(10) . . ? C17 C16 C15 112.42(10) . . ? C17 C16 C21 120.27(10) . . ? C6 C1 H1 119.9 . . ? C2 C1 C6 120.27(11) . . ? C2 C1 H1 119.9 . . ? C9 C10 H10 120.1 . . ? C11 C10 C9 119.70(11) . . ? C11 C10 H10 120.2 . . ? C1 C2 H2 119.9 . . ? C1 C2 C3 120.29(11) . . ? C3 C2 H2 119.9 . . ? C19 C18 H18 120.8 . . ? C19 C18 C17 118.49(11) . . ? C17 C18 H18 120.8 . . ? C20 C19 H19 120.0 . . ? C18 C19 C20 120.09(11) . . ? C18 C19 H19 120.0 . . ? C10 C11 H11 119.8 . . ? C12 C11 C10 120.43(11) . . ? C12 C11 H11 119.8 . . ? C11 C12 H12 120.1 . . ? C13 C12 C11 119.80(11) . . ? C13 C12 H12 120.1 . . ? C2 C3 H3 120.2 . . ? C4 C3 C2 119.69(11) . . ? C4 C3 H3 120.2 . . ? C20 C21 C16 116.08(11) . . ? C20 C21 C22 120.04(10) . . ? C16 C21 C22 123.82(10) . . ? C21 C22 C23 111.87(10) . . ? C25 C22 C21 109.63(10) . . ? C25 C22 C23 106.61(11) . . ? C24 C22 C21 110.55(11) . . ? C24 C22 C25 110.66(12) . . ? C24 C22 C23 107.44(10) . . ? C16 C17 H17 119.0 . . ? C18 C17 C16 121.92(11) . . ? C18 C17 H17 119.0 . . ? C9 C14 H14 120.0 . . ? C9 C14 C13 120.00(11) . . ? C13 C14 H14 120.0 . . ? C5 C4 C3 120.44(11) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C12 C13 C14 120.20(11) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? data_frm_0m_sad _database_code_depnum_ccdc_archive 'CCDC 882415' #TrackingRef '- Compound 5 Form II.cif' _audit_creation_date 2012-05-11 _audit_creation_method ; Olex2 1.1 (compiled Nov 1 2011 20:42:30, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C50 H46 N4 O2' _chemical_formula_sum 'C50 H46 N4 O2' _chemical_formula_weight 734.91 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.7885(5) _cell_length_b 10.0808(3) _cell_length_c 21.5264(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.4180(10) _cell_angle_gamma 90.00 _cell_volume 3981.78(18) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9922 _cell_measurement_temperature 100.00 _cell_measurement_theta_max 67.757 _cell_measurement_theta_min 4.206 _exptl_absorpt_coefficient_mu 0.585 _exptl_absorpt_correction_T_max 0.7530 _exptl_absorpt_correction_T_min 0.6191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0910 before and 0.0638 after correction. The Ratio of minimum to maximum transmission is 0.8222. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1560 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.09 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of \w scans, each set at different \f and/or 2\q angles, with additional \f scans, each set at different \w and/or 2\q angles, to aid absorption correction parameters. Each image (15.0 s exposure) covering -0.50\ degrees in \w or \f. The crystal to detector distance was 5.00 cm ; _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_unetI/netI 0.0298 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 16975 _diffrn_reflns_theta_full 67.80 _diffrn_reflns_theta_max 67.80 _diffrn_reflns_theta_min 4.21 _diffrn_ambient_temperature 100 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'Bruker Pt 135 CCD area detector' _diffrn_measured_fraction_theta_full 0.906 _diffrn_measured_fraction_theta_max 0.906 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Pt 135 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_collimation 'focused optics' _diffrn_radiation_monochromator 'Bruker Helios multilayer optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54188 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'Microstar rotating anode' _diffrn_source_target Cu _diffrn_source_type 'rotating anode' _reflns_number_gt 3105 _reflns_number_total 3282 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)' _computing_data_collection 'PROTEUM2 (Bruker, 2010)' _computing_data_reduction 'SAINT v7.60A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.236 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.039 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 256 _refine_ls_number_reflns 3282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0367 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+3.1160P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0963 _refine_ls_wR_factor_ref 0.0976 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.01933(4) 0.66420(9) 0.22304(4) 0.0206(2) Uani 1 1 d . . . N3 N -0.07936(5) 0.53007(10) 0.16896(5) 0.0204(2) Uani 1 1 d . . . N1 N -0.15877(5) 0.70928(10) 0.15725(5) 0.0206(2) Uani 1 1 d . . . C5 C -0.09508(6) 0.76133(12) 0.16215(5) 0.0195(3) Uani 1 1 d . . . C6 C -0.20541(7) 0.47614(12) 0.16911(6) 0.0204(3) Uani 1 1 d . . . C18 C -0.08224(7) 0.90443(12) 0.16216(6) 0.0215(3) Uani 1 1 d . . . C2 C -0.14562(6) 0.56853(12) 0.16246(5) 0.0196(3) Uani 1 1 d . . . C19 C -0.01200(7) 0.95641(13) 0.16923(6) 0.0261(3) Uani 1 1 d . . . H1 H 0.0288 0.8985 0.1751 0.031 Uiso 1 1 calc R . . C12 C 0.00219(6) 0.64477(12) 0.11253(6) 0.0200(3) Uani 1 1 d . . . C13 C 0.05897(7) 0.55407(13) 0.11613(6) 0.0245(3) Uani 1 1 d . . . H14 H 0.0736 0.5005 0.1530 0.029 Uiso 1 1 calc R . . C16 C 0.01488(7) 0.70600(13) 0.00744(6) 0.0254(3) Uani 1 1 d . . . H11 H -0.0008 0.7571 -0.0301 0.030 Uiso 1 1 calc R . . C4 C -0.03712(6) 0.65221(12) 0.16743(6) 0.0195(3) Uani 1 1 d . . . C17 C -0.01937(7) 0.72056(12) 0.05800(6) 0.0226(3) Uani 1 1 d . . . H10 H -0.0579 0.7829 0.0553 0.027 Uiso 1 1 calc R . . C23 C -0.14177(8) 0.99153(13) 0.15410(6) 0.0284(3) Uani 1 1 d . . . H5 H -0.1897 0.9574 0.1502 0.034 Uiso 1 1 calc R . . C15 C 0.07181(7) 0.61745(13) 0.01149(6) 0.0266(3) Uani 1 1 d . . . H12 H 0.0956 0.6083 -0.0230 0.032 Uiso 1 1 calc R . . C14 C 0.09405(7) 0.54207(13) 0.06594(7) 0.0281(3) Uani 1 1 d . . . H13 H 0.1335 0.4818 0.0689 0.034 Uiso 1 1 calc R . . C26 C -0.32265(7) 0.67862(14) 0.07777(6) 0.0284(3) Uani 1 1 d . . . H23A H -0.3396 0.7261 0.0376 0.043 Uiso 1 1 calc R . . H23B H -0.2815 0.7265 0.1040 0.043 Uiso 1 1 calc R . . H23C H -0.3625 0.6729 0.1005 0.043 Uiso 1 1 calc R . . C20 C -0.00184(8) 1.09269(14) 0.16762(7) 0.0325(3) Uani 1 1 d . . . H2 H 0.0460 1.1278 0.1725 0.039 Uiso 1 1 calc R . . C25 C -0.36365(7) 0.47099(14) 0.02011(6) 0.0294(3) Uani 1 1 d . . . H25A H -0.4062 0.4757 0.0396 0.044 Uiso 1 1 calc R . . H25B H -0.3520 0.3779 0.0138 0.044 Uiso 1 1 calc R . . H25C H -0.3745 0.5166 -0.0211 0.044 Uiso 1 1 calc R . . C11 C -0.18855(7) 0.40069(14) 0.22484(6) 0.0262(3) Uani 1 1 d . . . H17 H -0.1418 0.4103 0.2521 0.031 Uiso 1 1 calc R . . C22 C -0.13089(9) 1.12677(14) 0.15189(7) 0.0354(3) Uani 1 1 d . . . H4 H -0.1715 1.1852 0.1455 0.042 Uiso 1 1 calc R . . C27 C -0.23751(7) 0.54482(14) 0.02667(6) 0.0288(3) Uani 1 1 d . . . H24A H -0.2555 0.5909 -0.0137 0.043 Uiso 1 1 calc R . . H24B H -0.2225 0.4547 0.0183 0.043 Uiso 1 1 calc R . . H24C H -0.1957 0.5932 0.0516 0.043 Uiso 1 1 calc R . . C9 C -0.30459(7) 0.29731(14) 0.20071(6) 0.0308(3) Uani 1 1 d . . . H19 H -0.3392 0.2374 0.2112 0.037 Uiso 1 1 calc R . . C8 C -0.32144(7) 0.36884(14) 0.14473(6) 0.0280(3) Uani 1 1 d . . . H20 H -0.3675 0.3546 0.1170 0.034 Uiso 1 1 calc R . . C24 C -0.29822(7) 0.53814(13) 0.06403(6) 0.0246(3) Uani 1 1 d . . . C10 C -0.23756(8) 0.31261(15) 0.24154(6) 0.0306(3) Uani 1 1 d . . . H18 H -0.2255 0.2638 0.2801 0.037 Uiso 1 1 calc R . . C7 C -0.27391(7) 0.46136(13) 0.12682(6) 0.0228(3) Uani 1 1 d . . . C21 C -0.06117(9) 1.17766(14) 0.15890(7) 0.0365(4) Uani 1 1 d . . . H3 H -0.0540 1.2708 0.1577 0.044 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 0.0155(4) 0.0277(5) 0.0191(4) -0.0004(3) 0.0046(3) -0.0009(3) N3 0.0185(5) 0.0209(5) 0.0214(5) -0.0005(4) 0.0031(4) -0.0020(4) N1 0.0193(5) 0.0212(6) 0.0208(5) -0.0012(4) 0.0036(4) -0.0005(4) C5 0.0191(6) 0.0230(6) 0.0161(6) -0.0010(5) 0.0033(5) 0.0003(5) C6 0.0189(6) 0.0208(6) 0.0223(6) -0.0038(5) 0.0061(5) -0.0019(5) C18 0.0259(7) 0.0204(6) 0.0187(6) -0.0005(5) 0.0062(5) 0.0001(5) C2 0.0196(6) 0.0212(6) 0.0178(6) -0.0019(5) 0.0036(5) -0.0016(5) C19 0.0287(7) 0.0245(7) 0.0264(7) -0.0019(5) 0.0085(5) -0.0022(5) C12 0.0154(6) 0.0210(6) 0.0225(6) -0.0039(5) 0.0015(5) -0.0040(5) C13 0.0217(7) 0.0248(7) 0.0257(7) 0.0000(5) 0.0022(5) 0.0013(5) C16 0.0247(7) 0.0280(7) 0.0227(6) -0.0004(5) 0.0035(5) -0.0037(5) C4 0.0159(6) 0.0192(6) 0.0219(6) -0.0005(5) 0.0006(5) -0.0013(5) C17 0.0189(6) 0.0229(7) 0.0250(6) -0.0019(5) 0.0023(5) -0.0005(5) C23 0.0308(7) 0.0254(7) 0.0290(7) -0.0009(6) 0.0066(6) 0.0026(5) C15 0.0230(7) 0.0310(7) 0.0274(7) -0.0058(6) 0.0089(5) -0.0048(5) C14 0.0215(7) 0.0285(7) 0.0347(7) -0.0050(6) 0.0069(6) 0.0030(5) C26 0.0220(7) 0.0305(7) 0.0307(7) 0.0016(6) 0.0012(5) -0.0002(5) C20 0.0400(8) 0.0271(7) 0.0332(7) -0.0030(6) 0.0138(6) -0.0106(6) C25 0.0251(7) 0.0329(8) 0.0276(7) 0.0019(6) -0.0002(6) -0.0044(5) C11 0.0224(7) 0.0312(7) 0.0233(6) -0.0013(6) 0.0012(5) -0.0049(5) C22 0.0460(9) 0.0238(7) 0.0371(8) 0.0004(6) 0.0109(7) 0.0086(6) C27 0.0264(7) 0.0362(8) 0.0236(6) 0.0023(6) 0.0047(5) -0.0024(6) C9 0.0269(7) 0.0370(8) 0.0298(7) 0.0032(6) 0.0091(6) -0.0118(6) C8 0.0195(7) 0.0361(8) 0.0276(7) -0.0006(6) 0.0031(5) -0.0074(5) C24 0.0200(6) 0.0276(7) 0.0252(6) 0.0009(5) 0.0025(5) -0.0033(5) C10 0.0315(8) 0.0369(8) 0.0231(6) 0.0047(6) 0.0049(6) -0.0073(6) C7 0.0195(6) 0.0251(7) 0.0240(6) -0.0019(5) 0.0055(5) -0.0015(5) C21 0.0587(10) 0.0192(7) 0.0342(8) -0.0008(6) 0.0159(7) -0.0033(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 O1 1.4960(16) 2 ? O1 C4 1.4236(14) . ? N3 C2 1.2824(16) . ? N3 C4 1.4691(15) . ? N1 C5 1.2899(15) . ? N1 C2 1.4405(16) . ? C5 C18 1.4626(17) . ? C5 C4 1.5349(16) . ? C6 C2 1.4896(16) . ? C6 C11 1.3980(18) . ? C6 C7 1.4155(17) . ? C18 C19 1.3974(18) . ? C18 C23 1.4030(18) . ? C19 H1 0.9500 . ? C19 C20 1.3885(19) . ? C12 C13 1.3945(17) . ? C12 C4 1.5241(17) . ? C12 C17 1.3861(18) . ? C13 H14 0.9500 . ? C13 C14 1.3865(19) . ? C16 H11 0.9500 . ? C16 C17 1.3862(18) . ? C16 C15 1.3815(19) . ? C17 H10 0.9500 . ? C23 H5 0.9500 . ? C23 C22 1.381(2) . ? C15 H12 0.9500 . ? C15 C14 1.384(2) . ? C14 H13 0.9500 . ? C26 H23A 0.9800 . ? C26 H23B 0.9800 . ? C26 H23C 0.9800 . ? C26 C24 1.5370(19) . ? C20 H2 0.9500 . ? C20 C21 1.386(2) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C25 C24 1.5373(18) . ? C11 H17 0.9500 . ? C11 C10 1.3813(19) . ? C22 H4 0.9500 . ? C22 C21 1.384(2) . ? C27 H24A 0.9800 . ? C27 H24B 0.9800 . ? C27 H24C 0.9800 . ? C27 C24 1.5320(18) . ? C9 H19 0.9500 . ? C9 C8 1.381(2) . ? C9 C10 1.3805(19) . ? C8 H20 0.9500 . ? C8 C7 1.4014(18) . ? C24 C7 1.5392(18) . ? C10 H18 0.9500 . ? C21 H3 0.9500 . ? 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 C4 O1 O1 104.73(9) . 