Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 B607574F rev cif.CIF 0 Km œST W _publ_contact_author_name 'Albrecht Berkessel' _publ_contact_author_address ; Institut für Organische Chemie der Universität zu Köln, Greinstrasse 4, D-50939 Köln, Germany Fax: +49-221-470-5102 Tel: +49-221-470-3283 E-mail: berkessel@uni-koeln.de ; _publ_requested_journal ; Organic & Biomolecular Chemistry ; _publ_section_title ; Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones ; data_1f _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 F6 N3 O, C3 H8 O' _chemical_formula_sum 'C26 H33 F6 N3 O2' _chemical_formula_weight 533.55 _chemical_absolute_configuration syn 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.2234(7) _cell_length_b 8.9069(5) _cell_length_c 21.5226(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.890(2) _cell_angle_gamma 90.00 _cell_volume 2726.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13589 _cell_measurement_theta_min 1.43 _cell_measurement_theta_max 27.00 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'Nonius KappaCCD' _diffrn_measurement_method 'Phi/Omega-Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13589 _diffrn_reflns_av_R_equivalents 0.1052 _diffrn_reflns_av_sigmaI/netI 0.2006 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6269 _reflns_number_gt 2709 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0460P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.8(10) _refine_ls_number_reflns 6269 _refine_ls_number_parameters 801 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2120 _refine_ls_R_factor_gt 0.0753 _refine_ls_wR_factor_ref 0.1431 _refine_ls_wR_factor_gt 0.1107 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.002 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 0.2961(4) 0.7357(8) 0.4914(3) 0.0213(18) Uani 1 1 d . . . H1 H 0.301(4) 0.851(6) 0.492(3) 0.026 Uiso 1 1 d . . . C2 C 0.3818(4) 0.6805(8) 0.4563(4) 0.0227(19) Uani 1 1 d . . . H2 H 0.382(4) 0.585(6) 0.450(3) 0.027 Uiso 1 1 d . . . C3 C 0.3875(5) 0.7585(9) 0.3929(4) 0.0285(19) Uani 1 1 d . . . H3A H 0.444(4) 0.715(6) 0.365(3) 0.022(17) Uiso 1 1 d . . . H3B H 0.401(4) 0.878(7) 0.403(3) 0.05(2) Uiso 1 1 d . . . C4 C 0.2970(6) 0.7330(10) 0.3550(4) 0.041(2) Uani 1 1 d . . . H4A H 0.313(5) 0.765(8) 0.317(4) 0.050 Uiso 1 1 d . . . H4B H 0.291(4) 0.615(8) 0.345(3) 0.050 Uiso 1 1 d . . . C5 C 0.2110(4) 0.7860(8) 0.3902(4) 0.033(2) Uani 1 1 d . . . H5A H 0.2142 0.8961 0.3962 0.040 Uiso 1 1 calc R . . H5B H 0.1533 0.7628 0.3658 0.040 Uiso 1 1 calc R . . C6 C 0.2068(5) 0.7088(9) 0.4531(4) 0.0244(18) Uani 1 1 d . . . H6A H 0.156(4) 0.752(6) 0.480(3) 0.024(17) Uiso 1 1 d . . . H6B H 0.193(4) 0.596(7) 0.452(3) 0.030(18) Uiso 1 1 d . . . C7 C 0.2675(4) 0.5208(7) 0.5598(3) 0.0289(19) Uani 1 1 d . . . H7A H 0.2978 0.4623 0.5265 0.035 Uiso 1 1 calc R . . H7B H 0.1986 0.5150 0.5531 0.035 Uiso 1 1 calc R . . C8 C 0.2932(5) 0.4517(7) 0.6228(3) 0.0264(18) Uani 1 1 d . . . C9 C 0.3851(5) 0.4516(8) 0.6434(4) 0.032(2) Uani 1 1 d . . . H9 H 0.429(4) 0.508(7) 0.621(3) 0.04(2) Uiso 1 1 d . . . C10 C 0.4096(5) 0.3833(8) 0.7005(4) 0.031(2) Uani 1 1 d . . . H10 H 0.478(4) 0.384(6) 0.715(3) 0.038 Uiso 1 1 d . . . C11 C 0.3419(5) 0.3154(8) 0.7359(4) 0.035(2) Uani 1 1 d . . . H11 H 0.358(4) 0.257(6) 0.778(3) 0.022(17) Uiso 1 1 d . . . C12 C 0.2500(5) 0.3151(8) 0.7147(4) 0.036(2) Uani 1 1 d . . . H12 H 0.198(5) 0.266(8) 0.739(4) 0.06(2) Uiso 1 1 d . . . C13 C 0.2257(5) 0.3850(8) 0.6588(4) 0.032(2) Uani 1 1 d . . . H13 H 0.158(4) 0.371(6) 0.644(3) 0.019(17) Uiso 1 1 d . . . C14 C 0.2428(5) 0.7719(8) 0.5992(4) 0.037(2) Uani 1 1 d . . . H14A H 0.2670 0.8749 0.5989 0.045 Uiso 1 1 calc R . . H14B H 0.2487 0.7307 0.6413 0.045 Uiso 1 1 calc R . . H14C H 0.1765 0.7721 0.5862 0.045 Uiso 1 1 calc R . . C15 C 0.5531(4) 0.6613(7) 0.4836(4) 0.0222(18) Uani 1 1 d . . . C16 C 0.7142(4) 0.6927(7) 0.5307(4) 0.0223(18) Uani 1 1 d . . . C17 C 0.7608(5) 0.7305(8) 0.5878(4) 0.0277(19) Uani 1 1 d . . . H17 H 0.717(4) 0.767(6) 0.622(3) 0.012(16) Uiso 1 1 d . . . C18 C 0.8565(5) 0.7254(7) 0.5918(4) 0.0241(18) Uani 1 1 d . . . C19 C 0.9112(5) 0.6825(7) 0.5425(4) 0.028(2) Uani 1 1 d . . . H19 H 0.984(4) 0.681(5) 0.537(3) 0.017(16) Uiso 1 1 d . . . C20 C 0.8658(4) 0.6475(7) 0.4863(4) 0.0211(18) Uani 1 1 d . . . C21 C 0.7693(5) 0.6501(7) 0.4803(4) 0.0240(19) Uani 1 1 d . . . H21 H 0.734(4) 0.636(5) 0.439(3) 0.013(16) Uiso 1 1 d . . . C22 C 0.9011(5) 0.7698(10) 0.6542(4) 0.039(2) Uani 1 1 d . . . C23 C 0.9267(5) 0.6108(8) 0.4320(4) 0.031(2) Uani 1 1 d . . . N1 N 0.2976(3) 0.6782(6) 0.5558(3) 0.0234(15) Uani 1 1 d . . . N2 N 0.4655(4) 0.7092(7) 0.4951(3) 0.0251(17) Uani 1 1 d . . . H2N H 0.456(5) 0.730(8) 0.529(3) 0.030 Uiso 1 1 d . . . N3 N 0.6172(4) 0.7033(6) 0.5294(3) 0.0251(17) Uani 1 1 d . . . H3N H 0.600(5) 0.747(8) 0.551(4) 0.030 Uiso 1 1 d . . . O1 O 0.5754(3) 0.5846(5) 0.4382(2) 0.0285(13) Uani 1 1 d . . . F1 F 0.8909(3) 0.9148(6) 0.6667(2) 0.0643(15) Uani 1 1 d . . . F2 F 0.8633(3) 0.6936(6) 0.7003(2) 0.0627(16) Uani 1 1 d . . . F3 F 0.9936(3) 0.7417(6) 0.6557(2) 0.0581(14) Uani 1 1 d . . . F4 F 0.9862(3) 0.4985(5) 0.4469(2) 0.0494(13) Uani 1 1 d . . . F5 F 0.9794(3) 0.7261(4) 0.4160(2) 0.0424(12) Uani 1 1 d . . . F6 F 0.8789(2) 0.5663(4) 0.3819(2) 0.0366(11) Uani 1 1 d . . . C24 C 1.2029(4) 0.3048(8) 0.0090(4) 0.0260(19) Uani 1 1 d . . . H24 H 1.194(4) 0.415(7) 0.005(3) 0.031 Uiso 1 1 d . . . C25 C 1.1160(5) 0.2505(8) 0.0430(4) 0.0252(19) Uani 1 1 d . . . H25 H 1.117(4) 0.152(7) 0.050(3) 0.030 Uiso 1 1 d . . . C26 C 1.1121(5) 0.3240(10) 0.1072(4) 0.032(2) Uani 1 1 d . . . H26A H 1.113(4) 0.427(7) 0.106(3) 0.03(2) Uiso 1 1 d . . . H26B H 1.053(5) 0.291(8) 0.128(4) 0.07(3) Uiso 1 1 d . . . C27 C 1.2010(4) 0.2902(8) 0.1456(4) 0.033(2) Uani 1 1 d . . . H27A H 1.1977 0.3434 0.1859 0.039 Uiso 1 1 calc R . . H27B H 1.2041 0.1812 0.1542 0.039 Uiso 1 1 calc R . . C28 C 1.2892(5) 0.3380(8) 0.1124(4) 0.035(2) Uani 1 1 d . . . H28A H 1.3452 0.3064 0.1370 0.042 Uiso 1 1 calc R . . H28B H 1.2905 0.4488 0.1088 0.042 Uiso 1 1 calc R . . C29 C 1.2928(5) 0.2676(9) 0.0472(4) 0.038(2) Uani 1 1 d . . . H29A H 1.2993 0.1573 0.0511 0.045 Uiso 1 1 calc R . . H29B H 1.3485 0.3061 0.0252 0.045 Uiso 1 1 calc R . . C30 C 1.2282(5) 0.0951(8) -0.0629(4) 0.026(2) Uani 1 1 d . . . H30A H 1.200(4) 0.042(7) -0.035(3) 0.031 Uiso 1 1 d . . . H30B H 1.295(4) 0.095(6) -0.050(3) 0.031 Uiso 1 1 d . . . C31 C 1.2010(5) 0.0334(7) -0.1262(4) 0.0275(19) Uani 1 1 d . . . C32 C 1.1057(5) 0.0308(9) -0.1454(4) 0.035(2) Uani 1 1 d . . . H32 H 1.055(4) 0.076(7) -0.120(3) 0.042 Uiso 1 1 d . . . C33 C 1.0809(6) -0.0236(8) -0.2021(5) 0.042(2) Uani 1 1 d . . . H33 H 1.021(4) -0.031(6) -0.218(3) 0.023(19) Uiso 1 1 d . . . C34 C 1.1467(6) -0.0831(8) -0.2406(4) 0.041(2) Uani 1 1 d . . . H34 H 1.1274 -0.1247 -0.2794 0.05(2) Uiso 1 1 calc R . . C35 C 1.2413(6) -0.0837(8) -0.2237(4) 0.038(2) Uani 1 1 d . . . H35 H 1.292(5) -0.134(7) -0.255(4) 0.046 Uiso 1 1 d . . . C36 C 1.2673(5) -0.0240(8) -0.1654(4) 0.039(2) Uani 1 1 d . . . H36 H 1.339(4) -0.017(6) -0.154(3) 0.031(18) Uiso 1 1 d . . . C37 C 1.2591(5) 0.3509(7) -0.0955(3) 0.0301(19) Uani 1 1 d . . . H37A H 1.3243 0.3513 -0.0800 0.036 Uiso 1 1 calc R . . H37B H 1.2338 0.4532 -0.0945 0.036 Uiso 1 1 calc R . . H37C H 1.2572 0.3134 -0.1383 0.036 Uiso 1 1 calc R . . C38 C 0.9476(5) 0.2389(8) 0.0135(4) 0.0285(19) Uani 1 1 d . . . C39 C 0.7848(5) 0.2672(7) -0.0327(4) 0.0256(19) Uani 1 1 d . . . C40 C 0.7388(5) 0.2932(7) -0.0885(4) 0.028(2) Uani 1 1 d . . . H40 H 0.766(5) 0.314(8) -0.139(4) 0.07(3) Uiso 1 1 d . . . C41 C 0.6416(5) 0.2841(8) -0.0935(4) 0.034(2) Uani 1 1 d . . . C42 C 0.5893(5) 0.2496(8) -0.0408(4) 0.035(2) Uani 1 1 d . . . H42 H 0.526(5) 0.244(7) -0.042(3) 0.042 Uiso 1 1 d . . . C43 C 0.6368(5) 0.2264(7) 0.0141(4) 0.0287(19) Uani 1 1 d . . . C44 C 0.7329(4) 0.2326(7) 0.0203(4) 0.0265(19) Uani 1 1 d . . . H44 H 0.770(4) 0.215(6) 0.062(3) 0.032 Uiso 1 1 d . . . C45 C 0.5942(6) 0.3140(12) -0.1536(5) 0.050(3) Uani 1 1 d . . . C46 C 0.5767(5) 0.1912(8) 0.0702(4) 0.037(2) Uani 1 1 d . . . O2 O 0.9244(3) 0.1605(5) 0.0588(3) 0.0321(14) Uani 1 1 d . . . N4 N 1.2027(4) 0.2539(5) -0.0565(3) 0.0241(15) Uani 1 1 d . . . N5 N 1.0344(4) 0.2875(7) 0.0047(3) 0.0279(18) Uani 1 1 d . . . H5N H 1.050(5) 0.321(8) -0.026(4) 0.034 Uiso 1 1 d . . . N6 N 0.8833(4) 0.2826(6) -0.0318(3) 0.0284(17) Uani 1 1 d . . . H6N H 0.905(5) 0.328(7) -0.064(3) 0.034 Uiso 1 1 d . . . F7 F 0.6055(5) 0.4546(7) -0.1718(3) 0.110(2) Uani 1 1 d . . . F8 F 0.6296(4) 0.2329(7) -0.1982(3) 0.0821(18) Uani 1 1 d . . . F9 F 0.5045(3) 0.2869(10) -0.1543(3) 0.129(3) Uani 1 1 d . . . F10 F 0.5146(3) 0.0854(5) 0.0610(2) 0.0613(16) Uani 1 1 d . . . F11 F 0.5267(3) 0.3150(5) 0.0871(2) 0.0516(14) Uani 1 1 d . . . F12 F 0.6277(3) 0.1544(4) 0.1211(2) 0.0436(13) Uani 1 1 d . . . C47 C -0.0210(5) 0.9107(8) 0.1817(4) 0.0313(19) Uani 1 1 d . . . H47 H -0.075(5) 0.833(7) 0.174(3) 0.05(2) Uiso 1 1 d . . . C48 C 0.0510(6) 0.8312(9) 0.2216(4) 0.050(2) Uani 1 1 d . . . H48A H 0.0719 0.7399 0.2004 0.060 Uiso 1 1 calc R . . H48B H 0.0232 0.8043 0.2614 0.060 Uiso 1 1 calc R . . H48C H 0.1050 0.8975 0.2289 0.060 Uiso 1 1 calc R . . C49 C -0.0597(5) 1.0525(8) 0.2108(4) 0.047(2) Uani 1 1 d . . . H49A H -0.0080 1.1226 0.2195 0.056 Uiso 1 1 calc R . . H49B H -0.0909 1.0272 0.2497 0.056 Uiso 1 1 calc R . . H49C H -0.1051 1.0994 0.1821 0.056 Uiso 1 1 calc R . . O3 O 0.0217(3) 0.9474(5) 0.1238(2) 0.0321(13) Uani 1 1 d . . . H3 H -0.0175 0.9922 0.1008 0.31(10) Uiso 1 1 calc R . . C50 C 0.5033(5) 0.3282(8) 0.3146(4) 0.031(2) Uani 1 1 d . . . H50 H 0.572(5) 0.296(7) 0.317(3) 0.04(2) Uiso 1 1 d . . . C51 C 0.4316(5) 0.2170(8) 0.2884(4) 0.045(2) Uani 1 1 d . . . H51A H 0.4242 0.1335 0.3176 0.054 Uiso 1 1 calc R . . H51B H 0.4534 0.1782 0.2485 0.054 Uiso 1 1 calc R . . H51C H 0.3710 0.2676 0.2823 0.054 Uiso 1 1 calc R . . C52 C 0.5105(6) 0.4676(9) 0.2761(4) 0.054(2) Uani 1 1 d . . . H52A H 0.4525 0.5261 0.2796 0.065 Uiso 1 1 calc R . . H52B H 0.5199 0.4402 0.2326 0.065 Uiso 1 1 calc R . . H52C H 0.5639 0.5279 0.2910 0.065 Uiso 1 1 calc R . . O4 O 0.4721(3) 0.3673(5) 0.3758(3) 0.0324(14) Uani 1 1 d . . . H4O H 0.505(4) 0.443(8) 0.384(3) 0.039 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 C1 0.019(4) 0.024(4) 0.020(5) 0.002(3) -0.004(3) -0.002(3) C2 0.013(4) 0.027(4) 0.028(5) -0.002(4) -0.003(3) 0.001(3) C3 0.022(4) 0.046(5) 0.018(5) 0.001(4) 0.005(4) -0.007(4) C4 0.036(5) 0.060(6) 0.028(6) 0.004(5) 0.004(4) -0.005(4) C5 0.018(4) 0.045(5) 0.036(6) 0.007(4) -0.005(4) -0.008(3) C6 0.016(4) 0.035(5) 0.022(5) 0.000(4) -0.001(4) 0.002(3) C7 0.025(4) 0.031(5) 0.031(6) -0.003(4) 0.001(4) -0.005(3) C8 0.024(4) 0.031(4) 0.024(5) -0.002(4) 0.005(4) 0.008(3) C9 0.035(5) 0.028(5) 0.035(6) 0.000(4) 0.004(4) 0.003(4) C10 0.031(4) 0.032(4) 0.032(6) 0.011(4) 0.005(4) 0.006(3) C11 0.033(5) 0.038(5) 0.035(6) 0.010(4) 0.008(4) 0.007(4) C12 0.038(5) 0.039(5) 0.031(6) 0.010(4) 0.013(4) 0.003(4) C13 0.029(5) 0.043(5) 0.025(6) -0.003(4) 0.002(4) 0.005(4) C14 0.043(5) 0.036(5) 0.033(6) 0.000(4) 0.014(4) 0.001(4) C15 0.015(4) 0.032(4) 0.020(5) 0.002(4) 0.003(4) -0.003(3) C16 0.018(4) 0.022(4) 0.026(5) 0.007(4) 0.000(4) 0.001(3) C17 0.025(5) 0.034(5) 0.024(6) 0.003(4) 0.003(4) -0.006(3) C18 0.019(4) 0.031(4) 0.022(5) 0.000(4) -0.006(4) -0.004(3) C19 0.015(4) 0.032(5) 0.037(6) 0.007(4) -0.002(4) -0.001(3) C20 0.014(4) 0.022(4) 0.027(5) 0.002(3) -0.004(4) -0.002(3) C21 0.024(4) 0.015(4) 0.033(6) 0.000(3) -0.009(4) 0.002(3) C22 0.020(4) 0.052(6) 0.044(7) 0.014(5) 0.001(4) -0.002(4) C23 0.018(4) 0.036(5) 0.040(6) 0.000(4) 0.002(4) -0.001(4) N1 0.018(3) 0.022(4) 0.030(5) -0.005(3) 0.001(3) 0.002(2) N2 0.017(3) 0.034(4) 0.024(5) -0.001(3) 0.002(3) -0.005(3) N3 0.016(4) 0.033(4) 0.026(5) -0.010(3) 0.004(3) 0.002(3) O1 0.020(3) 0.038(3) 0.027(4) -0.007(2) 0.002(2) 0.004(2) F1 0.076(4) 0.068(4) 0.048(4) -0.026(3) -0.021(3) -0.002(3) F2 0.041(3) 0.120(4) 0.027(4) 0.021(3) -0.007(2) -0.028(3) F3 0.033(3) 0.105(4) 0.036(4) -0.001(3) -0.014(3) -0.005(2) F4 0.042(3) 0.058(3) 0.048(3) -0.002(2) 0.007(2) 0.023(2) F5 0.027(2) 0.055(3) 0.046(3) -0.003(2) 0.007(2) -0.019(2) F6 0.029(2) 0.049(3) 0.032(3) -0.008(2) 0.000(2) -0.0070(19) C24 0.017(4) 0.036(5) 0.025(6) 0.001(4) -0.005(4) 0.000(3) C25 0.029(5) 0.019(4) 0.028(6) 0.001(4) -0.003(4) 0.005(3) C26 0.031(5) 0.037(5) 0.028(6) -0.001(4) 0.004(4) -0.003(4) C27 0.028(4) 0.051(5) 0.020(5) -0.002(4) -0.003(4) -0.003(3) C28 0.028(4) 0.043(5) 0.035(6) 0.000(4) -0.013(4) -0.005(3) C29 0.019(4) 0.054(5) 0.040(7) -0.002(4) 0.002(4) -0.001(3) C30 0.026(4) 0.034(5) 0.018(5) -0.003(4) -0.002(4) -0.003(3) C31 0.034(5) 0.017(4) 0.032(6) 0.006(4) 0.002(4) -0.002(3) C32 0.033(5) 0.036(5) 0.035(6) 0.006(4) 0.004(4) -0.007(4) C33 0.030(5) 0.036(5) 0.059(8) 0.003(5) -0.001(5) -0.009(4) C34 0.043(5) 0.037(5) 0.044(7) 0.002(4) -0.006(5) -0.012(4) C35 0.048(6) 0.038(5) 0.029(6) -0.004(4) 0.002(4) -0.008(4) C36 0.028(5) 0.050(5) 0.038(7) -0.006(4) 0.008(4) -0.002(4) C37 0.031(4) 0.035(4) 0.025(5) 0.002(4) 0.002(4) -0.006(3) C38 0.025(5) 0.019(4) 0.041(6) -0.010(4) 0.001(4) 0.002(3) C39 0.027(5) 0.011(4) 0.038(6) -0.006(4) 0.002(4) -0.002(3) C40 0.024(5) 0.027(4) 0.033(6) -0.003(4) -0.007(4) 0.006(3) C41 0.023(5) 0.041(5) 0.038(7) -0.006(4) -0.008(4) 0.007(3) C42 0.019(4) 0.042(5) 0.044(7) -0.006(4) -0.002(5) 0.004(4) C43 0.030(5) 0.020(4) 0.036(6) -0.001(4) 0.003(4) 0.005(3) C44 0.016(4) 0.022(4) 0.042(6) -0.005(4) -0.003(4) 0.005(3) C45 0.033(6) 0.089(8) 0.027(7) -0.016(6) -0.004(5) 0.004(5) C46 0.030(5) 0.036(5) 0.044(7) 0.002(4) -0.007(4) 0.007(4) O2 0.025(3) 0.035(3) 0.036(4) 0.009(3) 0.003(3) 0.000(2) N4 0.032(3) 0.012(3) 0.028(5) 0.001(3) -0.002(3) -0.001(2) N5 0.022(4) 0.039(4) 0.023(5) 0.009(3) 0.002(3) -0.001(3) N6 0.018(4) 0.038(4) 0.029(5) 0.006(3) -0.002(3) 0.002(3) F7 0.160(6) 0.089(5) 0.079(6) 0.020(4) -0.055(4) 0.015(4) F8 0.079(4) 0.123(5) 0.044(5) -0.016(4) -0.016(3) 0.013(3) F9 0.026(3) 0.314(9) 0.047(5) 0.014(5) -0.018(3) -0.003(4) F10 0.040(3) 0.072(3) 0.072(4) 0.001(3) 0.010(3) -0.033(3) F11 0.037(3) 0.062(3) 0.057(4) 0.003(2) 0.011(3) 0.016(2) F12 0.034(3) 0.053(3) 0.043(4) 0.004(2) 0.007(2) 0.0038(19) C47 0.037(5) 0.037(5) 0.020(6) 0.002(4) 0.002(4) 0.002(4) C48 0.058(5) 0.060(6) 0.031(6) 0.015(4) -0.012(5) -0.002(4) C49 0.061(6) 0.047(5) 0.032(6) 0.001(4) 0.018(5) -0.009(4) O3 0.033(3) 0.041(3) 0.022(4) 0.002(2) 0.004(3) 0.003(2) C50 0.027(4) 0.036(5) 0.031(6) 0.007(4) 0.004(4) -0.008(3) C51 0.056(5) 0.048(5) 0.030(6) -0.005(4) 0.004(4) -0.005(4) C52 0.068(6) 0.059(6) 0.036(6) 0.000(5) 0.017(5) 0.003(4) O4 0.034(3) 0.033(3) 0.030(4) -0.002(3) 