# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Boc-Aic-Aic-OEt _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Boc-Aic-Aic-OEt _chemical_formula_moiety ? _chemical_formula_sum 'C19 H36 N2 O5' _chemical_formula_weight 372.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.633(4) _cell_length_b 11.242(5) _cell_length_c 40.783(18) _cell_angle_alpha 89.932(8) _cell_angle_beta 89.996(10) _cell_angle_gamma 82.953(10) _cell_volume 4383(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour colorles _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.129 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.990 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 55478 _diffrn_reflns_av_R_equivalents 0.2147 _diffrn_reflns_av_sigmaI/netI 0.3701 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -53 _diffrn_reflns_limit_l_max 54 _diffrn_reflns_theta_min 1.00 _diffrn_reflns_theta_max 28.44 _reflns_number_total 21030 _reflns_number_gt 6500 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 Ver.2010.11-3' _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0045(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 21030 _refine_ls_number_parameters 970 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2952 _refine_ls_R_factor_gt 0.0914 _refine_ls_wR_factor_ref 0.3591 _refine_ls_wR_factor_gt 0.2195 _refine_ls_goodness_of_fit_ref 0.795 _refine_ls_restrained_S_all 0.795 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1850(7) 0.7536(5) 0.47660(15) 0.0290(15) Uani 1 1 d . . . C2 C 0.1347(9) 0.6361(6) 0.48750(17) 0.047(2) Uani 1 1 d . . . H2A H 0.0589 0.6190 0.4737 0.070 Uiso 1 1 calc R . . H2B H 0.1034 0.6432 0.5098 0.070 Uiso 1 1 calc R . . H2C H 0.2103 0.5723 0.4858 0.070 Uiso 1 1 calc R . . C3 C 0.3114(8) 0.7782(7) 0.49662(16) 0.047(2) Uani 1 1 d . . . H3A H 0.3830 0.7111 0.4950 0.071 Uiso 1 1 calc R . . H3B H 0.2846 0.7903 0.5192 0.071 Uiso 1 1 calc R . . H3C H 0.3464 0.8488 0.4884 0.071 Uiso 1 1 calc R . . C4 C 0.0682(8) 0.8574(6) 0.47774(17) 0.0412(18) Uani 1 1 d . . . H4A H 0.1014 0.9281 0.4691 0.062 Uiso 1 1 calc R . . H4B H 0.0387 0.8715 0.5000 0.062 Uiso 1 1 calc R . . H4C H -0.0094 0.8381 0.4649 0.062 Uiso 1 1 calc R . . C5 C 0.1615(7) 0.7195(5) 0.41722(13) 0.0204(13) Uani 1 1 d . . . C6 C 0.1820(7) 0.7021(5) 0.35611(14) 0.0240(14) Uani 1 1 d . . . C7 C 0.0563(7) 0.7961(5) 0.34872(15) 0.0285(15) Uani 1 1 d . . . H7A H -0.0194 0.7844 0.3632 0.043 Uiso 1 1 calc R . . H7B H 0.0272 0.7878 0.3264 0.043 Uiso 1 1 calc R . . H7C H 0.0826 0.8749 0.3519 0.043 Uiso 1 1 calc R . . C8 C 0.3032(7) 0.7161(5) 0.33235(14) 0.0255(14) Uani 1 1 d . . . H8A H 0.3330 0.7939 0.3351 0.038 Uiso 1 1 calc R . . H8B H 0.2722 0.7077 0.3102 0.038 Uiso 1 1 calc R . . H8C H 0.3799 0.6555 0.3369 0.038 Uiso 1 1 calc R . . C9 C 0.1429(7) 0.5732(5) 0.35489(13) 0.0219(13) Uani 1 1 d . . . H9A H 0.2232 0.5187 0.3620 0.026 Uiso 1 1 calc R . . H9B H 0.0681 0.5669 0.3705 0.026 Uiso 1 1 calc R . . C10 C 0.0962(7) 0.5318(5) 0.32125(13) 0.0224(13) Uani 1 1 d . . . H10A H 0.0228 0.5900 0.3125 0.027 Uiso 1 1 calc R . . H10B H 0.1744 0.5253 0.3061 0.027 Uiso 1 1 calc R . . C11 C 0.0426(6) 0.4107(5) 0.32489(13) 0.0203(13) Uani 1 1 d . . . C12 C 0.1201(6) 0.1890(5) 0.33258(13) 0.0205(13) Uani 1 1 d . . . C13 C 0.2537(7) 0.1099(5) 0.32257(14) 0.0254(14) Uani 1 1 d . . . H13A H 0.2622 0.1097 0.2991 0.038 Uiso 1 1 calc R . . H13B H 0.2498 0.0296 0.3302 0.038 Uiso 1 1 calc R . . H13C H 0.3332 0.1407 0.3321 0.038 Uiso 1 1 calc R . . C14 C -0.0038(6) 0.1470(5) 0.31398(14) 0.0252(14) Uani 1 1 d . . . H14A H -0.0892 0.1931 0.3210 0.038 Uiso 1 1 calc R . . H14B H -0.0081 0.0637 0.3185 0.038 Uiso 1 1 calc R . . H14C H 0.0085 0.1578 0.2909 0.038 Uiso 1 1 calc R . . C15 C 0.0953(7) 0.1844(5) 0.37002(13) 0.0225(13) Uani 1 1 d . . . H15A H 0.0099 0.2359 0.3753 0.027 Uiso 1 1 calc R . . H15B H 0.0815 0.1031 0.3760 0.027 Uiso 1 1 calc R . . C16 C 0.2146(7) 0.2227(5) 0.39072(14) 0.0276(14) Uani 1 1 d . . . H16A H 0.2964 0.1638 0.3883 0.033 Uiso 1 1 calc R . . H16B H 0.2386 0.2986 0.3825 0.033 Uiso 1 1 calc R . . C17 C 0.1787(8) 0.2358(5) 0.42628(15) 0.0291(15) Uani 1 1 d . . . C18 C 0.2669(8) 0.2922(6) 0.47847(15) 0.0411(18) Uani 1 1 d . . . H18A H 0.1708 0.3249 0.4828 0.049 Uiso 1 1 calc R . . H18B H 0.3269 0.3495 0.4862 0.049 Uiso 1 1 calc R . . C19 C 0.3004(8) 0.1765(6) 0.49706(16) 0.0416(18) Uani 1 1 d . . . H19A H 0.2327 0.1235 0.4918 0.062 Uiso 1 1 calc R . . H19B H 0.2977 0.1925 0.5202 0.062 Uiso 1 1 calc R . . H19C H 0.3921 0.1396 0.4911 0.062 Uiso 1 1 calc R . . C20 C 0.6615(7) 0.9871(5) 0.40441(14) 0.0258(14) Uani 1 1 d . . . C21 C 0.5435(7) 1.0143(6) 0.42893(16) 0.0351(17) Uani 1 1 d . . . H21A H 0.4704 0.9662 0.4241 0.053 Uiso 1 1 calc R . . H21B H 0.5072 1.0976 0.4276 0.053 Uiso 1 1 calc R . . H21C H 0.5782 0.9963 0.4507 0.053 Uiso 1 1 calc R . . C22 C 0.7822(8) 1.0574(5) 0.41264(18) 0.0400(18) Uani 1 1 d . . . H22A H 0.8129 1.0394 0.4347 0.060 Uiso 1 1 calc R . . H22B H 0.7517 1.1416 0.4107 0.060 Uiso 1 1 calc R . . H22C H 0.8582 1.0354 0.3978 0.060 Uiso 1 1 calc R . . C23 C 0.6127(8) 1.0090(6) 0.36929(16) 0.0391(18) Uani 1 1 d . . . H23A H 0.6892 0.9863 0.3546 0.059 Uiso 1 1 calc R . . H23B H 0.5798 1.0924 0.3663 0.059 Uiso 1 1 calc R . . H23C H 0.5382 0.9621 0.3647 0.059 Uiso 1 1 calc R . . C24 C 0.6534(7) 0.7687(5) 0.40468(13) 0.0218(13) Uani 1 1 d . . . C25 C 0.6973(7) 0.5430(5) 0.41069(13) 0.0211(13) Uani 1 1 d . . . C26 C 0.5843(7) 0.5331(5) 0.43741(14) 0.0289(15) Uani 1 1 d . . . H26A H 0.6238 0.5433 0.4587 0.043 Uiso 1 1 calc R . . H26B H 0.5522 0.4556 0.4362 0.043 Uiso 1 1 calc R . . H26C H 0.5069 0.5942 0.4339 0.043 Uiso 1 1 calc R . . C27 C 0.8289(7) 0.4594(5) 0.41859(15) 0.0269(14) Uani 1 1 d . . . H27A H 0.8943 0.4605 0.4009 0.040 Uiso 1 1 calc R . . H27B H 0.8057 0.3794 0.4215 0.040 Uiso 1 1 calc R . . H27C H 0.8699 0.4854 0.4384 0.040 Uiso 1 1 calc R . . C28 C 0.6416(6) 0.5175(5) 0.37633(12) 0.0197(13) Uani 1 1 d . . . H28A H 0.7066 0.5415 0.3602 0.024 Uiso 1 1 calc R . . H28B H 0.5531 0.5674 0.3731 0.024 Uiso 1 1 calc R . . C29 C 0.6193(6) 0.3859(5) 0.36952(14) 0.0229(13) Uani 1 1 d . . . H29A H 0.7088 0.3360 0.3702 0.028 Uiso 1 1 calc R . . H29B H 0.5606 0.3585 0.3866 0.028 Uiso 1 1 calc R . . C30 C 0.5523(7) 0.3724(5) 0.33691(13) 0.0200(13) Uani 1 1 d . . . C31 C 0.5914(6) 0.3723(5) 0.27535(13) 0.0211(13) Uani 1 1 d . . . C32 C 0.4721(7) 0.4709(5) 0.26699(14) 0.0289(15) Uani 1 1 d . . . H32A H 0.3946 0.4649 0.2814 0.043 Uiso 1 1 calc R . . H32B H 0.4430 0.4616 0.2447 0.043 Uiso 1 1 calc R . . H32C H 0.5040 0.5480 0.2696 0.043 Uiso 1 1 calc R . . C33 C 0.7185(7) 0.3902(5) 0.25486(14) 0.0286(15) Uani 1 1 d . . . H33A H 0.7463 0.4677 0.2594 0.043 Uiso 1 1 calc R . . H33B H 0.6959 0.3852 0.2320 0.043 Uiso 1 1 calc R . . H33C H 0.7939 0.3292 0.2602 0.043 Uiso 1 1 calc R . . C34 C 0.5428(6) 0.2494(5) 0.26802(13) 0.0212(13) Uani 1 1 d . . . H34A H 0.4536 0.2457 0.2788 0.025 Uiso 1 1 calc R . . H34B H 0.5275 0.2436 0.2446 0.025 Uiso 1 1 calc R . . C35 C 0.6437(7) 0.1414(5) 0.27880(15) 0.0288(15) Uani 1 1 d . . . H35A H 0.7327 0.1437 0.2678 0.035 Uiso 1 1 calc R . . H35B H 0.6596 0.1465 0.3022 0.035 Uiso 1 1 calc R . . C36 C 0.5906(7) 0.0244(5) 0.27130(14) 0.0226(13) Uani 1 1 d . . . C37 C 0.6274(8) -0.1861(5) 