2 ? C2 N3 C4 105.11(10) . . ? C5 N1 C2 104.70(10) . . ? N1 C5 C18 123.46(11) . . ? N1 C5 C4 110.21(10) . . ? C18 C5 C4 126.33(10) . . ? C11 C6 C2 112.72(11) . . ? C11 C6 C7 120.10(11) . . ? C7 C6 C2 127.17(11) . . ? C19 C18 C5 121.45(11) . . ? C19 C18 C23 119.20(12) . . ? C23 C18 C5 119.34(11) . . ? N3 C2 N1 116.90(10) . . ? N3 C2 C6 122.34(11) . . ? N1 C2 C6 120.20(10) . . ? C18 C19 H1 120.0 . . ? C20 C19 C18 120.00(13) . . ? C20 C19 H1 120.0 . . ? C13 C12 C4 118.79(11) . . ? C17 C12 C13 119.29(11) . . ? C17 C12 C4 121.83(11) . . ? C12 C13 H14 120.0 . . ? C14 C13 C12 120.00(12) . . ? C14 C13 H14 120.0 . . ? C17 C16 H11 119.9 . . ? C15 C16 H11 119.9 . . ? C15 C16 C17 120.19(12) . . ? O1 C4 N3 111.15(9) . . ? O1 C4 C5 112.94(9) . . ? O1 C4 C12 104.98(9) . . ? N3 C4 C5 102.96(9) . . ? N3 C4 C12 109.29(9) . . ? C12 C4 C5 115.62(10) . . ? C12 C17 C16 120.40(12) . . ? C12 C17 H10 119.8 . . ? C16 C17 H10 119.8 . . ? C18 C23 H5 119.9 . . ? C22 C23 C18 120.14(13) . . ? C22 C23 H5 119.9 . . ? C16 C15 H12 120.1 . . ? C16 C15 C14 119.79(12) . . ? C14 C15 H12 120.1 . . ? C13 C14 H13 119.8 . . ? C15 C14 C13 120.31(12) . . ? C15 C14 H13 119.8 . . ? H23A C26 H23B 109.5 . . ? H23A C26 H23C 109.5 . . ? H23B C26 H23C 109.5 . . ? C24 C26 H23A 109.5 . . ? C24 C26 H23B 109.5 . . ? C24 C26 H23C 109.5 . . ? C19 C20 H2 119.9 . . ? C21 C20 C19 120.25(13) . . ? C21 C20 H2 119.9 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? C6 C11 H17 118.9 . . ? C10 C11 C6 122.16(12) . . ? C10 C11 H17 118.9 . . ? C23 C22 H4 119.8 . . ? C23 C22 C21 120.38(14) . . ? C21 C22 H4 119.8 . . ? H24A C27 H24B 109.5 . . ? H24A C27 H24C 109.5 . . ? H24B C27 H24C 109.5 . . ? C24 C27 H24A 109.5 . . ? C24 C27 H24B 109.5 . . ? C24 C27 H24C 109.5 . . ? C8 C9 H19 119.9 . . ? C10 C9 H19 119.9 . . ? C10 C9 C8 120.23(12) . . ? C9 C8 H20 118.4 . . ? C9 C8 C7 123.19(12) . . ? C7 C8 H20 118.4 . . ? C26 C24 C25 106.96(11) . . ? C26 C24 C7 109.80(11) . . ? C25 C24 C7 111.45(11) . . ? C27 C24 C26 110.33(11) . . ? C27 C24 C25 106.49(11) . . ? C27 C24 C7 111.66(11) . . ? C11 C10 H18 120.9 . . ? C9 C10 C11 118.30(12) . . ? C9 C10 H18 120.9 . . ? C6 C7 C24 124.68(11) . . ? C8 C7 C6 115.98(11) . . ? C8 C7 C24 119.34(11) . . ? C20 C21 H3 120.0 . . ? C22 C21 C20 120.01(13) . . ? C22 C21 H3 120.0 . . ? data_mono_sad _database_code_depnum_ccdc_archive 'CCDC 882416' #TrackingRef '- Compound 6 Form I.cif' _audit_creation_date 2012-05-11 _audit_creation_method ; Olex2 1.1-alpha (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C50 H46 N4 O2' _chemical_formula_sum 'C50 H46 N4 O2' _chemical_formula_weight 734.91 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'I 1 2/a 1' _space_group_name_Hall '-I 2ya' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y, -z' 3 'x+1/2, y+1/2, z+1/2' 4 '-x+1, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, -y, z' 7 '-x+1/2, -y+1/2, -z+1/2' 8 'x, -y+1/2, z+1/2' _cell_length_a 16.1305(10) _cell_length_b 15.4759(6) _cell_length_c 16.6219(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.2670(10) _cell_angle_gamma 90.00 _cell_volume 4137.9(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9878 _cell_measurement_temperature 160 _cell_measurement_theta_max 62.97 _cell_measurement_theta_min 3.91 _exptl_absorpt_coefficient_mu 0.563 _exptl_absorpt_correction_T_max 0.7523 _exptl_absorpt_correction_T_min 0.6748 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0842 before and 0.0628 after correction. The Ratio of minimum to maximum transmission is 0.8970. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1560 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of \w scans, each set at different \f and/or 2\q angles. Each image(3.0 s exposure) covering -0.50\ degrees in \w. The crystal to detector distance was 5.00 cm ; _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_unetI/netI 0.0265 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 15378 _diffrn_reflns_theta_full 63.42 _diffrn_reflns_theta_max 63.42 _diffrn_reflns_theta_min 3.91 _diffrn_ambient_temperature 160 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'Bruker Pt 135 CCD area detector' _diffrn_measured_fraction_theta_full 0.946 _diffrn_measured_fraction_theta_max 0.946 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_collimation 'focused optics' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54188 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'Microstar rotating anode' _diffrn_source_target Cu _diffrn_source_type 'rotating anode' _diffrn_special_details 'Crystal cooled at 120K/hr from 290K - phase transition occurs between 150K and 145K. Data were collected >10K above the phase transition' _diffrn_standards_number 0 _reflns_number_gt 3005 _reflns_number_total 3209 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)' _computing_data_collection 'Proteum2 (Bruker, 2010)' _computing_data_reduction 'SAINT v7.60A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.235 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.042 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 3209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0498 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0716P)^2^+2.9964P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1357 _refine_ls_wR_factor_ref 0.1379 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 0.46204(6) 0.52282(7) 0.51168(6) 0.0426(3) Uani 1 1 d . . . N3 N 0.53797(8) 0.55915(8) 0.63477(7) 0.0413(3) Uani 1 1 d . A . N1 N 0.62705(9) 0.64603(9) 0.56646(8) 0.0466(4) Uani 1 1 d . A . C4 C 0.49272(10) 0.59151(10) 0.56124(9) 0.0411(4) Uani 1 1 d . . . C12 C 0.4101(6) 0.6341(7) 0.5809(5) 0.0425(6) Uani 0.267(11) 1 d PG A 1 C13 C 0.3358(7) 0.5891(6) 0.5838(8) 0.0643(12) Uani 0.267(11) 1 d PG A 1 H13 H 0.3338 0.5290 0.5722 0.077 Uiso 0.267(11) 1 calc PR A 1 C14 C 0.2645(6) 0.6321(8) 0.6036(9) 0.0859(16) Uani 0.267(11) 1 d PG A 1 H14 H 0.2137 0.6013 0.6056 0.103 Uiso 0.267(11) 1 calc PR A 1 C15 C 0.2674(7) 0.7200(8) 0.6206(7) 0.0816(11) Uani 0.267(11) 1 d PG A 1 H15 H 0.2186 0.7494 0.6341 0.098 Uiso 0.267(11) 1 calc PR A 1 C16 C 0.3417(9) 0.7650(6) 0.6177(7) 0.0668(10) Uani 0.267(11) 1 d PG A 1 H16 H 0.3437 0.8251 0.6293 0.080 Uiso 0.267(11) 1 calc PR A 1 C17 C 0.4131(7) 0.7221(8) 0.5978(6) 0.0494(8) Uani 0.267(11) 1 d PG A 1 H17 H 0.4639 0.7528 0.5958 0.059 Uiso 0.267(11) 1 calc PR A 1 C8 C 0.61090(10) 0.59122(10) 0.63377(9) 0.0416(4) Uani 1 1 d . . . C9 C 0.67866(10) 0.57474(10) 0.69548(9) 0.0427(4) Uani 1 1 d . A . C18 C 0.54742(11) 0.68851(10) 0.44296(10) 0.0472(4) Uani 1 1 d . . . C11 C 0.73369(11) 0.50015(12) 0.81404(11) 0.0513(4) Uani 1 1 d . A . H11 H 0.7256 0.4595 0.8556 0.062 Uiso 1 1 calc R . . C1 C 0.80972(10) 0.54163(11) 0.81312(10) 0.0457(4) Uani 1 1 d . A . C24 C 0.88095(11) 0.52455(12) 0.87702(11) 0.0520(4) Uani 1 1 d . . . C2 C 0.66931(11) 0.51592(11) 0.75655(11) 0.0494(4) Uani 1 1 d . . . H2 H 0.6181 0.4860 0.7590 0.059 Uiso 1 1 calc R A . C3 C 0.55892(10) 0.64453(10) 0.52118(9) 0.0426(4) Uani 1 1 d . A . C5 C 0.81759(12) 0.60056(15) 0.75167(13) 0.0678(6) Uani 1 1 d . . . H5 H 0.8687 0.6307 0.7492 0.081 Uiso 1 1 calc R B . C6 C 0.75395(12) 0.61707(14) 0.69397(12) 0.0639(5) Uani 1 1 d . A . H6 H 0.7618 0.6580 0.6526 0.077 Uiso 1 1 calc R . . C19 C 0.47679(13) 0.67529(12) 0.39124(11) 0.0562(5) Uani 1 1 d . A . H19 H 0.4350 0.6362 0.4056 0.067 Uiso 1 1 calc R . . C20 C 0.46764(15) 0.71946(14) 0.31859(11) 0.0663(6) Uani 1 1 d . . . H20 H 0.4196 0.7103 0.2830 0.080 Uiso 1 1 calc R A . C23 C 0.60873(13) 0.74483(12) 0.42022(11) 0.0586(5) Uani 1 1 d . A . H23 H 0.6580 0.7530 0.4544 0.070 Uiso 1 1 calc R . . C21 C 0.52772(17) 0.77629(15) 0.29780(13) 0.0749(7) Uani 1 1 d . A . H21 H 0.5206 0.8072 0.2484 0.090 Uiso 1 1 calc R . . C22 C 0.59800(16) 0.78858(14) 0.34822(13) 0.0746(6) Uani 1 1 d . . . H22 H 0.6396 0.8277 0.3333 0.089 Uiso 1 1 calc R A . C26 C 0.96602(17) 0.5291(2) 0.84162(19) 0.0770(8) Uani 0.741(2) 1 d P B 1 H26A H 0.9664 0.4904 0.7950 0.115 Uiso 0.741(2) 1 calc PR B 1 H26B H 1.0094 0.5114 0.8827 0.115 Uiso 0.741(2) 1 calc PR B 1 H26C H 0.9765 0.5885 0.8246 0.115 Uiso 0.741(2) 1 calc PR B 1 C25 C 0.8787(2) 0.5938(2) 0.94218(19) 0.0805(9) Uani 0.741(2) 1 d P B 1 H25A H 0.8828 0.6511 0.9176 0.121 Uiso 0.741(2) 1 calc PR B 1 H25B H 0.9254 0.5853 0.9825 0.121 Uiso 0.741(2) 1 calc PR B 1 H25C H 0.8263 0.5896 0.9683 0.121 Uiso 0.741(2) 1 calc PR B 1 C27 C 0.8751(2) 0.4351(2) 0.9166(2) 0.0866(10) Uani 0.741(2) 1 d P B 1 H27A H 0.8245 0.4320 0.9456 0.130 Uiso 0.741(2) 1 calc PR B 1 H27B H 0.9238 0.4260 0.9545 0.130 Uiso 0.741(2) 1 calc PR B 1 H27C H 0.8734 0.3903 0.8748 0.130 Uiso 0.741(2) 1 calc PR B 1 C23A C 0.9442(5) 0.5978(7) 0.8802(6) 0.0770(8) Uani 0.259(2) 1 d P B 2 H23A H 0.9657 0.6050 0.8270 0.115 Uiso 0.259(2) 1 calc PR B 2 H23B H 0.9902 0.5841 0.9200 0.115 Uiso 0.259(2) 1 calc PR B 2 H23C H 0.9175 0.6515 0.8957 0.115 Uiso 0.259(2) 1 calc PR B 2 C25A C 0.8470(6) 0.5201(7) 0.9584(5) 0.0805(9) Uani 0.259(2) 1 d P B 2 H25D H 0.8129 0.5714 0.9665 0.121 Uiso 0.259(2) 1 calc PR B 2 H25E H 0.8930 0.5180 1.0003 0.121 Uiso 0.259(2) 1 calc PR B 2 H25F H 0.8127 0.4681 0.9617 0.121 Uiso 0.259(2) 1 calc PR B 2 C24A C 0.9203(6) 0.4435(6) 0.8500(7) 0.0866(10) Uani 0.259(2) 1 d P B 2 H24A H 0.8801 0.3961 0.8499 0.130 Uiso 0.259(2) 1 calc PR B 2 H24B H 0.9687 0.4296 0.8868 0.130 Uiso 0.259(2) 1 calc PR B 2 H24C H 0.9381 0.4515 0.7953 0.130 Uiso 0.259(2) 1 calc PR B 2 C12A C 0.4185(2) 0.6438(2) 0.58256(15) 0.0425(6) Uani 0.733(11) 1 d PG A 2 C13A C 0.3539(3) 0.5990(2) 0.6145(3) 0.0643(12) Uani 0.733(11) 1 d PG A 2 H13A H 0.3573 0.5381 0.6210 0.077 Uiso 0.733(11) 1 calc PR A 2 C14A C 0.2843(3) 0.6433(3) 0.6370(4) 0.0859(16) Uani 0.733(11) 1 d PG A 2 H14A H 0.2402 0.6127 0.6588 0.103 Uiso 0.733(11) 1 calc PR A 2 C15A C 0.2794(3) 0.7325(3) 0.6275(2) 0.0816(11) Uani 0.733(11) 1 d PG A 2 H15A H 0.2318 0.7628 0.6428 0.098 Uiso 0.733(11) 1 calc PR A 2 C16A C 0.3440(3) 0.7773(2) 0.5955(3) 0.0668(10) Uani 0.733(11) 1 d PG A 2 H16A H 0.3406 0.8382 0.5890 0.080 Uiso 0.733(11) 1 calc PR A 2 C17A C 0.4136(2) 0.7329(2) 0.5731(3) 0.0494(8) Uani 0.733(11) 1 d PG A 2 H17A H 0.4578 0.7635 0.5512 0.059 Uiso 0.733(11) 1 calc PR A 2 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 0.0394(6) 0.0432(6) 0.0446(6) -0.0051(5) -0.0003(5) 0.0060(5) N3 0.0456(8) 0.0418(7) 0.0360(7) 0.0007(6) -0.0005(6) 0.0016(6) N1 0.0527(8) 0.0458(8) 0.0417(7) 0.0013(6) 0.0054(6) -0.0009(6) C4 0.0478(9) 0.0383(8) 0.0367(8) -0.0015(7) -0.0013(7) 0.0024(7) C12 0.0481(12) 0.0428(13) 0.0366(8) 0.0017(8) 0.0025(8) 0.0030(9) C13 0.067(2) 0.0544(14) 0.075(3) 0.0177(18) 0.028(2) 0.0075(14) C14 0.073(2) 0.080(2) 0.112(4) 0.029(3) 0.049(3) 0.0150(18) C15 0.076(2) 0.083(2) 0.0902(19) 0.0174(15) 0.0376(15) 0.0322(18) C16 0.0834(16) 0.0532(15) 0.067(3) 0.0110(14) 0.0270(19) 0.0232(13) C17 0.0597(11) 0.0456(14) 0.044(2) 0.0034(15) 0.0122(15) 0.0046(10) C8 0.0473(9) 0.0403(8) 0.0375(8) -0.0032(7) 0.0046(7) 0.0029(7) C9 0.0455(9) 0.0431(9) 0.0394(8) -0.0040(7) 0.0026(7) 0.0029(7) C18 0.0626(11) 0.0399(9) 0.0398(9) 0.0010(7) 0.0083(8) 0.0066(8) C11 0.0531(10) 0.0497(9) 0.0497(10) 0.0089(8) -0.0048(8) -0.0041(8) C1 0.0451(9) 0.0454(9) 0.0464(9) -0.0053(7) 0.0007(7) 0.0008(7) C24 0.0472(9) 0.0540(10) 0.0533(10) -0.0004(8) -0.0053(8) -0.0002(8) C2 0.0452(9) 0.0485(10) 0.0537(10) 0.0053(8) -0.0020(8) -0.0056(8) C3 0.0521(9) 0.0383(8) 0.0377(8) -0.0021(7) 0.0059(7) 0.0035(7) C5 0.0475(10) 0.0849(14) 0.0696(13) 0.0212(11) -0.0063(9) -0.0167(10) C6 0.0523(11) 0.0798(13) 0.0587(11) 0.0218(10) -0.0023(9) -0.0125(10) C19 0.0695(12) 0.0538(10) 0.0448(9) 0.0058(8) 0.0012(9) 0.0049(9) C20 0.0891(15) 0.0654(12) 0.0437(10) 0.0061(9) 0.0001(10) 0.0170(11) C23 0.0740(13) 0.0524(10) 0.0509(10) 0.0035(8) 0.0147(9) -0.0028(9) C21 0.1121(19) 0.0657(13) 0.0489(11) 0.0187(10) 0.0192(12) 0.0160(13) C22 0.1037(18) 0.0637(13) 0.0589(12) 0.0153(10) 0.0232(13) -0.0048(12) C26 0.0481(14) 0.111(3) 0.0702(18) 0.0066(16) -0.0041(12) 0.0066(15) C25 0.0744(19) 0.097(2) 0.0662(17) -0.0198(17) -0.0199(15) 0.0105(17) C27 0.0664(18) 0.081(2) 0.106(2) 0.0357(19) -0.0350(16) -0.0072(15) C23A 0.0481(14) 0.111(3) 0.0702(18) 0.0066(16) -0.0041(12) 0.0066(15) C25A 0.0744(19) 0.097(2) 0.0662(17) -0.0198(17) -0.0199(15) 0.0105(17) C24A 0.0664(18) 0.081(2) 0.106(2) 0.0357(19) -0.0350(16) -0.0072(15) C12A 0.0481(12) 0.0428(13) 0.0366(8) 0.0017(8) 0.0025(8) 0.0030(9) C13A 0.067(2) 0.0544(14) 0.075(3) 0.0177(18) 0.028(2) 0.0075(14) C14A 0.073(2) 0.080(2) 0.112(4) 0.029(3) 0.049(3) 0.0150(18) C15A 0.076(2) 0.083(2) 0.0902(19) 0.0174(15) 0.0376(15) 0.0322(18) C16A 0.0834(16) 0.0532(15) 0.067(3) 0.0110(14) 0.0270(19) 0.0232(13) C17A 0.0597(11) 0.0456(14) 0.044(2) 0.0034(15) 0.0122(15) 0.0046(10) _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 O1 1.490(2) 5_666 ? O1 C4 1.4118(19) . ? N3 C4 1.4645(19) . ? N3 C8 1.278(2) . ? N1 C8 1.443(2) . ? N1 C3 1.285(2) . ? C4 C12 1.543(9) . ? C4 C3 1.537(2) . ? C4 C12A 1.508(3) . ? C12 C13 1.3900 . ? C12 C17 1.3900 . ? C13 H13 0.9500 . ? C13 C14 1.3900 . ? C14 H14 0.9500 . ? C14 C15 1.3900 . ? C15 H15 0.9500 . ? C15 C16 1.3900 . ? C16 H16 0.9500 . ? C16 C17 1.3900 . ? C17 H17 0.9500 . ? C8 C9 1.465(2) . ? C9 C2 1.380(2) . ? C9 C6 1.382(2) . ? C18 C3 1.467(2) . ? C18 C19 1.390(3) . ? C18 C23 1.392(3) . ? C11 H11 0.9500 . ? C11 C1 1.385(2) . ? C11 C2 1.380(2) . ? C1 C24 1.529(2) . ? C1 C5 1.382(3) . ? C24 C26 1.534(3) . ? C24 C25 1.527(4) . ? C24 C27 1.539(4) . ? C24 C23A 1.524(10) . ? C24 C25A 1.499(10) . ? C24 C24A 1.491(11) . ? C2 H2 0.9500 . ? C5 H5 0.9500 . ? C5 C6 1.376(3) . ? C6 H6 0.9500 . ? C19 H19 0.9500 . ? C19 C20 1.386(3) . ? C20 H20 0.9500 . ? C20 C21 1.372(3) . ? C23 H23 0.9500 . ? C23 C22 1.375(3) . ? C21 H21 0.9500 . ? C21 C22 1.372(3) . ? C22 H22 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C23A H23A 0.9800 . ? C23A H23B 0.9800 . ? C23A H23C 0.9800 . ? C25A H25D 0.9800 . ? C25A H25E 0.9800 . ? C25A H25F 0.9800 . ? C24A H24A 0.9800 . ? C24A H24B 0.9800 . ? C24A H24C 0.9800 . ? C12A C13A 1.3900 . ? C12A C17A 1.3900 . ? C13A H13A 0.9500 . ? C13A C14A 1.3900 . ? C14A H14A 0.9500 . ? C14A C15A 1.3900 . ? C15A H15A 0.9500 . ? C15A C16A 1.3900 . ? C16A H16A 0.9500 . ? C16A C17A 1.3900 . ? C17A H17A 0.9500 . ? 