0.007(3) -0.011(2) _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 N1 1.477(9) . ? C1 C6 1.523(9) . ? C1 C2 1.525(9) . ? C1 H1 1.03(5) . ? C2 N2 1.466(8) . ? C2 C3 1.534(10) . ? C2 H2 0.86(5) . ? C3 C4 1.532(10) . ? C3 H3A 1.09(6) . ? C3 H3B 1.10(6) . ? C4 C5 1.523(11) . ? C4 H4A 0.91(8) . ? C4 H4B 1.08(7) . ? C5 C6 1.519(10) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 1.01(6) . ? C6 H6B 1.02(6) . ? C7 N1 1.469(8) . ? C7 C8 1.528(9) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.374(9) . ? C8 C13 1.378(9) . ? C9 C10 1.411(10) . ? C9 H9 0.94(7) . ? C10 C11 1.378(10) . ? C10 H10 1.02(6) . ? C11 C12 1.377(10) . ? C11 H11 1.06(6) . ? C12 C13 1.394(10) . ? C12 H12 1.01(7) . ? C13 H13 1.01(5) . ? C14 N1 1.484(8) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O1 1.237(8) . ? C15 N2 1.345(8) . ? C15 N3 1.384(9) . ? C16 N3 1.382(8) . ? C16 C21 1.400(10) . ? C16 C17 1.428(9) . ? C17 C18 1.363(9) . ? C17 H17 1.02(6) . ? C18 C19 1.380(10) . ? C18 C22 1.529(10) . ? C19 C20 1.397(10) . ? C19 H19 1.04(5) . ? C20 C21 1.377(8) . ? C20 C23 1.500(10) . ? C21 H21 1.03(6) . ? C22 F2 1.322(8) . ? C22 F1 1.328(8) . ? C22 F3 1.339(7) . ? C23 F5 1.321(8) . ? C23 F6 1.325(8) . ? C23 F4 1.347(7) . ? N2 H2N 0.76(7) . ? N3 H3N 0.66(7) . ? C24 N4 1.479(9) . ? C24 C25 1.525(9) . ? C24 C29 1.545(9) . ? C24 H24 0.99(6) . ? C25 N5 1.452(9) . ? C25 C26 1.532(11) . ? C25 H25 0.89(6) . ? C26 C27 1.529(9) . ? C26 H26A 0.92(6) . ? C26 H26B 1.01(8) . ? C27 C28 1.514(10) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.538(10) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 N4 1.467(8) . ? C30 C31 1.512(10) . ? C30 H30A 0.87(6) . ? C30 H30B 0.99(6) . ? C31 C36 1.375(9) . ? C31 C32 1.411(9) . ? C32 C33 1.354(11) . ? C32 H32 1.00(7) . ? C33 C34 1.367(11) . ? C33 H33 0.92(6) . ? C34 C35 1.389(10) . ? C34 H34 0.9500 . ? C35 C36 1.407(10) . ? C35 H35 1.09(7) . ? C36 H36 1.05(6) . ? C37 N4 1.454(8) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 O2 1.248(9) . ? C38 N5 1.324(9) . ? C38 N6 1.383(9) . ? C39 C40 1.380(10) . ? C39 C44 1.401(10) . ? C39 N6 1.408(8) . ? C40 C41 1.388(9) . ? C40 H40 1.17(9) . ? C41 C42 1.399(11) . ? C41 C45 1.474(11) . ? C42 C43 1.368(10) . ? C42 H42 0.90(6) . ? C43 C44 1.373(9) . ? C43 C46 1.522(10) . ? C44 H44 1.04(6) . ? C45 F9 1.298(9) . ? C45 F8 1.309(10) . ? C45 F7 1.323(10) . ? C46 F10 1.305(8) . ? C46 F12 1.345(8) . ? C46 F11 1.366(8) . ? N5 H5N 0.76(7) . ? N6 H6N 0.87(7) . ? C47 O3 1.433(8) . ? C47 C48 1.504(9) . ? C47 C49 1.518(9) . ? C47 H47 1.04(7) . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? O3 H3 0.8400 . ? C50 O4 1.440(9) . ? C50 C52 1.497(10) . ? C50 C51 1.524(9) . ? C50 H50 1.02(6) . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? O4 H4O 0.84(6) . ? 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 N1 C1 C6 117.0(6) . . ? N1 C1 C2 110.7(5) . . ? C6 C1 C2 110.3(6) . . ? N1 C1 H1 110(3) . . ? C6 C1 H1 103(3) . . ? C2 C1 H1 106(3) . . ? N2 C2 C1 108.0(6) . . ? N2 C2 C3 111.9(6) . . ? C1 C2 C3 110.4(5) . . ? N2 C2 H2 105(4) . . ? C1 C2 H2 114(4) . . ? C3 C2 H2 107(5) . . ? C4 C3 C2 110.6(6) . . ? C4 C3 H3A 106(3) . . ? C2 C3 H3A 113(3) . . ? C4 C3 H3B 113(3) . . ? C2 C3 H3B 106(4) . . ? H3A C3 H3B 109(4) . . ? C5 C4 C3 111.3(7) . . ? C5 C4 H4A 125(5) . . ? C3 C4 H4A 102(5) . . ? C5 C4 H4B 110(4) . . ? C3 C4 H4B 109(3) . . ? H4A C4 H4B 98(6) . . ? C6 C5 C4 110.3(6) . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? C6 C5 H5B 109.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C5 C6 C1 111.5(6) . . ? C5 C6 H6A 112(3) . . ? C1 C6 H6A 104(3) . . ? C5 C6 H6B 116(4) . . ? C1 C6 H6B 109(3) . . ? H6A C6 H6B 105(5) . . ? N1 C7 C8 111.7(6) . . ? N1 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C13 119.0(7) . . ? C9 C8 C7 119.9(7) . . ? C13 C8 C7 121.0(6) . . ? C8 C9 C10 120.2(8) . . ? C8 C9 H9 119(4) . . ? C10 C9 H9 121(4) . . ? C11 C10 C9 120.4(7) . . ? C11 C10 H10 120(4) . . ? C9 C10 H10 119(4) . . ? C12 C11 C10 119.0(8) . . ? C12 C11 H11 118(3) . . ? C10 C11 H11 123(3) . . ? C11 C12 C13 120.4(8) . . ? C11 C12 H12 122(4) . . ? C13 C12 H12 117(4) . . ? C8 C13 C12 120.9(7) . . ? C8 C13 H13 123(3) . . ? C12 C13 H13 116(3) . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C15 N2 124.8(6) . . ? O1 C15 N3 122.6(6) . . ? N2 C15 N3 112.6(6) . . ? N3 C16 C21 124.9(7) . . ? N3 C16 C17 116.9(7) . . ? C21 C16 C17 118.2(6) . . ? C18 C17 C16 119.8(7) . . ? C18 C17 H17 125(3) . . ? C16 C17 H17 115(3) . . ? C17 C18 C19 122.3(7) . . ? C17 C18 C22 116.6(7) . . ? C19 C18 C22 121.1(6) . . ? C18 C19 C20 118.0(6) . . ? C18 C19 H19 131(3) . . ? C20 C19 H19 111(3) . . ? C21 C20 C19 121.5(7) . . ? C21 C20 C23 121.2(7) . . ? C19 C20 C23 117.3(6) . . ? C20 C21 C16 120.1(7) . . ? C20 C21 H21 123(3) . . ? C16 C21 H21 116(3) . . ? F2 C22 F1 107.5(7) . . ? F2 C22 F3 107.3(6) . . ? F1 C22 F3 106.7(6) . . ? F2 C22 C18 111.0(6) . . ? F1 C22 C18 112.6(6) . . ? F3 C22 C18 111.5(7) . . ? F5 C23 F6 107.8(6) . . ? F5 C23 F4 106.3(6) . . ? F6 C23 F4 106.5(6) . . ? F5 C23 C20 111.8(6) . . ? F6 C23 C20 113.8(6) . . ? F4 C23 C20 110.2(6) . . ? C7 N1 C1 112.7(5) . . ? C7 N1 C14 110.1(5) . . ? C1 N1 C14 113.3(5) . . ? C15 N2 C2 125.9(6) . . ? C15 N2 H2N 115(6) . . ? C2 N2 H2N 116(6) . . ? C16 N3 C15 129.9(6) . . ? C16 N3 H3N 115(7) . . ? C15 N3 H3N 114(7) . . ? N4 C24 C25 111.7(6) . . ? N4 C24 C29 115.5(6) . . ? C25 C24 C29 110.2(6) . . ? N4 C24 H24 103(4) . . ? C25 C24 H24 105(3) . . ? C29 C24 H24 111(3) . . ? N5 C25 C24 107.6(6) . . ? N5 C25 C26 112.0(6) . . ? C24 C25 C26 109.8(6) . . ? N5 C25 H25 109(4) . . ? C24 C25 H25 113(4) . . ? C26 C25 H25 106(5) . . ? C27 C26 C25 111.2(6) . . ? C27 C26 H26A 102(4) . . ? C25 C26 H26A 114(4) . . ? C27 C26 H26B 113(5) . . ? C25 C26 H26B 109(5) . . ? H26A C26 H26B 108(6) . . ? C28 C27 C26 112.0(7) . . ? C28 C27 H27A 109.2 . . ? C26 C27 H27A 109.2 . . ? C28 C27 H27B 109.2 . . ? C26 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? C27 C28 C29 110.8(6) . . ? C27 C28 H28A 109.5 . . ? C29 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? C29 C28 H28B 109.5 . . ? H28A C28 H28B 108.1 . . ? C28 C29 C24 111.1(6) . . ? C28 C29 H29A 109.4 . . ? C24 C29 H29A 109.4 . . ? C28 C29 H29B 109.4 . . ? C24 C29 H29B 109.4 . . ? H29A C29 H29B 108.0 . . ? N4 C30 C31 112.1(6) . . ? N4 C30 H30A 110(4) . . ? C31 C30 H30A 109(5) . . ? N4 C30 H30B 102(3) . . ? C31 C30 H30B 119(4) . . ? H30A C30 H30B 104(6) . . ? C36 C31 C32 118.7(8) . . ? C36 C31 C30 121.3(7) . . ? C32 C31 C30 120.1(7) . . ? C33 C32 C31 120.4(8) . . ? C33 C32 H32 118(4) . . ? C31 C32 H32 122(4) . . ? C32 C33 C34 120.9(8) . . ? C32 C33 H33 126(4) . . ? C34 C33 H33 113(4) . . ? C33 C34 C35 120.8(9) . . ? C33 C34 H34 119.6 . . ? C35 C34 H34 119.6 . . ? C34 C35 C36 118.2(8) . . ? C34 C35 H35 119(4) . . ? C36 C35 H35 123(4) . . ? C31 C36 C35 120.9(7) . . ? C31 C36 H36 120(3) . . ? C35 C36 H36 119(3) . . ? N4 C37 H37A 109.5 . . ? N4 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? N4 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O2 C38 N5 123.6(7) . . ? O2 C38 N6 121.9(6) . . ? N5 C38 N6 114.4(7) . . ? C40 C39 C44 119.8(7) . . ? C40 C39 N6 116.9(7) . . ? C44 C39 N6 123.2(7) . . ? C39 C40 C41 121.0(8) . . ? C39 C40 H40 132(4) . . ? C41 C40 H40 107(4) . . ? C40 C41 C42 119.5(8) . . ? C40 C41 C45 119.9(8) . . ? C42 C41 C45 120.6(7) . . ? C43 C42 C41 118.2(7) . . ? C43 C42 H42 119(5) . . ? C41 C42 H42 123(5) . . ? C42 C43 C44 123.7(8) . . ? C42 C43 C46 116.2(6) . . ? C44 C43 C46 120.2(7) . . ? C43 C44 C39 117.9(8) . . ? C43 C44 H44 124(4) . . ? C39 C44 H44 118(3) . . ? F9 C45 F8 106.1(8) . . ? F9 C45 F7 107.3(8) . . ? F8 C45 F7 104.8(9) . . ? F9 C45 C41 114.4(8) . . ? F8 C45 C41 111.6(8) . . ? F7 C45 C41 112.0(7) . . ? F10 C46 F12 107.6(6) . . ? F10 C46 F11 105.6(6) . . ? F12 C46 F11 104.8(6) . . ? F10 C46 C43 114.6(7) . . ? F12 C46 C43 113.2(6) . . ? F11 C46 C43 110.3(6) . . ? C37 N4 C30 112.2(6) . . ? C37 N4 C24 112.0(5) . . ? C30 N4 C24 112.9(6) . . ? C38 N5 C25 125.7(6) . . ? C38 N5 H5N 122(6) . . ? C25 N5 H5N 110(6) . . ? C38 N6 C39 129.0(7) . . ? C38 N6 H6N 117(5) . . ? C39 N6 H6N 114(5) . . ? O3 C47 C48 108.1(6) . . ? O3 C47 C49 109.3(6) . . ? C48 C47 C49 113.8(7) . . ? O3 C47 H47 110(4) . . ? C48 C47 H47 105(4) . . ? C49 C47 H47 110(4) . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C47 C49 H49A 109.5 . . ? C47 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C47 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C47 O3 H3 109.5 . . ? O4 C50 C52 109.3(6) . . ? O4 C50 C51 106.4(6) . . ? C52 C50 C51 112.8(7) . . ? O4 C50 H50 109(4) . . ? C52 C50 H50 101(4) . . ? C51 C50 H50 118(3) . . ? 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 . . ? C50 O4 H4O 101(5) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.255 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.058 #===END data_1g _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 F6 N3 O' _chemical_formula_sum 'C21 H25 F6 N3 O' _chemical_formula_weight 449.44 _chemical_absolute_configuration syn 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.3840(10) _cell_length_b 9.9690(10) _cell_length_c 12.6230(10) _cell_angle_alpha 81.560(10) _cell_angle_beta 89.690(10) _cell_angle_gamma 71.130(10) _cell_volume 1104.19(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6801 _cell_measurement_theta_min 1.63 _cell_measurement_theta_max 27.00 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Phi/Omega-Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6801 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.1019 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4749 _reflns_number_gt 2757 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0840P)^2^+0.2790P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.4(11) _refine_ls_number_reflns 4749 _refine_ls_number_parameters 569 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1332 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1760 _refine_ls_wR_factor_gt 0.1491 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0265(6) 0.6890(7) -0.1140(5) 0.0412(15) Uani 1 1 d . . . H1 H -0.0758 0.6833 -0.1157 0.049 Uiso 1 1 calc R . . C2 C 0.0082(6) 0.8492(6) -0.1413(4) 0.0297(13) Uani 1 1 d . . . H2 H 0.1086 0.8590 -0.1471 0.036 Uiso 1 1 calc R . . C3 C -0.0779(6) 0.9111(7) -0.2486(5) 0.0379(14) Uani 1 1 d . . . H3A H -0.0830 1.0106 -0.2670 0.046 Uiso 1 1 calc R . . H3B H -0.1802 0.9090 -0.2419 0.046 Uiso 1 1 calc R . . C4 C -0.0054(7) 0.8293(8) -0.3391(5) 0.0469(16) Uani 1 1 d . . . H4A H -0.0700 0.8671 -0.4036 0.056 Uiso 1 1 calc R . . H4B H 0.0905 0.8440 -0.3537 0.056 Uiso 1 1 calc R . . C5 C 0.0196(8) 0.6718(8) -0.3112(5) 0.0510(17) Uani 1 1 d . . . H5A H 0.0757 0.6222 -0.3666 0.061 Uiso 1 1 calc R . . H5B H -0.0770 0.6556 -0.3080 0.061 Uiso 1 1 calc R . . C6 C 0.1065(7) 0.6109(8) -0.2033(5) 0.0477(17) Uani 1 1 d . . . H6A H 0.1178 0.5099 -0.1859 0.057 Uiso 1 1 calc R . . H6B H 0.2065 0.6194 -0.2086 0.057 Uiso 1 1 calc R . . C7 C 0.2500(7) 0.6067(8) 0.0077(6) 0.0536(18) Uani 1 1 d . . . H7A H 0.2676 0.6937 -0.0255 0.064 Uiso 1 1 calc R . . H7B H 0.3076 0.5292 -0.0293 0.064 Uiso 1 1 calc R . . C8 C 0.3041(9) 0.5740(8) 0.1231(6) 0.067(2) Uani 1 1 d . . . H8 H 0.2427 0.6243 0.1720 0.080 Uiso 1 1 calc R . . C9 C 0.4342(9) 0.4777(10) 0.1588(7) 0.076(2) Uani 1 1 d . . . H9A H 0.4977 0.4259 0.1115 0.091 Uiso 1 1 calc R . . H9B H 0.4625 0.4615 0.2312 0.091 Uiso 1 1 calc R . . C10 C 0.0647(8) 0.4914(8) 0.0337(6) 0.060(2) Uani 1 1 d . . . H10A H 0.1165 0.4517 0.1032 0.072 Uiso 1 1 calc R . . H10B H 0.1079 0.4240 -0.0153 0.072 Uiso 1 1 calc R . . C11 C -0.1005(10) 0.5078(10) 0.0436(7) 0.075(2) Uani 1 1 d . . . H11 H -0.1608 0.5817 0.0774 0.089 Uiso 1 1 calc R . . C12 C -0.1634(12) 0.4209(12) 0.0059(8) 0.094(3) Uani 1 1 d . . . H12A H -0.1051 0.3464 -0.0281 0.112 Uiso 1 1 calc R . . H12B H -0.2656 0.4349 0.0138 0.112 Uiso 1 1 calc R . . C13 C -0.0014(6) 0.9782(6) 0.0143(4) 0.0314(13) Uani 1 1 d . . . C14 C -0.0624(6) 1.0844(7) 0.1830(5) 0.0380(14) Uani 1 1 d . . . C15 C -0.1695(6) 1.1067(7) 0.2609(5) 0.0365(14) Uani 1 1 d . . . H15 H -0.2586 1.0873 0.2510 0.044 Uiso 1 1 calc R . . C16 C -0.1445(7) 1.1581(7) 0.3541(5) 0.0427(16) Uani 1 1 d . . . C17 C -0.0132(7) 1.1855(7) 0.3699(5) 0.0443(16) Uani 1 1 d . . . H17 H 0.0053 1.2168 0.4327 0.053 Uiso 1 1 calc R . . C18 C 0.0912(6) 1.1664(7) 0.2922(5) 0.0370(14) Uani 1 1 d . . . C19 C 0.0682(6) 1.1186(7) 0.1976(5) 0.0378(14) Uani 1 1 d . . . H19 H 0.1389 1.1096 0.1449 0.045 Uiso 1 1 calc R . . C20 C -0.2619(7) 1.1808(9) 0.4350(5) 0.056(2) Uani 1 1 d . . . C21 C 0.2388(7) 1.1927(8) 0.3118(5) 0.0440(16) Uani 1 1 d . . . N1 N 0.0900(6) 0.6250(6) -0.0044(4) 0.0452(13) Uani 1 1 d . . . N2 N -0.0699(4) 0.9304(5) -0.0593(3) 0.0348(12) Uani 1 1 d . . . H2N H -0.1660 0.9493 -0.0574 0.042 Uiso 1 1 calc R . . N3 N -0.0955(5) 1.0343(6) 0.0919(4) 0.0355(12) Uani 1 1 d . . . H3N H -0.181(7) 1.028(7) 0.087(5) 0.043 Uiso 1 1 d . . . O1 O 0.1314(4) 0.9744(4) 0.0105(3) 0.0362(10) Uani 1 1 d . . . F1 F -0.3286(6) 1.0800(8) 0.4476(4) 0.110(2) Uani 1 1 d . . . F2 F -0.2077(5) 1.1786(6) 0.5315(3) 0.0765(14) Uani 1 1 d . . . F3 F -0.3697(6) 1.3008(7) 0.4106(4) 0.125(3) Uani 1 1 d . . . F4 F 0.3216(4) 1.0966(5) 0.3927(3) 0.0737(13) Uani 1 1 d . . . F5 F 0.2148(5) 1.3206(5) 0.3427(4) 0.0712(13) Uani 1 1 d . . . F6 F 0.3239(4) 1.1868(5) 0.2282(3) 0.0565(11) Uani 1 1 d . . . C22 C 0.3872(7) 1.1776(7) -0.2422(5) 0.0397(15) Uani 1 1 d . . . H22 H 0.3001 1.2545 -0.2232 0.048 Uiso 1 1 calc R . . C23 C 0.4947(6) 1.1241(7) -0.1435(5) 0.0423(16) Uani 1 1 d . . . H23 H 0.5866 1.0519 -0.1618 0.051 Uiso 1 1 calc R . . C24 C 0.5371(7) 1.2480(8) -0.1108(6) 0.0528(18) Uani 1 1 d . . . H24A H 0.4475 1.3202 -0.0918 0.063 Uiso 1 1 calc R . . H24B H 0.6063 1.2134 -0.0485 0.063 Uiso 1 1 calc R . . C25 C 0.6106(8) 1.3145(8) -0.2023(7) 0.063(2) Uani 1 1 d . . . H25C H 0.6350 1.3943 -0.1807 0.075 Uiso 1 1 calc R . . H25D H 0.7040 1.2438 -0.2177 0.075 Uiso 1 1 calc R . . C26 C 0.5088(8) 1.3667(8) -0.3019(6) 0.061(2) Uani 1 1 d . . . H26A H 0.5610 1.4031 -0.3599 0.073 Uiso 1 1 calc R . . H26B H 0.4200 1.4446 -0.2890 0.073 Uiso 1 1 calc R . . C27 C 0.4618(8) 1.2464(9) -0.3338(6) 0.060(2) Uani 1 1 d . . . H27A H 0.5498 1.1737 -0.3544 0.072 Uiso 1 1 calc R . . H27B H 0.3917 1.2835 -0.3955 0.072 Uiso 1 1 calc R . . C28 C 0.4397(15) 0.9499(10) -0.3126(7) 0.102(4) Uani 1 1 d . . . H28A H 0.4049 0.9517 -0.3851 0.122 Uiso 1 1 calc R . . H28B H 0.5347 0.9691 -0.3169 0.122 Uiso 1 1 calc R . . C29 C 0.4661(11) 0.8107(12) -0.2553(11) 0.109(4) Uani 1 1 d . . . H29 H 0.3861 0.7772 -0.2652 0.131 Uiso 1 1 calc R . . C30 C 0.553(3) 0.7345(18) -0.204(2) 0.35(2) Uani 1 1 d . . . H30A