0.28036(16) 0.0336(16) Uani 1 1 d . . . H37A H 0.6433 -0.2098 0.2577 0.040 Uiso 1 1 calc R . . H37B H 0.5286 -0.1851 0.2851 0.040 Uiso 1 1 calc R . . C38 C 0.7120(8) -0.2721(6) 0.30250(18) 0.047(2) Uani 1 1 d . . . H38A H 0.8090 -0.2760 0.2967 0.070 Uiso 1 1 calc R . . H38B H 0.6822 -0.3500 0.3003 0.070 Uiso 1 1 calc R . . H38C H 0.6993 -0.2456 0.3248 0.070 Uiso 1 1 calc R . . C39 C 0.6839(7) 1.2529(6) 0.02351(14) 0.0293(15) Uani 1 1 d . . . C40 C 0.5677(8) 1.3580(6) 0.02196(16) 0.0393(18) Uani 1 1 d . . . H40A H 0.4918 1.3419 0.0359 0.059 Uiso 1 1 calc R . . H40B H 0.5350 1.3687 -0.0002 0.059 Uiso 1 1 calc R . . H40C H 0.6033 1.4296 0.0293 0.059 Uiso 1 1 calc R . . C41 C 0.8097(8) 1.2792(7) 0.00311(16) 0.048(2) Uani 1 1 d . . . H41A H 0.8393 1.3536 0.0101 0.072 Uiso 1 1 calc R . . H41B H 0.7839 1.2848 -0.0196 0.072 Uiso 1 1 calc R . . H41C H 0.8849 1.2157 0.0060 0.072 Uiso 1 1 calc R . . C42 C 0.6334(9) 1.1364(6) 0.01260(16) 0.0438(19) Uani 1 1 d . . . H42A H 0.7067 1.0714 0.0157 0.066 Uiso 1 1 calc R . . H42B H 0.6082 1.1419 -0.0102 0.066 Uiso 1 1 calc R . . H42C H 0.5533 1.1222 0.0254 0.066 Uiso 1 1 calc R . . C43 C 0.6625(7) 1.2191(5) 0.08296(15) 0.0257(14) Uani 1 1 d . . . C44 C 0.6836(6) 1.2020(5) 0.14399(13) 0.0199(13) Uani 1 1 d . . . C45 C 0.5573(7) 1.2957(5) 0.15112(15) 0.0291(15) Uani 1 1 d . . . H45A H 0.5836 1.3746 0.1481 0.044 Uiso 1 1 calc R . . H45B H 0.5272 1.2870 0.1733 0.044 Uiso 1 1 calc R . . H45C H 0.4823 1.2841 0.1364 0.044 Uiso 1 1 calc R . . C46 C 0.8017(7) 1.2175(5) 0.16766(14) 0.0259(14) Uani 1 1 d . . . H46A H 0.8779 1.1555 0.1640 0.039 Uiso 1 1 calc R . . H46B H 0.7689 1.2125 0.1898 0.039 Uiso 1 1 calc R . . H46C H 0.8331 1.2944 0.1642 0.039 Uiso 1 1 calc R . . C47 C 0.6430(7) 1.0738(5) 0.14520(13) 0.0226(13) Uani 1 1 d . . . H47A H 0.5678 1.0685 0.1296 0.027 Uiso 1 1 calc R . . H47B H 0.7226 1.0189 0.1379 0.027 Uiso 1 1 calc R . . C48 C 0.5963(6) 1.0313(5) 0.17865(13) 0.0215(13) Uani 1 1 d . . . H48A H 0.6748 1.0240 0.1937 0.026 Uiso 1 1 calc R . . H48B H 0.5238 1.0900 0.1875 0.026 Uiso 1 1 calc R . . C49 C 0.5408(6) 0.9111(5) 0.17542(13) 0.0201(13) Uani 1 1 d . . . C50 C 0.6211(6) 0.6882(5) 0.16747(13) 0.0210(13) Uani 1 1 d . . . C51 C 0.4963(7) 0.6476(5) 0.18573(14) 0.0270(14) Uani 1 1 d . . . H51A H 0.5058 0.6616 0.2088 0.041 Uiso 1 1 calc R . . H51B H 0.4935 0.5636 0.1820 0.041 Uiso 1 1 calc R . . H51C H 0.4114 0.6921 0.1779 0.041 Uiso 1 1 calc R . . C52 C 0.7551(7) 0.6100(5) 0.17775(14) 0.0244(14) Uani 1 1 d . . . H52A H 0.8345 0.6418 0.1685 0.037 Uiso 1 1 calc R . . H52B H 0.7526 0.5297 0.1700 0.037 Uiso 1 1 calc R . . H52C H 0.7625 0.6094 0.2012 0.037 Uiso 1 1 calc R . . C53 C 0.5961(7) 0.6843(5) 0.13020(13) 0.0228(13) Uani 1 1 d . . . H53A H 0.5817 0.6033 0.1242 0.027 Uiso 1 1 calc R . . H53B H 0.5109 0.7362 0.1251 0.027 Uiso 1 1 calc R . . C54 C 0.7144(7) 0.7222(5) 0.10937(13) 0.0271(15) Uani 1 1 d . . . H54A H 0.7391 0.7977 0.1176 0.032 Uiso 1 1 calc R . . H54B H 0.7958 0.6628 0.1117 0.032 Uiso 1 1 calc R . . C55 C 0.6789(8) 0.7362(5) 0.07393(14) 0.0265(15) Uani 1 1 d . . . C56 C 0.7679(8) 0.7933(6) 0.02161(15) 0.0380(18) Uani 1 1 d . . . H56A H 0.8293 0.8498 0.0140 0.046 Uiso 1 1 calc R . . H56B H 0.6723 0.8272 0.0171 0.046 Uiso 1 1 calc R . . C57 C 0.8004(8) 0.6768(6) 0.00321(15) 0.0404(18) Uani 1 1 d . . . H57A H 0.8960 0.6447 0.0070 0.061 Uiso 1 1 calc R . . H57B H 0.7857 0.6909 -0.0198 0.061 Uiso 1 1 calc R . . H57C H 0.7399 0.6207 0.0108 0.061 Uiso 1 1 calc R . . C58 C 0.1611(7) 1.4876(5) 0.09563(15) 0.0263(14) Uani 1 1 d . . . C59 C 0.1134(8) 1.5096(6) 0.13064(15) 0.0387(18) Uani 1 1 d . . . H59A H 0.0409 1.4609 0.1356 0.058 Uiso 1 1 calc R . . H59B H 0.0781 1.5926 0.1334 0.058 Uiso 1 1 calc R . . H59C H 0.1911 1.4891 0.1452 0.058 Uiso 1 1 calc R . . C60 C 0.0433(7) 1.5154(5) 0.07095(15) 0.0343(16) Uani 1 1 d . . . H60A H 0.0774 1.4942 0.0494 0.051 Uiso 1 1 calc R . . H60B H 0.0102 1.5995 0.0716 0.051 Uiso 1 1 calc R . . H60C H -0.0319 1.4702 0.0763 0.051 Uiso 1 1 calc R . . C61 C 0.2828(8) 1.5575(5) 0.08745(18) 0.0411(18) Uani 1 1 d . . . H61A H 0.3552 1.5404 0.1035 0.062 Uiso 1 1 calc R . . H61B H 0.2508 1.6418 0.0875 0.062 Uiso 1 1 calc R . . H61C H 0.3189 1.5342 0.0662 0.062 Uiso 1 1 calc R . . C62 C 0.1546(7) 1.2676(5) 0.09520(13) 0.0223(13) Uani 1 1 d . . . C63 C 0.1977(6) 1.0432(5) 0.08906(13) 0.0207(13) Uani 1 1 d . . . C64 C 0.0847(7) 1.0336(5) 0.06294(14) 0.0273(15) Uani 1 1 d . . . H64A H 0.0059 1.0926 0.0671 0.041 Uiso 1 1 calc R . . H64B H 0.0554 0.9550 0.0637 0.041 Uiso 1 1 calc R . . H64C H 0.1221 1.0471 0.0416 0.041 Uiso 1 1 calc R . . C65 C 0.3290(7) 0.9585(5) 0.08129(14) 0.0275(15) Uani 1 1 d . . . H65A H 0.3695 0.9830 0.0613 0.041 Uiso 1 1 calc R . . H65B H 0.3053 0.8784 0.0789 0.041 Uiso 1 1 calc R . . H65C H 0.3952 0.9604 0.0988 0.041 Uiso 1 1 calc R . . C66 C 0.1413(6) 1.0172(5) 0.12391(13) 0.0194(13) Uani 1 1 d . . . H66A H 0.2061 1.0412 0.1401 0.023 Uiso 1 1 calc R . . H66B H 0.0526 1.0668 0.1271 0.023 Uiso 1 1 calc R . . C67 C 0.1199(6) 0.8856(5) 0.13038(13) 0.0180(12) Uani 1 1 d . . . H67A H 0.0609 0.8585 0.1134 0.022 Uiso 1 1 calc R . . H67B H 0.2096 0.8359 0.1296 0.022 Uiso 1 1 calc R . . C68 C 0.0524(7) 0.8720(5) 0.16376(13) 0.0194(13) Uani 1 1 d . . . C69 C 0.0918(6) 0.8733(5) 0.22467(13) 0.0211(13) Uani 1 1 d . . . C70 C 0.2201(7) 0.8909(5) 0.24501(14) 0.0285(15) Uani 1 1 d . . . H70A H 0.2942 0.8283 0.2401 0.043 Uiso 1 1 calc R . . H70B H 0.1972 0.8884 0.2679 0.043 Uiso 1 1 calc R . . H70C H 0.2497 0.9672 0.2398 0.043 Uiso 1 1 calc R . . C71 C -0.0285(7) 0.9712(5) 0.23294(14) 0.0277(15) Uani 1 1 d . . . H71A H 0.0016 1.0486 0.2296 0.042 Uiso 1 1 calc R . . H71B H -0.0555 0.9633 0.2554 0.042 Uiso 1 1 calc R . . H71C H -0.1069 0.9629 0.2190 0.042 Uiso 1 1 calc R . . C72 C 0.0422(7) 0.7498(5) 0.23203(14) 0.0249(14) Uani 1 1 d . . . H72A H 0.0264 0.7439 0.2554 0.030 Uiso 1 1 calc R . . H72B H -0.0466 0.7462 0.2211 0.030 Uiso 1 1 calc R . . C73 C 0.1440(7) 0.6419(5) 0.22131(15) 0.0286(15) Uani 1 1 d . . . H73A H 0.1603 0.6473 0.1979 0.034 Uiso 1 1 calc R . . H73B H 0.2327 0.6443 0.2324 0.034 Uiso 1 1 calc R . . C74 C 0.0907(7) 0.5238(5) 0.22876(14) 0.0229(13) Uani 1 1 d . . . C75 C 0.1273(8) 0.3146(5) 0.21994(16) 0.0356(17) Uani 1 1 d . . . H75A H 0.0285 0.3154 0.2152 0.043 Uiso 1 1 calc R . . H75B H 0.1433 0.2911 0.2426 0.043 Uiso 1 1 calc R . . C76 C 0.2127(9) 0.2285(6) 0.19777(18) 0.049(2) Uani 1 1 d . . . H76A H 0.1974 0.2534 0.1754 0.074 Uiso 1 1 calc R . . H76B H 0.1855 0.1498 0.2006 0.074 Uiso 1 1 calc R . . H76C H 0.3100 0.2270 0.2031 0.074 Uiso 1 1 calc R . . N1 N 0.2368(5) 0.7232(4) 0.38942(11) 0.0237(11) Uani 1 1 d . . . H1 H 0.3217 0.7387 0.3911 0.028 Uiso 1 1 calc R . . N2 N 0.1396(5) 0.3140(4) 0.32293(11) 0.0219(11) Uani 1 1 d . . . H2 H 0.2204 0.3253 0.3154 0.026 Uiso 1 1 calc R . . N3 N 0.7385(5) 0.6665(4) 0.41116(11) 0.0221(11) Uani 1 1 d . . . H3 H 0.8241 0.6734 0.4160 0.026 Uiso 1 1 calc R . . N4 N 0.6340(5) 0.3811(4) 0.31012(10) 0.0217(11) Uani 1 1 d . . . H4 H 0.7192 0.3929 0.3137 0.026 Uiso 1 1 calc R . . N5 N 0.7383(5) 1.2231(4) 0.11039(11) 0.0240(11) Uani 1 1 d . . . H5 H 0.8231 1.2387 0.1086 0.029 Uiso 1 1 calc R . . N6 N 0.6405(5) 0.8136(4) 0.17729(10) 0.0181(10) Uani 1 1 d . . . H6 H 0.7213 