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 C4 O1 O1 104.45(12) . 5_666 ? C8 N3 C4 104.98(13) . . ? C3 N1 C8 104.34(13) . . ? O1 C4 N3 111.15(12) . . ? O1 C4 C12 100.0(4) . . ? O1 C4 C3 111.96(12) . . ? O1 C4 C12A 106.94(18) . . ? N3 C4 C12 110.7(3) . . ? N3 C4 C3 103.00(12) . . ? N3 C4 C12A 110.01(15) . . ? C3 C4 C12 120.2(4) . . ? C12A C4 C12 7.5(5) . . ? C12A C4 C3 113.84(18) . . ? C13 C12 C4 123.6(7) . . ? C13 C12 C17 120.0 . . ? C17 C12 C4 116.4(7) . . ? C12 C13 H13 120.0 . . ? C14 C13 C12 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 H14 120.0 . . ? C13 C14 C15 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 H15 120.0 . . ? C14 C15 C16 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 H16 120.0 . . ? C17 C16 C15 120.0 . . ? C17 C16 H16 120.0 . . ? C12 C17 H17 120.0 . . ? C16 C17 C12 120.0 . . ? C16 C17 H17 120.0 . . ? N3 C8 N1 117.24(14) . . ? N3 C8 C9 124.26(15) . . ? N1 C8 C9 118.49(14) . . ? C2 C9 C8 120.88(15) . . ? C2 C9 C6 118.06(16) . . ? C6 C9 C8 121.05(15) . . ? C19 C18 C3 121.57(16) . . ? C19 C18 C23 119.37(16) . . ? C23 C18 C3 119.06(16) . . ? C1 C11 H11 118.9 . . ? C2 C11 H11 118.9 . . ? C2 C11 C1 122.12(16) . . ? C11 C1 C24 122.18(16) . . ? C5 C1 C11 116.35(16) . . ? C5 C1 C24 121.46(16) . . ? C1 C24 C26 111.89(17) . . ? C1 C24 C27 112.70(17) . . ? C26 C24 C27 106.9(2) . . ? C25 C24 C1 108.37(17) . . ? C25 C24 C26 108.0(2) . . ? C25 C24 C27 108.9(2) . . ? C23A C24 C1 111.3(4) . . ? C23A C24 C26 50.4(4) . . ? C23A C24 C25 60.3(4) . . ? C23A C24 C27 135.8(4) . . ? C25A C24 C1 109.2(4) . . ? C25A C24 C26 138.2(4) . . ? C25A C24 C25 50.4(4) . . ? C25A C24 C27 62.3(4) . . ? C25A C24 C23A 107.0(5) . . ? C24A C24 C1 104.5(4) . . ? C24A C24 C26 60.7(4) . . ? C24A C24 C25 147.0(4) . . ? C24A C24 C27 54.0(4) . . ? C24A C24 C23A 109.7(5) . . ? C24A C24 C25A 115.3(6) . . ? C9 C2 H2 119.7 . . ? C11 C2 C9 120.55(16) . . ? C11 C2 H2 119.7 . . ? N1 C3 C4 110.32(13) . . ? N1 C3 C18 123.84(15) . . ? C18 C3 C4 125.84(14) . . ? C1 C5 H5 118.9 . . ? C6 C5 C1 122.20(17) . . ? C6 C5 H5 118.9 . . ? C9 C6 H6 119.6 . . ? C5 C6 C9 120.70(18) . . ? C5 C6 H6 119.6 . . ? C18 C19 H19 120.2 . . ? C20 C19 C18 119.70(19) . . ? C20 C19 H19 120.2 . . ? C19 C20 H20 119.9 . . ? C21 C20 C19 120.3(2) . . ? C21 C20 H20 119.9 . . ? C18 C23 H23 120.0 . . ? C22 C23 C18 119.9(2) . . ? C22 C23 H23 120.0 . . ? C20 C21 H21 119.9 . . ? C20 C21 C22 120.13(19) . . ? C22 C21 H21 119.9 . . ? C23 C22 H22 119.7 . . ? C21 C22 C23 120.6(2) . . ? C21 C22 H22 119.7 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? C24 C23A H23A 109.5 . . ? C24 C23A H23B 109.5 . . ? C24 C23A H23C 109.5 . . ? H23A C23A H23B 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? C24 C25A H25D 109.5 . . ? C24 C25A H25E 109.5 . . ? C24 C25A H25F 109.5 . . ? H25D C25A H25E 109.5 . . ? H25D C25A H25F 109.5 . . ? H25E C25A H25F 109.5 . . ? C24 C24A H24A 109.5 . . ? C24 C24A H24B 109.5 . . ? C24 C24A H24C 109.5 . . ? H24A C24A H24B 109.5 . . ? H24A C24A H24C 109.5 . . ? H24B C24A H24C 109.5 . . ? C13A C12A C4 116.9(2) . . ? C13A C12A C17A 120.0 . . ? C17A C12A C4 123.1(2) . . ? C12A C13A H13A 120.0 . . ? C14A C13A C12A 120.0 . . ? C14A C13A H13A 120.0 . . ? C13A C14A H14A 120.0 . . ? C13A C14A C15A 120.0 . . ? C15A C14A H14A 120.0 . . ? C14A C15A H15A 120.0 . . ? C14A C15A C16A 120.0 . . ? C16A C15A H15A 120.0 . . ? C15A C16A H16A 120.0 . . ? C17A C16A C15A 120.0 . . ? C17A C16A H16A 120.0 . . ? C12A C17A H17A 120.0 . . ? C16A C17A C12A 120.0 . . ? C16A C17A H17A 120.0 . . ? data_mono_sad_100k _database_code_depnum_ccdc_archive 'CCDC 882417' #TrackingRef '- Compound 6 Form II.cif' _audit_creation_date 2012-03-27 _audit_creation_method ; Olex2 1.1 (compiled Nov 1 2011 20:42:30, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C50 H46 N4 O2' _chemical_formula_sum 'C50 H46 N4 O2' _chemical_formula_weight 734.91 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 16.0313(4) _cell_length_b 30.9627(9) _cell_length_c 16.5171(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.7920(10) _cell_angle_gamma 90.00 _cell_volume 8180.7(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9740 _cell_measurement_temperature 100 _cell_measurement_theta_max 63.120 _cell_measurement_theta_min 3.038 _exptl_absorpt_coefficient_mu 0.570 _exptl_absorpt_correction_T_max 0.7523 _exptl_absorpt_correction_T_min 0.6656 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0947 before and 0.0719 after correction. The Ratio of minimum to maximum transmission is 0.8848. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 3120 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of \w scans, each set at different \f and/or 2\q angles, with additional \f scans, each set at different \w and/or 2\q angles, to aid absorption correction parameters. Each image (1.0 s exposure) covering -0.50\ degrees in \w or \f. The crystal to detector distance was 5.00 cm ; _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_unetI/netI 0.0338 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 62341 _diffrn_reflns_theta_full 63.30 _diffrn_reflns_theta_max 63.30 _diffrn_reflns_theta_min 2.76 _diffrn_ambient_temperature 100 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'Bruker Pt 135 CCD area detector' _diffrn_measured_fraction_theta_full 0.962 _diffrn_measured_fraction_theta_max 0.962 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Pt 135 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_collimation 'focused optics' _diffrn_radiation_monochromator 'Bruker Helios multilayer optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54188 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'Microstar rotating anode' _diffrn_source_target Cu _diffrn_source_type 'rotating anode' _diffrn_special_details 'Sample undergoes phase transition between 150K and 145K' _reflns_number_gt 11361 _reflns_number_total 12830 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_collection 'Proteum2 (Bruker, 2010)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.347 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.050 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 1032 _refine_ls_number_reflns 12830 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0577 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0795P)^2^+3.8133P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1604 _refine_ls_wR_factor_ref 0.1659 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O2A O 0.77371(7) 0.63770(4) 0.23645(7) 0.0307(3) Uani 1 1 d . A . O2 O 0.27641(7) 0.61196(4) 0.22958(7) 0.0298(3) Uani 1 1 d . . . O1A O 0.69630(7) 0.61638(4) 0.26138(7) 0.0317(3) Uani 1 1 d . A . O1 O 0.20002(7) 0.63552(4) 0.25153(7) 0.0304(3) Uani 1 1 d . B . N3 N 0.20131(9) 0.59113(5) 0.10705(8) 0.0300(3) Uani 1 1 d . . . N2A N 0.77201(9) 0.59902(5) 0.38516(9) 0.0309(3) Uani 1 1 d . C . N4 N 0.10917(9) 0.55030(5) 0.17871(9) 0.0328(4) Uani 1 1 d . . . N1 N 0.36605(10) 0.69809(5) 0.30179(9) 0.0337(4) Uani 1 1 d . B . N2 N 0.27745(9) 0.65503(4) 0.37344(8) 0.0298(3) Uani 1 1 d . B . N3A N 0.69983(9) 0.65311(5) 0.11036(8) 0.0309(3) Uani 1 1 d . A . C44A C 0.67868(12) 0.69967(6) 0.21940(11) 0.0322(4) Uani 1 1 d . A . N4A N 0.61115(10) 0.70022(5) 0.17294(9) 0.0354(4) Uani 1 1 d . A . N1A N 0.86173(10) 0.55530(5) 0.31631(9) 0.0354(4) Uani 1 1 d . . . C8A C 0.84580(11) 0.58315(6) 0.38373(10) 0.0310(4) Uani 1 1 d . . . C44 C 0.17698(11) 0.55148(5) 0.22463(11) 0.0298(4) Uani 1 1 d . . . C26A C 0.74488(11) 0.67085(6) 0.18286(10) 0.0308(4) Uani 1 1 d . . . C45 C 0.18633(11) 0.53174(6) 0.30546(11) 0.0323(4) Uani 1 1 d . . . C6 C 0.28438(12) 0.71826(6) 0.17842(11) 0.0351(4) Uani 1 1 d . . . C33A C 0.62706(11) 0.67060(6) 0.10847(10) 0.0317(4) Uani 1 1 d . . . C27A C 0.8206(2) 0.69522(13) 0.16003(18) 0.0316(6) Uani 0.684(9) 1 d PG A 1 C28A C 0.8834(3) 0.67111(12) 0.1275(3) 0.0512(13) Uani 0.684(9) 1 d PG A 1 H28A H 0.8771 0.6408 0.1210 0.061 Uiso 0.684(9) 1 calc PR A 1 C29A C 0.9554(3) 0.69139(16) 0.1044(3) 0.0682(17) Uani 0.684(9) 1 d PG A 1 H29A H 0.9984 0.6749 0.0821 0.082 Uiso 0.684(9) 1 calc PR A 1 C30A C 0.9647(3) 0.73578(15) 0.1138(2) 0.0607(11) Uani 0.684(9) 1 d PG A 1 H30A H 1.0139 0.7496 0.0980 0.073 Uiso 0.684(9) 1 calc PR A 1 C31A C 0.9018(3) 0.75989(11) 0.1464(3) 0.0501(11) Uani 0.684(9) 1 d PG A 1 H31A H 0.9082 0.7902 0.1529 0.060 Uiso 0.684(9) 1 calc PR A 1 C32A C 0.8298(2) 0.73961(13) 0.1695(3) 0.0370(9) Uani 0.684(9) 1 d PG A 1 H32A H 0.7869 0.7561 0.1917 0.044 Uiso 0.684(9) 1 calc PR A 1 C27 C 0.32265(11) 0.55080(6) 0.16490(10) 0.0304(4) Uani 1 1 d . . . C9A C 0.91404(11) 0.59185(6) 0.44458(11) 0.0324(4) Uani 1 1 d . . . C26 C 0.24517(11) 0.57637(6) 0.18261(10) 0.0296(4) Uani 1 1 d . . . C35 C 0.07029(11) 0.61339(6) -0.01516(11) 0.0357(4) Uani 1 1 d . . . H35 H 0.1225 0.6276 -0.0183 0.043 Uiso 1 1 calc R . . C34A C 0.56001(11) 0.66165(6) 0.04616(10) 0.0318(4) Uani 1 1 d . A . C7A C 0.79285(12) 0.55532(6) 0.27183(11) 0.0323(4) Uani 1 1 d . C . C45A C 0.68994(12) 0.72355(6) 0.29598(11) 0.0361(4) Uani 1 1 d . . . C40A C 0.36009(11) 0.63695(6) -0.13891(11) 0.0340(4) Uani 1 1 d . A . C7 C 0.29726(11) 0.69671(5) 0.25748(11) 0.0305(4) Uani 1 1 d . B . C9 C 0.41933(11) 0.66361(6) 0.43203(11) 0.0317(4) Uani 1 1 d . B . C19 C 0.23136(11) 0.67039(5) 0.29959(10) 0.0301(4) Uani 1 1 d . . . C35A C 0.56710(11) 0.62856(6) -0.00915(11) 0.0321(4) Uani 1 1 d . . . H35A H 0.6163 0.6114 -0.0069 0.039 Uiso 1 1 calc R A . C37A C 0.43082(11) 0.64467(6) -0.07361(11) 0.0321(4) Uani 1 1 d . . . C20 C 0.1494(7) 0.6931(5) 0.3194(6) 0.0318(6) Uani 0.259(13) 1 d PG B 1 C25 C 0.0744(8) 0.6711(4) 0.3252(8) 0.0465(11) Uani 0.259(13) 1 d PG B 1 H25 H 0.0717 0.6409 0.3152 0.056 Uiso 0.259(13) 1 calc PR B 1 C24 C 0.0034(7) 0.6933(5) 0.3458(9) 0.0589(14) Uani 0.259(13) 1 d PG B 1 H24 H -0.0478 0.6783 0.3498 0.071 Uiso 0.259(13) 1 calc PR B 1 C23 C 0.0075(10) 0.7375(5) 0.3605(8) 0.0567(9) Uani 0.259(13) 1 d PG B 1 H23 H -0.0410 0.7527 0.3746 0.068 Uiso 0.259(13) 1 calc PR B 1 C22 C 0.0824(12) 0.7595(4) 0.3547(9) 0.0459(9) Uani 0.259(13) 1 d PG B 1 H22 H 0.0852 0.7897 0.3648 0.055 Uiso 0.259(13) 1 calc PR B 1 C21 C 0.1534(9) 0.7373(5) 0.3342(8) 0.0340(8) Uani 0.259(13) 1 d PG B 1 H21 H 0.2046 0.7523 0.3302 0.041 Uiso 0.259(13) 1 calc PR B 1 C8 C 0.35089(11) 0.67134(5) 0.37074(11) 0.0306(4) Uani 1 1 d . . . C37 C -0.07207(11) 0.60240(6) -0.07013(11) 0.0322(4) Uani 1 1 d . . . C13A C 0.96743(12) 0.62525(6) 0.56853(12) 0.0393(5) Uani 1 1 d . . . H13A H 0.9576 0.6427 0.6143 0.047 Uiso 1 1 calc R . . C32 C 0.32886(12) 0.50672(6) 0.17925(12) 0.0370(4) Uani 1 1 d . . . H32 H 0.2840 0.4918 0.2016 0.044 Uiso 1 1 calc R . . C36 C 0.00568(12) 0.62223(6) -0.07195(11) 0.0373(4) Uani 1 1 d . . . H36 H 0.0145 0.6425 -0.1137 0.045 Uiso 1 1 calc R . . C6A C 0.78003(13) 0.53225(6) 0.19474(11) 0.0363(4) Uani 1 1 d . . . C33 C 0.12707(11) 0.57570(6) 0.10889(10) 0.0303(4) Uani 1 1 d . . . C34 C 0.05961(11) 0.58395(6) 0.04644(11) 0.0310(4) Uani 1 1 d . . . C15A C 1.11899(12) 0.61589(6) 0.62519(12) 0.0398(5) Uani 1 1 d . . . C50 C 0.25757(12) 0.53882(6) 0.35721(11) 0.0374(4) Uani 1 1 d . . . H50 H 0.3005 0.5574 0.3410 0.045 Uiso 1 1 calc R . . C19A C 0.72643(11) 0.58231(6) 0.31217(10) 0.0316(4) Uani 1 1 d . . . C12A C 1.04739(12) 0.60832(6) 0.56095(11) 0.0345(4) Uani 1 1 d . D . C14A C 0.90245(12) 0.61746(6) 0.51171(12) 0.0389(5) Uani 1 1 d . . . H14A H 0.8491 0.6298 0.5186 0.047 Uiso 1 1 calc R . . C15 C 0.62392(12) 0.63752(6) 0.61126(12) 0.0385(4) Uani 1 1 d . . . C39A C 0.48717(13) 0.68661(7) 0.04087(13) 0.0462(5) Uani 