H 0.6393 0.7552 -0.1878 0.426 Uiso 1 1 calc R . . H30B H 0.5428 0.6468 -0.1753 0.426 Uiso 1 1 calc R . . C31 C 0.1862(11) 1.1263(9) -0.3293(6) 0.070(2) Uani 1 1 d . . . H31A H 0.1567 1.0487 -0.3500 0.084 Uiso 1 1 calc R . . H31B H 0.1998 1.1851 -0.3944 0.084 Uiso 1 1 calc R . . C32 C 0.0627(9) 1.2151(9) -0.2694(6) 0.061(2) Uani 1 1 d . . . H32 H 0.0503 1.1770 -0.1995 0.073 Uiso 1 1 calc R . . C33 C -0.0292(10) 1.3421(10) -0.3077(8) 0.074(3) Uani 1 1 d . . . H33A H -0.0202 1.3836 -0.3773 0.089 Uiso 1 1 calc R . . H33B H -0.1038 1.3913 -0.2655 0.089 Uiso 1 1 calc R . . C34 C 0.5088(6) 0.9718(7) 0.0303(4) 0.0331(13) Uani 1 1 d . . . C35 C 0.4842(6) 0.8267(7) 0.2014(4) 0.0339(13) Uani 1 1 d . . . C36 C 0.3768(6) 0.8020(7) 0.2720(5) 0.0392(15) Uani 1 1 d . . . H36 H 0.2754 0.8369 0.2499 0.047 Uiso 1 1 calc R . . C37 C 0.4187(7) 0.7270(7) 0.3732(5) 0.0400(15) Uani 1 1 d . . . C38 C 0.5677(7) 0.6751(7) 0.4086(5) 0.0446(16) Uani 1 1 d . . . H38 H 0.5955 0.6237 0.4771 0.054 Uiso 1 1 calc R . . C39 C 0.6745(7) 0.7001(8) 0.3416(5) 0.0439(16) Uani 1 1 d . . . C40 C 0.6356(6) 0.7758(7) 0.2378(5) 0.0385(14) Uani 1 1 d . . . H40 H 0.7096 0.7921 0.1934 0.046 Uiso 1 1 calc R . . C41 C 0.2997(8) 0.6992(9) 0.4432(6) 0.0548(19) Uani 1 1 d . . . C42 C 0.8363(8) 0.6488(11) 0.3773(6) 0.068(2) Uani 1 1 d . . . N4 N 0.3305(7) 1.0652(6) -0.2671(4) 0.0541(15) Uani 1 1 d . . . N5 N 0.4259(5) 1.0566(6) -0.0557(4) 0.0378(13) Uani 1 1 d . . . H5N H 0.350(8) 1.054(8) -0.066(6) 0.045 Uiso 1 1 d . . . N6 N 0.4328(5) 0.9020(6) 0.0994(4) 0.0363(12) Uani 1 1 d . . . H6N H 0.348(8) 0.914(7) 0.079(5) 0.044 Uiso 1 1 d . . . O2 O 0.6430(4) 0.9574(5) 0.0449(3) 0.0424(11) Uani 1 1 d . . . F7 F 0.1685(4) 0.8034(6) 0.4278(4) 0.0830(16) Uani 1 1 d . . . F8 F 0.2691(7) 0.5825(7) 0.4281(5) 0.120(2) Uani 1 1 d . . . F9 F 0.3371(5) 0.6820(6) 0.5465(3) 0.0883(17) Uani 1 1 d . . . F10 F 0.8812(7) 0.5277(9) 0.4333(8) 0.186(5) Uani 1 1 d . . . F11 F 0.8680(7) 0.7271(11) 0.4343(10) 0.215(6) Uani 1 1 d . . . F12 F 0.9296(6) 0.6386(13) 0.3043(5) 0.207(6) 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 0.034(3) 0.046(4) 0.043(4) -0.011(3) -0.006(3) -0.010(3) C2 0.021(2) 0.033(3) 0.038(3) -0.012(3) 0.001(2) -0.011(2) C3 0.030(3) 0.048(4) 0.038(3) -0.009(3) 0.003(2) -0.015(3) C4 0.044(3) 0.056(5) 0.044(4) -0.010(3) 0.005(3) -0.019(3) C5 0.056(4) 0.052(5) 0.048(4) -0.022(3) 0.003(3) -0.015(3) C6 0.039(3) 0.045(4) 0.061(4) -0.012(3) -0.002(3) -0.015(3) C7 0.047(4) 0.041(4) 0.065(5) -0.008(3) -0.021(3) -0.003(3) C8 0.066(5) 0.057(5) 0.070(5) -0.012(4) -0.034(4) -0.008(4) C9 0.062(5) 0.077(6) 0.078(6) -0.005(5) -0.030(4) -0.011(4) C10 0.056(4) 0.056(5) 0.063(5) 0.003(4) -0.018(4) -0.016(4) C11 0.081(6) 0.074(6) 0.064(5) 0.013(5) -0.005(4) -0.029(5) C12 0.091(6) 0.104(8) 0.089(7) 0.031(6) -0.022(5) -0.054(6) C13 0.025(3) 0.035(3) 0.032(3) 0.003(3) -0.007(2) -0.009(2) C14 0.036(3) 0.040(4) 0.034(3) -0.006(3) -0.007(3) -0.008(3) C15 0.024(3) 0.050(4) 0.036(3) -0.005(3) 0.001(2) -0.012(3) C16 0.040(3) 0.050(4) 0.028(3) -0.002(3) -0.004(3) -0.002(3) C17 0.043(3) 0.051(4) 0.033(3) -0.014(3) -0.004(3) -0.004(3) C18 0.043(3) 0.034(4) 0.033(3) -0.005(3) -0.005(3) -0.012(3) C19 0.027(3) 0.045(4) 0.040(3) -0.010(3) 0.005(2) -0.008(3) C20 0.038(4) 0.086(6) 0.040(4) -0.015(4) 0.003(3) -0.011(4) C21 0.045(4) 0.048(5) 0.045(4) -0.009(3) -0.010(3) -0.021(3) N1 0.045(3) 0.039(4) 0.048(3) -0.005(3) -0.012(2) -0.010(3) N2 0.017(2) 0.053(3) 0.036(3) -0.019(2) 0.0044(19) -0.009(2) N3 0.026(2) 0.055(4) 0.032(3) -0.015(2) 0.003(2) -0.018(2) O1 0.024(2) 0.051(3) 0.037(2) -0.0053(19) 0.0016(16) -0.0167(18) F1 0.105(4) 0.179(6) 0.099(4) -0.075(4) 0.063(3) -0.098(4) F2 0.068(3) 0.123(4) 0.037(2) -0.022(2) 0.009(2) -0.024(3) F3 0.085(3) 0.145(5) 0.067(3) 0.017(3) 0.034(3) 0.053(4) F4 0.053(2) 0.105(4) 0.064(3) -0.002(3) -0.024(2) -0.032(3) F5 0.063(2) 0.071(3) 0.098(3) -0.046(3) 0.011(2) -0.031(2) F6 0.043(2) 0.085(3) 0.056(2) -0.024(2) 0.0068(18) -0.034(2) C22 0.046(3) 0.032(4) 0.038(3) -0.006(3) 0.008(3) -0.008(3) C23 0.026(3) 0.050(4) 0.039(3) -0.002(3) 0.008(2) 0.001(3) C24 0.037(3) 0.063(5) 0.059(4) -0.009(4) 0.005(3) -0.017(3) C25 0.046(4) 0.043(5) 0.089(6) 0.005(4) 0.011(4) -0.007(3) C26 0.043(4) 0.057(5) 0.072(5) 0.011(4) 0.022(4) -0.012(4) C27 0.051(4) 0.061(5) 0.047(4) 0.007(4) 0.014(3) 0.005(4) C28 0.180(11) 0.050(6) 0.059(5) -0.014(5) 0.006(6) -0.011(6) C29 0.055(5) 0.059(7) 0.189(13) 0.009(7) -0.006(7) 0.004(5) C30 0.44(4) 0.062(10) 0.52(4) -0.036(16) -0.38(4) -0.024(16) C31 0.123(7) 0.061(5) 0.046(4) -0.007(4) -0.011(5) -0.057(6) C32 0.075(5) 0.070(6) 0.055(5) 0.007(4) -0.017(4) -0.054(5) C33 0.072(5) 0.072(6) 0.091(6) 0.009(5) -0.025(5) -0.051(5) C34 0.025(3) 0.039(4) 0.036(3) -0.009(3) 0.006(2) -0.009(3) C35 0.033(3) 0.041(4) 0.029(3) -0.009(3) -0.005(2) -0.013(3) C36 0.028(3) 0.049(4) 0.042(4) -0.008(3) 0.002(3) -0.014(3) C37 0.044(3) 0.037(4) 0.037(3) 0.002(3) 0.003(3) -0.014(3) C38 0.047(4) 0.044(4) 0.035(3) 0.002(3) -0.007(3) -0.009(3) C39 0.035(3) 0.056(5) 0.042(4) 0.000(3) -0.006(3) -0.019(3) C40 0.027(3) 0.047(4) 0.038(3) -0.004(3) 0.001(2) -0.009(3) C41 0.060(5) 0.058(5) 0.045(4) 0.006(4) 0.009(3) -0.023(4) C42 0.046(4) 0.109(7) 0.043(4) 0.013(5) -0.028(4) -0.027(5) N4 0.088(4) 0.037(4) 0.035(3) -0.006(3) -0.005(3) -0.017(3) N5 0.027(2) 0.055(4) 0.030(3) -0.002(2) 0.002(2) -0.014(3) N6 0.022(2) 0.060(4) 0.032(3) -0.002(2) -0.004(2) -0.020(2) O2 0.022(2) 0.062(3) 0.042(2) -0.001(2) -0.0021(17) -0.0160(19) F7 0.045(2) 0.104(4) 0.074(3) 0.030(3) 0.020(2) -0.007(2) F8 0.140(5) 0.110(5) 0.150(5) -0.047(4) 0.089(4) -0.087(4) F9 0.066(3) 0.143(5) 0.040(3) 0.014(3) 0.008(2) -0.025(3) F10 0.066(4) 0.158(8) 0.281(11) 0.111(8) -0.078(5) -0.026(4) F11 0.065(4) 0.211(9) 0.371(14) -0.187(10) -0.099(6) 0.019(4) F12 0.031(3) 0.445(16) 0.082(4) 0.024(6) -0.018(3) -0.017(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.476(8) . ? C1 C6 1.520(9) . ? C1 C2 1.536(9) . ? C1 H1 0.9800 . ? C2 N2 1.456(7) . ? C2 C3 1.520(8) . ? C2 H2 0.9800 . ? C3 C4 1.529(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.498(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.529(9) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N1 1.459(8) . ? C7 C8 1.499(10) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.317(10) . ? C8 H8 0.9300 . ? C9 H9A 0.9300 . ? C9 H9B 0.9300 . ? C10 N1 1.440(9) . ? C10 C11 1.512(11) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.334(12) . ? C11 H11 0.9300 . ? C12 H12A 0.9300 . ? C12 H12B 0.9300 . ? C13 O1 1.236(6) . ? C13 N2 1.356(7) . ? C13 N3 1.372(7) . ? C14 C15 1.392(8) . ? C14 N3 1.394(7) . ? C14 C19 1.394(8) . ? C15 C16 1.400(8) . ? C15 H15 0.9300 . ? C16 C17 1.367(9) . ? C16 C20 1.484(9) . ? C17 C18 1.371(8) . ? C17 H17 0.9300 . ? C18 C19 1.392(8) . ? C18 C21 1.519(8) . ? C19 H19 0.9300 . ? C20 F3 1.288(9) . ? C20 F2 1.317(8) . ? C20 F1 1.337(10) . ? C21 F6 1.317(7) . ? C21 F5 1.337(8) . ? C21 F4 1.343(8) . ? N2 H2N 0.8600 . ? N3 H3N 0.83(6) . ? C22 N4 1.459(8) . ? C22 C23 1.525(8) . ? C22 C27 1.538(9) . ? C22 H22 0.9800 . ? C23 N5 1.467(8) . ? C23 C24 1.525(10) . ? C23 H23 0.9800 . ? C24 C25 1.519(10) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.505(11) . ? C25 H25C 0.9700 . ? C25 H25D 0.9700 . ? C26 C27 1.509(11) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.413(14) . ? C28 N4 1.458(11) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.058(17) . ? C29 H29 0.9300 . ? C30 H30A 0.9300 . ? C30 H30B 0.9300 . ? C31 N4 1.470(10) . ? C31 C32 1.491(12) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.304(12) . ? C32 H32 0.9300 . ? C33 H33A 0.9300 . ? C33 H33B 0.9300 . ? C34 O2 1.233(6) . ? C34 N5 1.346(7) . ? C34 N6 1.375(8) . ? C35 N6 1.394(7) . ? C35 C36 1.399(8) . ? C35 C40 1.400(8) . ? C36 C37 1.371(8) . ? C36 H36 0.9300 . ? C37 C38 1.376(8) . ? C37 C41 1.490(9) . ? C38 C39 1.368(9) . ? C38 H38 0.9300 . ? C39 C40 1.398(8) . ? C39 C42 1.485(9) . ? C40 H40 0.9300 . ? C41 F7 1.322(8) . ? C41 F9 1.324(8) . ? C41 F8 1.325(9) . ? C42 F11 1.238(11) . ? C42 F10 1.248(10) . ? C42 F12 1.260(10) . ? N5 H5N 0.74(7) . ? N6 H6N 0.81(7) . ? 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 N1 C1 C6 115.6(5) . . ? N1 C1 C2 113.4(5) . . ? C6 C1 C2 109.4(5) . . ? N1 C1 H1 105.8 . . ? C6 C1 H1 105.8 . . ? C2 C1 H1 105.8 . . ? N2 C2 C3 109.4(4) . . ? N2 C2 C1 112.1(5) . . ? C3 C2 C1 109.9(5) . . ? N2 C2 H2 108.5 . . ? C3 C2 H2 108.5 . . ? C1 C2 H2 108.5 . . ? C2 C3 C4 112.8(5) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 111.8(5) . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C4 C5 C6 111.0(5) . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C1 C6 C5 111.7(5) . . ? C1 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? C1 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? N1 C7 C8 112.0(6) . . ? N1 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C7 123.4(8) . . ? C9 C8 H8 118.3 . . ? C7 C8 H8 118.3 . . ? C8 C9 H9A 120.0 . . ? C8 C9 H9B 120.0 . . ? H9A C9 H9B 120.0 . . ? N1 C10 C11 112.9(6) . . ? N1 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? N1 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 122.9(10) . . ? C12 C11 H11 118.6 . . ? C10 C11 H11 118.6 . . ? C11 C12 H12A 120.0 . . ? C11 C12 H12B 120.0 . . ? H12A C12 H12B 120.0 . . ? O1 C13 N2 123.3(5) . . ? O1 C13 N3 123.5(5) . . ? N2 C13 N3 113.1(4) . . ? C15 C14 N3 117.5(5) . . ? C15 C14 C19 118.9(5) . . ? N3 C14 C19 123.6(5) . . ? C14 C15 C16 120.6(5) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 120.0(5) . . ? C17 C16 C20 121.1(6) . . ? C15 C16 C20 118.9(5) . . ? C16 C17 C18 119.4(5) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 122.0(5) . . ? C17 C18 C21 119.0(5) . . ? C19 C18 C21 119.0(6) . . ? C18 C19 C14 119.0(6) . . ? C18 C19 H19 120.5 . . ? C14 C19 H19 120.5 . . ? F3 C20 F2 107.3(7) . . ? F3 C20 F1 105.4(7) . . ? F2 C20 F1 104.7(6) . . ? F3 C20 C16 112.6(6) . . ? F2 C20 C16 112.8(5) . . ? F1 C20 C16 113.4(6) . . ? F6 C21 F5 107.5(5) . . ? F6 C21 F4 107.3(5) . . ? F5 C21 F4 105.3(5) . . ? F6 C21 C18 114.2(5) . . ? F5 C21 C18 111.2(5) . . ? F4 C21 C18 110.9(5) . . ? C10 N1 C7 109.8(5) . . ? C10 N1 C1 113.5(5) . . ? C7 N1 C1 112.9(5) . . ? C13 N2 C2 124.4(4) . . ? C13 N2 H2N 117.8 . . ? C2 N2 H2N 117.8 . . ? C13 N3 C14 129.1(5) . . ? C13 N3 H3N 114(4) . . ? C14 N3 H3N 116(4) . . ? N4 C22 C23 110.8(5) . . ? N4 C22 C27 116.2(5) . . ? C23 C22 C27 109.5(5) . . ? N4 C22 H22 106.6 . . ? C23 C22 H22 106.6 . . ? C27 C22 H22 106.6 . . ? N5 C23 C24 111.4(5) . . ? N5 C23 C22 110.2(5) . . ? C24 C23 C22 109.8(5) . . ? N5 C23 H23 108.4 . . ? C24 C23 H23 108.4 . . ? C22 C23 H23 108.4 . . ? C25 C24 C23 110.4(6) . . ? C25 C24 H24A 109.6 . . ? C23 C24 H24A 109.6 . . ? C25 C24 H24B 109.6 . . ? C23 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? C26 C25 C24 111.5(6) . . ? C26 C25 H25C 109.3 . . ? C24 C25 H25C 109.3 . . ? C26 C25 H25D 109.3 . . ? C24 C25 H25D 109.3 . . ? H25C C25 H25D 108.0 . . ? C25 C26 C27 110.5(6) . . ? C25 C26 H26A 109.6 . . ? C27 C26 H26A 109.6 . . ? C25 C26 H26B 109.6 . . ? C27 C26 H26B 109.6 . . ? H26A C26 H26B 108.1 . . ? C26 C27 C22 112.0(6) . . ? C26 C27 H27A 109.2 . . ? C22 C27 H27A 109.2 . . ? C26 C27 H27B 109.2 . . ? C22 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? C29 C28 N4 115.3(9) . . ? C29 C28 H28A 108.5 . . ? N4 C28 H28A 108.5 . . ? C29 C28 H28B 108.5 . . ? N4 C28 H28B 108.5 . . ? H28A C28 H28B 107.5 . . ? C30 C29 C28 136.7(18) . . ? C30 C29 H29 111.6 . . ? C28 C29 H29 111.6 . . ? C29 C30 H30A 120.0 . . ? C29 C30 H30B 120.0 . . ? H30A C30 H30B 120.0 . . ? N4 C31 C32 113.2(6) . . ? N4 C31 H31A 108.9 . . ? C32 C31 H31A 108.9 . . ? N4 C31 H31B 108.9 . . ? C32 C31 H31B 108.9 . . ? H31A C31 H31B 107.8 . . ? C33 C32 C31 124.8(8) . . ? C33 C32 H32 117.6 . . ? C31 C32 H32 117.6 . . ? C32 C33 H33A 120.0 . . ? C32 C33 H33B 120.0 . . ? H33A C33 H33B 120.0 . . ? O2 C34 N5 122.2(5) . . ? O2 C34 N6 122.9(5) . . ? N5 C34 N6 114.9(5) . . ? N6 C35 C36 117.6(5) . . ? N6 C35 C40 124.3(5) . . ? C36 C35 C40 118.1(5) . . ? C37 C36 C35 121.1(5) . . ? C37 C36 H36 119.4 . . ? C35 C36 H36 119.4 . . ? C36 C37 C38 120.8(6) . . ? C36 C37 C41 118.6(5) . . ? C38 C37 C41 120.6(6) . . ? C39 C38 C37 119.2(5) . . ? C39 C38 H38 120.4 . . ? C37 C38 H38 120.4 . . ? C38 C39 C40 121.4(5) . . ? C38 C39 C42 121.0(6) . . ? C40 C39 C42 117.6(6) . . ? C39 C40 C35 119.4(5) . . ? C39 C40 H40 120.3 . . ? C35 C40 H40 120.3 . . ? F7 C41 F9 106.0(6) . . ? F7 C41 F8 104.7(7) . . ? F9 C41 F8 106.1(6) . . ? F7 C41 C37 113.6(6) . . ? F9 C41 C37 112.6(6) . . ? F8 C41 C37 113.2(6) . . ? F11 C42 F10 103.6(9) . . ? F11 C42 F12 104.3(9) . . ? F10 C42 F12 103.3(10) . . ? F11 C42 C39 112.9(8) . . ? F10 C42 C39 115.1(7) . . ? F12 C42 C39 116.2(6) . . ? C28 N4 C22 114.9(7) . . ? C28 N4 C31 113.4(6) . . ? C22 N4 C31 111.3(5) . . ? C34 N5 C23 121.5(5) . . ? C34 N5 H5N 119(6) . . ? C23 N5 H5N 117(6) . . ? C34 N6 C35 126.3(4) . . ? C34 N6 H6N 114(5) . . ? C35 N6 H6N 119(5) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.420 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.051 #===END data_5a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 F12 N4 O2, C H4 O' _chemical_formula_sum 'C29 H32 F12 N4 O3' _chemical_formula_weight 712.59 _chemical_absolute_configuration syn 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' 'F' 'F' 0.0171 0.0103 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.0545(8) _cell_length_b 15.0943(13) _cell_length_c 21.3967(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3247.