0.8252 0.1848 0.022 Uiso 1 1 calc R . . N7 N 0.2382(5) 1.1665(4) 0.08900(11) 0.0214(11) Uani 1 1 d . . . H7 H 0.3240 1.1734 0.0845 0.026 Uiso 1 1 calc R . . N8 N 0.1330(5) 0.8820(4) 0.18985(11) 0.0227(11) Uani 1 1 d . . . H8 H 0.2177 0.8948 0.1861 0.027 Uiso 1 1 calc R . . O1 O 0.2443(5) 0.7406(4) 0.44323(9) 0.0287(10) Uani 1 1 d . . . O2 O 0.0414(5) 0.6984(4) 0.41934(10) 0.0281(10) Uani 1 1 d . . . O3 O -0.0824(5) 0.4044(3) 0.33097(10) 0.0271(10) Uani 1 1 d . . . O4 O 0.0708(5) 0.2173(4) 0.43939(11) 0.0416(12) Uani 1 1 d . . . O5 O 0.2860(5) 0.2763(4) 0.44306(10) 0.0322(11) Uani 1 1 d . . . O6 O 0.7279(4) 0.8624(3) 0.40857(10) 0.0250(10) Uani 1 1 d . . . O7 O 0.5310(5) 0.7763(3) 0.39618(10) 0.0289(10) Uani 1 1 d . . . O8 O 0.4271(5) 0.3560(4) 0.33449(9) 0.0270(10) Uani 1 1 d . . . O9 O 0.4925(5) 0.0118(4) 0.25388(11) 0.0364(11) Uani 1 1 d . . . O10 O 0.6694(5) -0.0684(3) 0.28570(10) 0.0310(11) Uani 1 1 d . . . O11 O 0.7446(5) 1.2410(4) 0.05662(9) 0.0282(10) Uani 1 1 d . . . O12 O 0.5417(4) 1.1971(4) 0.08056(9) 0.0256(10) Uani 1 1 d . . . O13 O 0.4175(4) 0.9043(3) 0.16908(10) 0.0258(10) Uani 1 1 d . . . O14 O 0.5702(5) 0.7182(4) 0.06083(11) 0.0410(12) Uani 1 1 d . . . O15 O 0.7858(5) 0.7756(4) 0.05684(10) 0.0320(11) Uani 1 1 d . . . O16 O 0.2286(4) 1.3629(3) 0.09145(10) 0.0251(10) Uani 1 1 d . . . O17 O 0.0323(5) 1.2763(3) 0.10387(10) 0.0282(10) Uani 1 1 d . . . O18 O -0.0726(4) 0.8549(3) 0.16567(9) 0.0249(10) Uani 1 1 d . . . O19 O -0.0070(5) 0.5124(4) 0.24608(11) 0.0377(12) Uani 1 1 d . . . O20 O 0.1697(5) 0.4327(3) 0.21430(10) 0.0290(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.026(4) 0.033(3) 0.027(3) -0.010(3) 0.001(3) 0.000(3) C2 0.056(6) 0.051(5) 0.034(4) 0.009(3) -0.005(4) -0.011(4) C3 0.053(6) 0.066(5) 0.024(4) -0.020(3) -0.007(3) -0.009(4) C4 0.041(5) 0.041(4) 0.039(4) -0.014(3) 0.003(3) 0.002(3) C5 0.014(4) 0.022(3) 0.024(3) -0.001(2) -0.002(3) 0.005(3) C6 0.024(4) 0.020(3) 0.028(3) -0.007(2) -0.002(3) -0.001(3) C7 0.026(4) 0.022(3) 0.037(4) -0.002(3) -0.002(3) 0.000(3) C8 0.022(4) 0.028(3) 0.028(3) 0.004(2) -0.001(3) -0.006(3) C9 0.025(4) 0.016(3) 0.023(3) -0.002(2) -0.001(3) 0.002(2) C10 0.024(4) 0.018(3) 0.025(3) -0.006(2) -0.002(3) -0.002(3) C11 0.013(4) 0.025(3) 0.021(3) -0.002(2) -0.003(2) 0.004(3) C12 0.017(4) 0.019(3) 0.025(3) -0.004(2) 0.000(2) -0.001(2) C13 0.029(4) 0.015(3) 0.031(3) -0.009(2) 0.002(3) 0.001(3) C14 0.016(4) 0.029(3) 0.030(3) -0.004(3) -0.005(3) -0.002(3) C15 0.021(4) 0.024(3) 0.021(3) 0.002(2) 0.004(3) -0.001(3) C16 0.023(4) 0.032(3) 0.029(3) 0.003(3) -0.004(3) -0.005(3) C17 0.028(4) 0.022(3) 0.034(4) 0.004(3) -0.010(3) 0.007(3) C18 0.039(5) 0.053(5) 0.029(4) -0.017(3) -0.007(3) 0.002(4) C19 0.038(5) 0.054(5) 0.031(4) 0.003(3) 0.001(3) 0.003(4) C20 0.028(4) 0.018(3) 0.031(3) 0.001(2) 0.000(3) 0.002(3) C21 0.035(5) 0.027(3) 0.041(4) -0.001(3) 0.000(3) 0.006(3) C22 0.038(5) 0.022(3) 0.062(5) 0.000(3) -0.006(4) -0.010(3) C23 0.046(5) 0.029(4) 0.040(4) 0.005(3) 0.002(3) 0.002(3) C24 0.026(4) 0.025(3) 0.013(3) -0.002(2) -0.002(3) 0.001(3) C25 0.025(4) 0.018(3) 0.021(3) -0.002(2) 0.001(2) -0.007(3) C26 0.031(4) 0.033(3) 0.025(3) -0.004(3) 0.001(3) -0.010(3) C27 0.029(4) 0.020(3) 0.031(3) 0.001(2) -0.003(3) 0.001(3) C28 0.018(4) 0.024(3) 0.017(3) 0.000(2) -0.002(2) 0.000(2) C29 0.016(4) 0.025(3) 0.028(3) -0.007(2) 0.000(3) -0.002(3) C30 0.021(4) 0.015(3) 0.025(3) -0.001(2) 0.000(3) -0.003(2) C31 0.018(4) 0.021(3) 0.024(3) -0.002(2) 0.006(3) -0.001(2) C32 0.033(4) 0.027(3) 0.025(3) -0.002(2) 0.003(3) 0.005(3) C33 0.030(4) 0.031(3) 0.024(3) -0.004(3) 0.006(3) -0.001(3) C34 0.019(4) 0.023(3) 0.022(3) -0.002(2) 0.002(2) -0.001(3) C35 0.025(4) 0.029(3) 0.034(3) -0.002(3) -0.006(3) -0.005(3) C36 0.022(4) 0.018(3) 0.029(3) -0.002(2) 0.002(3) -0.005(3) C37 0.036(5) 0.024(3) 0.042(4) 0.000(3) -0.002(3) -0.009(3) C38 0.053(6) 0.025(4) 0.064(5) 0.006(3) -0.019(4) -0.011(3) C39 0.025(4) 0.041(4) 0.023(3) 0.007(3) -0.001(3) -0.006(3) C40 0.038(5) 0.042(4) 0.035(4) 0.010(3) -0.005(3) 0.004(3) C41 0.042(5) 0.065(5) 0.035(4) 0.015(3) 0.011(3) -0.002(4) C42 0.055(6) 0.043(4) 0.034(4) -0.005(3) 0.001(3) -0.004(4) C43 0.025(4) 0.021(3) 0.031(3) 0.005(2) -0.001(3) -0.004(3) C44 0.021(4) 0.019(3) 0.019(3) 0.000(2) 0.003(2) 0.001(2) C45 0.024(4) 0.025(3) 0.039(4) -0.004(3) 0.003(3) -0.002(3) C46 0.023(4) 0.032(3) 0.023(3) -0.002(2) 0.000(3) -0.005(3) C47 0.021(4) 0.025(3) 0.022(3) -0.001(2) 0.001(2) -0.003(3) C48 0.018(4) 0.022(3) 0.024(3) 0.002(2) 0.003(3) 0.003(2) C49 0.016(4) 0.027(3) 0.016(3) 0.003(2) 0.002(2) 0.000(3) C50 0.020(4) 0.017(3) 0.026(3) -0.003(2) 0.000(3) -0.006(2) C51 0.022(4) 0.029(3) 0.031(3) 0.000(3) 0.006(3) -0.008(3) C52 0.032(4) 0.014(3) 0.028(3) 0.000(2) -0.001(3) -0.004(3) C53 0.024(4) 0.017(3) 0.028(3) -0.002(2) 0.000(3) -0.001(2) C54 0.029(4) 0.029(3) 0.024(3) -0.003(2) 0.004(3) -0.005(3) C55 0.033(5) 0.021(3) 0.025(3) -0.005(2) 0.005(3) 0.002(3) C56 0.041(5) 0.042(4) 0.029(4) 0.013(3) 0.002(3) 0.004(3) C57 0.040(5) 0.055(5) 0.026(4) -0.004(3) 0.004(3) -0.003(4) C58 0.023(4) 0.019(3) 0.035(4) -0.002(2) -0.004(3) 0.003(3) C59 0.051(6) 0.030(4) 0.034(4) -0.008(3) 0.003(3) -0.003(3) C60 0.039(5) 0.027(3) 0.035(4) 0.002(3) -0.004(3) 0.005(3) C61 0.040(5) 0.024(3) 0.059(5) 0.002(3) 0.006(4) -0.002(3) C62 0.018(4) 0.023(3) 0.024(3) 0.005(2) -0.003(3) 0.002(3) C63 0.020(4) 0.019(3) 0.024(3) -0.001(2) -0.001(2) -0.006(2) C64 0.027(4) 0.029(3) 0.027(3) 0.008(3) 0.001(3) -0.008(3) C65 0.036(4) 0.020(3) 0.025(3) 0.001(2) 0.010(3) 0.005(3) C66 0.022(4) 0.019(3) 0.017(3) -0.001(2) -0.001(2) -0.001(2) C67 0.017(4) 0.018(3) 0.019(3) -0.003(2) 0.003(2) -0.003(2) C68 0.018(4) 0.017(3) 0.021(3) -0.002(2) -0.002(3) 0.003(2) C69 0.018(4) 0.024(3) 0.022(3) -0.002(2) 0.000(2) -0.004(3) C70 0.033(4) 0.029(3) 0.024(3) -0.003(3) -0.002(3) -0.008(3) C71 0.024(4) 0.031(3) 0.026(3) 0.000(3) -0.002(3) 0.004(3) C72 0.023(4) 0.028(3) 0.023(3) 0.003(2) 0.004(3) 0.003(3) C73 0.025(4) 0.025(3) 0.036(4) 0.002(3) 0.011(3) -0.004(3) C74 0.015(4) 0.028(3) 0.025(3) 0.001(2) -0.002(3) -0.001(3) C75 0.039(5) 0.023(3) 0.046(4) -0.005(3) 0.005(3) -0.007(3) C76 0.064(6) 0.029(4) 0.057(5) -0.001(3) 0.018(4) -0.016(4) N1 0.017(3) 0.025(3) 0.030(3) -0.008(2) 0.003(2) -0.008(2) N2 0.013(3) 0.022(3) 0.030(3) 0.002(2) 0.000(2) -0.001(2) N3 0.019(3) 0.020(2) 0.027(3) -0.001(2) -0.004(2) -0.003(2) N4 0.015(3) 0.032(3) 0.018(2) -0.003(2) -0.003(2) -0.003(2) N5 0.017(3) 0.029(3) 0.027(3) 0.001(2) 0.005(2) -0.005(2) N6 0.012(3) 0.022(2) 0.021(2) -0.0020(19) -0.0043(19) -0.001(2) N7 0.012(3) 0.023(3) 0.030(3) -0.001(2) 0.004(2) -0.004(2) N8 0.020(3) 0.028(3) 0.021(3) 0.001(2) 0.000(2) -0.004(2) O1 0.022(3) 0.039(2) 0.025(2) -0.0071(18) 0.0005(19) -0.005(2) O2 0.016(3) 0.037(2) 0.031(2) -0.0053(18) 0.0004(19) -0.004(2) O3 0.017(3) 0.030(2) 0.034(2) -0.0042(18) -0.0005(19) 0.0012(19) O4 0.030(3) 0.062(3) 0.031(3) 0.003(2) 0.008(2) 0.000(3) O5 0.029(3) 0.035(2) 0.033(2) -0.0029(19) -0.006(2) -0.007(2) O6 0.020(3) 0.016(2) 0.040(2) -0.0046(17) -0.0042(19) -0.0033(17) O7 0.019(3) 0.027(2) 0.040(3) -0.0029(18) -0.004(2) 0.0006(19) O8 0.018(3) 0.036(2) 0.028(2) -0.0038(18) 0.0025(18) -0.007(2) O9 0.034(3) 0.031(2) 0.045(3) 0.001(2) -0.015(2) -0.010(2) O10 0.033(3) 0.020(2) 0.041(3) 0.0006(18) -0.008(2) -0.0037(19) O11 