1 1 d . . . H39A H 0.4807 0.7095 0.0782 0.055 Uiso 1 1 calc R A . C40 C -0.14359(12) 0.61236(6) -0.13298(11) 0.0358(4) Uani 1 1 d . . . C38A C 0.42483(13) 0.67809(7) -0.01815(13) 0.0468(5) Uani 1 1 d . A . H38A H 0.3761 0.6956 -0.0211 0.056 Uiso 1 1 calc R . . C14 C 0.41078(12) 0.63388(6) 0.49385(12) 0.0362(4) Uani 1 1 d . . . H14 H 0.3597 0.6186 0.4968 0.043 Uiso 1 1 calc R B . C5A C 0.70830(14) 0.53825(6) 0.14358(11) 0.0418(5) Uani 1 1 d . . . H5A H 0.6664 0.5579 0.1584 0.050 Uiso 1 1 calc R . . C12 C 0.55182(11) 0.64801(6) 0.54918(11) 0.0337(4) Uani 1 1 d . B . C50A C 0.75843(13) 0.71621(6) 0.35085(12) 0.0416(5) Uani 1 1 d . A . H50A H 0.7990 0.6951 0.3391 0.050 Uiso 1 1 calc R . . C36A C 0.50365(11) 0.62023(6) -0.06755(11) 0.0324(4) Uani 1 1 d . A . H36A H 0.5099 0.5972 -0.1046 0.039 Uiso 1 1 calc R . . C11 C 0.55912(12) 0.67782(7) 0.48695(13) 0.0456(5) Uani 1 1 d . . . H11 H 0.6101 0.6933 0.4840 0.055 Uiso 1 1 calc R E . C31 C 0.40023(13) 0.48446(6) 0.16112(13) 0.0446(5) Uani 1 1 d . . . H31 H 0.4039 0.4542 0.1707 0.054 Uiso 1 1 calc R . . C38 C -0.08093(13) 0.57258(7) -0.00854(14) 0.0499(6) Uani 1 1 d . . . H38 H -0.1329 0.5581 -0.0057 0.060 Uiso 1 1 calc R . . C5 C 0.21315(13) 0.71068(6) 0.12721(11) 0.0410(5) Uani 1 1 d . . . H5 H 0.1723 0.6905 0.1423 0.049 Uiso 1 1 calc R . . C13 C 0.47568(12) 0.62646(6) 0.55083(12) 0.0381(4) Uani 1 1 d . B . H13 H 0.4684 0.6060 0.5926 0.046 Uiso 1 1 calc R . . C43A C 0.27517(12) 0.63699(7) -0.10072(13) 0.0456(5) Uani 1 1 d . . . H43A H 0.2760 0.6156 -0.0569 0.068 Uiso 1 1 calc R A . H43B H 0.2309 0.6296 -0.1422 0.068 Uiso 1 1 calc R . . H43C H 0.2645 0.6657 -0.0788 0.068 Uiso 1 1 calc R . . C30 C 0.46588(13) 0.50582(7) 0.12935(14) 0.0494(5) Uani 1 1 d . . . H30 H 0.5153 0.4906 0.1180 0.059 Uiso 1 1 calc R . . C1 C 0.34471(14) 0.74732(6) 0.15471(12) 0.0416(5) Uani 1 1 d . . . H1 H 0.3941 0.7521 0.1886 0.050 Uiso 1 1 calc R . . C42A C 0.36154(13) 0.67350(7) -0.20133(13) 0.0445(5) Uani 1 1 d . . . H42A H 0.3559 0.7013 -0.1740 0.067 Uiso 1 1 calc R A . H42B H 0.3151 0.6698 -0.2424 0.067 Uiso 1 1 calc R . . H42C H 0.4146 0.6728 -0.2276 0.067 Uiso 1 1 calc R . . C39 C -0.01684(13) 0.56331(7) 0.04873(13) 0.0467(5) Uani 1 1 d . . . H39 H -0.0252 0.5427 0.0899 0.056 Uiso 1 1 calc R . . C20A C 0.6460(4) 0.5580(3) 0.3323(6) 0.0352(9) Uani 0.663(18) 1 d PG C 1 C25A C 0.5709(5) 0.5801(2) 0.3362(6) 0.0524(17) Uani 0.663(18) 1 d PG C 1 H25A H 0.5683 0.6102 0.3254 0.063 Uiso 0.663(18) 1 calc PR C 1 C24A C 0.4994(5) 0.5581(2) 0.3559(6) 0.0597(19) Uani 0.663(18) 1 d PG C 1 H24A H 0.4481 0.5731 0.3586 0.072 Uiso 0.663(18) 1 calc PR C 1 C23A C 0.5031(5) 0.5140(2) 0.3717(5) 0.0588(18) Uani 0.663(18) 1 d PG C 1 H23A H 0.4543 0.4989 0.3852 0.071 Uiso 0.663(18) 1 calc PR C 1 C22A C 0.5783(6) 0.4919(2) 0.3678(5) 0.0638(15) Uani 0.663(18) 1 d PG C 1 H22A H 0.5808 0.4618 0.3786 0.077 Uiso 0.663(18) 1 calc PR C 1 C21A C 0.6497(5) 0.5139(3) 0.3481(6) 0.0519(11) Uani 0.663(18) 1 d PG C 1 H21A H 0.7011 0.4989 0.3454 0.062 Uiso 0.663(18) 1 calc PR C 1 C28 C 0.38764(12) 0.57200(7) 0.13131(13) 0.0444(5) Uani 1 1 d . . . H28 H 0.3834 0.6020 0.1199 0.053 Uiso 1 1 calc R . . C1A C 0.84128(14) 0.50353(6) 0.17179(12) 0.0432(5) Uani 1 1 d . . . H1A H 0.8909 0.4995 0.2056 0.052 Uiso 1 1 calc R . . C42 C -0.13986(14) 0.57996(8) -0.20244(13) 0.0540(6) Uani 1 1 d . . . H42D H -0.0876 0.5839 -0.2292 0.081 Uiso 1 1 calc R . . H42E H -0.1874 0.5847 -0.2418 0.081 Uiso 1 1 calc R . . H42F H -0.1421 0.5505 -0.1809 0.081 Uiso 1 1 calc R . . C2 C 0.33261(17) 0.76918(7) 0.08210(13) 0.0534(6) Uani 1 1 d . . . H2 H 0.3735 0.7892 0.0664 0.064 Uiso 1 1 calc R . . C48A C 0.70875(16) 0.77056(7) 0.43924(13) 0.0523(6) Uani 1 1 d . A . H48A H 0.7154 0.7868 0.4880 0.063 Uiso 1 1 calc R . . C10 C 0.49454(12) 0.68562(7) 0.42939(12) 0.0430(5) Uani 1 1 d . B . H10 H 0.5016 0.7062 0.3877 0.052 Uiso 1 1 calc R . . C46A C 0.63049(14) 0.75437(6) 0.31438(12) 0.0439(5) Uani 1 1 d . A . H46A H 0.5830 0.7592 0.2779 0.053 Uiso 1 1 calc R . . C49A C 0.76732(15) 0.73960(7) 0.42244(12) 0.0470(5) Uani 1 1 d . . . H49A H 0.8137 0.7344 0.4600 0.056 Uiso 1 1 calc R A . C29 C 0.45911(14) 0.54958(7) 0.11414(15) 0.0545(6) Uani 1 1 d . . . H29 H 0.5040 0.5645 0.0917 0.065 Uiso 1 1 calc R . . C10A C 0.99274(13) 0.57455(7) 0.43633(12) 0.0463(5) Uani 1 1 d . D . H10A H 1.0021 0.5567 0.3910 0.056 Uiso 1 1 calc R . . C43 C -0.22879(13) 0.60809(8) -0.09614(14) 0.0497(5) Uani 1 1 d . . . H43D H -0.2383 0.5778 -0.0820 0.075 Uiso 1 1 calc R . . H43E H -0.2731 0.6177 -0.1358 0.075 Uiso 1 1 calc R . . H43F H -0.2293 0.6260 -0.0472 0.075 Uiso 1 1 calc R . . C4 C 0.20225(15) 0.73267(7) 0.05418(12) 0.0478(5) Uani 1 1 d . . . H4 H 0.1539 0.7275 0.0191 0.057 Uiso 1 1 calc R . . C2A C 0.82937(16) 0.48095(7) 0.09947(13) 0.0523(6) Uani 1 1 d . . . H2A H 0.8708 0.4612 0.0842 0.063 Uiso 1 1 calc R . . C11A C 1.05757(13) 0.58299(8) 0.49327(13) 0.0489(5) Uani 1 1 d . . . H11A H 1.1111 0.5710 0.4858 0.059 Uiso 1 1 calc R D . C4A C 0.69784(15) 0.51574(7) 0.07141(12) 0.0486(5) Uani 1 1 d . . . H4A H 0.6490 0.5201 0.0367 0.058 Uiso 1 1 calc R . . C46 C 0.12283(12) 0.50512(6) 0.33100(12) 0.0383(4) Uani 1 1 d . . . H46 H 0.0737 0.5006 0.2968 0.046 Uiso 1 1 calc R . . C3A C 0.75798(16) 0.48697(7) 0.04957(13) 0.0524(6) Uani 1 1 d . . . H3A H 0.7502 0.4713 0.0002 0.063 Uiso 1 1 calc R . . C48 C 0.20310(15) 0.49193(7) 0.45617(13) 0.0487(5) Uani 1 1 d . . . H48 H 0.2092 0.4778 0.5073 0.058 Uiso 1 1 calc R . . C41A C 0.36899(13) 0.59384(7) -0.18269(13) 0.0448(5) Uani 1 1 d . . . H41A H 0.4211 0.5938 -0.2105 0.067 Uiso 1 1 calc R A . H41B H 0.3215 0.5899 -0.2225 0.067 Uiso 1 1 calc R . . H41C H 0.3701 0.5702 -0.1431 0.067 Uiso 1 1 calc R . . C47 C 0.13160(14) 0.48549(7) 0.40597(13) 0.0474(5) Uani 1 1 d . . . H47 H 0.0883 0.4674 0.4233 0.057 Uiso 1 1 calc R . . C49 C 0.26541(13) 0.51876(6) 0.43197(12) 0.0425(5) Uani 1 1 d . . . H49 H 0.3140 0.5235 0.4669 0.051 Uiso 1 1 calc R . . C3 C 0.26149(16) 0.76216(7) 0.03217(13) 0.0531(6) Uani 1 1 d . . . H3 H 0.2532 0.7776 -0.0174 0.064 Uiso 1 1 calc R . . C47A C 0.64045(15) 0.77791(7) 0.38530(13) 0.0525(6) Uani 1 1 d . . . H47A H 0.6003 0.7992 0.3971 0.063 Uiso 1 1 calc R A . C41 C -0.13755(14) 0.65810(7) -0.16652(16) 0.0592(6) Uani 1 1 d . . . H41D H -0.1342 0.6788 -0.1215 0.089 Uiso 1 1 calc R . . H41E H -0.1872 0.6643 -0.2025 0.089 Uiso 1 1 calc R . . H41F H -0.0874 0.6606 -0.1971 0.089 Uiso 1 1 calc R . . C17A C 1.20469(15) 0.61400(10) 0.58905(16) 0.0567(7) Uani 0.898(3) 1 d P D 1 H17A H 1.2145 0.5848 0.5691 0.085 Uiso 0.898(3) 1 calc PR D 1 H17B H 1.2484 0.6215 0.6310 0.085 Uiso 0.898(3) 1 calc PR D 1 H17C H 1.2059 0.6346 0.5440 0.085 Uiso 0.898(3) 1 calc PR D 1 C17 C 0.69100(16) 0.67262(9) 0.61392(18) 0.0550(7) Uani 0.854(3) 1 d P E 1 H17G H 0.7142 0.6749 0.5607 0.083 Uiso 0.854(3) 1 calc PR E 1 H17H H 0.7357 0.6651 0.6549 0.083 Uiso 0.854(3) 1 calc PR E 1 H17I H 0.6662 0.7003 0.6279 0.083 Uiso 0.854(3) 1 calc PR E 1 C16 C 0.66342(15) 0.59515(8) 0.58506(16) 0.0486(6) Uani 0.854(3) 1 d P E 1 H16G H 0.6213 0.5722 0.5832 0.073 Uiso 0.854(3) 1 calc PR E 1 H16H H 0.7097 0.5874 0.6241 0.073 Uiso 0.854(3) 1 calc PR E 1 H16I H 0.6845 0.5988 0.5311 0.073 Uiso 0.854(3) 1 calc PR E 1 C18A C 1.11636(19) 0.58000(12) 0.68846(18) 0.0735(10) Uani 0.898(3) 1 d P D 1 H18A H 1.0638 0.5818 0.7155 0.110 Uiso 0.898(3) 1 calc PR D 1 H18B H 1.1636 0.5833 0.7288 0.110 Uiso 0.898(3) 1 calc PR D 1 H18C H 1.1200 0.5519 0.6617 0.110 Uiso 0.898(3) 1 calc PR D 1 C18 C 0.59248(17) 0.63272(12) 0.69522(15) 0.0610(8) Uani 0.854(3) 1 d P E 1 H18G H 0.5630 0.6591 0.7095 0.091 Uiso 0.854(3) 1 calc PR E 1 H18H H 0.6399 0.6279 0.7347 0.091 Uiso 0.854(3) 1 calc PR E 1 H18I H 0.5542 0.6081 0.6959 0.091 Uiso 0.854(3) 1 calc PR E 1 C16A C 1.11328(18) 0.65999(10) 0.6650(2) 0.0785(11) Uani 0.898(3) 1 d P D 1 H16A H 1.1121 0.6825 0.6232 0.118 Uiso 0.898(3) 1 calc PR D 1 H16B H 1.1620 0.6643 0.7032 0.118 Uiso 0.898(3) 1 calc PR D 1 H16C H 1.0621 0.6616 0.6942 0.118 Uiso 0.898(3) 1 calc PR D 1 C1B C 0.7110(10) 0.6441(6) 0.5834(11) 0.0550(7) Uani 0.146(3) 1 d P E 2 H1BA H 0.7194 0.6253 0.5370 0.083 Uiso 0.146(3) 1 calc PR E 2 H1BB H 0.7523 0.6371 0.6279 0.083 Uiso 0.146(3) 1 calc PR E 2 H1BC H 0.7179 0.6743 0.5674 0.083 Uiso 0.146(3) 1 calc PR E 2 C1C C 0.6246(9) 0.5905(5) 0.6453(10) 0.0486(6) Uani 0.146(3) 1 d P E 2 H1CA H 0.5836 0.5880 0.6864 0.073 Uiso 0.146(3) 1 calc PR E 2 H1CB H 0.6805 0.5837 0.6698 0.073 Uiso 0.146(3) 1 calc PR E 2 H1CC H 0.6104 0.5702 0.6009 0.073 Uiso 0.146(3) 1 calc PR E 2 C1D C 0.6160(10) 0.6697(7) 0.6861(9) 0.0610(8) Uani 0.146(3) 1 d P E 2 H1DA H 0.6309 0.6990 0.6700 0.091 Uiso 0.146(3) 1 calc PR E 2 H1DB H 0.6539 0.6603 0.7317 0.091 Uiso 0.146(3) 1 calc PR E 2 H1DC H 0.5583 0.6694 0.7025 0.091 Uiso 0.146(3) 1 calc PR E 2 C18B C 1.0858(18) 0.6111(12) 0.7055(16) 0.0735(10) Uani 0.102(3) 1 d P D 2 H18D H 1.0533 0.6368 0.7177 0.110 Uiso 0.102(3) 1 calc PR D 2 H18E H 1.1322 0.6077 0.7467 0.110 Uiso 0.102(3) 1 calc PR D 2 H18F H 1.0497 0.5856 0.7057 0.110 Uiso 0.102(3) 1 calc PR D 2 C16B C 1.1596(16) 0.6540(9) 0.5942(18) 0.0785(11) Uani 0.102(3) 1 d P D 2 H16D H 1.1825 0.6470 0.5421 0.118 Uiso 0.102(3) 1 calc PR D 2 H16E H 1.2050 0.6631 0.6330 0.118 Uiso 0.102(3) 1 calc PR D 2 H16F H 1.1188 0.6774 0.5864 0.118 Uiso 0.102(3) 1 calc PR D 2 C17B C 1.1837(13) 0.5776(8) 0.6230(14) 0.0567(7) Uani 0.102(3) 1 d P D 2 H17D H 1.1537 0.5500 0.6227 0.085 Uiso 0.102(3) 1 calc PR D 2 H17E H 1.2229 0.5790 0.6710 0.085 Uiso 0.102(3) 1 calc PR D 2 H17F H 1.2146 0.5799 0.5740 0.085 Uiso 0.102(3) 1 calc PR D 2 C27B C 0.8304(5) 0.6906(3) 0.1608(4) 0.0316(6) Uani 0.316(9) 1 d PG A 2 C28B C 0.9031(6) 0.6663(3) 0.1590(6) 0.0512(13) Uani 0.316(9) 1 d PG A 2 H28B H 0.9025 0.6364 0.1719 0.061 Uiso 0.316(9) 1 calc PR A 2 C29B C 0.9769(5) 0.6858(4) 0.1381(7) 0.0682(17) Uani 0.316(9) 1 d PG A 2 H29B H 1.0266 0.6692 0.1368 0.082 Uiso 0.316(9) 1 calc PR A 2 C30B C 0.9778(6) 0.7295(4) 0.1191(6) 0.0607(11) Uani 0.316(9) 1 d PG A 2 H30B H 1.0282 0.7428 0.1048 0.073 Uiso 0.316(9) 1 calc PR A 2 C31B C 0.9051(8) 0.7538(3) 0.1210(6) 0.0501(11) Uani 0.316(9) 1 d PG A 2 H31B H 0.9057 0.7837 0.1080 0.060 Uiso 0.316(9) 1 calc PR A 2 C32B C 0.8313(6) 0.7343(3) 0.1419(5) 0.0370(9) Uani 0.316(9) 1 d PG A 2 H32B H 0.7816 0.7509 0.1431 0.044 Uiso 0.316(9) 1 calc PR A 2 C20B C 0.6571(8) 0.5552(6) 0.3351(12) 0.0352(9) Uani 0.337(18) 1 d PG C 2 C25B C 0.5844(9) 0.5750(4) 0.3581(10) 0.0524(17) Uani 0.337(18) 1 d PG C 2 H25B H 0.5793 0.6055 0.3562 0.063 Uiso 0.337(18) 1 calc PR C 2 C24B C 0.5192(8) 0.5500(4) 0.3839(9) 0.0597(19) Uani 0.337(18) 1 d PG C 2 H24B H 0.4696 0.5634 0.3996 0.072 Uiso 0.337(18) 1 calc PR C 2 C23B C 0.5267(8) 0.5053(4) 0.3867(8) 0.0588(18) Uani 0.337(18) 1 d PG C 2 H23B H 0.4821 0.4882 0.4044 0.071 Uiso 0.337(18) 1 calc PR C 2 C22B C 0.5993(9) 0.4855(4) 0.3637(11) 0.0638(15) Uani 0.337(18) 1 d PG C 2 H22B H 0.6044 0.4550 0.3656 0.077 Uiso 0.337(18) 1 calc PR C 2 C21B C 0.6645(8) 0.5105(6) 0.3379(13) 0.0519(11) Uani 0.337(18) 1 d PG C 2 H21B H 0.7142 0.4971 0.3222 0.062 Uiso 0.337(18) 1 calc PR C 2 C1E C 0.1560(2) 0.69647(16) 0.32192(18) 0.0318(6) Uani 0.741(13) 1 d PG B 2 C1J C 0.0914(3) 0.67385(12) 0.3547(4) 0.0465(11) Uani 0.741(13) 1 d PG B 2 H1J H 0.0949 0.6434 0.3606 0.056 Uiso 0.741(13) 1 calc PR B 2 C1I C 0.0215(3) 0.69583(14) 0.3787(4) 0.0589(14) Uani 0.741(13) 1 d PG B 2 H1I H -0.0227 0.6804 0.4011 0.071 Uiso 0.741(13) 1 calc PR B 2 C1H C 0.0164(3) 0.74042(14) 0.3700(3) 0.0567(9) Uani 0.741(13) 1 d PG B 2 H1H H -0.0313 0.7554 0.3865 0.068 Uiso 0.741(13) 1 calc PR B 2 C1G C 0.0811(4) 0.76304(11) 0.3373(3) 0.0459(9) Uani 0.741(13) 1 d PG B 2 H1G H 0.0776 0.7935 0.3314 0.055 Uiso 0.741(13) 1 calc PR B 2 C1F C 0.1509(3) 0.74106(16) 0.3132(3) 0.0340(8) Uani 0.741(13) 1 d PG B 2 H1F H 0.1951 0.7565 0.2909 0.041 Uiso 0.741(13) 1 calc PR B 2 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 O2A 0.0269(6) 0.0326(6) 0.0327(6) 0.0036(5) 0.0027(5) -0.0051(5) O2 0.0257(6) 0.0293(6) 0.0344(6) -0.0030(5) 0.0033(5) 0.0046(5) O1A 0.0275(6) 0.0344(7) 