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11456 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.00 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max .2 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .06 _e_exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'Nonius KappaCCD' _diffrn_measurement_method 'Phi/Omega-Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11456 _diffrn_reflns_av_R_equivalents 0.0726 _diffrn_reflns_av_sigmaI/netI 0.1321 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3913 _reflns_number_gt 1750 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0506P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(10) _refine_ls_number_reflns 3913 _refine_ls_number_parameters 545 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1547 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1156 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 0.879 _refine_ls_restrained_S_all 0.879 _refine_ls_shift/su_max 0.029 _refine_ls_shift/su_mean 0.003 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 F1 F 0.4814(5) -0.0657(3) 0.14748(17) 0.1173(18) Uani 1 1 d . . . F2 F 0.5901(5) -0.1606(4) 0.19573(17) 0.1341(19) Uani 1 1 d . . . F3 F 0.4104(5) -0.1946(3) 0.15698(18) 0.1141(16) Uani 1 1 d . . . F4 F 0.650(3) -0.4397(7) 0.0502(11) 0.138(11) Uani 0.62(3) 1 d P . . F5 F 0.654(4) -0.4100(8) -0.0435(12) 0.163(15) Uani 0.62(3) 1 d P . . F6 F 0.8269(12) -0.4060(8) 0.0089(14) 0.106(7) Uani 0.62(3) 1 d P . . F4A F 0.5830(17) -0.4261(12) -0.0018(17) 0.090(7) Uani 0.38(3) 1 d P . . F5A F 0.764(5) -0.3969(10) -0.0431(16) 0.117(16) Uani 0.38(3) 1 d P . . F6A F 0.747(5) -0.4268(11) 0.0529(14) 0.124(17) Uani 0.38(3) 1 d P . . F7 F 1.5136(3) 0.49018(19) -0.36215(12) 0.0588(9) Uani 1 1 d . . . F8 F 1.5691(3) 0.62728(18) -0.36904(13) 0.0567(9) Uani 1 1 d . . . F9 F 1.7059(4) 0.5344(2) -0.32952(13) 0.0688(10) Uani 1 1 d . . . F10 F 1.4608(3) 0.76031(18) -0.09268(13) 0.0540(8) Uani 1 1 d . . . F11 F 1.6112(4) 0.7959(2) -0.15804(13) 0.0699(10) Uani 1 1 d . . . F12 F 1.4075(5) 0.8163(2) -0.18062(17) 0.0952(15) Uani 1 1 d . . . O1 O 0.7773(4) 0.0426(2) 0.01116(13) 0.0427(10) Uani 1 1 d . . . O2 O 1.2975(4) 0.3466(2) -0.21072(13) 0.0427(9) Uani 1 1 d . . . N1 N 0.7763(5) 0.0643(3) -0.0934(2) 0.0446(13) Uani 1 1 d . . . N2 N 0.7389(5) -0.0747(3) -0.0534(2) 0.0415(12) Uani 1 1 d . . . N3 N 1.2520(5) 0.3266(3) -0.10683(18) 0.0430(12) Uani 1 1 d . . . N4 N 1.3558(5) 0.4523(3) -0.1388(2) 0.0446(13) Uani 1 1 d . . . C1 C 0.8251(6) 0.1565(3) -0.0904(2) 0.0411(14) Uani 1 1 d . . . C2 C 0.9745(6) 0.1589(3) -0.0972(2) 0.0368(13) Uani 1 1 d . . . C3 C 1.0330(5) 0.2518(3) -0.0937(2) 0.0345(12) Uani 1 1 d . . . C4 C 0.9575(6) 0.3122(3) -0.1403(2) 0.0421(14) Uani 1 1 d . . . C5 C 0.8051(6) 0.3110(3) -0.1391(2) 0.0472(14) Uani 1 1 d . . . C6 C 0.7599(7) 0.2131(4) -0.1408(3) 0.0454(15) Uani 1 1 d . . . C7 C 1.1783(6) 0.2437(3) -0.1126(2) 0.0424(15) Uani 1 1 d . . . C8 C 1.0259(6) 0.2879(3) -0.0253(2) 0.0479(15) Uani 1 1 d . . . H8A H 1.0893 0.2556 0.0009 0.072 Uiso 1 1 calc R . . H8B H 0.9357 0.2797 -0.0089 0.072 Uiso 1 1 calc R . . H8C H 1.0482 0.3511 -0.0251 0.072 Uiso 1 1 calc R . . C9 C 0.7556(6) 0.3550(4) -0.1992(3) 0.0696(18) Uani 1 1 d . . . H9A H 0.6584 0.3514 -0.2010 0.104 Uiso 1 1 calc R . . H9B H 0.7938 0.3245 -0.2354 0.104 Uiso 1 1 calc R . . H9C H 0.7830 0.4173 -0.1996 0.104 Uiso 1 1 calc R . . C10 C 0.7436(6) 0.3613(4) -0.0849(3) 0.0602(16) Uani 1 1 d . . . H10A H 0.7810 0.4212 -0.0832 0.090 Uiso 1 1 calc R . . H10B H 0.7631 0.3302 -0.0457 0.090 Uiso 1 1 calc R . . H10C H 0.6471 0.3649 -0.0908 0.090 Uiso 1 1 calc R . . C11 C 0.7653(6) 0.0133(3) -0.0428(2) 0.0399(13) Uani 1 1 d . . . C12 C 1.2997(5) 0.3736(3) -0.1557(2) 0.0402(13) Uani 1 1 d . . . C13 C 0.6980(5) -0.1365(3) -0.0078(2) 0.0411(13) Uani 1 1 d . . . C14 C 0.6282(6) -0.1110(4) 0.0456(2) 0.0455(15) Uani 1 1 d . . . C15 C 0.5874(6) -0.1748(3) 0.0873(2) 0.0512(15) Uani 1 1 d . . . C16 C 0.6093(7) -0.2639(4) 0.0771(3) 0.0580(17) Uani 1 1 d . . . C17 C 0.6781(6) -0.2892(3) 0.0227(3) 0.0503(16) Uani 1 1 d . . . C18 C 0.7233(6) -0.2259(3) -0.0191(2) 0.0433(14) Uani 1 1 d . . . C19 C 0.5165(8) -0.1482(4) 0.1453(3) 0.0673(19) Uani 1 1 d . . . C20 C 0.6993(10) -0.3853(4) 0.0095(3) 0.0624(18) Uani 1 1 d . . . C21 C 1.4143(5) 0.5177(3) -0.1757(2) 0.0376(13) Uani 1 1 d . . . C22 C 1.4624(6) 0.5034(3) -0.2361(2) 0.0404(13) Uani 1 1 d . . . C23 C 1.5211(5) 0.5736(3) -0.2679(2) 0.0411(13) Uani 1 1 d . . . C24 C 1.5315(6) 0.6568(4) -0.2417(2) 0.0437(14) Uani 1 1 d . . . C25 C 1.4838(5) 0.6700(3) -0.1820(2) 0.0420(14) Uani 1 1 d . . . C26 C 1.4256(5) 0.6020(3) -0.1497(2) 0.0396(14) Uani 1 1 d . . . C27 C 1.5763(6) 0.5555(3) -0.3313(2) 0.0464(15) Uani 1 1 d . . . C28 C 1.4899(7) 0.7593(4) -0.1532(3) 0.0535(16) Uani 1 1 d . . . O3 O 1.8183(5) 0.9241(3) -0.18620(16) 0.0573(12) Uani 1 1 d . . . C29 C 1.9540(7) 0.9328(4) -0.2023(3) 0.0633(17) Uani 1 1 d . . . H29A H 1.9620 0.9690 -0.2402 0.095 Uiso 1 1 calc R . . H29B H 1.9921 0.8741 -0.2100 0.095 Uiso 1 1 calc R . . H29C H 2.0020 0.9615 -0.1680 0.095 Uiso 1 1 calc R . . H1A H 0.786(4) 0.178(3) -0.047(2) 0.036(12) Uiso 1 1 d . . . H2A H 0.997(5) 0.132(3) -0.135(2) 0.054(16) Uiso 1 1 d . . . H2B H 1.008(5) 0.110(3) -0.065(2) 0.045(14) Uiso 1 1 d . . . H4A H 0.987(4) 0.295(2) -0.1806(17) 0.014(10) Uiso 1 1 d . . . H4B H 0.984(4) 0.379(3) -0.1311(18) 0.036(12) Uiso 1 1 d . . . H5A H 0.792(4) 0.183(3) -0.187(2) 0.047(13) Uiso 1 1 d . . . H5B H 0.677(5) 0.213(3) -0.135(2) 0.025(15) Uiso 1 1 d . . . H7A H 1.225(4) 0.193(3) -0.0841(19) 0.043(13) Uiso 1 1 d . . . H7B H 1.189(5) 0.230(3) -0.160(2) 0.062(16) Uiso 1 1 d . . . H14 H 0.619(4) -0.042(3) 0.0485(19) 0.038(13) Uiso 1 1 d . . . H16 H 0.582(5) -0.305(3) 0.107(2) 0.046(16) Uiso 1 1 d . . . H18 H 0.782(5) -0.250(3) -0.053(2) 0.052(15) Uiso 1 1 d . . . H22 H 1.453(4) 0.441(3) -0.2574(18) 0.041(13) Uiso 1 1 d . . . H24 H 1.576(5) 0.701(3) -0.2610(19) 0.033(14) Uiso 1 1 d . . . H26 H 1.396(5) 0.614(3) -0.107(2) 0.041(14) Uiso 1 1 d . . . H1 H 0.762(5) 0.047(3) -0.129(2) 0.045(17) Uiso 1 1 d . . . H2 H 0.761(5) -0.094(3) -0.090(2) 0.031(14) Uiso 1 1 d . . . H3 H 1.250(5) 0.362(3) -0.071(2) 0.045(15) Uiso 1 1 d . . . H4 H 1.354(4) 0.464(3) -0.1049(17) 0.014(13) Uiso 1 1 d . . . H3A H 1.783(9) 0.900(5) -0.218(4) 0.15(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.200(5) 0.064(3) 0.088(3) -0.002(2) 0.074(3) 0.010(3) F2 0.130(4) 0.227(6) 0.045(2) -0.015(3) 0.000(3) 0.032(4) F3 0.116(4) 0.126(4) 0.100(3) -0.034(3) 0.054(3) -0.049(3) F4 0.21(2) 0.035(5) 0.17(2) 0.018(7) 0.102(18) 0.008(9) F5 0.31(3) 0.035(6) 0.144(19) -0.015(9) -0.14(2) 0.007(13) F6 0.079(8) 0.051(6) 0.186(19) -0.024(8) 0.016(9) 0.011(4) F4A 0.084(13) 0.063(9) 0.123(18) 0.020(11) -0.014(12) -0.012(7) F5A 0.22(3) 0.028(6) 0.11(2) -0.009(11) 0.07(2) -0.016(14) F6A 0.21(4) 0.051(9) 0.11(2) 0.019(11) -0.12(3) -0.001(16) F7 0.081(3) 0.0483(18) 0.0470(16) -0.0048(15) 0.0170(18) -0.0150(18) F8 0.072(3) 0.0469(17) 0.0516(17) 0.0136(15) 0.0136(18) -0.0031(17) F9 0.053(3) 0.087(3) 0.066(2) 0.0080(18) 0.0132(19) 0.017(2) F10 0.067(2) 0.0446(17) 0.0501(17) -0.0092(15) 0.0051(17) -0.0119(16) F11 0.094(3) 0.070(2) 0.0455(17) -0.0084(16) 0.0135(19) -0.042(2) F12 0.151(4) 0.0414(19) 0.094(3) -0.0080(19) -0.059(3) 0.010(2) O1 0.064(3) 0.0353(19) 0.0286(17) -0.0040(16) -0.0017(18) -0.0044(18) O2 0.057(3) 0.040(2) 0.0312(18) -0.0021(16) 0.0075(17) -0.0070(18) N1 0.058(4) 0.045(3) 0.031(2) -0.008(2) 0.004(2) -0.014(2) N2 0.058(4) 0.034(3) 0.032(2) -0.005(2) 0.002(2) -0.004(2) N3 0.059(4) 0.039(3) 0.032(2) -0.003(2) 0.005(2) -0.007(2) N4 0.069(4) 0.038(3) 0.027(2) -0.008(2) 0.008(2) -0.013(2) C1 0.052(4) 0.036(3) 0.035(3) -0.001(3) -0.002(3) -0.006(3) C2 0.044(4) 0.029(3) 0.038(3) -0.002(3) 0.010(3) -0.001(3) C3 0.036(4) 0.038(3) 0.030(2) 0.004(2) -0.002(3) -0.002(3) C4 0.057(4) 0.035(3) 0.034(3) 0.007(3) -0.003(3) 0.001(3) C5 0.038(4) 0.044(3) 0.059(3) 0.016(3) -0.001(3) -0.005(3) C6 0.032(4) 0.051(4) 0.053(4) 0.006(3) 0.001(3) 0.003(3) C7 0.054(5) 0.034(3) 0.039(3) -0.002(3) -0.001(3) -0.005(3) C8 0.054(4) 0.050(3) 0.040(3) 0.002(3) -0.004(3) 0.001(3) C9 0.066(5) 0.063(4) 0.080(4) 0.027(3) -0.016(4) -0.004(4) C10 0.052(4) 0.049(3) 0.079(4) 0.002(3) 0.005(4) 0.007(3) C11 0.046(4) 0.032(3) 0.042(3) -0.005(3) 0.004(3) -0.007(3) C12 0.044(4) 0.037(3) 0.039(3) -0.001(3) 0.002(3) -0.002(3) C13 0.045(4) 0.038(3) 0.040(3) -0.003(3) -0.006(3) -0.005(3) C14 0.050(4) 0.043(4) 0.043(3) -0.004(3) 0.000(3) -0.006(3) C15 0.061(5) 0.044(3) 0.048(3) -0.004(3) 0.003(3) -0.012(3) C16 0.076(5) 0.050(4) 0.048(3) 0.008(3) -0.001(3) -0.014(4) C17 0.057(4) 0.038(3) 0.056(3) -0.002(3) -0.011(3) -0.004(3) C18 0.051(4) 0.039(3) 0.040(3) -0.006(3) -0.004(3) 0.000(3) C19 0.090(6) 0.058(4) 0.055(4) 0.003(3) 0.012(4) -0.023(4) C20 0.075(7) 0.048(4) 0.065(5) 0.009(4) -0.008(5) -0.001(5) C21 0.039(4) 0.035(3) 0.039(3) 0.004(3) -0.007(3) -0.004(3) C22 0.046(4) 0.036(3) 0.039(3) 0.001(3) 0.001(3) -0.001(3) C23 0.038(4) 0.043(3) 0.042(3) 0.006(3) 0.005(3) -0.001(3) C24 0.043(4) 0.042(3) 0.046(3) 0.010(3) 0.001(3) -0.006(3) C25 0.046(4) 0.039(3) 0.041(3) 0.003(3) -0.003(3) -0.004(3) C26 0.042(4) 0.041(3) 0.036(3) 0.003(3) -0.004(3) -0.006(3) C27 0.055(5) 0.038(3) 0.046(3) 0.007(3) 0.007(3) 0.000(3) C28 0.063(5) 0.041(3) 0.057(4) -0.002(3) -0.008(3) -0.012(3) O3 0.071(4) 0.063(3) 0.038(2) -0.014(2) 0.013(2) -0.018(2) C29 0.067(5) 0.066(4) 0.057(3) -0.010(3) 0.009(4) -0.006(4) _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 F1 C19 1.294(7) . ? F2 C19 1.321(7) . ? F3 C19 1.300(7) . ? F4 F6A 1.00(2) . ? F4 C20 1.297(12) . ? F4 F4A 1.31(2) . ? F5 F5A 1.11(3) . ? F5 F4A 1.17(2) . ? F5 C20 1.275(14) . ? F6 F6A 1.28(3) . ? F6 F5A 1.29(3) . ? F6 C20 1.320(12) . ? F4A C20 1.343(17) . ? F5A C20 1.310(19) . ? F6A C20 1.219(16) . ? F7 C27 1.344(6) . ? F8 C27 1.352(5) . ? F9 C27 1.342(6) . ? F10 C28 1.327(6) . ? F11 C28 1.343(6) . ? F12 C28 1.332(6) . ? O1 C11 1.243(5) . ? O2 C12 1.245(5) . ? N1 C11 1.333(6) . ? N1 C1 1.477(6) . ? N1 H1 0.81(5) . ? N2 C11 1.373(6) . ? N2 C13 1.410(6) . ? N2 H2 0.85(4) . ? N3 C12 1.352(6) . ? N3 C7 1.460(6) . ? N3 H3 0.93(5) . ? N4 C12 1.365(6) . ? N4 C21 1.394(6) . ? N4 H4 0.75(4) . ? C1 C2 1.510(7) . ? C1 C6 1.525(7) . ? C1 H1A 1.06(4) . ? C2 C3 1.522(7) . ? C2 H2A 0.93(5) . ? C2 H2B 1.07(5) . ? C3 C7 1.521(8) . ? C3 C4 1.549(7) . ? C3 C8 1.563(6) . ? C4 C5 1.533(8) . ? C4 H4A 0.95(4) . ? C4 H4B 1.06(4) . ? C5 C10 1.517(7) . ? C5 C9 1.531(7) . ? C5 C6 1.546(7) . ? C6 H5A 1.14(4) . ? C6 H5B 0.85(4) . ? C7 H7A 1.08(5) . ? C7 H7B 1.03(5) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C13 C14 1.395(7) . ? C13 C18 1.396(7) . ? C14 C15 1.375(7) . ? C14 H14 1.05(4) . ? C15 C16 1.380(7) . ? C15 C19 1.487(8) . ? C16 C17 1.407(8) . ? C16 H16 0.92(5) . ? C17 C18 1.384(7) . ? C17 C20 1.493(8) . ? C18 H18 1.00(5) . ? C21 C26 1.393(6) . ? C21 C22 1.396(6) . ? C22 C23 1.391(6) . ? C22 H22 1.05(4) . ? C23 C24 1.381(7) . ? C23 C27 1.491(6) . ? C24 C25 1.379(7) . ? C24 H24 0.90(4) . ? C25 C26 1.369(6) . ? C25 C28 1.483(7) . ? C26 H26 0.97(4) . ? O3 C29 1.414(7) . ? O3 H3A 0.85(8) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 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 F6A F4 C20 62.5(14) . . ? F6A F4 F4A 121(2) . . ? C20 F4 F4A 61.9(9) . . ? F5A F5 F4A 129(2) . . ? F5A F5 C20 66.1(14) . . ? F4A F5 C20 66.5(13) . . ? F6A F6 F5A 110.6(16) . . ? F6A F6 C20 56.0(10) . . ? F5A F6 C20 60.2(12) . . ? F5 F4A F4 111.4(19) . . ? F5 F4A C20 60.5(11) . . ? F4 F4A C20 58.4(10) . . ? F5 F5A F6 118(2) . . ? F5 F5A C20 62.9(15) . . ? F6 F5A C20 61.0(13) . . ? F4 F6A C20 70.7(14) . . ? F4 F6A F6 128(2) . . ? C20 F6A F6 63.8(13) . . ? C11 N1 C1 122.4(4) . . ? C11 N1 H1 124(3) . . ? C1 N1 H1 114(3) . . ? C11 N2 C13 125.6(4) . . ? C11 N2 H2 115(3) . . ? C13 N2 H2 119(3) . . ? C12 N3 C7 124.3(4) . . ? C12 N3 H3 110(3) . . ? C7 N3 H3 124(3) . . ? C12 N4 C21 129.8(4) . . ? C12 N4 H4 117(3) . . ? C21 N4 H4 114(3) . . ? N1 C1 C2 110.4(4) . . ? N1 C1 C6 110.7(4) . . ? C2 C1 C6 110.2(5) . . ? N1 C1 H1A 102(2) . . ? C2 C1 H1A 117(2) . . ? C6 C1 H1A 107(2) . . ? C1 C2 C3 113.7(4) . . ? C1 C2 H2A 108(3) . . ? C3 C2 H2A 110(3) . . ? C1 C2 H2B 104(3) . . ? C3 C2 H2B 119(2) . . ? H2A C2 H2B 100(4) . . ? C7 C3 C2 106.5(4) . . ? C7 C3 C4 110.3(4) . . ? C2 C3 C4 108.7(4) . . ? C7 C3 C8 108.7(4) . . ? C2 C3 C8 110.4(4) . . ? C4 C3 C8 112.0(4) . . ? C5 C4 C3 118.1(4) . . ? C5 C4 H4A 109(2) . . ? C3 C4 H4A 106(2) . . ? C5 C4 H4B 105(2) . . ? C3 C4 H4B 108(2) . . ? H4A C4 H4B 111(3) . . ? C10 C5 C9 107.0(4) . . ? C10 C5 C4 114.5(5) . . ? C9 C5 C4 107.8(4) . . ? C10 C5 C6 112.1(5) . . ? C9 C5 C6 107.4(5) . . ? C4 C5 C6 107.7(5) . . ? C1 C6 C5 113.1(5) . . ? C1 C6 H5A 106(2) . . ? C5 C6 H5A 108(2) . . ? C1 C6 H5B 109(3) . . ? C5 C6 H5B 106(3) . . ? H5A C6 H5B 114(4) . . ? N3 C7 C3 113.3(4) . . ? N3 C7 H7A 110(2) . . ? C3 C7 H7A 109(2) . . ? N3 C7 H7B 102(3) . . ? C3 C7 H7B 112(3) . . ? H7A C7 H7B 111(3) . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O1 C11 N1 122.8(5) . . ? O1 C11 N2 121.0(5) . . ? N1 C11 N2 116.2(4) . . ? O2 C12 N3 123.6(5) . . ? O2 C12 N4 122.9(5) . . ? N3 C12 N4 113.4(4) . . ? C14 C13 C18 120.0(5) . . ? C14 C13 N2 122.1(5) . . ? C18 C13 N2 117.8(5) . . ? C15 C14 C13 119.3(5) . . ? C15 C14 H14 129(2) . . ? C13 C14 H14 112(2) . . ? C14 C15 C16 122.1(5) . . ? C14 C15 C19 119.7(5) . . ? C16 C15 C19 118.2(5) . . ? C15 C16 C17 118.3(6) . . ? C15 C16 H16 120(3) . . ? C17 C16 H16 122(3) . . ? C18 C17 C16 120.5(5) . . ? C18 C17 C20 120.1(6) . . ? C16 C17 C20 119.4(6) . . ? C17 C18 C13 119.7(5) . . ? C17 C18 H18 114(3) . . ? C13 C18 H18 126(3) . . ? F1 C19 F3 106.7(6) . . ? F1 C19 F2 105.1(6) . . ? F3 C19 F2 103.1(5) . . ? F1 C19 C15 114.8(5) . . ? F3 C19 C15 114.0(5) . . ? F2 C19 C15 112.0(6) . . ? F6A C20 F5 131.8(11) . . ? F6A C20 F4 46.8(12) . . ? F5 C20 F4 106.0(13) . . ? F6A C20 F5A 113.1(19) . . ? F5 C20 F5A 51.0(11) . . ? F4 C20 F5A 133.0(9) . . ? F6A C20 F6 60.2(17) . . ? F5 C20 F6 105.4(14) . . ? F4 C20 F6 103.3(10) . . ? F5A C20 F6 58.8(16) . . ? F6A C20 F4A 104.1(14) . . ? F5 C20 F4A 53.1(11) . . ? F4 C20 F4A 59.6(10) . . ? F5A C20 F4A 102.3(16) . . ? F6 C20 F4A 137.3(9) . . ? F6A C20 C17 114.3(10) . . ? F5 C20 C17 113.7(8) . . ? F4 C20 C17 115.7(8) . . ? F5A C20 C17 111.3(9) . . ? F6 C20 C17 111.8(7) . . ? F4A C20 C17 110.8(10) . . ? C26 C21 N4 117.0(4) . . ? C26 C21 C22 118.9(5) . . ? N4 C21 C22 124.1(4) . . ? C23 C22 C21 118.8(4) . . ? C23 C22 H22 121(2) . . ? C21 C22 H22 120(2) . . ? C24 C23 C22 121.8(5) . . ? C24 C23 C27 120.5(5) . . ? C22 C23 C27 117.7(4) . . ? C25 C24 C23 118.8(5) . . ? C25 C24 H24 119(3) . . ? C23 C24 H24 122(3) . . ? C26 C25 C24 120.6(5) . . ? C26 C25 C28 119.3(5) . . ? C24 C25 C28 120.1(5) . . ? C25 C26 C21 121.1(5) . . ? C25 C26 H26 118(3) . . ? C21 C26 H26 121(3) . . ? F9 C27 F7 107.2(4) . . ? F9 C27 F8 105.1(4) . . ? F7 C27 F8 105.7(4) . . ? F9 C27 C23 112.3(5) . . ? F7 C27 C23 113.9(5) . . ? F8 C27 C23 112.1(4) . . ? F10 C28 F12 106.6(5) . . ? F10 C28 F11 105.7(4) . . ? F12 C28 F11 105.3(5) . . ? F10 C28 C25 114.0(5) . . ? F12 C28 C25 112.2(5) . . ? F11 C28 C25 112.3(5) . . ? C29 O3 H3A 104(6) . . ? O3 C29 H29A 109.5 . . ? O3 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O3 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.295 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.047 #===END data_9 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 F6 N3 O' _chemical_formula_sum 'C20 H21 F6 N3 O' _chemical_formula_weight 433.40 _chemical_absolute_configuration syn 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.5778(9) _cell_length_b 18.5187(16) _cell_length_c 11.1532(13) _cell_angle_alpha 90.00 _cell_angle_beta 100.724(3) _cell_angle_gamma 90.00 _cell_volume 2146.