0.021(3) 0.037(2) 0.027(2) 0.0069(18) 0.0012(19) -0.0063(19) O12 0.015(3) 0.036(2) 0.026(2) 0.0029(17) 0.0002(18) -0.0028(19) O13 0.010(3) 0.031(2) 0.036(2) 0.0063(18) -0.0010(19) 0.0001(18) O14 0.031(3) 0.058(3) 0.033(3) 0.000(2) 0.000(2) -0.006(2) O15 0.030(3) 0.034(2) 0.032(2) 0.0014(19) 0.010(2) -0.002(2) O16 0.020(3) 0.0126(19) 0.043(3) 0.0003(17) 0.0018(19) -0.0024(17) O17 0.019(3) 0.024(2) 0.042(3) 0.0022(18) 0.004(2) -0.0016(19) O18 0.018(3) 0.031(2) 0.026(2) 0.0026(17) -0.0027(18) -0.0042(19) O19 0.036(3) 0.034(3) 0.044(3) -0.002(2) 0.016(2) -0.008(2) O20 0.028(3) 0.023(2) 0.037(2) -0.0004(18) 0.008(2) -0.0073(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.476(7) . ? C1 C3 1.519(10) . ? C1 C4 1.519(9) . ? C1 C2 1.527(9) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 O2 1.212(7) . ? C5 N1 1.349(7) . ? C5 O1 1.366(7) . ? C6 N1 1.487(7) . ? C6 C7 1.535(8) . ? C6 C8 1.540(8) . ? C6 C9 1.542(8) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.534(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.521(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O3 1.240(7) . ? C11 N2 1.346(7) . ? C12 N2 1.493(7) . ? C12 C13 1.528(8) . ? C12 C14 1.537(8) . ? C12 C15 1.547(7) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.531(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.494(9) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O4 1.209(8) . ? C17 O5 1.364(8) . ? C18 O5 1.464(7) . ? C18 C19 1.506(9) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 O6 1.478(7) . ? C20 C21 1.517(9) . ? C20 C23 1.518(9) . ? C20 C22 1.521(9) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 O7 1.222(7) . ? C24 N3 1.353(7) . ? C24 O6 1.355(7) . ? C25 N3 1.490(7) . ? C25 C27 1.517(8) . ? C25 C28 1.540(8) . ? C25 C26 1.554(8) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.546(7) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.494(8) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 O8 1.246(7) . ? C30 N4 1.357(7) . ? C31 N4 1.483(7) . ? C31 C33 1.517(8) . ? C31 C32 1.534(8) . ? C31 C34 1.541(8) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 C35 1.523(8) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.501(8) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 O9 1.204(7) . ? C36 O10 1.346(7) . ? C37 O10 1.447(7) . ? C37 C38 1.490(9) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 O11 1.471(7) . ? C39 C42 1.519(9) . ? C39 C40 1.526(9) . ? C39 C41 1.528(9) . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 O12 1.223(7) . ? C43 N5 1.340(8) . ? C43 O11 1.374(7) . ? C44 N5 1.497(7) . ? C44 C46 1.519(8) . ? C44 C45 1.536(8) . ? C44 C47 1.539(8) . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C47 C48 1.530(7) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 C49 1.519(8) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C49 O13 1.228(7) . ? C49 N6 1.368(7) . ? C50 N6 1.499(7) . ? C50 C52 1.529(8) . ? C50 C51 1.531(8) . ? C50 C53 1.541(8) . ? C51 H51A 0.9600 . ? C51 H51B 0.9600 . ? C51 H51C 0.9600 . ? C52 H52A 0.9600 . ? C52 H52B 0.9600 . ? C52 H52C 0.9600 . ? C53 C54 1.523(8) . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C54 C55 1.489(8) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C55 O14 1.215(8) . ? C55 O15 1.362(7) . ? C56 O15 1.457(7) . ? C56 C57 1.510(9) . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? C57 H57A 0.9600 . ? C57 H57B 0.9600 . ? C57 H57C 0.9600 . ? C58 O16 1.482(7) . ? C58 C59 1.511(8) . ? C58 C60 1.520(9) . ? C58 C61 1.525(9) . ? C59 H59A 0.9600 . ? C59 H59B 0.9600 . ? C59 H59C 0.9600 . ? C60 H60A 0.9600 . ? C60 H60B 0.9600 . ? C60 H60C 0.9600 . ? C61 H61A 0.9600 . ? C61 H61B 0.9600 . ? C61 H61C 0.9600 . ? C62 O17 1.222(7) . ? C62 N7 1.334(7) . ? C62 O16 1.366(7) . ? C63 N7 1.484(7) . ? C63 C65 1.521(8) . ? C63 C64 1.537(8) . ? C63 C66 1.562(7) . ? C64 H64A 0.9600 . ? C64 H64B 0.9600 . ? C64 H64C 0.9600 . ? C65 H65A 0.9600 . ? C65 H65B 0.9600 . ? C65 H65C 0.9600 . ? C66 C67 1.541(7) . ? C66 H66A 0.9700 . ? C66 H66B 0.9700 . ? C67 C68 1.524(7) . ? C67 H67A 0.9700 . ? C67 H67B 0.9700 . ? C68 O18 1.244(7) . ? C68 N8 1.330(7) . ? C69 N8 1.481(7) . ? C69 C70 1.521(8) . ? C69 C71 1.536(8) . ? C69 C72 1.552(8) . ? C70 H70A 0.9600 . ? C70 H70B 0.9600 . ? C70 H70C 0.9600 . ? C71 H71A 0.9600 . ? C71 H71B 0.9600 . ? C71 H71C 0.9600 . ? C72 C73 1.527(8) . ? C72 H72A 0.9700 . ? C72 H72B 0.9700 . ? C73 C74 1.511(8) . ? C73 H73A 0.9700 . ? C73 H73B 0.9700 . ? C74 O19 1.197(7) . ? C74 O20 1.337(7) . ? C75 O20 1.454(7) . ? C75 C76 1.496(9) . ? C75 H75A 0.9700 . ? C75 H75B 0.9700 . ? C76 H76A 0.9600 . ? C76 H76B 0.9600 . ? C76 H76C 0.9600 . ? N1 H1 0.8600 . ? N2 H2 0.8600 . ? N3 H3 0.8600 . ? N4 H4 0.8600 . ? N5 H5 0.8600 . ? N6 H6 0.8600 . ? N7 H7 0.8600 . ? N8 H8 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 101.8(5) . . ? O1 C1 C4 110.2(5) . . ? C3 C1 C4 112.2(6) . . ? O1 C1 C2 110.0(5) . . ? C3 C1 C2 110.4(6) . . ? C4 C1 C2 111.8(6) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 N1 126.5(5) . . ? O2 C5 O1 124.8(5) . . ? N1 C5 O1 108.6(5) . . ? N1 C6 C7 109.5(5) . . ? N1 C6 C8 105.7(5) . . ? C7 C6 C8 110.5(5) . . ? N1 C6 C9 108.2(4) . . ? C7 C6 C9 112.2(5) . . ? C8 C6 C9 110.5(5) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C6 115.4(4) . . ? C10 C9 H9A 108.4 . . ? C6 C9 H9A 108.4 . . ? C10 C9 H9B 108.4 . . ? C6 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? C11 C10 C9 109.2(4) . . ? C11 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? O3 C11 N2 123.3(5) . . ? O3 C11 C10 120.6(5) . . ? N2 C11 C10 116.0(5) . . ? N2 C12 C13 106.4(5) . . ? N2 C12 C14 110.6(5) . . ? C13 C12 C14 108.6(5) . . ? N2 C12 C15 109.2(4) . . ? C13 C12 C15 111.5(5) . . ? C14 C12 C15 110.3(5) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C12 114.2(5) . . ? C16 C15 H15A 108.7 . . ? C12 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C12 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C17 C16 C15 113.0(5) . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16B 109.0 . . ? C15 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? O4 C17 O5 122.6(6) . . ? O4 C17 C16 127.3(6) . . ? O5 C17 C16 110.1(6) . . ? O5 C18 C19 112.3(5) . . ? O5 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? O5 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O6 C20 C21 110.0(4) . . ? O6 C20 C23 110.5(5) . . ? C21 C20 C23 112.3(6) . . ? O6 C20 C22 101.4(5) . . ? C21 C20 C22 110.6(6) . . ? C23 C20 C22 111.5(5) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O7 C24 N3 126.4(6) . . ? O7 C24 O6 125.3(5) . . ? N3 C24 O6 108.3(5) . . ? N3 C25 C27 106.0(5) . . ? N3 C25 C28 109.0(4) . . ? C27 C25 C28 111.2(5) . . ? N3 C25 C26 109.0(4) . . ? C27 C25 C26 110.3(5) . . ? C28 C25 C26 111.2(5) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 C29 115.8(4) . . ? C25 C28 H28A 108.3 . . ? C29 C28 H28A 108.3 . . ? C25 C28 H28B 108.3 . . ? C29 C28 H28B 108.3 . . ? H28A C28 H28B 107.4 . . ? C30 C29 C28 111.8(4) . . ? C30 C29 H29A 109.3 . . ? C28 C29 H29A 109.3 . . ? C30 C29 H29B 109.3 . . ? C28 C29 H29B 109.3 . . ? H29A C29 H29B 107.9 . . ? O8 C30 N4 121.8(5) . . ? O8 C30 C29 121.6(5) . . ? N4 C30 C29 116.6(5) . . ? N4 C31 C33 106.4(5) . . ? N4 C31 C32 110.6(4) . . ? C33 C31 C32 109.1(5) . . ? N4 C31 C34 111.3(4) . . ? C33 C31 C34 110.6(5) . . ? C32 C31 C34 108.8(5) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 C31 115.1(5) . . ? C35 C34 H34A 108.5 . . ? C31 C34 H34A 108.5 . . ? C35 C34 H34B 108.5 . . ? C31 C34 H34B 108.5 . . ? H34A C34 H34B 107.5 . . ? C36 C35 C34 112.7(5) . . ? C36 C35 H35A 109.0 . . ? C34 C35 H35A 109.0 . . ? C36 C35 H35B 109.0 . . ? C34 C35 H35B 109.0 . . ? H35A C35 H35B 107.8 . . ? O9 C36 O10 122.8(5) . . ? O9 C36 C35 125.5(5) . . ? O10 C36 C35 111.7(5) . . ? O10 C37 C38 108.0(5) . . ? O10 C37 H37A 110.1 . . ? C38 C37 H37A 110.1 . . ? O10 C37 H37B 110.1 . . ? C38 C37 H37B 110.1 . . ? H37A C37 H37B 108.4 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O11 C39 C42 110.9(5) . . ? O11 C39 C40 110.7(5) . . ? C42 C39 C40 111.9(6) . . ? O11 C39 C41 101.6(5) . . ? C42 C39 C41 110.6(6) . . ? C40 C39 C41 110.6(5) . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C39 C42 H42A 109.5 . . ? C39 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C39 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? O12 C43 N5 127.6(5) . . ? O12 C43 O11 123.8(6) . . ? N5 C43 O11 108.6(5) . . ? N5 C44 C46 106.3(5) . . ? N5 C44 C45 109.2(4) . . ? C46 C44 C45 110.0(5) . . ? N5 C44 C47 108.2(4) . . ? C46 C44 C47 111.6(5) . . ? C45 C44 C47 111.5(5) . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C44 C46 H46A 109.5 . . ? C44 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C44 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C48 C47 C44 115.9(4) . . ? C48 C47 H47A 108.3 . . ? C44 C47 H47A 108.3 . . ? C48 C47 H47B 108.3 . . ? C44 C47 H47B 108.3 . . ? H47A C47 H47B 107.4 . . ? C49 C48 C47 110.4(4) . . ? C49 C48 H48A 109.6 . . ? C47 C48 H48A 109.6 . . ? C49 C48 H48B 109.6 . . ? C47 C48 H48B 109.6 . . ? H48A C48 H48B 108.1 . . ? O13 C49 N6 123.5(5) . . ? O13 C49 C48 121.5(5) . . ? N6 C49 C48 114.8(5) . . ? N6 C50 C52 105.9(5) . . ? N6 C50 C51 110.1(4) . . ? C52 C50 C51 109.5(5) . . ? N6 C50 C53 109.3(4) . . ? C52 C50 C53 112.2(5) . . ? C51 C50 C53 109.9(5) . . ? C50 C51 H51A 109.5 . . ? C50 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C50 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C50 C52 H52A 109.5 . . ? C50 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C50 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C54 C53 C50 114.6(5) . . ? C54 C53 H53A 108.6 . . ? C50 C53 H53A 108.6 . . ? C54 C53 H53B 108.6 . . ? C50 C53 H53B 108.6 . . ? H53A C53 H53B 107.6 . . ? C55 C54 C53 113.6(6) . . ? C55 C54 H54A 108.8 . . ? C53 C54 H54A 108.8 . . ? C55 C54 H54B 108.8 . . ? C53 C54 H54B 108.8 . . ? H54A C54 H54B 107.7 . . ? O14 C55 O15 122.1(6) . . ? O14 C55 C54 126.9(6) . . ? O15 C55 C54 111.0(6) . . ? O15 C56 C57 111.3(5) . . ? O15 C56 H56A 109.4 . . ? C57 C56 H56A 109.4 . . ? O15 C56 H56B 109.4 . . ? C57 C56 H56B 109.4 . . ? H56A C56 H56B 108.0 . . ? C56 C57 H57A 109.5 . . ? C56 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C56 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? O16 C58 C59 110.7(5) . . ? O16 C58 C60 110.3(5) . . ? C59 C58 C60 112.9(6) . . ? O16 C58 C61 100.7(5) . . ? C59 C58 C61 111.1(5) . . ? C60 C58 C61 110.6(5) . . ? C58 C59 H59A 109.5 . . ? C58 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C58 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C58 C60 H60A 109.5 . . ? C58 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C58 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? C58 C61 H61A 109.5 . . ? C58 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C58 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? O17 C62 N7 126.7(5) . . ? O17 C62 O16 124.0(5) . . ? N7 C62 O16 109.2(5) . . ? N7 C63 C65 106.9(5) . . ? N7 C63 C64 109.6(4) . . ? C65 C63 C64 110.7(5) . . ? N7 C63 C66 108.2(4) . . ? C65 C63 C66 110.8(4) . . ? C64 C63 C66 110.6(5) . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C63 C65 H65A 109.5 . . ? C63 C65 H65B 109.5 . . ? H65A C65 H65B 109.5 . . ? C63 C65 H65C 109.5 . . ? H65A C65 H65C 109.5 . . ? H65B C65 H65C 109.5 . . ? C67 C66 C63 115.1(4) . . ? C67 C66 H66A 108.5 . . ? C63 C66 H66A 108.5 . . ? C67 C66 H66B 108.5 . . ? C63 C66 H66B 108.5 . . ? H66A C66 H66B 107.5 . . ? C68 C67 C66 110.9(4) . . ? C68 C67 H67A 109.5 . . ? C66 C67 H67A 109.5 . . ? C68 C67 H67B 109.5 . . ? C66 C67 H67B 109.5 . . ? H67A C67 H67B 108.0 . . ? O18 C68 N8 123.3(5) . . ? O18 C68 C67 120.3(5) . . ? N8 C68 C67 116.4(5) . . ? N8 C69 C70 106.6(5) . . ? N8 C69 C71 110.4(4) . . ? C70 C69 C71 109.9(5) . . ? N8 C69 C72 111.0(4) . . ? C70 C69 C72 110.9(5) . . ? C71 C69 C72 108.1(5) . . ? C69 C70 H70A 109.5 . . ? C69 C70 H70B 109.5 . . ? H70A C70 H70B 109.5 . . ? C69 C70 H70C 109.5 . . ? H70A C70 H70C 109.5 . . ? H70B C70 H70C 109.5 . . ? C69 C71 H71A 109.5 . . ? C69 C71 H71B 109.5 . . ? H71A C71 H71B 109.5 . . ? C69 C71 H71C 109.5 . . ? H71A C71 H71C 109.5 . . ? H71B C71 H71C 109.5 . . ? C73 C72 C69 114.6(5) . . ? C73 C72 H72A 108.6 . . ? C69 C72 H72A 108.6 . . ? C73 C72 H72B 108.6 . . ? C69 C72 H72B 108.6 . . ? H72A C72 H72B 107.6 . . ? C74 C73 C72 112.7(5) . . ? C74 C73 H73A 109.0 . . ? C72 C73 H73A 109.0 . . ? C74 C73 H73B 109.0 . . ? C72 C73 H73B 109.0 . . ? H73A C73 H73B 107.8 . . ? O19 C74 O20 124.1(5) . . ? O19 C74 C73 124.7(5) . . ? O20 C74 C73 111.2(5) . . ? O20 C75 C76 107.6(5) . . ? O20 C75 H75A 110.2 . . ? C76 C75 H75A 110.2 . . ? O20 C75 H75B 110.2 . . ? C76 C75 H75B 110.2 . . ? H75A C75 H75B 108.5 . . ? C75 C76 H76A 109.5 . . ? C75 C76 H76B 109.5 . . ? H76A C76 H76B 109.5 . . ? C75 C76 H76C 109.5 . . ? H76A C76 H76C 109.5 . . ? H76B C76 H76C 109.5 . . ? C5 N1 C6 124.1(5) . . ? C5 N1 H1 118.0 . . ? C6 N1 H1 118.0 . . ? C11 N2 C12 126.1(5) . . ? C11 N2 H2 117.0 . . ? C12 N2 H2 117.0 . . ? C24 N3 C25 125.8(5) . . ? C24 N3 H3 117.1 . . ? C25 N3 H3 117.1 . . ? C30 N4 C31 126.7(5) . . ? C30 N4 H4 116.7 . . ? C31 N4 H4 116.7 . . ? C43 N5 C44 123.7(5) . . ? C43 N5 H5 118.1 . . ? C44 N5 H5 118.1 . . ? C49 N6 C50 125.6(5) . . ? C49 N6 H6 117.2 . . ? C50 N6 H6 117.2 . . ? C62 N7 C63 126.5(5) . . ? C62 N7 H7 116.7 . . ? C63 N7 H7 116.7 . . ? C68 N8 C69 126.7(5) . . ? C68 N8 H8 116.6 . . ? C69 N8 H8 116.6 . . ? C5 O1 C1 120.4(5) . . ? C17 O5 C18 116.6(5) . . ? C24 O6 C20 121.0(5) . . ? C36 O10 C37 116.6(5) . . ? C43 O11 C39 120.2(5) . . ? C55 O15 C56 117.8(5) . . ? C62 O16 C58 121.3(5) . . ? C74 O20 C75 115.7(5) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 28.44 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.361 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.078 _database_code_depnum_ccdc_archive 'CCDC 943867' ####################################################################### # # 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_Boc-Aic-Aic-Aic-OEt _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common gammatripeptide _chemical_melting_point ? _chemical_formula_moiety 'C25 H47 N3 O6' _chemical_formula_sum 'C25 H47 N3 O6' _chemical_formula_weight 485.66 _chemical_compound_source synthesis _exptl_crystal_recrystallization_method MeOH/Water _diffrn_ambient_temperature 100(2) _diffrn_ambient_pressure 101.325 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.633(5) _cell_length_b 18.305(8) _cell_length_c 33.028(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5824(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX2 