0.0333(6) 0.0034(5) 0.0032(5) -0.0055(5) O1 0.0258(6) 0.0307(6) 0.0349(7) -0.0024(5) 0.0042(5) 0.0054(5) N3 0.0311(8) 0.0307(8) 0.0284(8) 0.0003(6) 0.0027(6) 0.0009(6) N2A 0.0341(8) 0.0316(8) 0.0271(7) 0.0005(6) 0.0021(6) -0.0020(7) N4 0.0350(8) 0.0310(8) 0.0331(8) 0.0025(6) 0.0057(7) -0.0003(7) N1 0.0391(9) 0.0301(8) 0.0326(8) -0.0010(6) 0.0078(7) 0.0007(7) N2 0.0323(8) 0.0278(7) 0.0294(8) 0.0001(6) 0.0026(6) 0.0031(6) N3A 0.0329(8) 0.0319(8) 0.0278(8) 0.0003(6) 0.0020(6) -0.0014(7) C44A 0.0391(10) 0.0286(9) 0.0294(9) 0.0034(7) 0.0059(8) -0.0019(8) N4A 0.0394(9) 0.0354(8) 0.0315(8) -0.0016(7) 0.0038(7) 0.0029(7) N1A 0.0441(9) 0.0324(8) 0.0300(8) 0.0007(7) 0.0047(7) 0.0007(7) C8A 0.0387(10) 0.0279(9) 0.0266(9) 0.0031(7) 0.0045(8) -0.0032(8) C44 0.0327(10) 0.0266(9) 0.0307(9) -0.0022(7) 0.0059(8) 0.0024(7) C26A 0.0363(10) 0.0298(9) 0.0263(9) 0.0020(7) 0.0009(8) -0.0024(8) C45 0.0374(10) 0.0283(9) 0.0317(9) 0.0006(8) 0.0067(8) 0.0043(8) C6 0.0477(11) 0.0275(9) 0.0314(10) -0.0002(8) 0.0120(9) 0.0069(8) C33A 0.0358(10) 0.0317(9) 0.0278(9) 0.0027(7) 0.0041(8) -0.0015(8) C27A 0.0331(13) 0.0353(14) 0.0263(9) -0.0010(8) 0.0019(9) -0.0020(11) C28A 0.051(3) 0.0439(16) 0.061(3) -0.019(2) 0.025(2) -0.0082(16) C29A 0.056(3) 0.062(2) 0.091(4) -0.029(3) 0.044(3) -0.0137(19) C30A 0.053(2) 0.067(2) 0.0653(17) -0.0089(15) 0.0285(15) -0.0218(19) C31A 0.0578(15) 0.0432(17) 0.051(3) 0.0010(17) 0.016(2) -0.0137(14) C32A 0.0428(12) 0.0366(15) 0.032(3) 0.0024(18) 0.0079(18) -0.0014(11) C27 0.0327(9) 0.0326(9) 0.0259(9) 0.0002(7) 0.0021(7) 0.0019(8) C9A 0.0367(10) 0.0307(9) 0.0299(9) 0.0032(8) 0.0034(8) -0.0013(8) C26 0.0322(9) 0.0277(9) 0.0288(9) -0.0015(7) 0.0017(8) 0.0002(7) C35 0.0286(9) 0.0422(11) 0.0368(10) 0.0055(8) 0.0049(8) -0.0040(8) C34A 0.0327(10) 0.0336(10) 0.0296(9) 0.0028(8) 0.0045(8) -0.0011(8) C7A 0.0413(11) 0.0277(9) 0.0282(9) 0.0032(7) 0.0039(8) -0.0039(8) C45A 0.0468(11) 0.0302(9) 0.0320(10) -0.0004(8) 0.0071(9) -0.0037(8) C40A 0.0302(9) 0.0359(10) 0.0358(10) 0.0019(8) 0.0018(8) 0.0007(8) C7 0.0369(10) 0.0253(9) 0.0301(9) -0.0032(7) 0.0072(8) 0.0033(8) C9 0.0322(9) 0.0304(9) 0.0327(9) -0.0045(8) 0.0044(8) 0.0023(8) C19 0.0335(9) 0.0277(9) 0.0292(9) -0.0006(7) 0.0032(8) 0.0036(8) C35A 0.0291(9) 0.0319(9) 0.0354(10) 0.0021(8) 0.0026(8) 0.0033(8) C37A 0.0313(9) 0.0323(9) 0.0330(9) 0.0051(8) 0.0050(8) 0.0000(8) C20 0.0351(12) 0.0323(13) 0.0285(9) 0.0025(8) 0.0050(8) 0.0043(10) C25 0.050(2) 0.0382(13) 0.054(3) 0.0113(18) 0.023(2) 0.0063(13) C24 0.053(2) 0.0535(16) 0.075(4) 0.019(2) 0.035(2) 0.0116(16) C23 0.0518(18) 0.0583(16) 0.0631(19) 0.0112(14) 0.0262(15) 0.0245(14) C22 0.0571(14) 0.0386(13) 0.043(3) 0.0069(13) 0.0124(18) 0.0182(12) C21 0.0401(11) 0.0348(14) 0.027(2) 0.0032(16) 0.0044(16) 0.0056(10) C8 0.0339(10) 0.0272(9) 0.0313(9) -0.0026(7) 0.0062(8) 0.0028(8) C37 0.0314(10) 0.0310(9) 0.0346(10) -0.0029(8) 0.0036(8) 0.0003(8) C13A 0.0415(11) 0.0367(10) 0.0388(10) -0.0084(8) -0.0028(9) 0.0037(9) C32 0.0347(10) 0.0326(10) 0.0446(11) -0.0030(8) 0.0096(9) -0.0015(8) C36 0.0359(10) 0.0414(11) 0.0351(10) 0.0081(8) 0.0051(8) -0.0015(9) C6A 0.0513(12) 0.0280(9) 0.0303(9) 0.0000(8) 0.0073(9) -0.0073(8) C33 0.0323(10) 0.0293(9) 0.0299(9) -0.0016(7) 0.0055(8) 0.0018(8) C34 0.0309(9) 0.0305(9) 0.0318(9) -0.0021(8) 0.0045(8) 0.0021(7) C15A 0.0362(10) 0.0434(11) 0.0395(11) -0.0007(9) 0.0000(9) -0.0021(9) C50 0.0415(11) 0.0356(10) 0.0354(10) 0.0018(8) 0.0041(9) 0.0009(8) C19A 0.0384(10) 0.0310(9) 0.0251(9) 0.0012(7) 0.0007(8) -0.0042(8) C12A 0.0345(10) 0.0349(10) 0.0342(10) 0.0048(8) 0.0034(8) -0.0023(8) C14A 0.0380(10) 0.0355(10) 0.0426(11) -0.0064(9) -0.0020(9) 0.0060(8) C15 0.0295(10) 0.0455(11) 0.0403(11) -0.0004(9) -0.0005(8) -0.0008(8) C39A 0.0412(11) 0.0528(12) 0.0439(11) -0.0151(10) -0.0013(9) 0.0111(10) C40 0.0330(10) 0.0368(10) 0.0373(10) 0.0008(8) 0.0008(8) -0.0022(8) C38A 0.0351(11) 0.0535(13) 0.0511(12) -0.0122(10) -0.0033(9) 0.0133(10) C14 0.0314(10) 0.0337(10) 0.0431(11) 0.0033(8) 0.0005(8) -0.0037(8) C5A 0.0544(12) 0.0360(10) 0.0345(10) -0.0020(8) 0.0009(9) -0.0072(9) C12 0.0304(9) 0.0336(10) 0.0372(10) -0.0059(8) 0.0020(8) 0.0025(8) C50A 0.0529(12) 0.0362(10) 0.0357(10) -0.0031(8) 0.0025(9) -0.0025(9) C36A 0.0332(10) 0.0305(9) 0.0335(9) -0.0022(8) 0.0034(8) 0.0014(8) C11 0.0320(10) 0.0577(13) 0.0471(12) 0.0057(10) 0.0021(9) -0.0112(9) C31 0.0442(11) 0.0326(10) 0.0586(13) 0.0019(9) 0.0149(10) 0.0070(9) C38 0.0348(11) 0.0531(13) 0.0606(14) 0.0192(11) -0.0052(10) -0.0143(10) C5 0.0492(12) 0.0398(11) 0.0344(10) 0.0039(9) 0.0050(9) 0.0038(9) C13 0.0383(11) 0.0334(10) 0.0419(11) 0.0051(8) -0.0016(9) -0.0015(8) C43A 0.0334(11) 0.0546(13) 0.0488(12) 0.0002(10) 0.0027(9) -0.0022(9) C30 0.0444(12) 0.0465(12) 0.0595(13) 0.0054(10) 0.0200(11) 0.0133(10) C1 0.0562(13) 0.0322(10) 0.0381(11) -0.0018(8) 0.0156(10) 0.0006(9) C42A 0.0422(11) 0.0470(12) 0.0436(11) 0.0062(9) -0.0024(9) 0.0002(9) C39 0.0390(11) 0.0502(12) 0.0505(12) 0.0194(10) -0.0019(10) -0.0101(10) C20A 0.0389(19) 0.0415(15) 0.0252(11) -0.0029(10) 0.0022(15) -0.0098(16) C25A 0.050(3) 0.0453(19) 0.065(5) -0.018(2) 0.027(3) -0.0100(17) C24A 0.043(3) 0.062(3) 0.077(5) -0.023(3) 0.027(3) -0.010(2) C23A 0.051(4) 0.072(3) 0.055(3) -0.007(2) 0.019(3) -0.030(3) C22A 0.050(4) 0.059(2) 0.083(2) 0.021(2) 0.011(3) -0.021(2) C21A 0.042(3) 0.0512(19) 0.063(3) 0.0206(19) 0.0046(19) -0.0109(19) C28 0.0440(12) 0.0374(11) 0.0538(12) 0.0110(9) 0.0173(10) 0.0041(9) C1A 0.0586(13) 0.0347(10) 0.0375(11) 0.0007(9) 0.0115(10) -0.0027(9) C42 0.0502(13) 0.0674(15) 0.0436(12) -0.0075(11) -0.0024(10) 0.0030(11) C2 0.0826(17) 0.0383(11) 0.0424(12) 0.0042(10) 0.0267(12) 0.0002(11) C48A 0.0723(16) 0.0462(12) 0.0400(12) -0.0136(10) 0.0148(11) -0.0116(11) C10 0.0378(11) 0.0509(12) 0.0405(11) 0.0091(9) 0.0043(9) -0.0068(9) C46A 0.0520(12) 0.0391(11) 0.0412(11) -0.0039(9) 0.0082(10) 0.0027(9) C49A 0.0616(14) 0.0454(12) 0.0337(10) -0.0024(9) 0.0012(10) -0.0118(11) C29 0.0451(12) 0.0484(12) 0.0735(16) 0.0151(11) 0.0300(12) 0.0053(10) C10A 0.0396(11) 0.0643(14) 0.0354(10) -0.0116(10) 0.0038(9) 0.0056(10) C43 0.0374(11) 0.0620(14) 0.0495(12) 0.0015(11) 0.0012(10) 0.0003(10) C4 0.0603(14) 0.0494(12) 0.0339(10) 0.0029(9) 0.0038(10) 0.0139(11) C2A 0.0782(16) 0.0360(11) 0.0455(12) -0.0069(10) 0.0253(12) -0.0054(11) C11A 0.0328(11) 0.0686(15) 0.0453(12) -0.0117(11) 0.0032(9) 0.0079(10) C4A 0.0702(15) 0.0426(12) 0.0328(10) -0.0022(9) 0.0027(10) -0.0165(11) C46 0.0416(11) 0.0360(10) 0.0377(10) 0.0018(8) 0.0063(9) -0.0015(9) C3A 0.0825(17) 0.0441(12) 0.0319(11) -0.0065(9) 0.0140(11) -0.0224(12) C48 0.0657(14) 0.0445(12) 0.0364(11) 0.0127(9) 0.0068(10) 0.0019(11) C41A 0.0368(11) 0.0465(12) 0.0496(12) -0.0067(10) -0.0073(9) 0.0005(9) C47 0.0574(13) 0.0419(11) 0.0440(12) 0.0094(9) 0.0118(10) -0.0049(10) C49 0.0482(12) 0.0423(11) 0.0364(11) 0.0029(9) -0.0022(9) 0.0060(9) C3 0.0827(17) 0.0442(12) 0.0342(11) 0.0103(9) 0.0175(12) 0.0156(12) C47A 0.0647(15) 0.0465(12) 0.0476(13) -0.0132(10) 0.0132(11) 0.0025(11) C41 0.0441(12) 0.0534(14) 0.0781(17) 0.0197(12) -0.0115(12) -0.0019(11) C17A 0.0378(13) 0.0783(19) 0.0536(15) -0.0095(14) -0.0012(11) -0.0087(13) C17 0.0410(14) 0.0522(16) 0.0690(18) 0.0062(14) -0.0182(13) -0.0090(12) C16 0.0388(13) 0.0505(14) 0.0551(15) 0.0018(12) -0.0077(11) 0.0076(11) C18A 0.0582(18) 0.099(2) 0.0596(17) 0.0337(18) -0.0253(14) -0.0264(17) C18 0.0391(14) 0.106(2) 0.0371(13) -0.0010(15) -0.0044(11) -0.0030(15) C16A 0.0482(16) 0.082(2) 0.101(2) -0.0504(19) -0.0291(16) 0.0130(15) C1B 0.0410(14) 0.0522(16) 0.0690(18) 0.0062(14) -0.0182(13) -0.0090(12) C1C 0.0388(13) 0.0505(14) 0.0551(15) 0.0018(12) -0.0077(11) 0.0076(11) C1D 0.0391(14) 0.106(2) 0.0371(13) -0.0010(15) -0.0044(11) -0.0030(15) C18B 0.0582(18) 0.099(2) 0.0596(17) 0.0337(18) -0.0253(14) -0.0264(17) C16B 0.0482(16) 0.082(2) 0.101(2) -0.0504(19) -0.0291(16) 0.0130(15) C17B 0.0378(13) 0.0783(19) 0.0536(15) -0.0095(14) -0.0012(11) -0.0087(13) C27B 0.0331(13) 0.0353(14) 0.0263(9) -0.0010(8) 0.0019(9) -0.0020(11) C28B 0.051(3) 0.0439(16) 0.061(3) -0.019(2) 0.025(2) -0.0082(16) C29B 0.056(3) 0.062(2) 0.091(4) -0.029(3) 0.044(3) -0.0137(19) C30B 0.053(2) 0.067(2) 0.0653(17) -0.0089(15) 0.0285(15) -0.0218(19) C31B 0.0578(15) 0.0432(17) 0.051(3) 0.0010(17) 0.016(2) -0.0137(14) C32B 0.0428(12) 0.0366(15) 0.032(3) 0.0024(18) 0.0079(18) -0.0014(11) C20B 0.0389(19) 0.0415(15) 0.0252(11) -0.0029(10) 0.0022(15) -0.0098(16) C25B 0.050(3) 0.0453(19) 0.065(5) -0.018(2) 0.027(3) -0.0100(17) C24B 0.043(3) 0.062(3) 0.077(5) -0.023(3) 0.027(3) -0.010(2) C23B 0.051(4) 0.072(3) 0.055(3) -0.007(2) 0.019(3) -0.030(3) C22B 0.050(4) 0.059(2) 0.083(2) 0.021(2) 0.011(3) -0.021(2) C21B 0.042(3) 0.0512(19) 0.063(3) 0.0206(19) 0.0046(19) -0.0109(19) C1E 0.0351(12) 0.0323(13) 0.0285(9) 0.0025(8) 0.0050(8) 0.0043(10) C1J 0.050(2) 0.0382(13) 0.054(3) 0.0113(18) 0.023(2) 0.0063(13) C1I 0.053(2) 0.0535(16) 0.075(4) 0.019(2) 0.035(2) 0.0116(16) C1H 0.0518(18) 0.0583(16) 0.0631(19) 0.0112(14) 0.0262(15) 0.0245(14) C1G 0.0571(14) 0.0386(13) 0.043(3) 0.0069(13) 0.0124(18) 0.0182(12) C1F 0.0401(11) 0.0348(14) 0.027(2) 0.0032(16) 0.0044(16) 0.0056(10) _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 O2A O1A 1.4876(16) . ? O2A C26A 1.413(2) . ? O2 O1 1.4906(16) . ? O2 C26 1.420(2) . ? O1A C19A 1.413(2) . ? O1 C19 1.413(2) . ? N3 C26 1.464(2) . ? N3 C33 1.285(2) . ? N2A C8A 1.283(2) . ? N2A C19A 1.462(2) . ? N4 C44 1.284(2) . ? N4 C33 1.440(2) . ? N1 C7 1.283(2) . ? N1 C8 1.442(2) . ? N2 C19 1.463(2) . ? N2 C8 1.285(2) . ? N3A C26A 1.464(2) . ? N3A C33A 1.285(2) . ? C44A N4A 1.285(2) . ? C44A C26A 1.540(2) . ? C44A C45A 1.466(3) . ? N4A C33A 1.441(2) . ? N1A C8A 1.444(2) . ? N1A C7A 1.285(2) . ? C8A C9A 1.461(3) . ? C44 C45 1.467(2) . ? C44 C26 1.540(2) . ? C26A C27A 1.498(4) . ? C26A C27B 1.566(8) . ? C45 C50 1.398(3) . ? C45 C46 1.397(3) . ? C6 C7 1.469(3) . ? C6 C5 1.395(3) . ? C6 C1 1.396(3) . ? C33A C34A 1.465(2) . ? C27A C28A 1.3900 . ? C27A C32A 1.3900 . ? C28A H28A 0.9500 . ? C28A C29A 1.3900 . ? C29A H29A 0.9500 . ? C29A C30A 1.3900 . ? C30A H30A 0.9500 . ? C30A C31A 1.3900 . ? C31A H31A 0.9500 . ? C31A C32A 1.3900 . ? C32A H32A 0.9500 . ? C27 C26 1.518(2) . ? C27 C32 1.388(2) . ? C27 C28 1.379(3) . ? C9A C14A 1.386(3) . ? C9A C10A 1.386(3) . ? C35 H35 0.9500 . ? C35 C36 1.378(3) . ? C35 C34 1.385(3) . ? C34A C35A 1.382(3) . ? C34A C39A 1.398(3) . ? C7A C6A 1.463(3) . ? C7A C19A 1.540(3) . ? C45A C50A 1.395(3) . ? C45A C46A 1.396(3) . ? C40A C37A 1.531(3) . ? C40A C43A 1.538(3) . ? C40A C42A 1.532(3) . ? C40A C41A 1.529(3) . ? C7 C19 1.537(2) . ? C9 C8 1.463(3) . ? C9 C14 1.388(3) . ? C9 C10 1.388(3) . ? C19 C20 1.545(12) . ? C19 C1E 1.518(4) . ? C35A H35A 0.9500 . ? C35A C36A 1.379(3) . ? C37A C38A 1.389(3) . ? C37A C36A 1.389(3) . ? C20 C25 1.3900 . ? C20 C21 1.3900 . ? C25 H25 0.9500 . ? C25 C24 1.3900 . ? C24 H24 0.9500 . ? C24 C23 1.3900 . ? C23 H23 0.9500 . ? C23 C22 1.3900 . ? C22 H22 0.9500 . ? C22 C21 1.3900 . ? C21 H21 0.9500 . ? C37 C36 1.391(3) . ? C37 C40 1.526(3) . ? C37 C38 1.388(3) . ? C13A H13A 0.9500 . ? C13A C12A 1.398(3) . ? C13A C14A 1.376(3) . ? C32 H32 0.9500 . ? C32 C31 1.385(3) . ? C36 H36 0.9500 . ? C6A C5A 1.394(3) . ? C6A C1A 1.396(3) . ? C33 C34 1.467(2) . ? C34 C39 1.385(3) . ? C15A C12A 1.529(3) . ? C15A C17A 1.535(3) . ? C15A C18A 1.528(3) . ? C15A C16A 1.521(3) . ? C15A C18B 1.47(3) . ? C15A C16B 1.46(3) . ? C15A C17B 1.58(2) . ? C50 H50 0.9500 . ? C50 C49 1.381(3) . ? C19A C20A 1.548(5) . ? C19A C20B 1.462(11) . ? C12A C11A 1.384(3) . ? C14A H14A 0.9500 . ? C15 C12 1.528(3) . ? C15 C17 1.527(3) . ? C15 C16 1.532(3) . ? C15 C18 1.514(3) . ? C15 C1B 1.513(17) . ? C15 C1C 1.560(15) . ? C15 C1D 1.599(18) . ? C39A H39A 0.9500 . ? C39A C38A 1.375(3) . ? C40 C42 1.528(3) . ? C40 C43 1.537(3) . ? C40 C41 1.526(3) . ? C38A H38A 0.9500 . ? C14 H14 0.9500 . ? C14 C13 1.375(3) . ? C5A H5A 0.9500 . ? C5A C4A 1.382(3) . ? C12 C11 1.392(3) . ? C12 C13 1.393(3) . ? C50A H50A 0.9500 . ? C50A C49A 1.386(3) . ? C36A H36A 0.9500 . ? C11 H11 0.9500 . ? C11 C10 1.380(3) . ? C31 H31 0.9500 . ? C31 C30 1.376(3) . ? C38 H38 0.9500 . ? C38 C39 1.380(3) . ? C5 H5 0.9500 . ? C5 C4 1.386(3) . ? C13 H13 0.9500 . ? C43A H43A 0.9800 . ? C43A H43B 0.9800 . ? C43A H43C 0.9800 . ? C30 H30 0.9500 . ? C30 C29 1.381(3) . ? C1 H1 0.9500 . ? C1 C2 1.379(3) . ? C42A H42A 0.9800 . ? C42A H42B 0.9800 . ? C42A H42C 0.9800 . ? C39 H39 0.9500 . ? C20A C25A 1.3900 . ? C20A C21A 1.3900 . ? C25A H25A 0.9500 . ? C25A C24A 1.3900 . ? C24A H24A 0.9500 . ? C24A C23A 1.3900 . ? C23A H23A 0.9500 . ? C23A C22A 1.3900 . ? C22A H22A 0.9500 . ? C22A C21A 1.3900 . ? C21A H21A 0.9500 . ? C28 H28 0.9500 . ? C28 C29 1.385(3) . ? C1A H1A 0.9500 . ? C1A C2A 1.386(3) . ? C42 H42D 0.9800 . ? C42 H42E 0.9800 . ? C42 H42F 0.9800 . ? C2 H2 0.9500 . ? C2 C3 1.379(3) . ? C48A H48A 0.9500 . ? C48A C49A 1.383(3) . ? C48A C47A 1.384(3) . ? C10 H10 0.9500 . ? C46A H46A 0.9500 . ? C46A C47A 1.380(3) . ? C49A H49A 0.9500 . ? C29 H29 0.9500 . ? C10A H10A 0.9500 . ? C10A C11A 1.380(3) . ? C43 H43D 0.9800 . ? C43 H43E 0.9800 . ? C43 H43F 0.9800 . ? C4 H4 0.9500 . ? C4 C3 1.383(3) . ? C2A H2A 0.9500 . ? C2A C3A 1.378(3) . ? C11A H11A 0.9500 . ? C4A H4A 0.9500 . ? C4A C3A 1.378(3) . ? C46 H46 0.9500 . ? C46 C47 1.378(3) . ? C3A H3A 0.9500 . ? C48 H48 0.9500 . ? C48 C47 1.384(3) . ? C48 C49 1.379(3) . ? C41A H41A 0.9800 . ? C41A H41B 0.9800 . ? C41A H41C 0.9800 . ? C47 H47 0.9500 . ? C49 H49 0.9500 . ? C3 H3 0.9500 . ? C47A H47A 0.9500 . ? C41 H41D 0.9800 . ? C41 H41E 0.9800 . ? C41 H41F 0.9800 . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C17 H17G 0.9800 . ? C17 H17H 0.9800 . ? C17 H17I 0.9800 . ? C16 H16G 0.9800 . ? C16 H16H 0.9800 . ? C16 H16I 0.9800 . ? C18A H18A 0.9800 . ? C18A H18B 0.9800 . ? C18A H18C 0.9800 . ? C18 H18G 0.9800 . ? C18 H18H 0.9800 . ? C18 H18I 0.9800 . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? C1B H1BA 0.9800 . ? C1B H1BB 0.9800 . ? C1B H1BC 0.9800 . ? C1C H1CA 0.9800 . ? C1C H1CB 0.9800 . ? C1C H1CC 0.9800 . ? C1D H1DA 0.9800 . ? C1D H1DB 0.9800 . ? C1D H1DC 0.9800 . ? C18B H18D 0.9800 . ? C18B H18E 0.9800 . ? C18B H18F 0.9800 . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 0.9800 . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C27B C28B 1.3900 . ? C27B C32B 1.3900 . ? C28B H28B 0.9500 . ? C28B C29B 1.3900 . ? C29B H29B 0.9500 . ? C29B C30B 1.3900 . ? C30B H30B 0.9500 . ? C30B C31B 1.3900 . ? C31B H31B 0.9500 . ? C31B C32B 1.3900 . ? C32B H32B 0.9500 . ? C20B C25B 1.3900 . ? C20B C21B 1.3900 . ? C25B H25B 0.9500 . ? C25B C24B 1.3900 . ? C24B H24B 0.9500 . ? C24B C23B 1.3900 . ? C23B H23B 0.9500 . ? C23B C22B 1.3900 . ? C22B H22B 0.9500 . ? C22B C21B 1.3900 . ? C21B H21B 0.9500 . ? C1E C1J 1.3900 . ? C1E C1F 1.3900 . ? C1J H1J 0.9500 . ? C1J C1I 1.3900 . ? C1I H1I 0.9500 . ? C1I C1H 1.3900 . ? C1H H1H 0.9500 . ? C1H C1G 1.3900 . ? C1G H1G 0.9500 . ? C1G C1F 1.3900 . ? C1F H1F 0.9500 . ? 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 C26A O2A O1A 104.56(11) . . ? C26 O2 O1 104.30(11) . . ? C19A O1A O2A 103.71(11) . . ? C19 O1 O2 104.09(11) . . ? C33 N3 C26 104.90(14) . . ? C8A N2A C19A 105.10(14) . . ? C44 N4 C33 104.58(14) . . ? C7 N1 C8 104.35(15) . . ? C8 N2 C19 104.87(14) . . ? C33A N3A C26A 105.05(14) . . ? N4A C44A C26A 110.41(15) . . ? N4A C44A C45A 124.01(17) . . ? C45A C44A C26A 125.58(16) . . ? C44A N4A C33A 104.45(15) . . ? C7A N1A C8A 104.56(15) . . ? N2A C8A N1A 116.96(16) . . ? N2A C8A C9A 124.49(16) . . ? N1A C8A C9A 118.55(16) . . ? N4 C44 C45 123.86(16) . . ? N4 C44 C26 110.27(15) . . ? C45 C44 C26 125.87(16) . . ? O2A C26A N3A 111.29(14) . . ? O2A C26A C44A 112.38(13) . . ? O2A C26A C27A 106.65(19) . . ? O2A C26A C27B 100.0(4) . . ? N3A C26A C44A 102.87(14) . . ? N3A C26A C27A 110.31(17) . . ? N3A C26A C27B 110.4(3) . . ? C44A C26A C27B 120.1(4) . . ? C27A C26A C44A 113.4(2) . . ? C27A C26A C27B 7.5(5) . . ? C50 C45 C44 121.42(16) . . ? C46 C45 C44 119.22(17) . . ? C46 C45 C50 119.36(17) . . ? C5 C6 C7 121.59(17) . . ? C5 C6 C1 119.53(18) . . ? C1 C6 C7 118.88(18) . . ? N3A C33A N4A 117.08(16) . . ? N3A C33A C34A 124.08(16) . . ? N4A C33A C34A 118.83(16) . . ? C28A C27A C26A 116.5(3) . . ? C28A C27A C32A 120.0 . . ? C32A C27A C26A 123.5(3) . . ? C27A C28A H28A 120.0 . . ? C29A C28A C27A 120.0 . . ? C29A C28A H28A 120.0 . . ? C28A C29A H29A 120.0 . . ? C30A C29A C28A 120.0 . . ? C30A C29A H29A 120.0 . . ? C29A C30A H30A 120.0 . . ? C29A C30A C31A 120.0 . . ? C31A C30A H30A 120.0 . . ? C30A C31A H31A 120.0 . . ? C32A C31A C30A 120.0 . . ? C32A C31A H31A 120.0 . . ? C27A C32A H32A 120.0 . . ? C31A C32A C27A 120.0 . . ? C31A C32A H32A 120.0 . . ? C32 C27 C26 122.03(16) . . ? C28 C27 C26 118.64(16) . . ? C28 C27 C32 119.30(17) . . ? C14A C9A C8A 121.47(17) . . ? C14A C9A C10A 118.11(17) . . ? C10A C9A C8A 120.42(17) . . ? O2 C26 N3 110.83(13) . . ? O2 C26 C44 112.18(13) . . ? O2 C26 C27 104.27(13) . . ? N3 C26 C44 103.01(14) . . ? N3 C26 C27 110.57(14) . . ? C27 C26 C44 116.13(14) . . ? C36 C35 H35 119.8 . . ? C36 C35 C34 120.45(17) . . ? C34 C35 H35 119.8 . . ? C35A C34A C33A 121.07(16) . . ? C35A C34A C39A 118.24(17) . . ? C39A C34A C33A 120.69(17) . . ? N1A C7A C6A 124.29(17) . . ? N1A C7A C19A 110.21(15) . . ? C6A C7A C19A 125.48(16) . . ? C50A C45A C44A 121.66(17) . . ? C50A C45A C46A 119.28(18) . . ? C46A C45A C44A 119.06(18) . . ? C37A C40A C43A 110.20(15) . . ? C37A C40A C42A 108.37(15) . . ? C42A C40A C43A 109.19(16) . . ? C41A C40A C37A 112.43(15) . . ? C41A C40A C43A 107.91(16) . . ? C41A C40A C42A 108.69(16) . . ? N1 C7 C6 123.84(17) . . ? N1 C7 C19 110.49(15) . . ? C6 C7 C19 125.66(16) . . ? C14 C9 C8 120.77(16) . . ? C14 C9 C10 118.47(17) . . ? C10 C9 C8 120.75(17) . . ? O1 C19 N2 111.18(13) . . ? O1 C19 C7 112.37(13) . . ? O1 C19 C20 101.0(6) . . ? O1 C19 C1E 106.5(2) . . ? N2 C19 C7 103.03(14) . . ? N2 C19 C20 111.2(4) . . ? N2 C19 C1E 109.64(16) . . ? C7 C19 C20 118.3(6) . . ? C1E C19 C7 114.2(2) . . ? C1E C19 C20 5.6(7) . . ? C34A C35A H35A 119.6 . . ? C36A C35A C34A 120.78(16) . . ? C36A C35A H35A 119.6 . . ? C38A C37A C40A 120.03(16) . . ? C36A C37A C40A 123.03(16) . . ? C36A C37A C38A 116.91(17) . . ? C25 C20 C19 122.9(10) . . ? C25 C20 C21 120.0 . . ? C21 C20 C19 117.1(10) . . ? C20 C25 H25 120.0 . . ? C20 C25 C24 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C24 H24 120.0 . . ? C23 C24 C25 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C23 H23 120.0 . . ? C24 C23 C22 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C22 H22 120.0 . . ? C21 C22 C23 120.0 . . ? C21 C22 H22 120.0 . . ? C20 C21 H21 120.0 . . ? C22 C21 C20 120.0 . . ? C22 C21 H21 120.0 . . ? N1 C8 C9 118.87(15) . . ? N2 C8 N1 117.14(16) . . ? N2 C8 C9 123.98(16) . . ? C36 C37 C40 121.99(16) . . ? C38 C37 C36 116.39(17) . . ? C38 C37 C40 121.61(16) . . ? C12A C13A H13A 119.0 . . ? C14A C13A H13A 119.0 . . ? C14A C13A C12A 122.03(18) . . ? C27 C32 H32 119.9 . . ? C31 C32 C27 120.23(17) . . ? C31 C32 H32 119.9 . . ? C35 C36 C37 122.12(17) . . ? C35 C36 H36 118.9 . . ? C37 C36 H36 118.9 . . ? C5A C6A C7A 121.70(18) . . ? C5A C6A C1A 119.17(18) . . ? C1A C6A C7A 119.12(18) . . ? N3 C33 N4 117.12(16) . . ? N3 C33 C34 124.03(16) . . ? N4 C33 C34 118.80(15) . . ? C35 C34 C33 120.67(16) . . ? C35 C34 C39 118.45(17) . . ? C39 C34 C33 120.86(16) . . ? C12A C15A C17A 111.99(17) . . ? C12A C15A C17B 109.5(8) . . ? C17A C15A C17B 49.9(9) . . ? C18A C15A C12A 108.05(17) . . ? C18A C15A C17A 107.7(2) . . ? C18A C15A C17B 61.1(9) . . ? C16A C15A C12A 111.94(18) . . ? C16A C15A C17A 106.5(2) . . ? C16A C15A C18A 110.6(2) . . ? C16A C15A C17B 138.0(8) . . ? C18B C15A C12A 108.1(10) . . ? C18B C15A C17A 137.3(11) . . ? C18B C15A C18A 44.0(14) . . ? C18B C15A C16A 70.4(14) . . ? C18B C15A C17B 102.9(16) . . ? C16B C15A C12A 102.3(10) . . ? C16B C15A C17A 57.4(10) . . ? C16B C15A C18A 149.6(10) . . ? C16B C15A C16A 57.8(11) . . ? C16B C15A C18B 126.6(17) . . ? C16B C15A C17B 106.9(13) . . ? C45 C50 H50 120.0 . . ? C49 C50 C45 119.92(18) . . ? C49 C50 H50 120.0 . . ? O1A C19A N2A 110.98(14) . . ? O1A C19A C7A 111.56(14) . . ? O1A C19A C20A 103.5(4) . . ? O1A C19A C20B 110.2(7) . . ? N2A C19A C7A 103.10(14) . . ? N2A C19A C20A 111.9(4) . . ? C7A C19A C20A 116.0(4) . . ? C20B C19A N2A 109.6(8) . . ? C20B C19A C7A 111.1(8) . . ? C20B C19A C20A 6.9(10) . . ? C13A C12A C15A 122.09(17) . . ? C11A C12A C13A 116.26(17) . . ? C11A C12A C15A 121.62(17) . . ? C9A C14A H14A 119.7 . . ? C13A C14A C9A 120.68(18) . . ? C13A C14A H14A 119.7 . . ? C12 C15 C16 107.51(17) . . ? C12 C15 C1C 115.3(6) . . ? C12 C15 C1D 106.9(6) . . ? C17 C15 C12 111.59(17) . . ? C17 C15 C16 108.30(19) . . ? C17 C15 C1C 131.7(6) . . ? C17 C15 C1D 68.1(7) . . ? C16 C15 C1C 46.3(6) . . ? C16 C15 C1D 143.8(7) . . ? C18 C15 C12 110.65(17) . . ? C18 C15 C17 108.7(2) . . ? C18 C15 C16 110.1(2) . . ? C18 C15 C1C 64.8(6) . . ? C18 C15 C1D 45.9(7) . . ? C1B C15 C12 116.1(6) . . ? C1B C15 C17 41.4(7) . . ? C1B C15 C16 67.8(7) . . ? C1B C15 C18 131.4(7) . . ? C1B C15 C1C 104.5(9) . . ? C1B C15 C1D 105.8(9) . . ? C1C C15 C1D 107.6(9) . . ? C34A C39A H39A 119.9 . . ? C38A C39A C34A 120.23(18) . . ? C38A C39A H39A 119.9 . . ? C37 C40 C42 108.23(16) . . ? C37 C40 C43 111.14(16) . . ? C37 C40 C41 111.81(16) . . ? C42 C40 C43 108.69(17) . . ? C41 C40 C42 109.28(18) . . ? C41 C40 C43 107.63(17) . . ? C37A C38A H38A 118.9 . . ? C39A C38A C37A 122.11(18) . . ? C39A C38A H38A 118.9 . . ? C9 C14 H14 119.8 . . ? C13 C14 C9 120.48(17) . . ? C13 C14 H14 119.8 . . ? C6A C5A H5A 119.9 . . ? C4A C5A C6A 120.3(2) . . ? C4A C5A H5A 119.9 . . ? C11 C12 C15 122.65(17) . . ? C11 C12 C13 116.66(17) . . ? C13 C12 C15 120.65(17) . . ? C45A C50A H50A 120.0 . . ? C49A C50A C45A 120.1(2) . . ? C49A C50A H50A 120.0 . . ? C35A C36A C37A 121.73(17) . . ? C35A C36A H36A 119.1 . . ? C37A C36A H36A 119.1 . . ? C12 C11 H11 119.0 . . ? C10 C11 C12 121.93(18) . . ? C10 C11 H11 119.0 . . ? C32 C31 H31 119.8 . . ? C30 C31 C32 120.44(18) . . ? C30 C31 H31 119.8 . . ? C37 C38 H38 118.9 . . ? C39 C38 C37 122.22(18) . . ? C39 C38 H38 118.9 . . ? C6 C5 H5 120.1 . . ? C4 C5 C6 119.7(2) . . ? C4 C5 H5 120.1 . . ? C14 C13 C12 122.05(18) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C40A C43A H43A 109.5 . . ? C40A C43A H43B 109.5 . . ? C40A C43A H43C 109.5 . . ? H43A C43A H43B 109.5 . . ? H43A C43A H43C 109.5 . . ? H43B C43A H43C 109.5 . . ? C31 C30 H30 120.4 . . ? C31 C30 C29 119.22(18) . . ? C29 C30 H30 120.4 . . ? C6 C1 H1 120.0 . . ? C2 C1 C6 120.0(2) . . ? C2 C1 H1 120.0 . . ? C40A C42A H42A 109.5 . . ? C40A C42A H42B 109.5 . . ? C40A C42A H42C 109.5 . . ? H42A C42A H42B 109.5 . . ? H42A C42A H42C 109.5 . . ? H42B C42A H42C 109.5 . . ? C34 C39 H39 119.8 . . ? C38 C39 C34 120.36(18) . . ? C38 C39 H39 119.8 . . ? C25A C20A C19A 120.5(5) . . ? C25A C20A C21A 120.0 . . ? C21A C20A C19A 119.5(5) . . ? C20A C25A H25A 120.0 . . ? C20A C25A C24A 120.0 . . ? C24A C25A H25A 120.0 . . ? C25A C24A H24A 120.0 . . ? C25A C24A C23A 120.0 . . ? C23A C24A H24A 120.0 . . ? C24A C23A H23A 120.0 . . ? C22A C23A C24A 120.0 . . ? C22A C23A H23A 120.0 . . ? C23A C22A H22A 120.0 . . ? C21A C22A C23A 120.0 . . ? C21A C22A H22A 120.0 . . ? C20A C21A H21A 120.0 . . ? C22A C21A C20A 120.0 . . ? C22A C21A H21A 120.0 . . ? C27 C28 H28 120.0 . . ? C27 C28 C29 120.09(18) . . ? C29 C28 H28 120.0 . . ? C6A C1A H1A 120.1 . . ? C2A C1A C6A 119.7(2) . . ? C2A C1A H1A 120.1 . . ? C40 C42 H42D 109.5 . . ? C40 C42 H42E 109.5 . . ? C40 C42 H42F 109.5 . . ? H42D C42 H42E 109.5 . . ? H42D C42 H42F 109.5 . . ? H42E C42 H42F 109.5 . . ? C1 C2 H2 119.8 . . ? C3 C2 C1 120.4(2) . . ? C3 C2 H2 119.8 . . ? C49A C48A H48A 119.9 . . ? C49A C48A C47A 120.24(19) . . ? C47A C48A H48A 119.9 . . ? C9 C10 H10 119.8 . . ? C11 C10 C9 120.41(18) . . ? C11 C10 H10 119.8 . . ? C45A C46A H46A 119.9 . . ? C47A C46A C45A 120.2(2) . . ? C47A C46A H46A 119.9 . . ? C50A C49A H49A 120.0 . . ? C48A C49A C50A 120.0(2) . . ? C48A C49A H49A 120.0 . . ? C30 C29 C28 120.70(19) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C9A C10A H10A 119.7 . . ? C11A C10A C9A 120.63(18) . . ? C11A C10A H10A 119.7 . . ? C40 C43 H43D 109.5 . . ? C40 C43 H43E 109.5 . . ? C40 C43 H43F 109.5 . . ? H43D C43 H43E 109.5 . . ? H43D C43 H43F 109.5 . . ? H43E C43 H43F 109.5 . . ? C5 C4 H4 119.9 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C1A C2A H2A 119.7 . . ? C3A C2A C1A 120.6(2) . . ? C3A C2A H2A 119.7 . . ? C12A C11A H11A 118.9 . . ? C10A C11A C12A 122.29(19) . . ? C10A C11A H11A 118.9 . . ? C5A C4A H4A 119.8 . . ? C3A C4A C5A 120.3(2) . . ? C3A C4A H4A 119.8 . . ? C45 C46 H46 120.0 . . ? C47 C46 C45 119.90(19) . . ? C47 C46 H46 120.0 . . ? C2A C3A C4A 119.90(19) . . ? C2A C3A H3A 120.0 . . ? C4A C3A H3A 120.0 . . ? C47 C48 H48 120.0 . . ? C49 C48 H48 120.0 . . ? C49 C48 C47 120.02(18) . . ? C40A C41A H41A 109.5 . . ? C40A C41A H41B 109.5 . . ? C40A C41A H41C 109.5 . . ? H41A C41A H41B 109.5 . . ? H41A C41A H41C 109.5 . . ? H41B C41A H41C 109.5 . . ? C46 C47 C48 120.41(19) . . ? C46 C47 H47 119.8 . . ? C48 C47 H47 119.8 . . ? C50 C49 H49 119.8 . . ? C48 C49 C50 120.37(19) . . ? C48 C49 H49 119.8 . . ? C2 C3 C4 120.10(19) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C48A C47A H47A 119.9 . . ? C46A C47A C48A 120.1(2) . . ? C46A C47A H47A 119.9 . . ? C40 C41 H41D 109.5 . . ? C40 C41 H41E 109.5 . . ? C40 C41 H41F 109.5 . . ? H41D C41 H41E 109.5 . . ? H41D C41 H41F 109.5 . . ? H41E C41 H41F 109.5 . . ? C15A C17A H17A 109.5 . . ? C15A C17A H17B 109.5 . . ? C15A C17A H17C 109.5 . . ? C15 C17 H17G 109.5 . . ? C15 C17 H17H 109.5 . . ? C15 C17 H17I 109.5 . . ? C15 C16 H16G 109.5 . . ? C15 C16 H16H 109.5 . . ? C15 C16 H16I 109.5 . . ? C15A C18A H18A 109.5 . . ? C15A C18A H18B 109.5 . . ? C15A C18A H18C 109.5 . . ? C15 C18 H18G 109.5 . . ? C15 C18 H18H 109.5 . . ? C15 C18 H18I 109.5 . . ? C15A C16A H16A 109.5 . . ? C15A C16A H16B 109.5 . . ? C15A C16A H16C 109.5 . . ? C15 C1B H1BA 109.5 . . ? C15 C1B H1BB 109.5 . . ? C15 C1B H1BC 109.5 . . ? H1BA C1B H1BB 109.5 . . ? H1BA C1B H1BC 109.5 . . ? H1BB C1B H1BC 109.5 . . ? C15 C1C H1CA 109.5 . . ? C15 C1C H1CB 109.5 . . ? C15 C1C H1CC 109.5 . . ? H1CA C1C H1CB 109.5 . . ? H1CA C1C H1CC 109.5 . . ? H1CB C1C H1CC 109.5 . . ? C15 C1D H1DA 109.5 . . ? C15 C1D H1DB 109.5 . . ? C15 C1D H1DC 109.5 . . ? H1DA C1D H1DB 109.5 . . ? H1DA C1D H1DC 109.5 . . ? H1DB C1D H1DC 109.5 . . ? C15A C18B H18D 109.5 . . ? C15A C18B H18E 109.5 . . ? C15A C18B H18F 109.5 . . ? H18D C18B H18E 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C15A C16B H16D 109.5 . . ? C15A C16B H16E 109.5 . . ? C15A C16B H16F 109.5 . . ? H16D C16B H16E 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? C15A C17B H17D 109.5 . . ? C15A C17B H17E 109.5 . . ? C15A C17B H17F 109.5 . . ? H17D C17B H17E 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C28B C27B C26A 122.9(6) . . ? C28B C27B C32B 120.0 . . ? C32B C27B C26A 117.1(6) . . ? C27B C28B H28B 120.0 . . ? C27B C28B C29B 120.0 . . ? C29B C28B H28B 120.0 . . ? C28B C29B H29B 120.0 . . ? C28B C29B C30B 120.0 . . ? C30B C29B H29B 120.0 . . ? C29B C30B H30B 120.0 . . ? C31B C30B C29B 120.0 . . ? C31B C30B H30B 120.0 . . ? C30B C31B H31B 120.0 . . ? C32B C31B C30B 120.0 . . ? C32B C31B H31B 120.0 . . ? C27B C32B H32B 120.0 . . ? C31B C32B C27B 120.0 . . ? C31B C32B H32B 120.0 . . ? C25B C20B C19A 119.0(11) . . ? C25B C20B C21B 120.0 . . ? C21B C20B C19A 121.0(11) . . ? C20B C25B H25B 120.0 . . ? C24B C25B C20B 120.0 . . ? C24B C25B H25B 120.0 . . ? C25B C24B H24B 120.0 . . ? C25B C24B C23B 120.0 . . ? C23B C24B H24B 120.0 . . ? C24B C23B H23B 120.0 . . ? C24B C23B C22B 120.0 . . ? C22B C23B H23B 120.0 . . ? C23B C22B H22B 120.0 . . ? C23B C22B C21B 120.0 . . ? C21B C22B H22B 120.0 . . ? C20B C21B H21B 120.0 . . ? C22B C21B C20B 120.0 . . ? C22B C21B H21B 120.0 . . ? C1J C1E C19 116.9(3) . . ? C1J C1E C1F 120.0 . . ? C1F C1E C19 123.1(3) . . ? C1E C1J H1J 120.0 . . ? C1E C1J C1I 120.0 . . ? C1I C1J H1J 120.0 . . ? C1J C1I H1I 120.0 . . ? C1H C1I C1J 120.0 . . ? C1H C1I H1I 120.0 . . ? C1I C1H H1H 120.0 . . ? C1I C1H C1G 120.0 . . ? C1G C1H H1H 120.0 . . ? C1H C1G H1G 120.0 . . ? C1H C1G C1F 120.0 . . ? C1F C1G H1G 120.0 . . ? C1E C1F H1F 120.0 . . ? C1G C1F C1E 120.0 . . ? C1G C1F H1F 120.0 . . ? data_mike _database_code_depnum_ccdc_archive 'CCDC 919639' #TrackingRef '16891_web_deposit_cif_file_0_RobertM.Edkins_1358263718.CN_dimer.cif' _audit_creation_date 2012-09-19 _audit_creation_method ; Olex2 1.1 (compiled Nov 1 2011 20:42:30, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C50 H46 N4' _chemical_formula_sum 'C50 H46 N4' _chemical_formula_weight 702.91 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 12.1735(2) _cell_length_b 12.2821(3) _cell_length_c 15.1686(3) _cell_angle_alpha 111.6050(4) _cell_angle_beta 101.1490(4) _cell_angle_gamma 98.8910(5) _cell_volume 2004.46(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9796 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 68.97 _cell_measurement_theta_min 3.26 _exptl_absorpt_coefficient_mu 0.521 _exptl_absorpt_correction_T_max 0.7532 _exptl_absorpt_correction_T_min 0.6246 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0648 before and 0.0340 after correction. The Ratio of minimum to maximum transmission is 0.8293. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 748 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of \w scans, each set at different \f and/or 2\q angles, with additional \f scans, each set at different \w and/or 2\q angles, to aid absorption correction parameters. Each image covering -0.50\ degrees in \w or \f. The crystal to detector distance was 5.00 cm ; _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_unetI/netI 0.0184 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 25172 _diffrn_reflns_theta_full 68.97 _diffrn_reflns_theta_max 68.97 _diffrn_reflns_theta_min 3.26 _diffrn_ambient_temperature 373.15 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'Bruker Pt 135 CCD area detector' _diffrn_measured_fraction_theta_full 0.894 _diffrn_measured_fraction_theta_max 0.894 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Pt 135 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_collimation 'focused optics' _diffrn_radiation_monochromator 'Bruker Helios multilayer optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54188 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'Microstar rotating anode' _diffrn_source_target Cu _diffrn_source_type 'rotating anode' _diffrn_standards_number 0 _reflns_number_gt 6470 _reflns_number_total 6673 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v8.18C (Bruker, 2012)' _computing_data_collection 'Proteum2 (Bruker, 2010)' _computing_data_reduction 'SAINT v8.18C (Bruker, 2012)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.181 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.038 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 493 _refine_ls_number_reflns 6673 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0373 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+0.7679P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0937 _refine_ls_wR_factor_ref 0.0943 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.74346(8) -0.05202(9) 0.38631(7) 0.0212(2) Uani 1 1 d . . . N3A N 0.98532(8) 0.21543(8) 0.37308(7) 0.0191(2) Uani 1 1 d . . . N1A N 1.04828(8) 0.04628(9) 0.27859(7) 0.0209(2) Uani 1 1 d . . . N3 N 0.86678(8) 0.01295(8) 0.31498(7) 0.0191(2) Uani 1 1 d . . . C9 C 0.95668(10) 0.34542(10) 0.67900(8) 0.0209(2) Uani 1 1 d . . . C21A C 1.26092(10) 0.34875(11) 0.55397(9) 0.0249(3) Uani 1 1 d . . . H21A H 1.2842 0.2759 0.5450 0.030 Uiso 1 1 calc R . . C9A C 0.75523(10) 0.13967(10) 0.03892(9) 0.0220(2) Uani 1 1 d . . . C22 C 0.62337(10) -0.24411(10) 0.25119(9) 0.0215(2) Uani 1 1 d . . . C11A C 0.78054(10) 0.14570(10) 0.20331(9) 0.0223(2) Uani 1 1 d . . . H11A H 0.7530 0.1602 0.2601 0.027 Uiso 1 1 calc R . . C6A C 0.88325(10) 0.11008(10) 0.20085(8) 0.0196(2) Uani 1 1 d . . . C8 C 0.84590(10) 0.31848(11) 0.61691(9) 0.0231(3) Uani 1 1 d . . . H8 H 0.7962 0.3697 0.6368 0.028 Uiso 1 1 calc R . . C2 C 0.83077(10) 0.03560(10) 0.39968(8) 0.0196(2) Uani 1 1 d . . . C7 C 0.80696(10) 0.21910(11) 0.52725(9) 0.0223(3) Uani 1 1 d . . . H7 H 0.7308 0.2026 0.4872 0.027 Uiso 1 1 calc R . . C4A C 1.09600(10) 0.23669(10) 0.40230(8) 0.0195(2) Uani 1 1 d . . . C10 C 1.02619(10) 0.26721(11) 0.64671(9) 0.0219(2) Uani 1 1 d . . . H10 H 1.1017 0.2824 0.6874 0.026 Uiso 1 1 calc R . . C8A C 0.85865(10) 0.10449(10) 0.03802(9) 0.0228(3) Uani 1 1 d . . . H8A H 0.8863 0.0899 -0.0187 0.027 Uiso 1 1 calc R . . C11 C 0.98777(10) 0.16764(10) 0.55648(9) 0.0217(2) Uani 1 1 d . . . H11 H 1.0371 0.1159 0.5366 0.026 Uiso 1 1 calc R . . C5 C 0.72067(10) -0.13594(10) 0.28987(8) 0.0204(2) Uani 1 1 d . . . C16A C 1.16674(10) 0.34924(10) 0.48502(8) 0.0204(2) Uani 1 1 d . . . C27 C 0.53687(11) -0.24147(11) 0.29918(10) 0.0293(3) Uani 1 1 d . . . H27 H 0.5438 -0.1725 0.3574 0.035 Uiso 1 1 calc R . . C4 C 0.79539(10) -0.09800(10) 0.24415(8) 0.0196(2) Uani 1 1 d . . . C15 C 1.12122(11) 0.47689(12) 0.83262(9) 0.0306(3) Uani 1 1 d . . . H15A H 1.1310 0.4068 0.8469 0.046 Uiso 1 1 calc R . . H15B H 1.1424 0.5494 0.8945 0.046 Uiso 1 1 calc R . . H15C H 1.1711 0.4878 0.7914 0.046 Uiso 1 1 calc R . . C5A C 1.13522(10) 0.12787(10) 0.34386(8) 0.0205(2) Uani 1 1 d . . . C17A C 1.13350(10) 0.45704(11) 0.49940(9) 0.0228(3) Uani 1 1 d . . . H17A H 1.0694 0.4579 0.4528 0.027 Uiso 1 1 calc R . . C6 C 0.87816(10) 0.14289(10) 0.49495(8) 0.0200(2) Uani 1 1 d . . . C21 C 0.70788(11) -0.16366(10) 0.06518(9) 0.0235(3) Uani 1 1 d . . . H21 H 0.6429 -0.1353 0.0810 0.028 Uiso 1 1 calc R . . C7A C 0.92251(10) 0.09011(10) 0.11782(9) 0.0215(2) Uani 1 1 d . . . H7A H 0.9930 0.0666 0.1153 0.026 Uiso 1 1 calc R . . C20A C 1.32026(11) 0.45449(12) 0.63539(9) 0.0285(3) Uani 1 1 d . . . H20A H 1.3843 0.4541 0.6822 0.034 Uiso 1 1 calc R . . C2A C 0.94687(10) 0.09502(10) 0.29119(8) 0.0194(2) Uani 1 1 d . . . C19 C 0.80416(12) -0.25690(11) -0.05602(9) 0.0305(3) Uani 1 1 d . . . H19 H 0.8058 -0.2916 -0.1229 0.037 Uiso 1 1 calc R . . C17 C 0.89503(11) -0.19600(10) 0.11601(9) 0.0243(3) Uani 1 1 d . . . H17 H 0.9585 -0.1903 0.1664 0.029 Uiso 1 1 calc R . . C24 C 0.51731(11) -0.44618(11) 0.13348(9) 0.0272(3) Uani 1 1 d . . . H24 H 0.5118 -0.5173 0.0774 0.033 Uiso 1 1 calc R . . C18A C 1.19290(11) 0.56239(11) 0.58076(9) 0.0268(3) Uani 1 1 d . . . H18A H 1.1698 0.6354 0.5901 0.032 Uiso 1 1 calc R . . C16 C 0.80111(10) -0.15267(10) 0.14063(8) 0.0210(2) Uani 1 1 d . . . C26A C 1.37874(12) -0.01412(13) 0.38799(10) 0.0317(3) Uani 1 1 d . . . H26A H 1.3893 -0.0848 0.3968 0.038 Uiso 1 1 calc R . . C12 C 0.99525(11) 0.45606(11) 0.77812(9) 0.0235(3) Uani 1 1 d . . . C12A C 0.68164(11) 0.14994(12) -0.05088(9) 0.0274(3) Uani 1 1 d . . . C10A C 0.71801(10) 0.16020(11) 0.12371(9) 0.0238(3) Uani 1 1 d . . . H10A H 0.6481 0.1847 0.1269 0.029 Uiso 1 1 calc R . . C18 C 0.89638(11) -0.24749(11) 0.01820(9) 0.0281(3) Uani 1 1 d . . . H18 H 0.9610 -0.2765 0.0020 0.034 Uiso 1 1 calc R . . C23 C 0.61325(11) -0.34907(11) 0.16791(9) 0.0234(3) Uani 1 1 d . . . H23 H 0.6722 -0.3539 0.1348 0.028 Uiso 1 1 calc R . . C19A C 1.28647(11) 0.56103(11) 0.64880(9) 0.0288(3) Uani 1 1 d . . . H19A H 1.3275 0.6333 0.7048 0.035 Uiso 1 1 calc R . . C22A C 1.25332(10) 0.10962(11) 0.35955(8) 0.0229(3) Uani 1 1 d . . . C27A C 1.26922(11) 0.00522(12) 0.37078(9) 0.0267(3) Uani 1 1 d . . . H27A H 1.2048 -0.0528 0.3666 0.032 Uiso 1 1 calc R . . C13 C 0.91868(12) 0.43542(12) 0.84303(9) 0.0302(3) Uani 1 1 d . . . H13A H 0.8380 0.4278 0.8113 0.045 Uiso 1 1 calc R . . H13B H 0.9438 0.5041 0.9076 0.045 Uiso 1 1 calc R . . H13C H 0.9255 0.3612 0.8515 0.045 Uiso 1 1 calc R . . C20 C 0.70934(12) -0.21549(11) -0.03241(9) 0.0283(3) Uani 1 1 d . . . H20 H 0.6455 -0.2227 -0.0832 0.034 Uiso 1 1 calc R . . C14 C 0.98207(12) 0.57037(11) 0.76199(9) 0.0292(3) Uani 1 1 d . . . H14A H 1.0308 0.5832 0.7205 0.044 Uiso 1 1 calc R . . H14B H 1.0059 0.6403 0.8258 0.044 Uiso 1 1 calc R . . H14C H 0.9011 0.5605 0.7294 0.044 Uiso 1 1 calc R . . C23A C 1.34848(11) 0.19368(12) 0.36521(10) 0.0312(3) Uani 1 1 d . . . H23A H 1.3385 0.2658 0.3586 0.037 Uiso 1 1 calc R . . C25A