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12334 _cell_measurement_theta_min 1.96 _cell_measurement_theta_max 26.99 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Phi/Omega-Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12334 _diffrn_reflns_av_R_equivalents 0.0972 _diffrn_reflns_av_sigmaI/netI 0.1262 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.99 _reflns_number_total 4834 _reflns_number_gt 2571 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0648P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(10) _refine_ls_number_reflns 4834 _refine_ls_number_parameters 618 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1530 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.005 _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 0.3181(7) 0.2325(3) 0.2481(6) 0.0569(19) Uani 1 1 d . . . H1A H 0.3669 0.1939 0.2216 0.068 Uiso 1 1 calc R . . H1B H 0.3737 0.2729 0.2732 0.068 Uiso 1 1 calc R . . H1C H 0.2510 0.2468 0.1822 0.068 Uiso 1 1 calc R . . C2 C 0.2589(6) 0.2069(3) 0.3553(6) 0.0371(15) Uani 1 1 d . . . H2 H 0.320(5) 0.200(2) 0.431(5) 0.021(13) Uiso 1 1 d . . . C3 C 0.1699(6) 0.2646(3) 0.3944(5) 0.0347(14) Uani 1 1 d . . . H3 H 0.1098 0.2808 0.3217 0.042 Uiso 1 1 calc . . . C4 C 0.2495(6) 0.3923(3) 0.3789(7) 0.0464(17) Uani 1 1 d . . . H4 H 0.195(7) 0.395(4) 0.298(7) 0.08(2) Uiso 1 1 d . . . C5 C 0.3271(8) 0.4495(4) 0.4258(9) 0.063(2) Uani 1 1 d . . . H5 H 0.326(7) 0.490(4) 0.376(7) 0.08(2) Uiso 1 1 d . . . C6 C 0.4013(7) 0.4461(3) 0.5391(9) 0.064(2) Uani 1 1 d . . . H6 H 0.4524 0.4853 0.5692 0.077 Uiso 1 1 calc . . . C7 C 0.4014(7) 0.3842(4) 0.6110(9) 0.060(2) Uani 1 1 d . . . H7 H 0.449(7) 0.374(3) 0.688(6) 0.06(2) Uiso 1 1 d . . . C8 C 0.3232(6) 0.3258(3) 0.5635(6) 0.0430(16) Uani 1 1 d . . . H8 H 0.3223 0.2843 0.6103 0.052 Uiso 1 1 calc . . . C9 C 0.2481(5) 0.3288(3) 0.4488(6) 0.0382(15) Uani 1 1 d . . . C10 C 0.0041(6) 0.2660(3) 0.5216(5) 0.0304(14) Uani 1 1 d . . . C11 C -0.1714(6) 0.2413(3) 0.6347(5) 0.0308(13) Uani 1 1 d . . . C12 C -0.2695(6) 0.1934(3) 0.6449(5) 0.0316(14) Uani 1 1 d . . . H12 H -0.272(5) 0.154(3) 0.593(5) 0.039(16) Uiso 1 1 d . . . C13 C -0.3555(6) 0.2068(3) 0.7200(5) 0.0360(15) Uani 1 1 d . . . C14 C -0.3442(7) 0.2691(3) 0.7916(6) 0.0412(16) Uani 1 1 d . . . H14 H -0.392(5) 0.277(3) 0.851(5) 0.029(15) Uiso 1 1 d . . . C15 C -0.2467(6) 0.3177(3) 0.7804(5) 0.0371(15) Uani 1 1 d . . . C16 C -0.1614(6) 0.3045(3) 0.7052(5) 0.0316(14) Uani 1 1 d . . . H16 H -0.0963 0.3375 0.7006 0.038 Uiso 1 1 calc . . . C17 C -0.2300(7) 0.3839(3) 0.8620(6) 0.0465(16) Uani 1 1 d . . . C18 C -0.4570(6) 0.1525(3) 0.7292(6) 0.0447(16) Uani 1 1 d . . . C19 C 0.0973(6) 0.1325(4) 0.2236(6) 0.0564(18) Uani 1 1 d . . . H19A H 0.1408 0.1355 0.1555 0.068 Uiso 1 1 calc R . . H19B H 0.0369 0.1716 0.2198 0.068 Uiso 1 1 calc R . . H19C H 0.0523 0.0874 0.2209 0.068 Uiso 1 1 calc R . . C20 C 0.2768(7) 0.0761(3) 0.3483(6) 0.0567(19) Uani 1 1 d . . . H20A H 0.2293 0.0325 0.3551 0.068 Uiso 1 1 calc R . . H20B H 0.3417 0.0820 0.4202 0.068 Uiso 1 1 calc R . . H20C H 0.3169 0.0731 0.2780 0.068 Uiso 1 1 calc R . . N1 N 0.1900(4) 0.1372(2) 0.3357(4) 0.0361(12) Uani 1 1 d . . . N2 N 0.0967(4) 0.2313(2) 0.4765(4) 0.0323(12) Uani 1 1 d . . . H2N H 0.094(5) 0.187(3) 0.471(5) 0.039 Uiso 1 1 d . . . N3 N -0.0829(5) 0.2225(2) 0.5635(5) 0.0338(13) Uani 1 1 d . . . H3N H -0.066(6) 0.187(3) 0.564(5) 0.041 Uiso 1 1 d . . . O1 O -0.0037(4) 0.33273(17) 0.5258(3) 0.0339(9) Uani 1 1 d . . . F1 F -0.4101(3) 0.09409(17) 0.7922(3) 0.0572(10) Uani 1 1 d . . . F2 F -0.5151(4) 0.1288(2) 0.6210(4) 0.0743(13) Uani 1 1 d . . . F3 F -0.5494(4) 0.1780(2) 0.7847(4) 0.0759(13) Uani 1 1 d . . . F4 F -0.3374(5) 0.4214(2) 0.8526(5) 0.1080(19) Uani 1 1 d . . . F5 F -0.1901(5) 0.3676(2) 0.9759(4) 0.0945(17) Uani 1 1 d . . . F6 F -0.1448(5) 0.43050(19) 0.8341(4) 0.0824(14) Uani 1 1 d . . . C21 C 0.3222(6) -0.0086(3) -0.1493(5) 0.0427(16) Uani 1 1 d . . . H21A H 0.3668 -0.0469 -0.1012 0.051 Uiso 1 1 calc R . . H21B H 0.2915 0.0256 -0.0967 0.051 Uiso 1 1 calc R . . H21C H 0.3797 0.0151 -0.1938 0.051 Uiso 1 1 calc R . . C22 C 0.2092(5) -0.0394(3) -0.2382(5) 0.0291(13) Uani 1 1 d . . . H22 H 0.149(5) -0.065(3) -0.190(5) 0.046(17) Uiso 1 1 d . . . C23 C 0.1330(5) 0.0200(3) -0.3181(5) 0.0309(14) Uani 1 1 d . . . H23 H 0.186(5) 0.046(3) -0.361(5) 0.037 Uiso 1 1 d . . . C24 C 0.1226(6) 0.1394(3) -0.2110(6) 0.0394(15) Uani 1 1 d . . . H24 H 0.191(6) 0.153(3) -0.254(5) 0.047(18) Uiso 1 1 d . . . C25 C 0.0684(8) 0.1833(4) -0.1321(7) 0.055(2) Uani 1 1 d . . . H25 H 0.116(6) 0.220(3) -0.122(5) 0.041(19) Uiso 1 1 d . . . C26 C -0.0331(8) 0.1621(4) -0.0828(6) 0.0521(19) Uani 1 1 d . . . H26 H -0.084(5) 0.188(3) -0.029(5) 0.039(16) Uiso 1 1 d . . . C27 C -0.0853(7) 0.0943(4) -0.1108(6) 0.0501(17) Uani 1 1 d . . . H27 H -0.173(8) 0.079(4) -0.076(7) 0.10(3) Uiso 1 1 d . . . C28 C -0.0338(6) 0.0500(3) -0.1895(6) 0.0426(16) Uani 1 1 d . . . H28 H -0.0702 0.0048 -0.2084 0.051 Uiso 1 1 calc . . . C29 C 0.0694(6) 0.0707(3) -0.2410(5) 0.0329(14) Uani 1 1 d . . . C30 C -0.0292(5) 0.0163(3) -0.5081(5) 0.0283(13) Uani 1 1 d . . . C31 C -0.1682(6) -0.0133(3) -0.7067(5) 0.0299(13) Uani 1 1 d . . . C32 C -0.1951(6) -0.0672(3) -0.7953(5) 0.0361(15) Uani 1 1 d . . . H32 H -0.157(4) -0.113(3) -0.777(4) 0.018(12) Uiso 1 1 d . . . C33 C -0.2781(6) -0.0563(3) -0.9028(5) 0.0352(14) Uani 1 1 d . . . C34 C -0.3396(6) 0.0100(3) -0.9297(6) 0.0348(14) Uani 1 1 d . . . H34 H -0.393(5) 0.017(3) -1.008(6) 0.042 Uiso 1 1 d . . . C35 C -0.3102(5) 0.0647(3) -0.8437(5) 0.0314(14) Uani 1 1 d . . . C36 C -0.2272(5) 0.0540(3) -0.7338(5) 0.0322(13) Uani 1 1 d . . . H36 H -0.213(5) 0.088(3) -0.670(5) 0.041(16) Uiso 1 1 d . . . C37 C -0.3721(7) 0.1379(3) -0.8704(6) 0.0455(16) Uani 1 1 d . . . C38 C -0.3061(8) -0.1170(4) -0.9931(7) 0.062(2) Uani 1 1 d . . . C39 C 0.3457(7) -0.0822(4) -0.3803(6) 0.059(2) Uani 1 1 d . . . H39A H 0.4253 -0.0802 -0.3227 0.064(8) Uiso 1 1 calc R . . H39B H 0.3306 -0.0365 -0.4212 0.064(8) Uiso 1 1 calc R . . H39C H 0.3505 -0.1194 -0.4392 0.064(8) Uiso 1 1 calc R . . C40 C 0.2589(7) -0.1677(3) -0.2563(6) 0.0547(19) Uani 1 1 d . . . H40A H 0.2664 -0.2044 -0.3153 0.064(8) Uiso 1 1 calc R . . H40B H 0.1863 -0.1780 -0.2187 0.064(8) Uiso 1 1 calc R . . H40C H 0.3358 -0.1668 -0.1950 0.064(8) Uiso 1 1 calc R . . N4 N 0.2410(5) -0.0978(2) -0.3165(4) 0.0409(13) Uani 1 1 d . . . N5 N 0.0393(5) -0.0170(2) -0.4107(4) 0.0328(12) Uani 1 1 d . . . H5N H 0.055(6) -0.056(3) -0.410(5) 0.039 Uiso 1 1 d . . . N6 N -0.0869(5) -0.0291(2) -0.5985(4) 0.0320(13) Uani 1 1 d . . . H6N H -0.079(6) -0.064(3) -0.580(5) 0.038 Uiso 1 1 d . . . O2 O -0.0431(4) 0.08302(18) -0.5154(3) 0.0354(10) Uani 1 1 d . . . F7 F -0.1966(5) -0.1469(2) -1.0129(4) 0.106(2) Uani 1 1 d . . . F8 F -0.3643(5) -0.0965(2) -1.1004(4) 0.0932(17) Uani 1 1 d . . . F9 F -0.3661(8) -0.1695(3) -0.9557(5) 0.160(3) Uani 1 1 d . . . F10 F -0.3007(4) 0.17960(19) -0.9287(4) 0.0777(13) Uani 1 1 d . . . F11 F -0.4874(4) 0.13414(19) -0.9406(3) 0.0716(13) Uani 1 1 d . . . F12 F -0.3842(3) 0.17298(16) -0.7705(3) 0.0542(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 0.068(5) 0.046(4) 0.066(5) 0.007(3) 0.038(4) 0.012(3) C2 0.046(4) 0.034(3) 0.033(4) 0.007(3) 0.012(3) 0.010(3) C3 0.039(4) 0.031(3) 0.035(3) 0.006(3) 0.008(3) 0.005(3) C4 0.041(4) 0.034(3) 0.072(5) 0.012(3) 0.029(4) 0.000(3) C5 0.061(5) 0.037(4) 0.102(7) 0.011(4) 0.042(5) -0.004(4) C6 0.048(5) 0.033(4) 0.118(7) -0.024(4) 0.036(5) -0.015(3) C7 0.041(5) 0.039(4) 0.100(7) -0.015(4) 0.011(5) 0.001(3) C8 0.043(4) 0.030(3) 0.053(4) 0.000(3) 0.001(3) 0.007(3) C9 0.033(4) 0.026(3) 0.059(4) 0.008(3) 0.017(3) 0.004(3) C10 0.039(4) 0.020(3) 0.031(3) -0.001(2) 0.004(3) -0.005(3) C11 0.041(4) 0.020(3) 0.033(3) 0.002(2) 0.012(3) 0.007(3) C12 0.037(4) 0.020(3) 0.037(4) -0.002(3) 0.005(3) -0.001(3) C13 0.039(4) 0.030(3) 0.039(4) 0.008(3) 0.009(3) 0.001(3) C14 0.052(5) 0.041(4) 0.035(4) 0.008(3) 0.022(3) 0.010(3) C15 0.050(4) 0.029(3) 0.032(3) 0.001(2) 0.008(3) 0.003(3) C16 0.042(4) 0.020(3) 0.032(3) -0.001(2) 0.006(3) -0.001(2) C17 0.060(5) 0.044(4) 0.039(4) -0.001(3) 0.019(3) -0.005(4) C18 0.033(4) 0.046(4) 0.055(4) 0.013(3) 0.008(4) 0.000(3) C19 0.056(4) 0.054(4) 0.055(4) -0.010(3) 0.000(4) 0.006(3) C20 0.079(5) 0.044(4) 0.047(4) -0.007(3) 0.009(4) 0.013(4) N1 0.041(3) 0.034(3) 0.033(3) 0.001(2) 0.003(2) 0.006(2) N2 0.036(3) 0.022(2) 0.041(3) 0.000(2) 0.013(2) 0.006(2) N3 0.046(3) 0.011(2) 0.047(3) 0.000(2) 0.015(3) 0.004(2) O1 0.042(2) 0.0153(19) 0.044(2) -0.0017(16) 0.0081(19) -0.0016(16) F1 0.047(2) 0.044(2) 0.082(3) 0.0271(19) 0.014(2) -0.0040(17) F2 0.067(3) 0.088(3) 0.060(3) 0.014(2) -0.007(2) -0.039(2) F3 0.050(3) 0.064(3) 0.124(4) 0.020(3) 0.045(3) 0.006(2) F4 0.088(4) 0.083(3) 0.146(5) -0.067(3) 0.004(3) 0.026(3) F5 0.185(5) 0.054(2) 0.040(3) -0.0119(19) 0.010(3) -0.004(3) F6 0.135(4) 0.042(2) 0.084(3) -0.024(2) 0.055(3) -0.021(2) C21 0.043(4) 0.039(3) 0.045(4) 0.005(3) 0.004(3) -0.004(3) C22 0.027(3) 0.026(3) 0.031(3) 0.002(2) -0.001(3) -0.003(2) C23 0.030(4) 0.029(3) 0.035(3) 0.000(3) 0.010(3) -0.007(2) C24 0.048(4) 0.031(3) 0.037(4) -0.006(3) 0.003(3) 0.001(3) C25 0.071(6) 0.030(4) 0.054(5) -0.009(3) -0.011(4) 0.000(4) C26 0.056(5) 0.051(4) 0.045(4) -0.012(3) -0.002(4) 0.019(4) C27 0.050(5) 0.060(4) 0.040(4) -0.007(3) 0.009(4) 0.010(3) C28 0.046(4) 0.035(3) 0.046(4) -0.009(3) 0.005(3) -0.007(3) C29 0.036(4) 0.023(3) 0.035(3) 0.003(2) -0.003(3) 0.001(2) C30 0.034(4) 0.023(3) 0.031(3) -0.001(2) 0.015(3) 0.000(2) C31 0.040(3) 0.022(3) 0.029(3) -0.005(2) 0.009(3) -0.002(2) C32 0.050(4) 0.022(3) 0.038(4) -0.005(3) 0.011(3) 0.005(3) C33 0.046(4) 0.027(3) 0.033(3) -0.003(2) 0.007(3) 0.006(3) C34 0.035(4) 0.037(3) 0.030(3) -0.002(3) 0.000(3) 0.001(3) C35 0.040(4) 0.025(3) 0.030(3) 0.004(2) 0.008(3) 0.005(2) C36 0.036(4) 0.027(3) 0.035(4) -0.005(3) 0.010(3) 0.000(3) C37 0.053(5) 0.038(4) 0.042(4) 0.000(3) 0.001(4) 0.010(3) C38 0.081(6) 0.042(4) 0.054(5) -0.013(4) -0.011(4) 0.017(4) C39 0.071(5) 0.057(4) 0.050(4) 0.010(4) 0.012(4) 0.030(4) C40 0.085(5) 0.025(3) 0.050(4) 0.006(3) 0.003(4) 0.008(3) N4 0.052(3) 0.036(3) 0.037(3) 0.006(2) 0.015(3) 0.011(2) N5 0.043(3) 0.020(2) 0.033(3) 0.001(2) 0.000(2) 0.002(2) N6 0.045(3) 0.016(2) 0.032(3) 0.001(2) -0.002(2) 0.002(2) O2 0.051(3) 0.016(2) 0.038(2) -0.0004(15) 0.004(2) 0.0026(16) F7 0.112(4) 0.094(3) 0.093(4) -0.061(3) -0.029(3) 0.056(3) F8 0.124(4) 0.076(3) 0.060(3) -0.034(2) -0.034(3) 0.049(3) F9 0.302(9) 0.092(4) 0.100(4) -0.060(3) 0.074(5) -0.116(5) F10 0.098(3) 0.040(2) 0.103(3) 0.027(2) 0.038(3) 0.022(2) F11 0.071(3) 0.057(2) 0.071(3) -0.017(2) -0.027(2) 0.035(2) F12 0.062(3) 0.0358(18) 0.061(2) -0.0113(17) 0.002(2) 0.0193(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.524(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.478(7) . ? C2 C3 1.541(8) . ? C2 H2 0.97(5) . ? C3 N2 1.444(7) . ? C3 C9 1.510(8) . ? C3 H3 0.9800 . ? C4 C5 1.381(10) . ? C4 C9 1.412(8) . ? C4 H4 0.98(7) . ? C5 C6 1.360(11) . ? C5 H5 0.93(8) . ? C6 C7 1.398(11) . ? C6 H6 0.9300 . ? C7 C8 1.405(9) . ? C7 H7 0.93(7) . ? C8 C9 1.375(8) . ? C8 H8 0.9300 . ? C10 O1 1.240(6) . ? C10 N2 1.345(7) . ? C10 N3 1.370(7) . ? C11 N3 1.380(7) . ? C11 C12 1.385(8) . ? C11 C16 1.404(7) . ? C12 C13 1.368(8) . ? C12 H12 0.93(6) . ? C13 C14 1.395(8) . ? C13 C18 1.490(8) . ? C14 C15 1.392(9) . ? C14 H14 0.91(6) . ? C15 C16 1.364(8) . ? C15 C17 1.517(9) . ? C16 H16 0.9300 . ? C17 F5 1.298(7) . ? C17 F4 1.318(8) . ? C17 F6 1.325(7) . ? C18 F2 1.323(7) . ? C18 F1 1.333(7) . ? C18 F3 1.337(7) . ? C19 N1 1.441(7) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N1 1.448(7) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N2 H2N 0.82(6) . ? N3 H3N 0.69(6) . ? C21 C22 1.515(8) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 N4 1.468(7) . ? C22 C23 1.544(7) . ? C22 H22 1.02(6) . ? C23 N5 1.461(7) . ? C23 C29 1.513(8) . ? C23 H23 0.93(6) . ? C24 C25 1.397(10) . ? C24 C29 1.407(8) . ? C24 H24 0.98(6) . ? C25 C26 1.352(10) . ? C25 H25 0.84(6) . ? C26 C27 1.385(10) . ? C26 H26 1.01(6) . ? C27 C28 1.384(9) . ? C27 H27 1.10(9) . ? C28 C29 1.379(8) . ? C28 H28 0.9300 . ? C30 O2 1.246(6) . ? C30 N5 1.338(7) . ? C30 N6 1.366(7) . ? C31 N6 1.376(7) . ? C31 C32 1.396(7) . ? C31 C36 1.402(7) . ? C32 C33 1.363(8) . ? C32 H32 0.95(5) . ? C33 C34 1.396(8) . ? C33 C38 1.502(8) . ? C34 C35 1.391(8) . ? C34 H34 0.95(6) . ? C35 C36 1.383(8) . ? C35 C37 1.510(8) . ? C36 H36 0.94(5) . ? C37 F12 1.317(7) . ? C37 F11 1.322(7) . ? C37 F10 1.332(7) . ? C38 F9 1.273(9) . ? C38 F8 1.297(7) . ? C38 F7 1.339(8) . ? C39 N4 1.453(8) . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C40 N4 1.454(7) . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? N5 H5N 0.73(6) . ? N6 H6N 0.69(6) . ? 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 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C1 114.8(5) . . ? N1 C2 C3 109.7(5) . . ? C1 C2 C3 111.6(5) . . ? N1 C2 H2 104(3) . . ? C1 C2 H2 114(3) . . ? C3 C2 H2 101(3) . . ? N2 C3 C9 113.6(5) . . ? N2 C3 C2 108.1(4) . . ? C9 C3 C2 110.0(5) . . ? N2 C3 H3 108.3 . . ? C9 C3 H3 108.3 . . ? C2 C3 H3 108.3 . . ? C5 C4 C9 119.7(7) . . ? C5 C4 H4 121(4) . . ? C9 C4 H4 120(4) . . ? C6 C5 C4 121.1(7) . . ? C6 C5 H5 122(5) . . ? C4 C5 H5 116(5) . . ? C5 C6 C7 120.6(6) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C8 118.6(7) . . ? C6 C7 H7 130(4) . . ? C8 C7 H7 111(4) . . ? C9 C8 C7 121.1(6) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C4 119.0(6) . . ? C8 C9 C3 121.3(5) . . ? C4 C9 C3 119.6(6) . . ? O1 C10 N2 123.3(5) . . ? O1 C10 N3 121.3(5) . . ? N2 C10 N3 115.4(4) . . ? N3 C11 C12 119.0(5) . . ? N3 C11 C16 123.0(5) . . ? C12 C11 C16 117.8(5) . . ? C13 C12 C11 121.8(5) . . ? C13 C12 H12 125(3) . . ? C11 C12 H12 113(3) . . ? C12 C13 C14 120.3(5) . . ? C12 C13 C18 119.3(5) . . ? C14 C13 C18 120.3(6) . . ? C15 C14 C13 118.0(6) . . ? C15 C14 H14 119(3) . . ? C13 C14 H14 123(3) . . ? C16 C15 C14 121.7(5) . . ? C16 C15 C17 119.8(5) . . ? C14 C15 C17 118.3(6) . . ? C15 C16 C11 120.3(5) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? F5 C17 F4 108.6(6) . . ? F5 C17 F6 105.7(6) . . ? F4 C17 F6 104.6(6) . . ? F5 C17 C15 112.2(5) . . ? F4 C17 C15 112.0(5) . . ? F6 C17 C15 113.2(5) . . ? F2 C18 F1 106.0(5) . . ? F2 C18 F3 106.5(5) . . ? F1 C18 F3 106.0(5) . . ? F2 C18 C13 112.3(5) . . ? F1 C18 C13 112.5(5) . . ? F3 C18 C13 113.1(5) . . ? N1 C19 H19A 109.5 . . ? N1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N1 C20 H20A 109.5 . . ? N1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 N1 C20 110.7(5) . . ? C19 N1 C2 114.7(5) . . ? C20 N1 C2 112.5(4) . . ? C10 N2 C3 123.1(4) . . ? C10 N2 H2N 119(4) . . ? C3 N2 H2N 113(4) . . ? C10 N3 C11 128.2(4) . . ? C10 N3 H3N 113(5) . . ? C11 N3 H3N 116(5) . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N4 C22 C21 115.2(5) . . ? N4 C22 C23 109.5(4) . . ? C21 C22 C23 111.9(4) . . ? N4 C22 H22 101(3) . . ? C21 C22 H22 109(3) . . ? C23 C22 H22 109(3) . . ? N5 C23 C29 112.2(5) . . ? N5 C23 C22 106.7(4) . . ? C29 C23 C22 110.7(5) . . ? N5 C23 H23 106(3) . . ? C29 C23 H23 110(3) . . ? C22 C23 H23 111(3) . . ? C25 C24 C29 118.9(7) . . ? C25 C24 H24 126(3) . . ? C29 C24 H24 115(3) . . ? C26 C25 C24 122.5(7) . . ? C26 C25 H25 133(4) . . ? C24 C25 H25 105(4) . . ? C25 C26 C27 119.0(7) . . ? C25 C26 H26 131(3) . . ? C27 C26 H26 110(3) . . ? C28 C27 C26 119.5(7) . . ? C28 C27 H27 122(4) . . ? C26 C27 H27 118(4) . . ? C29 C28 C27 122.4(6) . . ? C29 C28 H28 118.8 . . ? C27 C28 H28 118.8 . . ? C28 C29 C24 117.7(6) . . ? C28 C29 C23 122.3(5) . . ? C24 C29 C23 119.7(6) . . ? O2 C30 N5 123.3(5) . . ? O2 C30 N6 122.1(5) . . ? N5 C30 N6 114.6(4) . . ? N6 C31 C32 118.7(5) . . ? N6 C31 C36 123.9(5) . . ? C32 C31 C36 117.3(5) . . ? C33 C32 C31 122.0(5) . . ? C33 C32 H32 120(3) . . ? C31 C32 H32 118(3) . . ? C32 C33 C34 121.2(5) . . ? C32 C33 C38 119.6(5) . . ? C34 C33 C38 119.2(5) . . ? C35 C34 C33 117.2(5) . . ? C35 C34 H34 124(3) . . ? C33 C34 H34 119(3) . . ? C36 C35 C34 122.1(5) . . ? C36 C35 C37 119.0(5) . . ? C34 C35 C37 119.0(5) . . ? C35 C36 C31 120.2(5) . . ? C35 C36 H36 124(3) . . ? C31 C36 H36 115(3) . . ? F12 C37 F11 107.6(5) . . ? F12 C37 F10 106.3(5) . . ? F11 C37 F10 106.6(5) . . ? F12 C37 C35 112.5(5) . . ? F11 C37 C35 112.9(5) . . ? F10 C37 C35 110.7(5) . . ? F9 C38 F8 110.3(7) . . ? F9 C38 F7 103.8(6) . . ? F8 C38 F7 104.2(6) . . ? F9 C38 C33 113.5(6) . . ? F8 C38 C33 113.6(5) . . ? F7 C38 C33 110.6(6) . . ? N4 C39 H39A 109.5 . . ? N4 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? N4 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? N4 C40 H40A 109.5 . . ? N4 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? N4 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 N4 C40 111.0(5) . . ? C39 N4 C22 115.1(5) . . ? C40 N4 C22 113.9(5) . . ? C30 N5 C23 123.5(4) . . ? C30 N5 H5N 123(5) . . ? C23 N5 H5N 110(5) . . ? C30 N6 C31 129.6(4) . . ? C30 N6 H6N 111(5) . . ? C31 N6 H6N 119(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.285 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.052 #===END data_17 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 2 (C15 H21 N5 O5), C H4 O, O H2 _chemical_formula_sum 'C31 H48 N10 O12' _chemical_formula_weight 752.79 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.1767(6) _cell_length_b 22.874(2) _cell_length_c 10.1933(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.158(3) _cell_angle_gamma 90.00 _cell_volume 1811.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7412 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.00 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max .3 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'Nonius KappaCCD' _diffrn_measurement_method 'Phi/Omega-Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7412 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4031 _reflns_number_gt 2818 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.1167P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(16) _refine_ls_number_reflns 4031 _refine_ls_number_parameters 501 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0883 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1739 _refine_ls_wR_factor_gt 0.1565 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2461(5) 0.36836(16) 0.4016(4) 0.0532(10) Uani 1 1 d . . . O2 O -0.2283(5) 0.39604(15) 0.0712(4) 0.0458(9) Uani 1 1 d . . . O3 O -0.3286(5) 0.47357(18) -0.0486(4) 0.0585(11) Uani 1 1 d . . . O4 O -0.0780(5) 0.66189(15) 0.1163(4) 0.0487(9) Uani 1 1 d . . . O5 O 0.0986(5) 0.66782(15) 0.3243(4) 0.0459(9) Uani 1 1 d . . . N1 N 0.7931(5) 0.34903(18) 0.7045(4) 0.0389(9) Uani 1 1 d . . . N2 N 0.4490(6) 0.3947(2) 0.5996(5) 0.0384(10) Uani 1 1 d . . . H2C H 0.487(7) 0.415(2) 0.651(6) 0.034(16) Uiso 1 1 d . . . N3 N 0.2812(6) 0.46539(19) 0.4578(5) 0.0417(10) Uani 1 1 d . . . H3C H 0.331(7) 0.486(2) 0.510(5) 0.031(15) Uiso 1 1 d . . . N4 N 0.0107(5) 0.64046(16) 0.2245(4) 0.0355(9) Uani 1 1 d . . . N5 N -0.2264(5) 0.44913(19) 0.0494(4) 0.0395(10) Uani 1 1 d . . . C1 C 0.6515(6) 0.32642(19) 0.7539(5) 0.0346(10) Uani 1 1 d . . . H1 H 0.6545 0.3499 0.8373 0.042 Uiso 1 1 calc R . . C2 C 0.4747(6) 0.33497(19) 0.6512(5) 0.0334(10) Uani 1 1 d . . . H2 H 0.4617 0.3080 0.5714 0.040 Uiso 1 1 calc R . . C3 C 0.3405(6) 0.3192(2) 0.7199(5) 0.0403(11) Uani 1 1 d . . . H3A H 0.3498 0.3468 0.7968 0.048 Uiso 1 1 calc R . . H3B H 0.2245 0.3239 0.6520 0.048 Uiso 1 1 calc R . . C4 C 0.3585(7) 0.2584(2) 0.7746(6) 0.0473(13) Uani 1 1 d . . . H4A H 0.3324 0.2304 0.6966 0.057 Uiso 1 1 calc R . . H4B H 0.2742 0.2519 0.8249 0.057 Uiso 1 1 calc R . . C5 C 0.5380(7) 0.2468(2) 0.8707(6) 0.0474(13) Uani 1 1 d . . . H5A H 0.5497 0.2050 0.8972 0.057 Uiso 1 1 calc R . . H5B H 0.5585 0.2704 0.9557 0.057 Uiso 1 1 calc R . . C6 C 0.6703(7) 0.2627(2) 0.7990(5) 0.0409(12) Uani 1 1 d . . . H6A H 0.7877 0.2559 0.8630 0.049 Uiso 1 1 calc R . . H6B H 0.6542 0.2372 0.7174 0.049 Uiso 1 1 calc R . . C7 C 0.9612(7) 0.3443(3) 0.8137(6) 0.0571(15) Uani 1 1 d . . . H7A H 1.0026 0.3039 0.8188 0.086 Uiso 1 1 calc R . . H7B H 0.9482 0.3555 0.9027 0.086 Uiso 1 1 calc R . . H7C H 1.0444 0.3704 0.7920 0.086 Uiso 1 1 calc R . . C8 C 0.8032(7) 0.3199(2) 0.5765(5) 0.0455(13) Uani 1 1 d . . . H8A H 0.8430 0.2795 0.5977 0.068 Uiso 1 1 calc R . . H8B H 0.8842 0.3412 0.5405 0.068 Uiso 1 1 calc R . . H8C H 0.6891 0.3198 0.5070 0.068 Uiso 1 1 calc R . . C9 C 0.3183(6) 0.4063(2) 0.4814(5) 0.0373(11) Uani 1 1 d . . . C10 C 0.1499(6) 0.4892(2) 0.3512(5) 0.0337(10) Uani 1 1 d . . . C11 C 0.0267(6) 0.4565(2) 0.2536(5) 0.0344(10) Uani 1 1 d . . . H11 H 0.0275 0.4150 0.2590 0.041 Uiso 1 1 calc R . . C12 C -0.0955(6) 0.4847(2) 0.1498(5) 0.0327(10) Uani 1 1 d . . . C13 C -0.1056(6) 0.5445(2) 0.1353(5) 0.0342(10) Uani 1 1 d . . . H13 H -0.1905 0.5630 0.0614 0.041 Uiso 1 1 calc R . . C14 C 0.0142(6) 0.5757(2) 0.2339(5) 0.0334(10) Uani 1 1 d . . . C15 C 0.1420(6) 0.5503(2) 0.3419(5) 0.0337(10) Uani 1 1 d . . . H15 H 0.2225 0.5738 0.4082 0.040 Uiso 1 1 calc R . . O6 O 0.3373(7) 0.12578(15) 0.6526(4) 0.0706(14) Uani 1 1 d . . . O7 O 0.4648(5) -0.17087(14) 0.7649(4) 0.0449(9) Uani 1 1 d . . . O8 O 0.6805(5) -0.16394(14) 0.9516(3) 0.0438(9) Uani 1 1 d . . . O9 O 0.9048(7) 0.0266(2) 1.1205(5) 0.098(2) Uani 1 1 d . . . O10 O 0.7860(5) 0.10294(17) 1.0125(4) 0.0606(11) Uani 1 1 d . . . N6 N 0.3995(5) 0.15438(18) 0.2838(4) 0.0407(9) Uani 1 1 d . . . N7 N 0.1949(6) 0.09974(18) 0.4340(4) 0.0410(10) Uani 1 1 d . . . H7D H 0.170(8) 0.071(3) 0.363(6) 0.054(16) Uiso 1 1 d . . . N8 N 0.3209(6) 0.02983(18) 0.5950(4) 0.0452(11) Uani 1 1 d . . . H8D H 0.263(6) 0.006(2) 0.525(5) 0.036(13) Uiso 1 1 d . . . N9 N 0.5718(5) -0.14228(17) 0.8529(4) 0.0350(9) Uani 1 1 d . . . N10 N 0.7914(6) 0.0503(2) 1.0289(5) 0.0515(12) Uani 1 1 d . . . C16 C 0.2135(6) 0.17066(19) 0.2569(4) 0.0311(9) Uani 1 1 d . . . H16 H 0.1435 0.1444 0.1818 0.037 Uiso 1 1 calc R . . C17 C 0.1576(5) 0.15921(19) 0.3838(4) 0.0297(9) Uani 1 1 d . . . H17 H 0.2241 0.1862 0.4586 0.036 Uiso 1 1 calc R . . C18 C -0.0341(6) 0.1731(2) 0.3532(5) 0.0411(11) Uani 1 1 d . . . H18A H -0.1029 0.1460 0.2814 0.049 Uiso 1 1 calc R . . H18B H -0.0669 0.1669 0.4378 0.049 Uiso 1 1 calc R . . C19 C -0.0756(7) 0.2360(2) 0.3040(6) 0.0492(13) Uani 1 1 d . . . H19A H -0.2008 0.2431 0.2816 0.059 Uiso 1 1 calc R . . H19B H -0.0144 0.2634 0.3781 0.059 Uiso 1 1 calc R . . C20 C -0.0207(7) 0.2464(2) 0.1774(5) 0.0424(12) Uani 1 1 d . . . H20A H -0.0440 0.2876 0.1475 0.051 Uiso 1 1 calc R . . H20B H -0.0888 0.2210 0.1013 0.051 Uiso 1 1 calc R . . C21 C 0.1719(6) 0.23330(19) 0.2074(5) 0.0352(10) Uani 1 1 d . . . H21A H 0.2040 0.2396 0.1225 0.042 Uiso 1 1 calc R . . H21B H 0.2403 0.2606 0.2789 0.042 Uiso 1 1 calc R . . C22 C 0.5186(6) 0.1852(3) 0.4009(5) 0.0460(12) Uani 1 1 d . . . H22A H 0.6359 0.1710 0.4153 0.069 Uiso 1 1 calc R . . H22B H 0.4858 0.1781 0.4841 0.069 Uiso 1 1 calc R . . H22C H 0.5136 0.2273 0.3815 0.069 Uiso 1 1 calc R . . C23 C 0.4535(7) 0.1636(3) 0.1609(6) 0.0590(16) Uani 1 1 d . . . H23A H 0.4559 0.2056 0.1425 0.089 Uiso 1 1 calc R . . H23B H 0.3719 0.1443 0.0813 0.089 Uiso 1 1 calc R . . H23C H 0.5686 0.1471 0.1767 0.089 Uiso 1 1 calc R . . C24 C 0.2895(7) 0.0885(2) 0.5662(5) 0.0419(12) Uani 1 1 d . . . C25 C 0.4387(6) 0.0071(2) 0.7134(4) 0.0332(10) Uani 1 1 d . . . C26 C 0.4478(6) -0.0532(2) 0.7278(5) 0.0342(10) Uani 1 1 d . . . H26 H 0.3712 -0.0772 0.6601 0.041 Uiso 1 1 calc R . . C27 C 0.5669(6) -0.07826(19) 0.8395(4) 0.0302(10) Uani 1 1 d . . . C28 C 0.6814(6) -0.0462(2) 0.9417(5) 0.0371(11) Uani 1 1 d . . . H28 H 0.7632 -0.0642 1.0186 0.045 Uiso 1 1 calc R . . C29 C 0.6696(6) 0.0140(2) 0.9253(5) 0.0374(11) Uani 1 1 d . . . C30 C 0.5516(6) 0.0414(2) 0.8165(5) 0.0368(11) Uani 1 1 d . . . H30 H 0.5465 0.0828 0.8112 0.044 Uiso 1 1 calc R . . O11 O 0.8167(8) 0.4647(2) 0.6481(6) 0.099(2) Uani 1 1 d . . . H11A H 0.7941 0.4313 0.6723 0.056(17) Uiso 1 1 calc R . . C31 C 0.980(2) 0.4613(6) 0.6014(15) 0.165(6) Uani 1 1 d . . . H31A H 1.0168 0.5009 0.5866 0.248 Uiso 1 1 calc R . . H31B H 0.9542 0.4391 0.5151 0.248 Uiso 1 1 calc R . . H31C H 1.0729 0.4418 0.6729 0.248 Uiso 1 1 calc R . . O12 O 0.5109(7) 0.03918(17) 0.3253(5) 0.095(2) 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 O1 0.065(2) 0.0365(19) 0.041(2) -0.0025(16) -0.0096(18) 0.0104(18) O2 0.047(2) 0.0340(19) 0.0472(19) -0.0105(16) 0.0023(16) -0.0009(16) O3 0.052(2) 0.058(3) 0.047(2) 0.0046(19) -0.0108(19) -0.0007(19) O4 0.059(2) 0.0336(18) 0.045(2) 0.0147(17) 0.0032(18) 0.0131(17) O5 0.051(2) 0.0341(18) 0.046(2) 0.0048(17) 0.0057(17) -0.0033(17) N1 0.032(2) 0.049(2) 0.0308(19) -0.0041(19) 0.0019(16) 0.0003(19) N2 0.040(2) 0.030(2) 0.034(2) -0.0033(19) -0.0058(18) 0.0026(19) N3 0.041(2) 0.027(2) 0.043(2) 0.002(2) -0.0070(19) 0.0024(19) N4 0.043(2) 0.025(2) 0.038(2) 0.0051(17) 0.0119(19) 0.0020(17) N5 0.038(2) 0.047(3) 0.031(2) -0.0023(19) 0.0070(18) 0.003(2) C1 0.034(2) 0.034(2) 0.031(2) -0.0050(19) 0.0019(19) 0.010(2) C2 0.033(2) 0.029(2) 0.032(2) -0.0032(18) 0.0018(18) 0.011(2) C3 0.029(2) 0.038(3) 0.048(3) -0.001(2) 0.004(2) 0.003(2) C4 0.057(3) 0.035(3) 0.051(3) -0.002(2) 0.018(3) 0.001(3) C5 0.065(4) 0.035(3) 0.043(3) 0.003(2) 0.018(3) 0.003(3) C6 0.047(3) 0.036(3) 0.035(2) 0.002(2) 0.006(2) 0.018(2) C7 0.032(3) 0.089(5) 0.045(3) -0.012(3) 0.005(2) 0.004(3) C8 0.049(3) 0.053(3) 0.032(2) 0.000(2) 0.010(2) -0.004(2) C9 0.036(2) 0.031(2) 0.037(3) -0.002(2) 0.001(2) 0.003(2) C10 0.034(2) 0.028(2) 0.033(2) 0.0039(18) 0.0015(19) 0.004(2) C11 0.037(2) 0.027(2) 0.035(2) 0.0006(19) 0.005(2) 0.002(2) C12 0.029(2) 0.033(2) 0.032(2) -0.0025(19) 0.0044(19) 0.003(2) C13 0.029(2) 0.039(3) 0.030(2) 0.005(2) 0.0031(19) 0.005(2) C14 0.034(2) 0.029(2) 0.034(2) 0.0039(19) 0.0054(19) -0.0002(19) C15 0.032(2) 0.029(2) 0.035(2) 0.0042(19) 0.0039(19) 0.000(2) O6 0.127(4) 0.0268(18) 0.0346(19) -0.0042(16) -0.008(2) 0.019(2) O7 0.053(2) 0.0297(18) 0.0447(19) -0.0032(16) 0.0037(17) -0.0011(16) O8 0.058(2) 0.0324(18) 0.0330(18) 0.0024(15) 0.0036(16) 0.0097(16) O9 0.105(4) 0.053(3) 0.082(3) -0.003(2) -0.050(3) 0.000(3) O10 0.061(2) 0.038(2) 0.066(3) -0.0137(19) -0.004(2) -0.0078(19) N6 0.032(2) 0.045(2) 0.044(2) -0.0041(19) 0.0098(17) -0.0026(18) N7 0.049(2) 0.029(2) 0.035(2) 0.0059(18) -0.0021(18) -0.0037(19) N8 0.060(3) 0.026(2) 0.034(2) 0.0012(18) -0.007(2) -0.004(2) N9 0.044(2) 0.028(2) 0.032(2) -0.0013(17) 0.0103(19) 0.0018(18) N10 0.047(3) 0.038(3) 0.053(3) -0.007(2) -0.009(2) -0.001(2) C16 0.032(2) 0.031(2) 0.029(2) -0.0051(18) 0.0064(17) -0.0040(19) C17 0.029(2) 0.030(2) 0.028(2) 0.0033(18) 0.0049(17) -0.0008(19) C18 0.033(2) 0.053(3) 0.038(2) 0.009(2) 0.012(2) 0.003(2) C19 0.039(3) 0.054(3) 0.054(3) 0.005(3) 0.015(2) 0.012(3) C20 0.049(3) 0.030(2) 0.041(3) 0.011(2) 0.002(2) 0.008(2) C21 0.039(2) 0.029(2) 0.036(2) 0.002(2) 0.009(2) -0.004(2) C22 0.029(2) 0.062(3) 0.041(3) 0.000(2) 0.003(2) -0.005(2) C23 0.042(3) 0.085(4) 0.054(3) -0.022(3) 0.021(3) -0.006(3) C24 0.054(3) 0.030(2) 0.037(3) 0.005(2) 0.008(2) 0.004(2) C25 0.037(2) 0.031(2) 0.027(2) 0.0035(19) 0.005(2) 0.003(2) C26 0.040(2) 0.033(2) 0.025(2) -0.0016(19) 0.0023(19) -0.004(2) C27 0.037(2) 0.027(2) 0.028(2) 0.0012(18) 0.0123(19) 0.005(2) C28 0.036(2) 0.034(2) 0.033(2) -0.002(2) -0.002(2) 0.004(2) C29 0.035(2) 0.034(3) 0.037(2) -0.007(2) 0.003(2) -0.003(2) C30 0.042(3) 0.024(2) 0.042(3) 0.0033(19) 0.011(2) -0.002(2) O11 0.109(4) 0.066(3) 0.085(4) 0.032(3) -0.024(3) -0.040(3) C31 0.225(16) 0.140(11) 0.156(12) -0.015(9) 0.096(12) -0.037(11) O12 0.121(4) 0.031(2) 0.076(3) -0.011(2) -0.051(3) 0.028(2) _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 C9 1.210(6) . ? O2 N5 1.236(5) . ? O3 N5 1.220(5) . ? O4 N4 1.218(5) . ? O5 N4 1.220(5) . ? N1 C7 1.479(6) . ? N1 C8 1.491(6) . ? N1 C1 1.492(6) . ? N2 C9 1.365(6) . ? N2 C2 1.455(6) . ? N2 H2C 0.70(6) . ? N3 C10 1.379(6) . ? N3 C9 1.389(6) . ? N3 H3C 0.74(5) . ? N4 C14 1.484(6) . ? N5 C12 1.473(6) . ? C1 C2 1.510(6) . ? C1 C6 1.523(6) . ? C1 H1 1.0000 . ? C2 C3 1.518(7) . ? C2 H2 1.0000 . ? C3 C4 1.489(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.512(8) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.526(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 C11 1.393(7) . ? C10 C15 1.399(6) . ? C11 C12 1.369(6) . ? C11 H11 0.9500 . ? C12 C13 1.377(7) . ? C13 C14 1.365(6) . ? C13 H13 0.9500 . ? C14 C15 1.388(6) . ? C15 H15 0.9500 . ? O6 C24 1.200(6) . ? O7 N9 1.228(5) . ? O8 N9 1.221(5) . ? O9 N10 1.219(6) . ? O10 N10 1.213(6) . ? N6 C22 1.465(6) . ? N6 C23 1.468(7) . ? N6 C16 1.506(6) . ? N7 C24 1.353(6) . ? N7 C17 1.452(6) . ? N7 H7D 0.95(6) . ? N8 C24 1.381(6) . ? N8 C25 1.390(6) . ? N8 H8D 0.90(6) . ? N9 C27 1.470(6) . ? N10 C29 1.464(6) . ? C16 C21 1.522(6) . ? C16 C17 1.523(6) . ? C16 H16 1.0000 . ? C17 C18 1.533(6) . ? C17 H17 1.0000 . ? C18 C19 1.526(8) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.511(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.537(7) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C25 C26 1.385(6) . ? C25 C30 1.403(7) . ? C26 C27 1.372(6) . ? C26 H26 0.9500 . ? C27 C28 1.375(7) . ? C28 C29 1.388(7) . ? C28 H28 0.9500 . ? C29 C30 1.373(7) . ? C30 H30 0.9500 . ? O11 C31 1.555(15) . ? O11 H11A 0.8400 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 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 C7 N1 C8 109.5(4) . . ? C7 N1 C1 111.0(4) . . ? C8 N1 C1 113.6(4) . . ? C9 N2 C2 119.2(4) . . ? C9 N2 H2C 125(5) . . ? C2 N2 H2C 112(4) . . ? C10 N3 C9 126.5(5) . . ? C10 N3 H3C 115(4) . . ? C9 N3 H3C 118(4) . . ? O4 N4 O5 125.3(4) . . ? O4 N4 C14 117.0(4) . . ? O5 N4 C14 117.6(4) . . ? O3 N5 O2 123.6(4) . . ? O3 N5 C12 118.7(4) . . ? O2 N5 C12 117.7(4) . . ? N1 C1 C2 113.4(4) . . ? N1 C1 C6 114.7(4) . . ? C2 C1 C6 108.6(4) . . ? N1 C1 H1 106.5 . . ? C2 C1 H1 106.5 . . ? C6 C1 H1 106.5 . . ? N2 C2 C1 111.8(4) . . ? N2 C2 C3 110.2(4) . . ? C1 C2 C3 108.8(4) . . ? N2 C2 H2 108.6 . . ? C1 C2 H2 108.6 . . ? C3 C2 H2 108.6 . . ? C4 C3 C2 113.2(4) . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.8 . . ? C3 C4 C5 111.6(4) . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 109.8(4) . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C1 C6 C5 110.6(4) . . ? C1 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O1 C9 N2 122.5(5) . . ? O1 C9 N3 123.2(4) . . ? N2 C9 N3 114.3(4) . . ? N3 C10 C11 124.2(4) . . ? N3 C10 C15 117.1(4) . . ? C11 C10 C15 118.7(4) . . ? C12 C11 C10 119.4(4) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 123.7(4) . . ? C11 C12 N5 118.3(4) . . ? C13 C12 N5 117.9(4) . . ? C14 C13 C12 115.8(4) . . ? C14 C13 H13 122.1 . . ? C12 C13 H13 122.1 . . ? C13 C14 C15 123.7(4) . . ? C13 C14 N4 118.6(4) . . ? C15 C14 N4 117.7(4) . . ? C14 C15 C10 118.7(4) . . ? C14 C15 H15 120.7 . . ? C10 C15 H15 120.7 . . ? C22 N6 C23 109.0(4) . . ? C22 N6 C16 114.0(4) . . ? C23 N6 C16 111.4(4) . . ? C24 N7 C17 121.4(4) . . ? C24 N7 H7D 123(4) . . ? C17 N7 H7D 115(3) . . ? C24 N8 C25 125.5(4) . . ? C24 N8 H8D 114(3) . . ? C25 N8 H8D 121(3) . . ? O8 N9 O7 123.8(4) . . ? O8 N9 C27 118.2(4) . . ? O7 N9 C27 118.0(4) . . ? O10 N10 O9 122.2(5) . . ? O10 N10 C29 118.4(4) . . ? O9 N10 C29 119.0(5) . . ? N6 C16 C21 113.7(4) . . ? N6 C16 C17 110.8(4) . . ? C21 C16 C17 110.4(4) . . ? N6 C16 H16 107.2 . . ? C21 C16 H16 107.2 . . ? C17 C16 H16 107.2 . . ? N7 C17 C16 112.0(4) . . ? N7 C17 C18 110.8(4) . . ? C16 C17 C18 110.5(4) . . ? N7 C17 H17 107.8 . . ? C16 C17 H17 107.8 . . ? C18 C17 H17 107.8 . . ? C19 C18 C17 111.8(4) . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? C19 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? C20 C19 C18 109.5(4) . . ? C20 C19 H19A 109.8 . . ? C18 C19 H19A 109.8 . . ? C20 C19 H19B 109.8 . . ? C18 C19 H19B 109.8 . . ? H19A C19 H19B 108.2 . . ? C19 C20 C21 111.0(4) . . ? C19 C20 H20A 109.4 . . ? C21 C20 H20A 109.4 . . ? C19 C20 H20B 109.4 . . ? C21 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? C16 C21 C20 111.0(4) . . ? C16 C21 H21A 109.4 . . ? C20 C21 H21A 109.4 . . ? C16 C21 H21B 109.4 . . ? C20 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? N6 C22 H22A 109.5 . . ? N6 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N6 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N6 C23 H23A 109.5 . . ? N6 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N6 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O6 C24 N7 123.4(4) . . ? O6 C24 N8 122.5(5) . . ? N7 C24 N8 114.0(4) . . ? C26 C25 N8 117.7(4) . . ? C26 C25 C30 118.4(4) . . ? N8 C25 C30 123.9(4) . . ? C27 C26 C25 120.4(4) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C26 C27 C28 123.0(4) . . ? C26 C27 N9 119.1(4) . . ? C28 C27 N9 117.9(4) . . ? C27 C28 C29 115.6(4) . . ? C27 C28 H28 122.2 . . ? C29 C28 H28 122.2 . . ? C30 C29 C28 123.7(4) . . ? C30 C29 N10 118.2(4) . . ? C28 C29 N10 118.1(4) . . ? C29 C30 C25 118.9(4) . . ? C29 C30 H30 120.6 . . ? C25 C30 H30 120.6 . . ? C31 O11 H11A 109.5 . . ? O11 C31 H31A 109.5 . . ? O11 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O11 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.679 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.063 #===END data_18 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H29 N3 O' _chemical_formula_sum 'C18 H29 N3 O' _chemical_formula_weight 303.44 _chemical_absolute_configuration syn 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.8168(3) _cell_length_b 16.6626(6) _cell_length_c 18.2008(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3583.71(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 18006 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 27.00 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.125 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'Nonius KappaCCD' _diffrn_measurement_method 'Phi/Omega-Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18006 _diffrn_reflns_av_R_equivalents 0.0926 _diffrn_reflns_av_sigmaI/netI 0.1111 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4342 _reflns_number_gt 2550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0431P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 5.3(18) _refine_ls_number_reflns 4342 _refine_ls_number_parameters 539 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1234 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0843 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 0.5554(3) 0.8775(2) 0.97818(18) 0.0268(9) Uani 1 1 d . . . H1 H 0.546(3) 0.8605(17) 1.0318(17) 0.031(9) Uiso 1 1 d . . . C2 C 0.6236(4) 0.8127(2) 0.9389(2) 0.0314(9) Uani 1 1 d . . . H2A H 0.636(3) 0.8302(19) 0.8854(19) 0.044(11) Uiso 1 1 d . . . H2B H 0.701(3) 0.812(2) 0.9542(16) 0.037(11) Uiso 1 1 d . . . C3 C 0.5684(4) 0.7305(2) 0.9466(2) 0.0413(11) Uani 1 1 d . . . H3A H 0.620(3) 0.691(2) 0.9220(19) 0.048(11) Uiso 1 1 d . . . H3B H 0.573(3) 0.7146(19) 0.9956(18) 0.033(10) Uiso 1 1 d . . . C4 C 0.4486(4) 0.7308(3) 0.9181(2) 0.0434(11) Uani 1 1 d . . . H4A H 0.450(3) 0.7380(18) 0.8644(19) 0.038(10) Uiso 1 1 d . . . H4B H 0.414(4) 0.675(2) 0.924(2) 0.061(13) Uiso 1 1 d . . . C5 C 0.3800(4) 0.7979(2) 0.9538(2) 0.0353(10) Uani 1 1 d . . . H5A H 0.371(3) 0.786(2) 1.007(2) 0.046(11) Uiso 1 1 d . . . H5B H 0.305(3) 0.7990(18) 0.9346(15) 0.022(9) Uiso 1 1 d . . . C6 C 0.4358(3) 0.8799(2) 0.94570(18) 0.0265(9) Uani 1 1 d . . . H6 H 0.441(3) 0.8940(17) 0.8932(18) 0.032 Uiso 1 1 d . . . C7 C 0.7164(3) 0.9559(3) 1.0205(2) 0.0512(12) Uani 1 1 d . . . H7A H 0.7742 0.9315 0.9890 0.061 Uiso 1 1 calc R . . H7B H 0.7088 0.9244 1.0657 0.061 Uiso 1 1 calc R . . H7C H 0.7389 1.0109 1.0328 0.061 Uiso 1 1 calc R . . C8 C 0.6227(4) 0.9970(2) 0.9113(2) 0.0539(12) Uani 1 1 d . . . H8A H 0.5501 0.9980 0.8853 0.065 Uiso 1 1 calc R . . H8B H 0.6785 0.9678 0.8818 0.065 Uiso 1 1 calc R . . H8C H 0.6491 1.0521 0.9193 0.065 Uiso 1 1 calc R . . C9 C 0.3088(3) 0.9977(2) 0.94054(17) 0.0236(8) Uani 1 1 d . . . C10 C 0.2114(3) 1.12681(19) 0.95252(15) 0.0209(8) Uani 1 1 d . . . C11 C 0.2722(3) 1.1978(2) 0.96488(15) 0.0216(8) Uani 1 1 d . . . C12 C 0.2302(3) 1.2690(2) 0.93757(16) 0.0223(8) Uani 1 1 d . . . H12 H 0.267(3) 1.3190(19) 0.9475(15) 0.027 Uiso 1 1 d . . . C13 C 0.1303(3) 1.27222(19) 0.89625(15) 0.0226(8) Uani 1 1 d . . . C14 C 0.0724(3) 1.2008(2) 0.88511(16) 0.0225(8) Uani 1 1 d . . . H14 H -0.003(3) 1.1996(19) 0.8589(15) 0.027 Uiso 1 1 d . . . C15 C 0.1101(3) 1.12804(19) 0.91395(15) 0.0210(8) Uani 1 1 d . . . C16 C 0.3822(3) 1.1958(2) 1.00615(17) 0.0326(9) Uani 1 1 d . . . H16A H 0.4350 1.1596 0.9812 0.039 Uiso 1 1 calc R . . H16B H 0.3688 1.1766 1.0563 0.039 Uiso 1 1 calc R . . H16C H 0.4145 1.2500 1.0079 0.039 Uiso 1 1 calc R . . C17 C 0.0395(3) 1.05300(19) 0.90450(16) 0.0285(9) Uani 1 1 d . . . H17A H 0.0384 1.0228 0.9507 0.034 Uiso 1 1 calc R . . H17B H 0.0723 1.0196 0.8657 0.034 Uiso 1 1 calc R . . H17C H -0.0379 1.0680 0.8910 0.034 Uiso 1 1 calc R . . C18 C 0.0876(4) 1.3511(2) 0.8665(2) 0.0312(10) Uani 1 1 d . . . H18A H 0.014(4) 1.344(2) 0.8346(19) 0.050(11) Uiso 1 1 d . . . H18B H 0.070(3) 1.390(2) 0.908(2) 0.043(10) Uiso 1 1 d . . . H18C H 0.136(3) 1.371(2) 0.837(2) 0.055(13) Uiso 1 1 d . . . N1 N 0.6087(3) 0.95714(18) 0.98181(15) 0.0389(8) Uani 1 1 d . . . N2 N 0.3668(3) 0.94239(17) 0.97956(15) 0.0287(7) Uani 1 1 d . . . H2N H 0.275(3) 1.0577(17) 1.0265(16) 0.020(9) Uiso 1 1 d . . . N3 N 0.2549(3) 1.05376(16) 0.98219(15) 0.0250(7) Uani 1 1 d . . . H3N H 0.368(3) 0.9464(19) 1.0272(18) 0.034(10) Uiso 1 1 d . . . O1 O 0.3037(2) 0.99706(13) 0.87222(11) 0.0285(6) Uani 1 1 d . . . C19 C 0.0680(3) 1.1445(2) 1.19388(18) 0.0243(8) Uani 1 1 d . . . H19 H 0.053(3) 1.1573(17) 1.2478(17) 0.029 Uiso 1 1 d . . . C20 C 0.0243(4) 1.2139(2) 1.14572(19) 0.0307(9) Uani 1 1 d . . . H20A H 0.050(3) 1.2026(17) 1.0939(17) 0.026(9) Uiso 1 1 d . . . H20B H -0.063(3) 1.215(2) 1.1468(15) 0.033(10) Uiso 1 1 d . . . C21 C 0.0756(3) 1.2938(2) 1.1695(2) 0.0347(10) Uani 1 1 d . . . H21A H 0.055(3) 1.3073(18) 1.2215(16) 0.030(9) Uiso 1 1 d . . . H21B H 0.045(4) 1.338(2) 1.137(2) 0.066(13) Uiso 1 1 d . . . C22 C 0.2045(3) 1.2907(2) 1.1657(2) 0.0312(9) Uani 1 1 d . . . H22A H 0.237(3) 1.3428(18) 1.1841(15) 0.023(9) Uiso 1 1 d . . . H22B H 0.229(3) 1.2850(18) 1.1130(18) 0.034(9) Uiso 1 1 d . . . C23 C 0.2497(3) 1.2193(2) 1.20894(16) 0.0272(8) Uani 1 1 d . . . H23A H 0.2353 1.2282 1.2619 0.033 Uiso 1 1 calc . . . H23B H 0.3327 1.2158 1.2019 0.033 Uiso 1 1 calc . . . C24 C 0.1958(3) 1.14003(19) 1.18579(17) 0.0214(8) Uani 1 1 d . . . H24 H 0.212(3) 1.1280(17) 1.1340(17) 0.026 Uiso 1 1 d . . . C25 C -0.1025(3) 1.0654(3) 1.2103(2) 0.0503(12) Uani 1 1 d . . . H25A H -0.1513 1.0968 1.1775 0.060 Uiso 1 1 calc R . . H25B H -0.1045 1.0887 1.2597 0.060 Uiso 1 1 calc R . . H25C H -0.1297 1.0099 1.2122 0.060 Uiso 1 1 calc R . . C26 C 0.0174(4) 1.0361(3) 1.1083(2) 0.0429(11) Uani 1 1 d . . . H26A H -0.024(4) 1.065(2) 1.074(2) 0.061(14) Uiso 1 1 d . . . H26B H 0.098(3) 1.034(2) 1.087(2) 0.052(12) Uiso 1 1 d . . . H26C H -0.011(3) 0.980(2) 1.1109(16) 0.042(11) Uiso 1 1 d . . . C27 C 0.2993(3) 1.01262(19) 1.19419(16) 0.0208(8) Uani 1 1 d . . . C28 C 0.3721(3) 0.87643(19) 1.21456(15) 0.0207(8) Uani 1 1 d . . . C29 C 0.3042(3) 0.8077(2) 1.21473(15) 0.0220(8) Uani 1 1 d . . . C30 C 0.3526(4) 0.7350(2) 1.19349(17) 0.0278(9) Uani 1 1 d . . . H30 H 0.308(3) 0.689(2) 1.1944(17) 0.039(11) Uiso 1 1 d . . . C31 C 0.4656(3) 0.7292(2) 1.17250(16) 0.0252(9) Uani 1 1 d . . . C32 C 0.5295(3) 0.7991(2) 1.17322(16) 0.0257(8) Uani 1 1 d . . . H32 H 0.610(3) 0.7984(19) 1.1614(15) 0.024(9) Uiso 1 1 d . . . C33 C 0.4859(3) 0.8730(2) 1.19445(15) 0.0236(8) Uani 1 1 d . . . C34 C 0.1837(3) 0.8119(2) 1.24006(17) 0.0335(9) Uani 1 1 d . . . H34A H 0.1440 0.8543 1.2130 0.040 Uiso 1 1 calc R . . H34B H 0.1817 0.8239 1.2928 0.040 Uiso 1 1 calc R . . H34C H 0.1465 0.7603 1.2310 0.040 Uiso 1 1 calc R . . C35 C 0.5589(3) 0.9468(2) 1.19569(17) 0.0320(9) Uani 1 1 d . . . H35A H 0.5387 0.9799 1.2382 0.038 Uiso 1 1 calc R . . H35B H 0.5469 0.9777 1.1505 0.038 Uiso 1 1 calc R . . H35C H 0.6386 0.9311 1.1992 0.038 Uiso 1 1 calc R . . C36 C 0.5154(5) 0.6498(2) 1.1516(2) 0.0404(12) Uani 1 1 d . . . H36A H 0.465(4) 0.619(2) 1.114(2) 0.070(13) Uiso 1 1 d . . . H36B H 0.583(4) 0.655(3) 1.126(2) 0.078(18) Uiso 1 1 d . . . H36C H 0.530(4) 0.616(2) 1.189(2) 0.056(13) Uiso 1 1 d . . . N4 N 0.0124(3) 1.06670(17) 1.18285(14) 0.0307(7) Uani 1 1 d . . . N5 N 0.2446(3) 1.07398(16) 1.22716(15) 0.0240(7) Uani 1 1 d . . . H5N H 0.220(3) 1.067(2) 1.2709(19) 0.045(12) Uiso 1 1 d . . . N6 N 0.3231(2) 0.94960(16) 1.23957(13) 0.0232(7) Uani 1 1 d . . . H6N H 0.289(3) 0.9482(18) 1.2811(17) 0.028 Uiso 1 1 d . . . O2 O 0.33019(19) 1.01385(12) 1.12886(11) 0.0250(6) 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 0.033(2) 0.026(2) 0.022(2) 0.0016(14) 0.0018(16) 0.0097(19) C2 0.030(3) 0.031(2) 0.033(2) 0.0018(15) 0.0014(19) 0.013(2) C3 0.053(3) 0.037(3) 0.034(2) 0.0033(18) 0.008(2) 0.021(2) C4 0.054(3) 0.029(2) 0.047(3) -0.0045(19) 0.012(2) 0.003(2) C5 0.035(3) 0.034(2) 0.037(2) -0.0046(17) 0.0001(19) 0.002(2) C6 0.034(2) 0.025(2) 0.0204(19) 0.0007(14) -0.0009(16) 0.0140(19) C7 0.037(3) 0.064(3) 0.053(2) -0.013(2) 0.000(2) -0.006(3) C8 0.058(3) 0.033(2) 0.070(3) 0.013(2) 0.002(2) 0.000(3) C9 0.024(2) 0.025(2) 0.021(2) 0.0006(14) 0.0015(15) 0.0035(18) C10 0.027(2) 0.0206(19) 0.0154(16) -0.0027(13) 0.0030(14) 0.0063(18) C11 0.017(2) 0.033(2) 0.0153(17) 0.0004(13) -0.0005(13) -0.0005(18) C12 0.020(2) 0.025(2) 0.0223(17) -0.0011(14) 0.0012(15) -0.0063(18) C13 0.024(2) 0.0253(19) 0.0183(17) -0.0020(14) 0.0034(15) 0.0056(18) C14 0.021(2) 0.028(2) 0.0186(18) -0.0032(14) -0.0006(14) 0.0036(19) C15 0.024(2) 0.0215(18) 0.0171(17) -0.0039(13) 0.0007(14) 0.0017(18) C16 0.027(2) 0.044(2) 0.0275(19) 0.0054(15) -0.0008(16) -0.008(2) C17 0.032(2) 0.030(2) 0.0226(17) -0.0005(15) -0.0011(15) -0.002(2) C18 0.037(3) 0.027(2) 0.029(2) 0.0033(17) 0.004(2) 0.000(2) N1 0.037(2) 0.0371(19) 0.0427(18) -0.0004(14) 0.0057(15) 0.0001(18) N2 0.036(2) 0.0348(18) 0.0155(16) 0.0000(12) 0.0003(13) 0.0156(17) N3 0.034(2) 0.0276(17) 0.0132(15) -0.0024(12) -0.0024(13) 0.0102(16) O1 0.0395(16) 0.0300(14) 0.0161(13) -0.0021(9) -0.0052(10) 0.0121(14) C19 0.026(2) 0.026(2) 0.0208(19) -0.0019(14) 0.0011(15) 0.0043(19) C20 0.027(3) 0.037(2) 0.028(2) 0.0014(15) -0.0031(17) 0.011(2) C21 0.038(3) 0.029(2) 0.037(2) 0.0023(17) -0.0015(18) 0.012(2) C22 0.035(3) 0.023(2) 0.036(2) -0.0008(16) 0.0010(18) 0.003(2) C23 0.024(2) 0.028(2) 0.0297(19) 0.0001(15) 0.0026(15) 0.0018(19) C24 0.028(2) 0.0203(19) 0.0158(17) 0.0018(13) 0.0012(15) 0.0012(18) C25 0.046(3) 0.061(3) 0.044(2) -0.008(2) 0.011(2) -0.017(3) C26 0.040(3) 0.048(3) 0.041(3) -0.013(2) 0.006(2) -0.011(3) C27 0.022(2) 0.0198(18) 0.0206(19) 0.0014(14) -0.0028(15) -0.0004(18) C28 0.031(2) 0.0179(18) 0.0128(16) 0.0022(12) -0.0016(15) 0.0044(19) C29 0.021(2) 0.028(2) 0.0168(16) 0.0007(13) -0.0029(14) 0.0009(19) C30 0.038(3) 0.023(2) 0.0226(19) 0.0021(15) -0.0076(16) -0.005(2) C31 0.033(3) 0.025(2) 0.0180(17) 0.0028(14) -0.0003(15) 0.0046(19) C32 0.027(2) 0.029(2) 0.0204(18) 0.0032(14) 0.0049(16) 0.007(2) C33 0.030(2) 0.0219(19) 0.0191(17) 0.0035(14) -0.0006(16) 0.0015(19) C34 0.032(2) 0.040(2) 0.0284(19) -0.0007(16) 0.0012(17) -0.005(2) C35 0.034(2) 0.028(2) 0.034(2) 0.0043(16) 0.0084(16) -0.001(2) C36 0.063(4) 0.023(2) 0.035(3) 0.0000(18) 0.000(3) 0.011(2) N4 0.0261(19) 0.0339(18) 0.0321(16) -0.0035(13) 0.0010(14) -0.0070(16) N5 0.032(2) 0.0256(17) 0.0145(16) 0.0010(12) 0.0040(13) 0.0097(15) N6 0.033(2) 0.0234(16) 0.0133(14) 0.0030(12) 0.0043(12) 0.0070(15) O2 0.0313(15) 0.0277(13) 0.0160(12) 0.0020(9) 0.0031(10) 0.0066(12) _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 N1 1.470(4) . ? C1 C2 1.526(5) . ? C1 C6 1.533(5) . ? C1 H1 1.02(3) . ? C2 C3 1.524(5) . ? C2 H2A 1.03(3) . ? C2 H2B 0.96(4) . ? C3 C4 1.508(6) . ? C3 H3A 1.01(4) . ? C3 H3B 0.93(3) . ? C4 C5 1.526(5) . ? C4 H4A 0.99(3) . ? C4 H4B 1.02(4) . ? C5 C6 1.525(5) . ? C5 H5A 1.00(3) . ? C5 H5B 0.96(3) . ? C6 N2 1.459(4) . ? C6 H6 0.99(3) . ? C7 