area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 80005 _diffrn_reflns_av_R_equivalents 0.2720 _diffrn_reflns_av_sigmaI/netI 0.1810 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 10226 _reflns_number_gt 5498 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 Ver.2010.11-3' _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1037P)^2^+8.9865P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0130(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_ls_number_reflns 10226 _refine_ls_number_parameters 604 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1965 _refine_ls_R_factor_gt 0.1057 _refine_ls_wR_factor_ref 0.2667 _refine_ls_wR_factor_gt 0.2218 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0050(7) 0.7649(5) 0.7913(3) 0.043(2) Uani 1 1 d . . . C2 C 1.0726(10) 0.6979(6) 0.7734(3) 0.077(3) Uani 1 1 d . . . H2A H 1.0118 0.6766 0.7537 0.115 Uiso 1 1 calc R . . H2B H 1.0906 0.6631 0.7945 0.115 Uiso 1 1 calc R . . H2C H 1.1585 0.7114 0.7607 0.115 Uiso 1 1 calc R . . C3 C 0.9594(11) 0.8159(6) 0.7588(3) 0.071(3) Uani 1 1 d . . . H3A H 0.8906 0.7925 0.7423 0.107 Uiso 1 1 calc R . . H3B H 1.0377 0.8291 0.7424 0.107 Uiso 1 1 calc R . . H3C H 0.9206 0.8591 0.7709 0.107 Uiso 1 1 calc R . . C4 C 1.0924(10) 0.8011(6) 0.8239(3) 0.068(3) Uani 1 1 d . . . H4A H 1.1747 0.8213 0.8119 0.102 Uiso 1 1 calc R . . H4B H 1.1180 0.7655 0.8439 0.102 Uiso 1 1 calc R . . H4C H 1.0398 0.8394 0.8365 0.102 Uiso 1 1 calc R . . C5 C 0.7851(8) 0.7763(4) 0.8306(3) 0.038(2) Uani 1 1 d . . . C6 C 0.5590(7) 0.7587(4) 0.8666(2) 0.0323(19) Uani 1 1 d . . . C7 C 0.4765(8) 0.8089(4) 0.8394(3) 0.042(2) Uani 1 1 d . . . H7A H 0.5270 0.8535 0.8353 0.063 Uiso 1 1 calc R . . H7B H 0.3886 0.8195 0.8517 0.063 Uiso 1 1 calc R . . H7C H 0.4616 0.7855 0.8137 0.063 Uiso 1 1 calc R . . C8 C 0.5988(8) 0.8013(4) 0.9055(2) 0.039(2) Uani 1 1 d . . . H8A H 0.6476 0.7694 0.9237 0.059 Uiso 1 1 calc R . . H8B H 0.5162 0.8190 0.9184 0.059 Uiso 1 1 calc R . . H8C H 0.6574 0.8418 0.8985 0.059 Uiso 1 1 calc R . . C9 C 0.4714(7) 0.6920(4) 0.8771(2) 0.0289(17) Uani 1 1 d . . . H9A H 0.4568 0.6638 0.8526 0.035 Uiso 1 1 calc R . . H9B H 0.3812 0.7085 0.8864 0.035 Uiso 1 1 calc R . . C10 C 0.5348(7) 0.6409(4) 0.9099(2) 0.0271(17) Uani 1 1 d . . . H10A H 0.5171 0.5906 0.9022 0.033 Uiso 1 1 calc R . . H10B H 0.6346 0.6478 0.9102 0.033 Uiso 1 1 calc R . . C11 C 0.4805(8) 0.6525(4) 0.9518(2) 0.0274(17) Uiso 1 1 d . . . C12 C 0.5414(7) 0.6533(4) 1.0256(2) 0.0313(18) Uani 1 1 d . . . C13 C 0.4540(9) 0.5864(4) 1.0387(3) 0.045(2) Uani 1 1 d . . . H13A H 0.3708 0.5842 1.0228 0.068 Uiso 1 1 calc R . . H13B H 0.4299 0.5910 1.0668 0.068 Uiso 1 1 calc R . . H13C H 0.5070 0.5426 1.0348 0.068 Uiso 1 1 calc R . . C14 C 0.6808(8) 0.6528(4) 1.0480(2) 0.037(2) Uani 1 1 d . . . H14A H 0.7399 0.6159 1.0366 0.056 Uiso 1 1 calc R . . H14B H 0.6653 0.6425 1.0762 0.056 Uiso 1 1 calc R . . H14C H 0.7244 0.6997 1.0453 0.056 Uiso 1 1 calc R . . C15 C 0.4605(7) 0.7229(3) 1.0378(2) 0.0228(16) Uiso 1 1 d . . . H15A H 0.3643 0.7174 1.0296 0.027 Uiso 1 1 calc R . . H15B H 0.4624 0.7276 1.0670 0.027 Uiso 1 1 calc R . . C16 C 0.5193(8) 0.7932(4) 1.0188(2) 0.0331(19) Uani 1 1 d . . . H16A H 0.6198 0.7906 1.0178 0.040 Uiso 1 1 calc R . . H16B H 0.4850 0.7986 0.9914 0.040 Uiso 1 1 calc R . . C17 C 0.4751(7) 0.8581(3) 1.0440(2) 0.0250(17) Uani 1 1 d . . . C18 C 0.5539(7) 0.9479(4) 1.0979(2) 0.0264(18) Uani 1 1 d . . . C19 C 0.5130(7) 1.0165(4) 1.0776(2) 0.0338(19) Uani 1 1 d . . . H19A H 0.5833 1.0302 1.0584 0.051 Uiso 1 1 calc R . . H19B H 0.5026 1.0545 1.0974 0.051 Uiso 1 1 calc R . . H19C H 0.4265 1.0094 1.0637 0.051 Uiso 1 1 calc R . . C20 C 0.6965(8) 0.9571(4) 1.1191(2) 0.0305(18) Uiso 1 1 d . . . H20A H 0.7159 0.9146 1.1352 0.046 Uiso 1 1 calc R . . H20B H 0.6941 0.9995 1.1363 0.046 Uiso 1 1 calc R . . H20C H 0.7677 0.9630 1.0991 0.046 Uiso 1 1 calc R . . C21 C 0.4426(7) 0.9222(4) 1.1295(2) 0.0327(19) Uani 1 1 d . . . H21A H 0.3531 0.9187 1.1161 0.039 Uiso 1 1 calc R . . H21B H 0.4671 0.8739 1.1392 0.039 Uiso 1 1 calc R . . C22 C 0.4300(8) 0.9735(4) 1.1654(2) 0.0349(19) Uani 1 1 d . . . H22A H 0.4157 1.0229 1.1556 0.042 Uiso 1 1 calc R . . H22B H 0.5162 0.9728 1.1806 0.042 Uiso 1 1 calc R . . C23 C 0.3106(8) 0.9527(4) 1.1934(3) 0.039(2) Uani 1 1 d . . . C24 C 0.2315(11) 0.9523(7) 1.2617(3) 0.072(3) Uani 1 1 d . . . H24A H 0.1427 0.9736 1.2545 0.086 Uiso 1 1 calc R . . H24B H 0.2202 0.8997 1.2635 0.086 Uiso 1 1 calc R . . C25 C 0.2785(11) 0.9811(7) 1.3001(3) 0.080(4) Uani 1 1 d . . . H25A H 0.3746 0.9690 1.3040 0.121 Uiso 1 1 calc R . . H25B H 0.2244 0.9602 1.3216 0.121 Uiso 1 1 calc R . . H25C H 0.2677 1.0332 1.3003 0.121 Uiso 1 1 calc R . . C26 C 0.0887(8) 0.2010(4) 0.1955(3) 0.038(2) Uani 1 1 d . . . C27 C 0.0097(8) 0.1681(5) 0.1613(3) 0.054(3) Uani 1 1 d . . . H27A H -0.0180 0.2059 0.1429 0.081 Uiso 1 1 calc R . . H27B H -0.0712 0.1438 0.1717 0.081 Uiso 1 1 calc R . . H27C H 0.0674 0.1334 0.1475 0.081 Uiso 1 1 calc R . . C28 C 0.0018(9) 0.2590(5) 0.2164(3) 0.057(3) Uani 1 1 d . . . H28A H 0.0599 0.2874 0.2340 0.086 Uiso 1 1 calc R . . H28B H -0.0701 0.2359 0.2320 0.086 Uiso 1 1 calc R . . H28C H -0.0393 0.2903 0.1964 0.086 Uiso 1 1 calc R . . C29 C 0.1417(9) 0.1467(5) 0.2261(3) 0.048(2) Uani 1 1 d . . . H29A H 0.1932 0.1091 0.2126 0.071 Uiso 1 1 calc R . . H29B H 0.0647 0.1253 0.2402 0.071 Uiso 1 1 calc R . . H29C H 0.2010 0.1713 0.2452 0.071 Uiso 1 1 calc R . . C30 C 0.3133(8) 0.2108(4) 0.1576(3) 0.035(2) Uani 1 1 d . . . C31 C 0.5315(7) 0.2470(4) 0.1218(2) 0.0325(19) Uani 1 1 d . . . C32 C 0.4906(8) 0.2149(4) 0.0810(2) 0.036(2) Uani 1 1 d . . . H32A H 0.4438 0.1692 0.0851 0.055 Uiso 1 1 calc R . . H32B H 0.5724 0.2071 0.0650 0.055 Uiso 1 1 calc R . . H32C H 0.4298 0.2481 0.0672 0.055 Uiso 1 1 calc R . . C33 C 0.6258(8) 0.1920(4) 0.1450(3) 0.041(2) Uani 1 1 d . . . H33A H 0.6650 0.2156 0.1683 0.062 Uiso 1 1 calc R . . H33B H 0.6991 0.1757 0.1275 0.062 Uiso 1 1 calc R . . H33C H 0.5715 0.1508 0.1535 0.062 Uiso 1 1 calc R . . C34 C 0.6072(7) 0.3204(4) 0.1175(2) 0.0330(19) Uani 1 1 d . . . H34A H 0.6112 0.3432 0.1440 0.040 Uiso 1 1 calc R . . H34B H 0.7020 0.3107 0.1092 0.040 Uiso 1 1 calc R . . C35 C 0.5447(7) 0.3745(4) 0.0882(2) 0.0303(18) Uani 1 1 d . . . H35A H 0.4448 0.3682 0.0880 0.036 Uiso 1 1 calc R . . H35B H 0.5640 0.4236 0.0978 0.036 Uiso 1 1 calc R . . C36 C 0.5978(7) 0.3673(4) 0.0455(2) 0.0292(18) Uani 1 1 d . . . C37 C 0.5361(7) 0.3728(4) -0.0283(2) 0.0306(19) Uani 1 1 d . . . C38 C 0.6346(8) 0.4381(4) -0.0384(3) 0.039(2) Uani 1 1 d . . . H38A H 0.5880 0.4833 -0.0326 0.058 Uiso 1 1 calc R . . H38B H 0.6591 0.4366 -0.0665 0.058 Uiso 1 1 calc R . . H38C H 0.7171 0.4346 -0.0222 0.058 Uiso 1 1 calc R . . C39 C 0.3948(8) 0.3858(4) -0.0502(3) 0.040(2) Uani 1 1 d . . . H39A H 0.3289 0.3497 -0.0416 0.060 Uiso 1 1 calc R . . H39B H 0.4079 0.3821 -0.0790 0.060 Uiso 1 1 calc R . . H39C H 0.3605 0.4336 -0.0436 0.060 Uiso 1 1 calc R . . C40 C 0.6052(7) 0.3016(4) -0.0420(3) 0.0320(18) Uani 1 1 d . . . H40A H 0.6231 0.3045 -0.0709 0.038 Uiso 1 1 calc R . . H40B H 0.6941 0.2971 -0.0284 0.038 Uiso 1 1 calc R . . C41 C 0.5212(7) 0.2337(4) -0.0337(2) 0.0318(18) Uani 1 1 d . . . H41A H 0.4326 0.2379 -0.0474 0.038 Uiso 1 1 calc R . . H41B H 0.5027 0.2309 -0.0048 0.038 