C 1.47280(11) 0.06838(13) 0.39247(10) 0.0338(3) Uani 1 1 d . . . H25A H 1.5477 0.0541 0.4037 0.041 Uiso 1 1 calc R . . C25 C 0.43020(11) -0.44039(12) 0.17978(11) 0.0334(3) Uani 1 1 d . . . H25 H 0.3637 -0.5060 0.1547 0.040 Uiso 1 1 calc R . . C14A C 0.61482(12) 0.24716(14) -0.01950(10) 0.0355(3) Uani 1 1 d . . . H14D H 0.5600 0.2240 0.0139 0.053 Uiso 1 1 calc R . . H14E H 0.5726 0.2551 -0.0779 0.053 Uiso 1 1 calc R . . H14F H 0.6691 0.3246 0.0255 0.053 Uiso 1 1 calc R . . C15A C 0.75691(14) 0.18469(17) -0.11086(11) 0.0442(4) Uani 1 1 d . . . H15D H 0.8166 0.2590 -0.0678 0.066 Uiso 1 1 calc R . . H15E H 0.7087 0.1979 -0.1639 0.066 Uiso 1 1 calc R . . H15F H 0.7936 0.1194 -0.1394 0.066 Uiso 1 1 calc R . . C24A C 1.45753(12) 0.17230(13) 0.38050(11) 0.0367(3) Uani 1 1 d . . . H24A H 1.5220 0.2289 0.3828 0.044 Uiso 1 1 calc R . . C26 C 0.44050(12) -0.33782(12) 0.26344(12) 0.0374(3) Uani 1 1 d . . . H26 H 0.3813 -0.3336 0.2964 0.045 Uiso 1 1 calc R . . C13A C 0.59452(16) 0.02841(15) -0.11433(12) 0.0541(5) Uani 1 1 d . . . H13D H 0.6359 -0.0339 -0.1390 0.081 Uiso 1 1 calc R . . H13E H 0.5439 0.0345 -0.1701 0.081 Uiso 1 1 calc R . . H13F H 0.5480 0.0067 -0.0745 0.081 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 0.0227(5) 0.0185(5) 0.0203(5) 0.0061(4) 0.0040(4) 0.0060(4) N3A 0.0228(5) 0.0166(5) 0.0177(5) 0.0075(4) 0.0036(4) 0.0055(4) N1A 0.0229(5) 0.0199(5) 0.0205(5) 0.0084(4) 0.0050(4) 0.0082(4) N3 0.0214(5) 0.0152(5) 0.0189(5) 0.0058(4) 0.0038(4) 0.0052(4) C9 0.0267(6) 0.0170(6) 0.0202(6) 0.0086(5) 0.0082(5) 0.0042(5) C21A 0.0252(6) 0.0241(6) 0.0239(6) 0.0082(5) 0.0048(5) 0.0087(5) C9A 0.0252(6) 0.0159(6) 0.0216(6) 0.0070(5) 0.0028(5) 0.0025(4) C22 0.0211(6) 0.0184(6) 0.0239(6) 0.0093(5) 0.0015(5) 0.0064(5) C11A 0.0264(6) 0.0205(6) 0.0194(6) 0.0067(5) 0.0065(5) 0.0077(5) C6A 0.0213(6) 0.0134(5) 0.0203(6) 0.0051(4) 0.0025(5) 0.0027(4) C8 0.0249(6) 0.0191(6) 0.0259(6) 0.0080(5) 0.0091(5) 0.0078(5) C2 0.0212(6) 0.0182(6) 0.0197(6) 0.0077(5) 0.0038(5) 0.0077(4) C7 0.0218(6) 0.0207(6) 0.0226(6) 0.0082(5) 0.0037(5) 0.0049(5) C4A 0.0223(6) 0.0197(6) 0.0183(6) 0.0097(5) 0.0048(5) 0.0063(5) C10 0.0240(6) 0.0209(6) 0.0201(6) 0.0092(5) 0.0032(5) 0.0056(5) C8A 0.0267(6) 0.0198(6) 0.0204(6) 0.0076(5) 0.0068(5) 0.0030(5) C11 0.0260(6) 0.0190(6) 0.0221(6) 0.0091(5) 0.0066(5) 0.0090(5) C5 0.0217(6) 0.0173(6) 0.0205(6) 0.0062(5) 0.0025(5) 0.0076(4) C16A 0.0217(6) 0.0202(6) 0.0196(6) 0.0078(5) 0.0069(5) 0.0047(5) C27 0.0258(6) 0.0214(6) 0.0368(7) 0.0061(5) 0.0097(6) 0.0083(5) C4 0.0209(6) 0.0149(5) 0.0203(6) 0.0054(5) 0.0016(5) 0.0066(4) C15 0.0341(7) 0.0250(7) 0.0231(6) 0.0033(5) 0.0028(5) 0.0039(5) C5A 0.0242(6) 0.0200(6) 0.0183(6) 0.0084(5) 0.0049(5) 0.0073(5) C17A 0.0237(6) 0.0229(6) 0.0220(6) 0.0097(5) 0.0051(5) 0.0063(5) C6 0.0252(6) 0.0162(6) 0.0197(6) 0.0083(5) 0.0066(5) 0.0047(4) C21 0.0256(6) 0.0171(6) 0.0241(6) 0.0061(5) 0.0046(5) 0.0034(5) C7A 0.0212(6) 0.0170(6) 0.0241(6) 0.0068(5) 0.0050(5) 0.0040(4) C20A 0.0246(6) 0.0328(7) 0.0219(6) 0.0068(5) 0.0010(5) 0.0077(5) C2A 0.0205(6) 0.0160(6) 0.0204(6) 0.0061(5) 0.0048(5) 0.0053(4) C19 0.0412(8) 0.0207(6) 0.0227(6) 0.0027(5) 0.0117(6) 0.0009(5) C17 0.0272(6) 0.0147(6) 0.0276(6) 0.0059(5) 0.0063(5) 0.0037(5) C24 0.0333(7) 0.0180(6) 0.0236(6) 0.0063(5) -0.0019(5) 0.0050(5) C18A 0.0312(7) 0.0205(6) 0.0270(7) 0.0075(5) 0.0081(5) 0.0071(5) C16 0.0257(6) 0.0132(5) 0.0218(6) 0.0059(5) 0.0061(5) 0.0027(4) C26A 0.0324(7) 0.0338(7) 0.0304(7) 0.0126(6) 0.0062(6) 0.0171(6) C12 0.0306(6) 0.0172(6) 0.0205(6) 0.0059(5) 0.0069(5) 0.0047(5) C12A 0.0296(7) 0.0274(7) 0.0223(6) 0.0109(5) 0.0007(5) 0.0049(5) C10A 0.0236(6) 0.0224(6) 0.0237(6) 0.0075(5) 0.0041(5) 0.0092(5) C18 0.0315(7) 0.0173(6) 0.0306(7) 0.0033(5) 0.0129(6) 0.0036(5) C23 0.0271(6) 0.0207(6) 0.0220(6) 0.0094(5) 0.0037(5) 0.0076(5) C19A 0.0294(7) 0.0239(6) 0.0228(6) 0.0015(5) 0.0041(5) 0.0025(5) C22A 0.0240(6) 0.0249(6) 0.0167(6) 0.0048(5) 0.0035(5) 0.0093(5) C27A 0.0258(6) 0.0277(7) 0.0255(6) 0.0093(5) 0.0052(5) 0.0103(5) C13 0.0407(7) 0.0248(7) 0.0231(6) 0.0066(5) 0.0121(6) 0.0068(5) C20 0.0348(7) 0.0217(6) 0.0217(6) 0.0067(5) 0.0021(5) 0.0012(5) C14 0.0413(7) 0.0182(6) 0.0243(6) 0.0060(5) 0.0070(6) 0.0059(5) C23A 0.0285(7) 0.0295(7) 0.0359(7) 0.0131(6) 0.0087(6) 0.0087(5) C25A 0.0234(6) 0.0416(8) 0.0310(7) 0.0083(6) 0.0038(6) 0.0144(6) C25 0.0243(6) 0.0214(6) 0.0453(8) 0.0102(6) 0.0006(6) -0.0002(5) C14A 0.0318(7) 0.0448(8) 0.0333(7) 0.0213(7) 0.0013(6) 0.0146(6) C15A 0.0473(9) 0.0697(11) 0.0361(8) 0.0367(8) 0.0157(7) 0.0279(8) C24A 0.0246(7) 0.0376(8) 0.0429(8) 0.0121(7) 0.0087(6) 0.0056(6) C26 0.0256(7) 0.0285(7) 0.0538(9) 0.0100(6) 0.0156(6) 0.0060(5) C13A 0.0691(11) 0.0345(8) 0.0352(9) 0.0133(7) -0.0209(8) -0.0053(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 N1 C2 1.3158(15) . ? N1 C5 1.3870(15) . ? N3A C4A 1.2865(15) . ? N3A C2A 1.4689(14) . ? N1A C5A 1.2810(15) . ? N1A C2A 1.4677(15) . ? N3 C2 1.3828(15) . ? N3 C4 1.4005(14) . ? N3 C2A 1.4823(15) . ? C9 C8 1.3988(17) . ? C9 C10 1.3942(16) . ? C9 C12 1.5339(16) . ? C21A H21A 0.9500 . ? C21A C16A 1.3970(17) . ? C21A C20A 1.3847(18) . ? C9A C8A 1.3937(17) . ? C9A C12A 1.5374(16) . ? C9A C10A 1.3946(17) . ? C22 C5 1.4776(16) . ? C22 C27 1.3889(18) . ? C22 C23 1.4016(17) . ? C11A H11A 0.9500 . ? C11A C6A 1.3897(17) . ? C11A C10A 1.3834(17) . ? C6A C7A 1.3842(17) . ? C6A C2A 1.5272(16) . ? C8 H8 0.9500 . ? C8 C7 1.3834(17) . ? C2 C6 1.4825(16) . ? C7 H7 0.9500 . ? C7 C6 1.3945(16) . ? C4A C16A 1.4710(16) . ? C4A C5A 1.5128(16) . ? C10 H10 0.9500 . ? C10 C11 1.3894(17) . ? C8A H8A 0.9500 . ? C8A C7A 1.3917(17) . ? C11 H11 0.9500 . ? C11 C6 1.3886(17) . ? C5 C4 1.3698(17) . ? C16A C17A 1.3969(16) . ? C27 H27 0.9500 . ? C27 C26 1.3868(18) . ? C4 C16 1.4838(16) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C15 C12 1.5275(18) . ? C5A C22A 1.4766(17) . ? C17A H17A 0.9500 . ? C17A C18A 1.3820(17) . ? C21 H21 0.9500 . ? C21 C16 1.3974(17) . ? C21 C20 1.3844(18) . ? C7A H7A 0.9500 . ? C20A H20A 0.9500 . ? C20A C19A 1.3877(18) . ? C19 H19 0.9500 . ? C19 C18 1.384(2) . ? C19 C20 1.3880(19) . ? C17 H17 0.9500 . ? C17 C16 1.3917(17) . ? C17 C18 1.3867(18) . ? C24 H24 0.9500 . ? C24 C23 1.3907(17) . ? C24 C25 1.378(2) . ? C18A H18A 0.9500 . ? C18A C19A 1.3881(19) . ? C26A H26A 0.9500 . ? C26A C27A 1.3824(18) . ? C26A C25A 1.379(2) . ? C12 C13 1.5389(17) . ? C12 C14 1.5376(17) . ? C12A C14A 1.5315(19) . ? C12A C15A 1.5287(19) . ? C12A C13A 1.5287(19) . ? C10A H10A 0.9500 . ? C18 H18 0.9500 . ? C23 H23 0.9500 . ? C19A H19A 0.9500 . ? C22A C27A 1.3912(18) . ? C22A C23A 1.3935(18) . ? C27A H27A 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C20 H20 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C23A H23A 0.9500 . ? C23A C24A 1.3851(19) . ? C25A H25A 0.9500 . ? C25A C24A 1.388(2) . ? C25 H25 0.9500 . ? C25 C26 1.388(2) . ? C14A H14D 0.9800 . ? C14A H14E 0.9800 . ? C14A H14F 0.9800 . ? C15A H15D 0.9800 . ? C15A H15E 0.9800 . ? C15A H15F 0.9800 . ? C24A H24A 0.9500 . ? C26 H26 0.9500 . ? C13A H13D 0.9800 . ? C13A H13E 0.9800 . ? C13A H13F 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 C2 N1 C5 106.46(10) . . ? C4A N3A C2A 105.85(9) . . ? C5A N1A C2A 105.92(9) . . ? C2 N3 C4 106.62(9) . . ? C2 N3 C2A 129.25(9) . . ? C4 N3 C2A 123.07(9) . . ? C8 C9 C12 119.59(10) . . ? C10 C9 C8 117.00(11) . . ? C10 C9 C12 123.40(11) . . ? C16A C21A H21A 120.0 . . ? C20A C21A H21A 120.0 . . ? C20A C21A C16A 119.93(11) . . ? C8A C9A C12A 121.99(11) . . ? C8A C9A C10A 117.07(11) . . ? C10A C9A C12A 120.88(11) . . ? C27 C22 C5 118.43(11) . . ? C27 C22 C23 118.21(11) . . ? C23 C22 C5 123.35(11) . . ? C6A C11A H11A 119.7 . . ? C10A C11A H11A 119.7 . . ? C10A C11A C6A 120.51(11) . . ? C11A C6A C2A 117.46(10) . . ? C7A C6A C11A 119.03(11) . . ? C7A C6A C2A 123.51(10) . . ? C9 C8 H8 119.2 . . ? C7 C8 C9 121.65(11) . . ? C7 C8 H8 119.2 . . ? N1 C2 N3 111.11(10) . . ? N1 C2 C6 121.56(10) . . ? N3 C2 C6 127.31(10) . . ? C8 C7 H7 119.6 . . ? C8 C7 C6 120.77(11) . . ? C6 C7 H7 119.6 . . ? N3A C4A C16A 122.18(10) . . ? N3A C4A C5A 109.63(10) . . ? C16A C4A C5A 128.07(10) . . ? C9 C10 H10 119.2 . . ? C11 C10 C9 121.59(11) . . ? C11 C10 H10 119.2 . . ? C9A C8A H8A 119.1 . . ? C7A C8A C9A 121.86(11) . . ? C7A C8A H8A 119.1 . . ? C10 C11 H11 119.6 . . ? C6 C11 C10 120.81(11) . . ? C6 C11 H11 119.6 . . ? N1 C5 C22 119.39(10) . . ? C4 C5 N1 110.16(10) . . ? C4 C5 C22 130.40(11) . . ? C21A C16A C4A 121.22(11) . . ? C17A C16A C21A 119.29(11) . . ? C17A C16A C4A 119.28(10) . . ? C22 C27 H27 119.5 . . ? C26 C27 C22 121.07(12) . . ? C26 C27 H27 119.5 . . ? N3 C4 C16 124.04(10) . . ? C5 C4 N3 105.65(10) . . ? C5 C4 C16 130.22(10) . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? N1A C5A C4A 109.99(10) . . ? N1A C5A C22A 122.51(10) . . ? C22A C5A C4A 127.41(10) . . ? C16A C17A H17A 119.7 . . ? C18A C17A C16A 120.62(11) . . ? C18A C17A H17A 119.7 . . ? C7 C6 C2 118.50(10) . . ? C11 C6 C2 123.25(10) . . ? C11 C6 C7 118.15(11) . . ? C16 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C20 C21 C16 120.63(11) . . ? C6A C7A C8A 119.96(11) . . ? C6A C7A H7A 120.0 . . ? C8A C7A H7A 120.0 . . ? C21A C20A H20A 119.9 . . ? C21A C20A C19A 120.23(12) . . ? C19A C20A H20A 119.9 . . ? N3A C2A N3 109.78(9) . . ? N3A C2A C6A 107.00(9) . . ? N1A C2A N3A 108.53(9) . . ? N1A C2A N3 108.23(9) . . ? N1A C2A C6A 113.74(9) . . ? N3 C2A C6A 109.51(9) . . ? C18 C19 H19 120.1 . . ? C18 C19 C20 119.77(12) . . ? C20 C19 H19 120.1 . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C18 C17 C16 120.31(12) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C25 C24 C23 120.69(12) . . ? C17A C18A H18A 120.2 . . ? C17A C18A C19A 119.67(11) . . ? C19A C18A H18A 120.2 . . ? C21 C16 C4 118.90(10) . . ? C17 C16 C4 122.18(11) . . ? C17 C16 C21 118.90(11) . . ? C27A C26A H26A 119.7 . . ? C25A C26A H26A 119.7 . . ? C25A C26A C27A 120.58(13) . . ? C9 C12 C13 108.31(10) . . ? C9 C12 C14 110.10(10) . . ? C15 C12 C9 112.43(10) . . ? C15 C12 C13 108.40(10) . . ? C15 C12 C14 107.89(10) . . ? C14 C12 C13 109.68(10) . . ? C14A C12A C9A 111.35(10) . . ? C15A C12A C9A 111.30(11) . . ? C15A C12A C14A 107.05(11) . . ? C15A C12A C13A 110.45(13) . . ? C13A C12A C9A 108.27(11) . . ? C13A C12A C14A 108.39(12) . . ? C9A C10A H10A 119.2 . . ? C11A C10A C9A 121.56(11) . . ? C11A C10A H10A 119.2 . . ? C19 C18 C17 120.41(12) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C22 C23 H23 119.8 . . ? C24 C23 C22 120.37(12) . . ? C24 C23 H23 119.8 . . ? C20A C19A C18A 120.26(11) . . ? C20A C19A H19A 119.9 . . ? C18A C19A H19A 119.9 . . ? C27A C22A C5A 118.11(11) . . ? C27A C22A C23A 119.41(11) . . ? C23A C22A C5A 122.47(11) . . ? C26A C27A C22A 120.04(12) . . ? C26A C27A H27A 120.0 . . ? C22A C27A H27A 120.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C21 C20 C19 119.97(12) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C22A C23A H23A 119.9 . . ? C24A C23A C22A 120.10(13) . . ? C24A C23A H23A 119.9 . . ? C26A C25A H25A 120.1 . . ? C26A C25A C24A 119.73(12) . . ? C24A C25A H25A 120.1 . . ? C24 C25 H25 120.3 . . ? C24 C25 C26 119.36(12) . . ? C26 C25 H25 120.3 . . ? C12A C14A H14D 109.5 . . ? C12A C14A H14E 109.5 . . ? C12A C14A H14F 109.5 . . ? H14D C14A H14E 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? C12A C15A H15D 109.5 . . ? C12A C15A H15E 109.5 . . ? C12A C15A H15F 109.5 . . ? H15D C15A H15E 109.5 . . ? H15D C15A H15F 109.5 . . ? H15E C15A H15F 109.5 . . ? C23A C24A C25A 120.12(13) . . ? C23A C24A H24A 119.9 . . ? C25A C24A H24A 119.9 . . ? C27 C26 C25 120.24(13) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C12A C13A H13D 109.5 . . ? C12A C13A H13E 109.5 . . ? C12A C13A H13F 109.5 . . ? H13D C13A H13E 109.5 . . ? H13D C13A H13F 109.5 . . ? H13E C13A H13F 109.5 . . ? _smtbx_masks_special_details ? loop_ _smtbx_masks_void_nr _smtbx_masks_void_average_x _smtbx_masks_void_average_y _smtbx_masks_void_average_z _smtbx_masks_void_volume _smtbx_masks_void_count_electrons _smtbx_masks_void_content 1 0.200 0.100 0.160 7.2 0.1 ? 2 0.500 0.500 0.500 127.5 18.4 ? 3 0.800 0.900 0.840 7.2 0.1 ?