Uiso 1 1 calc R . . C42 C 0.5909(7) 0.1633(4) -0.0470(2) 0.0278(17) Uani 1 1 d . . . C43 C 0.5393(7) 0.0354(4) -0.0730(2) 0.0272(17) Uani 1 1 d . . . C44 C 0.5875(8) -0.0062(4) -0.0348(3) 0.038(2) Uani 1 1 d . . . H44A H 0.6693 0.0166 -0.0240 0.057 Uiso 1 1 calc R . . H44B H 0.6080 -0.0560 -0.0418 0.057 Uiso 1 1 calc R . . H44C H 0.5151 -0.0052 -0.0148 0.057 Uiso 1 1 calc R . . C45 C 0.4034(7) 0.0021(4) -0.0891(3) 0.035(2) Uani 1 1 d . . . H45A H 0.3322 0.0065 -0.0689 0.052 Uiso 1 1 calc R . . H45B H 0.4178 -0.0486 -0.0954 0.052 Uiso 1 1 calc R . . H45C H 0.3754 0.0276 -0.1132 0.052 Uiso 1 1 calc R . . C46 C 0.6522(8) 0.0318(4) -0.1052(2) 0.0356(19) Uani 1 1 d . . . H46A H 0.7403 0.0439 -0.0927 0.043 Uiso 1 1 calc R . . H46B H 0.6586 -0.0182 -0.1149 0.043 Uiso 1 1 calc R . . C47 C 0.6306(8) 0.0813(4) -0.1410(2) 0.036(2) Uani 1 1 d . . . H47A H 0.6372 0.1317 -0.1322 0.043 Uiso 1 1 calc R . . H47B H 0.5383 0.0736 -0.1519 0.043 Uiso 1 1 calc R . . C48 C 0.7371(10) 0.0672(5) -0.1736(3) 0.045(2) Uani 1 1 d . . . C49 C 0.7846(11) 0.0092(6) -0.2363(3) 0.065(3) Uani 1 1 d . . . H49A H 0.8621 -0.0172 -0.2246 0.078 Uiso 1 1 calc R . . H49B H 0.8199 0.0525 -0.2497 0.078 Uiso 1 1 calc R . . C50 C 0.7076(10) -0.0380(6) -0.2657(3) 0.068(3) Uani 1 1 d . . . H50A H 0.6704 -0.0797 -0.2517 0.102 Uiso 1 1 calc R . . H50B H 0.7698 -0.0542 -0.2865 0.102 Uiso 1 1 calc R . . H50C H 0.6331 -0.0106 -0.2776 0.102 Uiso 1 1 calc R . . N1 N 0.6853(6) 0.7327(3) 0.84611(18) 0.0338(16) Uani 1 1 d . . . H1 H 0.6964 0.6863 0.8438 0.041 Uiso 1 1 calc R . . N2 N 0.5728(6) 0.6502(3) 0.98204(17) 0.0260(14) Uani 1 1 d . . . H2 H 0.6589 0.6466 0.9754 0.031 Uiso 1 1 calc R . . N3 N 0.5744(6) 0.8876(3) 1.06807(18) 0.0286(15) Uani 1 1 d . . . H3 H 0.6569 0.8701 1.0659 0.034 Uiso 1 1 calc R . . N4 N 0.4055(6) 0.2618(3) 0.14692(19) 0.0320(16) Uani 1 1 d . . . H4 H 0.3915 0.3058 0.1550 0.038 Uiso 1 1 calc R . . N5 N 0.5045(6) 0.3723(3) 0.01523(18) 0.0270(15) Uani 1 1 d . . . H5 H 0.4186 0.3754 0.0220 0.032 Uiso 1 1 calc R . . N6 N 0.5038(7) 0.1111(3) -0.06187(17) 0.0282(15) Uiso 1 1 d . . . H6 H 0.4185 0.1238 -0.0651 0.034 Uiso 1 1 calc R . . O1 O 0.8773(5) 0.7322(3) 0.81010(19) 0.0491(16) Uani 1 1 d . . . O2 O 0.7933(6) 0.8409(3) 0.8338(2) 0.0517(16) Uani 1 1 d . . . O3 O 0.3522(5) 0.6641(2) 0.95796(14) 0.0307(12) Uiso 1 1 d . . . O4 O 0.3516(5) 0.8816(3) 1.04428(16) 0.0351(13) Uani 1 1 d . . . O5 O 0.2018(6) 0.9227(3) 1.18263(18) 0.0481(15) Uani 1 1 d . . . O6 O 0.3345(6) 0.9702(3) 1.23139(18) 0.0458(15) Uani 1 1 d . . . O7 O 0.2074(5) 0.2449(3) 0.17930(16) 0.0388(14) Uani 1 1 d . . . O8 O 0.3147(5) 0.1463(3) 0.15015(17) 0.0420(14) Uani 1 1 d . . . O9 O 0.7248(5) 0.3591(3) 0.03885(15) 0.0321(12) Uiso 1 1 d . . . O10 O 0.7200(5) 0.1545(3) -0.04466(16) 0.0335(13) Uani 1 1 d . . . O11 O 0.8576(6) 0.0863(3) -0.17252(19) 0.0482(16) Uani 1 1 d . . . O12 O 0.6839(6) 0.0294(3) -0.20474(17) 0.0467(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.010(4) 0.052(5) 0.068(6) 0.021(5) 0.012(4) -0.009(4) C2 0.033(6) 0.084(8) 0.114(9) 0.016(7) 0.035(6) 0.006(5) C3 0.047(7) 0.097(9) 0.070(7) 0.030(6) 0.012(6) 0.001(6) C4 0.033(6) 0.109(9) 0.062(7) 0.000(6) 0.002(5) -0.027(6) C5 0.022(4) 0.019(4) 0.074(6) 0.004(4) 0.001(4) -0.001(3) C6 0.017(4) 0.031(4) 0.049(5) 0.006(4) 0.000(4) 0.011(3) C7 0.021(4) 0.041(5) 0.064(6) 0.007(4) 0.004(4) 0.011(4) C8 0.022(4) 0.037(5) 0.059(6) -0.002(4) 0.004(4) 0.000(4) C9 0.007(3) 0.038(4) 0.042(5) -0.010(4) -0.001(3) 0.000(3) C10 0.015(4) 0.025(4) 0.041(5) -0.003(3) -0.001(3) 0.000(3) C12 0.009(4) 0.040(5) 0.045(5) -0.001(4) 0.002(3) 0.004(3) C13 0.035(5) 0.037(5) 0.064(6) -0.004(4) 0.013(5) -0.010(4) C14 0.026(4) 0.047(5) 0.039(5) -0.001(4) -0.002(4) 0.014(4) C16 0.019(4) 0.039(5) 0.041(5) -0.011(4) -0.002(4) 0.008(3) C17 0.004(3) 0.017(3) 0.055(5) -0.006(3) 0.005(3) 0.001(3) C18 0.014(4) 0.020(4) 0.045(5) -0.005(3) 0.005(3) -0.009(3) C19 0.017(4) 0.029(4) 0.055(5) -0.003(4) -0.003(4) 0.005(3) C21 0.015(4) 0.034(4) 0.048(5) -0.002(4) 0.002(4) 0.002(3) C22 0.024(4) 0.024(4) 0.057(5) -0.009(4) 0.007(4) -0.007(3) C23 0.022(5) 0.046(5) 0.048(6) 0.002(4) 0.012(4) 0.001(4) C24 0.050(7) 0.116(10) 0.050(7) -0.013(6) 0.029(5) -0.013(6) C25 0.066(8) 0.110(10) 0.066(8) 0.003(7) 0.038(6) 0.003(7) C26 0.020(4) 0.040(5) 0.055(5) 0.005(4) 0.007(4) -0.006(4) C27 0.017(4) 0.089(7) 0.057(6) 0.015(5) -0.009(4) -0.018(4) C28 0.025(5) 0.067(6) 0.080(7) 0.005(5) 0.009(5) 0.006(4) C29 0.030(5) 0.061(6) 0.051(5) 0.021(5) -0.003(4) -0.015(4) C30 0.016(4) 0.029(5) 0.060(6) 0.005(4) -0.005(4) 0.009(3) C31 0.011(4) 0.039(4) 0.048(5) 0.000(4) 0.004(3) 0.016(3) C32 0.013(4) 0.036(5) 0.060(6) -0.004(4) 0.003(4) -0.001(3) C33 0.023(4) 0.044(5) 0.057(6) 0.016(4) 0.000(4) 0.014(4) C34 0.010(4) 0.038(5) 0.051(5) 0.002(4) -0.001(4) -0.005(3) C35 0.008(4) 0.031(4) 0.051(5) 0.000(4) 0.001(4) -0.002(3) C36 0.006(3) 0.033(4) 0.049(5) -0.012(4) 0.000(4) -0.003(3) C37 0.009(4) 0.024(4) 0.059(6) -0.001(4) -0.003(4) -0.001(3) C38 0.026(4) 0.029(4) 0.060(6) 0.000(4) 0.011(4) -0.008(3) C39 0.020(4) 0.045(5) 0.055(6) -0.003(4) 0.003(4) 0.010(4) C40 0.009(4) 0.036(4) 0.052(5) -0.002(4) -0.003(4) 0.007(3) C41 0.014(4) 0.027(4) 0.054(5) -0.012(4) -0.005(4) -0.010(3) C42 0.020(4) 0.030(4) 0.034(5) -0.002(4) -0.006(4) 0.001(3) C43 0.016(4) 0.012(3) 0.053(5) -0.005(3) -0.002(4) 0.001(3) C44 0.017(4) 0.033(4) 0.064(6) -0.002(4) 0.001(4) 0.004(3) C45 0.013(4) 0.028(4) 0.062(6) -0.005(4) 0.002(4) -0.013(3) C46 0.016(4) 0.041(5) 0.050(5) -0.006(4) 0.009(4) -0.001(4) C47 0.022(4) 0.040(5) 0.046(5) -0.007(4) 0.005(4) -0.004(4) C48 0.053(6) 0.041(5) 0.041(5) -0.009(4) 0.000(5) 0.001(4) C49 0.067(7) 0.059(6) 0.068(7) -0.031(5) 0.019(6) -0.020(5) C50 0.040(6) 0.075(7) 0.089(8) -0.036(6) -0.003(6) -0.001(5) N1 0.018(3) 0.033(4) 0.050(4) 0.003(3) 0.005(3) -0.008(3) N2 0.010(3) 0.026(3) 0.042(4) -0.001(3) -0.001(3) 0.004(3) N3 0.004(3) 0.031(3) 0.050(4) -0.001(3) -0.001(3) 0.004(3) N4 0.011(3) 0.024(3) 0.062(4) -0.004(3) 0.005(3) 0.006(3) N5 0.010(3) 0.025(3) 0.046(4) -0.004(3) 0.007(3) 0.000(2) O1 0.019(3) 0.050(4) 0.077(4) 0.004(3) 0.020(3) -0.005(3) O2 0.031(3) 0.034(4) 0.090(5) 0.007(3) 0.003(3) 0.000(3) O4 0.012(3) 0.035(3) 0.058(4) -0.009(3) 0.001(3) 0.006(2) O5 0.029(3) 0.040(3) 0.075(4) -0.013(3) 0.011(3) -0.009(3) O6 0.029(3) 0.057(4) 0.052(4) 0.000(3) 0.003(3) -0.004(3) O7 0.019(3) 0.038(3) 0.059(4) 0.001(3) 0.009(3) 0.002(2) O8 0.024(3) 0.033(3) 0.068(4) 0.004(3) 0.000(3) -0.004(2) O10 0.006(3) 0.034(3) 0.060(4) -0.009(3) 0.000(2) 0.002(2) O11 0.025(3) 0.046(3) 0.074(4) -0.010(3) 0.005(3) -0.010(3) O12 0.029(3) 0.054(4) 0.057(4) -0.011(3) 0.006(3) -0.012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C3 1.488(12) . ? C1 O1 1.503(8) . ? C1 C2 1.509(13) . ? C1 C4 1.519(12) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 O2 1.190(8) . ? C5 N1 1.349(9) . ? C5 O1 1.378(10) . ? C6 N1 1.472(9) . ? C6 C7 1.513(10) . ? C6 C9 1.524(10) . ? C6 C8 1.550(11) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.556(10) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.494(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O3 1.270(8) . ? C11 N2 1.338(9) . ? C12 N2 1.470(9) . ? C12 C14 1.535(10) . ? C12 C15 1.547(10) . ? C12 C13 1.548(11) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.540(10) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.510(9) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O4 1.265(8) . ? C17 N3 1.357(9) . ? C18 C19 1.479(10) . ? C18 N3 1.492(9) . ? C18 C20 1.551(10) . ? C18 C21 1.568(10) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.517(10) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.524(11) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 O5 1.236(10) . ? C23 O6 1.315(10) . ? C24 C25 1.447(14) . ? C24 O6 1.447(10) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.487(11) . ? C26 O7 1.497(9) . ? C26 C29 1.507(11) . ? C26 C28 1.518(12) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 O8 1.206(9) . ? C30 N4 1.336(10) . ? C30 O7 1.394(9) . ? C31 N4 1.495(9) . ? C31 C32 1.522(11) . ? C31 C34 1.536(10) . ? C31 C33 1.558(10) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 C35 1.510(10) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.506(10) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 O9 1.252(8) . ? C36 N5 1.347(9) . ? C37 N5 1.470(10) . ? C37 C40 1.533(10) . ? C37 C39 1.560(10) . ? C37 C38 1.562(10) . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C40 C41 1.508(10) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 C42 1.519(10) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 O10 1.256(8) . ? C42 N6 1.363(9) . ? C43 N6 1.474(8) . ? C43 C46 1.522(10) . ? C43 C45 1.540(10) . ? C43 C44 1.545(10) . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 C47 1.504(11) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 C48 1.511(11) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 O11 1.213(10) . ? C48 O12 1.340(10) . ? C49 O12 1.472(10) . ? C49 C50 1.496(13) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? N1 H1 0.8600 . ? N2 H2 0.8600 . ? N3 H3 0.8600 . ? N4 H4 0.8600 . ? N5 H5 0.8600 . ? N6 H6 0.8600 . ? 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 C3 C1 O1 107.8(7) . . ? C3 C1 C2 110.9(8) . . ? O1 C1 C2 101.0(7) . . ? C3 C1 C4 113.6(9) . . ? O1 C1 C4 109.5(7) . . ? C2 C1 C4 113.1(8) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 N1 127.0(8) . . ? O2 C5 O1 125.6(7) . . ? N1 C5 O1 107.4(6) . . ? N1 C6 C7 110.8(6) . . ? N1 C6 C9 107.7(6) . . ? C7 C6 C9 109.3(6) . . ? N1 C6 C8 109.8(6) . . ? C7 C6 C8 108.6(6) . . ? C9 C6 C8 110.6(6) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 C10 114.9(6) . . ? C6 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? C6 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C11 C10 C9 115.0(6) . . ? C11 C10 H10A 108.5 . . ? C9 C10 H10A 108.5 . . ? C11 C10 H10B 108.5 . . ? C9 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? O3 C11 N2 122.2(6) . . ? O3 C11 C10 120.8(6) . . ? N2 C11 C10 117.0(6) . . ? N2 C12 C14 107.0(6) . . ? N2 C12 C15 113.0(6) . . ? C14 C12 C15 108.6(6) . . ? N2 C12 C13 110.9(6) . . ? C14 C12 C13 109.6(6) . . ? C15 C12 C13 107.7(6) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C12 113.4(6) . . ? C16 C15 H15A 108.9 . . ? C12 C15 H15A 108.9 . . ? C16 C15 H15B 108.9 . . ? C12 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 109.2(6) . . ? C17 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? C17 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? O4 C17 N3 121.5(6) . . ? O4 C17 C16 122.5(6) . . ? N3 C17 C16 115.9(6) . . ? C19 C18 N3 111.2(6) . . ? C19 C18 C20 110.4(6) . . ? N3 C18 C20 105.2(6) . . ? C19 C18 C21 112.0(6) . . ? N3 C18 C21 108.0(5) . . ? C20 C18 C21 109.8(6) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C18 112.9(6) . . ? C22 C21 H21A 109.0 . . ? C18 C21 H21A 109.0 . . ? C22 C21 H21B 109.0 . . ? C18 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C21 C22 C23 112.4(6) . . ? C21 C22 H22A 109.1 . . ? C23 C22 H22A 109.1 . . ? C21 C22 H22B 109.1 . . ? C23 C22 H22B 109.1 . . ? H22A C22 H22B 107.9 . . ? O5 C23 O6 122.1(7) . . ? O5 C23 C22 125.1(8) . . ? O6 C23 C22 112.8(7) . . ? C25 C24 O6 108.0(9) . . ? C25 C24 H24A 110.1 . . ? O6 C24 H24A 110.1 . . ? C25 C24 H24B 110.1 . . ? O6 C24 H24B 110.1 . . ? H24A C24 H24B 108.4 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 O7 109.7(6) . . ? C27 C26 C29 114.6(7) . . ? O7 C26 C29 109.6(6) . . ? C27 C26 C28 110.2(7) . . ? O7 C26 C28 102.0(6) . . ? C29 C26 C28 110.0(7) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O8 C30 N4 128.5(7) . . ? O8 C30 O7 123.4(7) . . ? N4 C30 O7 108.0(6) . . ? N4 C31 C32 110.6(6) . . ? N4 C31 C34 106.1(6) . . ? C32 C31 C34 112.3(6) . . ? N4 C31 C33 108.5(6) . . ? C32 C31 C33 109.7(6) . . ? C34 C31 C33 109.5(6) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 C31 116.3(6) . . ? C35 C34 H34A 108.2 . . ? C31 C34 H34A 108.2 . . ? C35 C34 H34B 108.2 . . ? C31 C34 H34B 108.2 . . ? H34A C34 H34B 107.4 . . ? C36 C35 C34 114.1(6) . . ? C36 C35 H35A 108.7 . . ? C34 C35 H35A 108.7 . . ? C36 C35 H35B 108.7 . . ? C34 C35 H35B 108.7 . . ? H35A C35 H35B 107.6 . . ? O9 C36 N5 122.0(7) . . ? O9 C36 C35 120.4(7) . . ? N5 C36 C35 117.5(6) . . ? N5 C37 C40 111.8(6) . . ? N5 C37 C39 105.9(6) . . ? C40 C37 C39 111.8(6) . . ? N5 C37 C38 109.8(6) . . ? C40 C37 C38 109.0(6) . . ? C39 C37 C38 108.4(6) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C37 C39 H39A 109.5 . . ? C37 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C37 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C41 C40 C37 114.5(6) . . ? C41 C40 H40A 108.6 . . ? C37 C40 H40A 108.6 . . ? C41 C40 H40B 108.6 . . ? C37 C40 H40B 108.6 . . ? H40A C40 H40B 107.6 . . ? C40 C41 C42 114.1(6) . . ? C40 C41 H41A 108.7 . . ? C42 C41 H41A 108.7 . . ? C40 C41 H41B 108.7 . . ? C42 C41 H41B 108.7 . . ? H41A C41 H41B 107.6 . . ? O10 C42 N6 122.8(6) . . ? O10 C42 C41 121.9(6) . . ? N6 C42 C41 115.2(6) . . ? N6 C43 C46 112.4(6) . . ? N6 C43 C45 105.1(6) . . ? C46 C43 C45 110.4(6) . . ? N6 C43 C44 109.3(6) . . ? C46 C43 C44 109.5(6) . . ? C45 C43 C44 110.1(6) . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C43 C45 H45A 109.5 . . ? C43 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C43 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C47 C46 C43 115.1(6) . . ? C47 C46 H46A 108.5 . . ? C43 C46 H46A 108.5 . . ? C47 C46 H46B 108.5 . . ? C43 C46 H46B 108.5 . . ? H46A C46 H46B 107.5 . . ? C46 C47 C48 111.4(7) . . ? C46 C47 H47A 109.3 . . ? C48 C47 H47A 109.3 . . ? C46 C47 H47B 109.3 . . ? C48 C47 H47B 109.3 . . ? H47A C47 H47B 108.0 . . ? O11 C48 O12 122.6(8) . . ? O11 C48 C47 125.3(8) . . ? O12 C48 C47 112.1(8) . . ? O12 C49 C50 106.1(8) . . ? O12 C49 H49A 110.5 . . ? C50 C49 H49A 110.5 . . ? O12 C49 H49B 110.5 . . ? C50 C49 H49B 110.5 . . ? H49A C49 H49B 108.7 . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C5 N1 C6 124.9(6) . . ? C5 N1 H1 117.5 . . ? C6 N1 H1 117.5 . . ? C11 N2 C12 126.3(6) . . ? C11 N2 H2 116.9 . . ? C12 N2 H2 116.9 . . ? C17 N3 C18 126.1(6) . . ? C17 N3 H3 117.0 . . ? C18 N3 H3 117.0 . . ? C30 N4 C31 124.0(6) . . ? C30 N4 H4 118.0 . . ? C31 N4 H4 118.0 . . ? C36 N5 C37 126.1(6) . . ? C36 N5 H5 117.0 . . ? C37 N5 H5 117.0 . . ? C42 N6 C43 127.2(6) . . ? C42 N6 H6 116.4 . . ? C43 N6 H6 116.4 . . ? C5 O1 C1 119.8(6) . . ? C23 O6 C24 119.0(7) . . ? C30 O7 C26 120.2(6) . . ? C48 O12 C49 114.9(7) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.470 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 943868'