N1 1.455(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N1 1.455(5) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 O1 1.245(3) . ? C9 N2 1.351(4) . ? C9 N3 1.361(4) . ? C10 C15 1.388(4) . ? C10 C11 1.402(4) . ? C10 N3 1.427(4) . ? C11 C12 1.378(4) . ? C11 C16 1.501(4) . ? C12 C13 1.400(4) . ? C12 H12 0.96(3) . ? C13 C14 1.388(4) . ? C13 C18 1.509(5) . ? C14 C15 1.394(4) . ? C14 H14 1.01(3) . ? C15 C17 1.513(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 1.05(4) . ? C18 H18B 1.01(4) . ? C18 H18C 0.86(4) . ? N2 H3N 0.87(3) . ? N3 H2N 0.84(3) . ? C19 N4 1.467(4) . ? C19 C24 1.518(5) . ? C19 C20 1.541(5) . ? C19 H19 1.02(3) . ? C20 C21 1.525(5) . ? C20 H20A 1.01(3) . ? C20 H20B 1.03(3) . ? C21 C22 1.526(5) . ? C21 H21A 1.00(3) . ? C21 H21B 1.01(4) . ? C22 C23 1.523(5) . ? C22 H22A 1.01(3) . ? C22 H22B 1.01(3) . ? C23 C24 1.527(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 N5 1.453(4) . ? C24 H24 0.98(3) . ? C25 N4 1.448(5) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N4 1.450(4) . ? C26 H26A 0.93(4) . ? C26 H26B 1.03(4) . ? C26 H26C 0.99(3) . ? C27 O2 1.244(4) . ? C27 N5 1.350(4) . ? C27 N6 1.365(4) . ? C28 C33 1.395(5) . ? C28 C29 1.398(4) . ? C28 N6 1.424(4) . ? C29 C30 1.396(5) . ? C29 C34 1.498(5) . ? C30 C31 1.392(5) . ? C30 H30 0.93(4) . ? C31 C32 1.388(5) . ? C31 C36 1.498(5) . ? C32 C33 1.390(5) . ? C32 H32 0.98(3) . ? C33 C35 1.503(4) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 1.04(4) . ? C36 H36B 0.93(5) . ? C36 H36C 0.91(4) . ? N5 H5N 0.86(3) . ? N6 H6N 0.86(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 115.7(3) . . ? N1 C1 C6 112.8(3) . . ? C2 C1 C6 109.0(3) . . ? N1 C1 H1 104.8(17) . . ? C2 C1 H1 108.2(17) . . ? C6 C1 H1 105.7(18) . . ? C3 C2 C1 111.5(3) . . ? C3 C2 H2A 113.9(18) . . ? C1 C2 H2A 108.6(19) . . ? C3 C2 H2B 112(2) . . ? C1 C2 H2B 112(2) . . ? H2A C2 H2B 98(3) . . ? C4 C3 C2 111.5(4) . . ? C4 C3 H3A 115(2) . . ? C2 C3 H3A 107(2) . . ? C4 C3 H3B 113(2) . . ? C2 C3 H3B 108(2) . . ? H3A C3 H3B 102(3) . . ? C3 C4 C5 110.8(4) . . ? C3 C4 H4A 109(2) . . ? C5 C4 H4A 110.0(19) . . ? C3 C4 H4B 109(2) . . ? C5 C4 H4B 114(2) . . ? H4A C4 H4B 103(3) . . ? C6 C5 C4 112.7(3) . . ? C6 C5 H5A 108(2) . . ? C4 C5 H5A 109(2) . . ? C6 C5 H5B 110.5(19) . . ? C4 C5 H5B 110.7(19) . . ? H5A C5 H5B 105(3) . . ? N2 C6 C5 110.9(3) . . ? N2 C6 C1 111.8(3) . . ? C5 C6 C1 109.7(3) . . ? N2 C6 H6 106.0(18) . . ? C5 C6 H6 109.6(18) . . ? C1 C6 H6 108.7(19) . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O1 C9 N2 123.0(3) . . ? O1 C9 N3 122.6(3) . . ? N2 C9 N3 114.4(3) . . ? C15 C10 C11 120.7(3) . . ? C15 C10 N3 121.0(3) . . ? C11 C10 N3 118.3(3) . . ? C12 C11 C10 118.9(3) . . ? C12 C11 C16 120.8(3) . . ? C10 C11 C16 120.4(3) . . ? C11 C12 C13 122.1(3) . . ? C11 C12 H12 120.9(19) . . ? C13 C12 H12 117.0(19) . . ? C14 C13 C12 117.4(3) . . ? C14 C13 C18 122.0(3) . . ? C12 C13 C18 120.6(3) . . ? C13 C14 C15 122.2(3) . . ? C13 C14 H14 121.3(19) . . ? C15 C14 H14 116.3(19) . . ? C10 C15 C14 118.6(3) . . ? C10 C15 C17 121.4(3) . . ? C14 C15 C17 120.0(3) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 112(2) . . ? C13 C18 H18B 110.7(19) . . ? H18A C18 H18B 109(3) . . ? C13 C18 H18C 111(3) . . ? H18A C18 H18C 104(3) . . ? H18B C18 H18C 111(3) . . ? C8 N1 C7 109.5(3) . . ? C8 N1 C1 114.9(3) . . ? C7 N1 C1 112.5(3) . . ? C9 N2 C6 123.3(3) . . ? C9 N2 H3N 119(2) . . ? C6 N2 H3N 118(2) . . ? C9 N3 C10 122.9(3) . . ? C9 N3 H2N 117(2) . . ? C10 N3 H2N 113(2) . . ? N4 C19 C24 112.9(3) . . ? N4 C19 C20 115.8(3) . . ? C24 C19 C20 108.4(3) . . ? N4 C19 H19 103.7(17) . . ? C24 C19 H19 106.2(18) . . ? C20 C19 H19 109.4(17) . . ? C21 C20 C19 111.1(3) . . ? C21 C20 H20A 108.2(17) . . ? C19 C20 H20A 107.0(17) . . ? C21 C20 H20B 112.5(19) . . ? C19 C20 H20B 109.4(19) . . ? H20A C20 H20B 108(2) . . ? C22 C21 C20 110.8(3) . . ? C22 C21 H21A 107.3(18) . . ? C20 C21 H21A 111.3(18) . . ? C22 C21 H21B 111(3) . . ? C20 C21 H21B 109(2) . . ? H21A C21 H21B 108(3) . . ? C23 C22 C21 110.7(3) . . ? C23 C22 H22A 111.4(17) . . ? C21 C22 H22A 110.0(19) . . ? C23 C22 H22B 108.5(18) . . ? C21 C22 H22B 109.5(18) . . ? H22A C22 H22B 107(3) . . ? C22 C23 C24 112.8(3) . . ? C22 C23 H23A 109.0 . . ? C24 C23 H23A 109.0 . . ? C22 C23 H23B 109.0 . . ? C24 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? N5 C24 C19 112.5(3) . . ? N5 C24 C23 110.3(3) . . ? C19 C24 C23 110.2(3) . . ? N5 C24 H24 105.4(17) . . ? C19 C24 H24 107.2(19) . . ? C23 C24 H24 111.1(18) . . ? N4 C25 H25A 109.5 . . ? N4 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N4 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N4 C26 H26A 116(3) . . ? N4 C26 H26B 114(2) . . ? H26A C26 H26B 104(3) . . ? N4 C26 H26C 105.8(18) . . ? H26A C26 H26C 110(3) . . ? H26B C26 H26C 107(3) . . ? O2 C27 N5 123.6(3) . . ? O2 C27 N6 122.0(3) . . ? N5 C27 N6 114.4(3) . . ? C33 C28 C29 121.4(3) . . ? C33 C28 N6 120.7(3) . . ? C29 C28 N6 117.9(3) . . ? C30 C29 C28 118.4(3) . . ? C30 C29 C34 121.0(3) . . ? C28 C29 C34 120.6(3) . . ? C31 C30 C29 122.0(4) . . ? C31 C30 H30 120(2) . . ? C29 C30 H30 118(2) . . ? C32 C31 C30 117.5(3) . . ? C32 C31 C36 122.0(4) . . ? C30 C31 C36 120.5(4) . . ? C31 C32 C33 123.0(3) . . ? C31 C32 H32 121(2) . . ? C33 C32 H32 116(2) . . ? C32 C33 C28 117.8(3) . . ? C32 C33 C35 121.1(3) . . ? C28 C33 C35 121.1(3) . . ? C29 C34 H34A 109.5 . . ? C29 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C29 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C31 C36 H36A 112(2) . . ? C31 C36 H36B 113(3) . . ? H36A C36 H36B 102(3) . . ? C31 C36 H36C 115(2) . . ? H36A C36 H36C 108(3) . . ? H36B C36 H36C 106(4) . . ? C25 N4 C26 110.8(3) . . ? C25 N4 C19 112.7(3) . . ? C26 N4 C19 114.8(3) . . ? C27 N5 C24 122.2(3) . . ? C27 N5 H5N 119(2) . . ? C24 N5 H5N 116(2) . . ? C27 N6 C28 123.3(3) . . ? C27 N6 H6N 117(2) . . ? C28 N6 H6N 117(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.198 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.050 #===END data_20 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H21 N3 S' _chemical_formula_sum 'C10 H21 N3 S' _chemical_formula_weight 215.36 _chemical_absolute_configuration ad 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' 'S' 'S' 0.1246 0.1234 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.5762(4) _cell_length_b 12.7340(4) _cell_length_c 16.3923(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2416.41(14) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13703 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 27.00 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.238 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'Nonius KappaCCD' _diffrn_measurement_method 'Phi/Omega-Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13703 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5270 _reflns_number_gt 4141 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0335P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(5) _refine_ls_number_reflns 5270 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0655 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _refine_ls_shift/su_max 0.002 _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 S1 S 0.20240(4) 0.92908(4) 0.17077(3) 0.03203(13) Uani 1 1 d . . . N1 N 0.28083(13) 1.15190(11) -0.03762(9) 0.0282(4) Uani 1 1 d . . . N2 N 0.25129(12) 0.93589(12) 0.01167(9) 0.0218(3) Uani 1 1 d . . . H2 H 0.2876(14) 0.9161(13) -0.0255(10) 0.014(5) Uiso 1 1 d . . . N3 N 0.36582(14) 0.83014(12) 0.08888(10) 0.0271(4) Uani 1 1 d . . . H3 H 0.4015(18) 0.8194(16) 0.0454(12) 0.038(6) Uiso 1 1 d . . . C1 C 0.18353(14) 1.08772(13) -0.06745(11) 0.0210(4) Uani 1 1 d . . . H1A H 0.2089(14) 1.0541(13) -0.1188(11) 0.026(5) Uiso 1 1 d . . . C2 C 0.15115(14) 1.00098(14) -0.00742(11) 0.0211(4) Uani 1 1 d . . . H2A H 0.1286(13) 1.0313(12) 0.0448(10) 0.015(4) Uiso 1 1 d . . . C3 C 0.05289(16) 0.93402(16) -0.04106(15) 0.0320(5) Uani 1 1 d . . . H3A H 0.0396(17) 0.8858(15) -0.0012(13) 0.041(6) Uiso 1 1 d . . . H3B H 0.0818(17) 0.8964(15) -0.0876(12) 0.035(6) Uiso 1 1 d . . . C4 C -0.05285(17) 0.99733(17) -0.06392(14) 0.0351(5) Uani 1 1 d . . . H4A H -0.0863(17) 1.0279(15) -0.0145(13) 0.044(6) Uiso 1 1 d . . . H4B H -0.1162(17) 0.9582(16) -0.0863(12) 0.042(6) Uiso 1 1 d . . . C5 C -0.01953(17) 1.08126(16) -0.12535(13) 0.0310(5) Uani 1 1 d . . . H5A H 0.0091(16) 1.0471(14) -0.1744(12) 0.038(5) Uiso 1 1 d . . . H5B H -0.0882(18) 1.1257(15) -0.1434(11) 0.037(5) Uiso 1 1 d . . . C6 C 0.07537(17) 1.15088(15) -0.09155(14) 0.0291(5) Uani 1 1 d . . . H6A H 0.0987(19) 1.2050(19) -0.1305(14) 0.061(7) Uiso 1 1 d . . . H6B H 0.0526(16) 1.1866(15) -0.0437(12) 0.031(5) Uiso 1 1 d . . . C7 C 0.25177(19) 1.21497(16) 0.03423(14) 0.0471(6) Uani 1 1 d . . . H7A H 0.1922 1.2664 0.0198 0.071 Uiso 1 1 calc R . . H7B H 0.3209 1.2518 0.0535 0.071 Uiso 1 1 calc R . . H7C H 0.2228 1.1689 0.0775 0.071 Uiso 1 1 calc R . . C8 C 0.32676(18) 1.22007(15) -0.10238(15) 0.0461(6) Uani 1 1 d . . . H8A H 0.2724 1.2775 -0.1127 0.069 Uiso 1 1 calc R . . H8B H 0.3372 1.1790 -0.1524 0.069 Uiso 1 1 calc R . . H8C H 0.4013 1.2491 -0.0852 0.069 Uiso 1 1 calc R . . C9 C 0.27620(15) 0.89686(13) 0.08593(11) 0.0203(4) Uani 1 1 d . . . C10 C 0.41073(17) 0.78289(15) 0.16264(12) 0.0323(5) Uani 1 1 d . . . H10A H 0.4182 0.8367 0.2050 0.048 Uiso 1 1 calc R . . H10B H 0.4867 0.7520 0.1515 0.048 Uiso 1 1 calc R . . H10C H 0.3577 0.7279 0.1813 0.048 Uiso 1 1 calc R . . S2 S 0.66573(4) 0.94011(4) 0.05374(3) 0.03485(14) Uani 1 1 d . . . N11 N 0.38181(12) 0.85068(10) -0.13909(8) 0.0198(3) Uani 1 1 d . . . N12 N 0.49957(13) 1.00715(11) -0.04665(8) 0.0212(3) Uani 1 1 d . . . H12 H 0.4356(16) 1.0448(13) -0.0517(10) 0.023(5) Uiso 1 1 d . . . N13 N 0.48785(14) 1.06861(13) 0.08165(9) 0.0274(4) Uani 1 1 d . . . H13 H 0.4239(16) 1.0912(14) 0.0677(11) 0.026(6) Uiso 1 1 d . . . C11 C 0.46390(13) 0.92383(13) -0.17939(10) 0.0178(4) Uani 1 1 d . . . H11A H 0.4152(12) 0.9880(11) -0.1977(9) 0.005(4) Uiso 1 1 d . . . C12 C 0.55473(15) 0.96529(14) -0.11978(11) 0.0204(4) Uani 1 1 d . . . H12A H 0.6026(12) 0.9074(11) -0.1021(9) 0.004(4) Uiso 1 1 d . . . C13 C 0.63102(16) 1.04845(15) -0.15968(12) 0.0243(4) Uani 1 1 d . . . H13A H 0.5814(15) 1.1066(13) -0.1734(10) 0.021(5) Uiso 1 1 d . . . H13B H 0.6857(15) 1.0737(13) -0.1210(10) 0.022(5) Uiso 1 1 d . . . C14 C 0.68968(16) 1.00677(15) -0.23680(11) 0.0254(4) Uani 1 1 d . . . H14A H 0.7456(14) 0.9497(12) -0.2235(9) 0.014(4) Uiso 1 1 d . . . H14B H 0.7399(16) 1.0609(15) -0.2624(11) 0.037(5) Uiso 1 1 d . . . C15 C 0.59966(16) 0.96494(14) -0.29597(11) 0.0229(4) Uani 1 1 d . . . H15A H 0.5514(14) 1.0232(12) -0.3148(10) 0.016(4) Uiso 1 1 d . . . H15B H 0.6363(16) 0.9413(15) -0.3450(12) 0.034(5) Uiso 1 1 d . . . C16 C 0.52433(16) 0.88115(14) -0.25600(11) 0.0217(4) Uani 1 1 d . . . H16A H 0.5709(15) 0.8208(14) -0.2413(10) 0.024(5) Uiso 1 1 d . . . H16B H 0.4658(14) 0.8594(12) -0.2944(10) 0.015(4) Uiso 1 1 d . . . C17 C 0.28457(15) 0.82359(15) -0.19169(11) 0.0281(4) Uani 1 1 d . . . H17A H 0.3119 0.7802 -0.2371 0.042 Uiso 1 1 calc R . . H17B H 0.2495 0.8880 -0.2131 0.042 Uiso 1 1 calc R . . H17C H 0.2270 0.7844 -0.1601 0.042 Uiso 1 1 calc R . . C18 C 0.43699(17) 0.75386(13) -0.10997(12) 0.0289(5) Uani 1 1 d . . . H18A H 0.4664 0.7139 -0.1566 0.043 Uiso 1 1 calc R . . H18B H 0.3802 0.7113 -0.0803 0.043 Uiso 1 1 calc R . . H18C H 0.5011 0.7717 -0.0735 0.043 Uiso 1 1 calc R . . C19 C 0.54631(15) 1.00808(14) 0.02807(11) 0.0226(4) Uani 1 1 d . . . C20 C 0.51060(19) 1.07090(16) 0.16880(11) 0.0386(5) Uani 1 1 d . . . H20A H 0.4997 1.0005 0.1916 0.058 Uiso 1 1 calc R . . H20B H 0.4572 1.1200 0.1952 0.058 Uiso 1 1 calc R . . H20C H 0.5903 1.0938 0.1783 0.058 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 S1 0.0298(2) 0.0466(3) 0.0197(2) -0.0029(2) 0.0060(2) 0.0067(2) N1 0.0274(8) 0.0171(8) 0.0402(10) -0.0015(7) -0.0042(7) -0.0035(7) N2 0.0235(8) 0.0222(8) 0.0197(8) -0.0003(8) 0.0086(7) 0.0038(7) N3 0.0335(10) 0.0274(9) 0.0205(9) 0.0016(8) 0.0069(8) 0.0096(7) C1 0.0217(9) 0.0190(9) 0.0225(10) -0.0012(8) 0.0016(8) 0.0010(7) C2 0.0196(9) 0.0225(9) 0.0211(10) -0.0019(9) 0.0044(8) 0.0035(8) C3 0.0249(10) 0.0260(11) 0.0449(14) 0.0032(12) 0.0052(9) -0.0045(10) C4 0.0218(10) 0.0425(12) 0.0410(14) -0.0065(11) 0.0009(10) -0.0040(10) C5 0.0259(10) 0.0380(12) 0.0291(11) -0.0077(10) -0.0040(9) 0.0084(10) C6 0.0279(11) 0.0300(11) 0.0295(12) -0.0039(10) -0.0026(9) 0.0051(9) C7 0.0428(12) 0.0368(12) 0.0617(16) -0.0217(12) -0.0124(11) 0.0002(10) C8 0.0336(12) 0.0301(11) 0.0746(17) 0.0199(12) -0.0051(11) -0.0071(10) C9 0.0206(10) 0.0183(9) 0.0220(10) -0.0012(8) 0.0014(8) -0.0036(7) C10 0.0411(11) 0.0280(11) 0.0279(11) 0.0018(9) -0.0002(9) 0.0086(9) S2 0.0245(2) 0.0550(3) 0.0250(3) 0.0047(3) -0.0065(2) 0.0042(2) N11 0.0212(8) 0.0197(8) 0.0185(8) 0.0012(6) 0.0015(6) -0.0005(6) N12 0.0177(7) 0.0309(9) 0.0151(8) -0.0033(7) -0.0010(7) 0.0047(7) N13 0.0268(9) 0.0370(9) 0.0184(8) -0.0063(8) -0.0003(7) -0.0036(8) C11 0.0193(8) 0.0179(9) 0.0162(9) 0.0046(8) 0.0016(7) 0.0032(7) C12 0.0182(9) 0.0268(10) 0.0162(9) 0.0020(8) 0.0025(7) 0.0071(8) C13 0.0197(9) 0.0290(11) 0.0241(11) -0.0007(9) 0.0011(8) -0.0009(8) C14 0.0215(10) 0.0300(11) 0.0246(10) -0.0001(9) 0.0056(8) 0.0006(9) C15 0.0276(10) 0.0234(10) 0.0178(10) 0.0014(8) 0.0077(8) 0.0041(8) C16 0.0264(11) 0.0196(10) 0.0191(10) -0.0003(8) 0.0033(8) 0.0040(8) C17 0.0278(10) 0.0291(10) 0.0273(11) -0.0016(9) 0.0012(9) -0.0033(9) C18 0.0355(11) 0.0229(10) 0.0284(12) 0.0055(8) 0.0074(9) 0.0025(9) C19 0.0207(9) 0.0290(10) 0.0180(10) 0.0022(9) -0.0007(8) -0.0076(8) C20 0.0545(13) 0.0448(12) 0.0166(10) -0.0060(10) 0.0020(9) -0.0132(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 S1 C9 1.6829(18) . ? N1 C7 1.465(2) . ? N1 C8 1.471(2) . ? N1 C1 1.475(2) . ? N2 C9 1.346(2) . ? N2 C2 1.459(2) . ? N2 H2 0.782(17) . ? N3 C9 1.342(2) . ? N3 C10 1.447(2) . ? N3 H3 0.84(2) . ? C1 C2 1.526(2) . ? C1 C6 1.540(2) . ? C1 H1A 0.989(17) . ? C2 C3 1.525(3) . ? C2 H2A 0.974(16) . ? C3 C4 1.513(3) . ? C3 H3A 0.91(2) . ? C3 H3B 0.96(2) . ? C4 C5 1.518(3) . ? C4 H4A 0.98(2) . ? C4 H4B 0.96(2) . ? C5 C6 1.517(3) . ? C5 H5A 0.97(2) . ? C5 H5B 1.02(2) . ? C6 H6A 0.98(2) . ? C6 H6B 0.94(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? S2 C19 1.6844(18) . ? N11 C17 1.459(2) . ? N11 C18 1.468(2) . ? N11 C11 1.486(2) . ? N12 C19 1.339(2) . ? N12 C12 1.459(2) . ? N12 H12 0.886(18) . ? N13 C19 1.350(2) . ? N13 C20 1.453(2) . ? N13 H13 0.826(19) . ? C11 C12 1.529(2) . ? C11 C16 1.537(2) . ? C11 H11A 1.037(14) . ? C12 C13 1.526(2) . ? C12 H12A 0.966(15) . ? C13 C14 1.530(2) . ? C13 H13A 0.964(17) . ? C13 H13B 0.951(18) . ? C14 C15 1.520(3) . ? C14 H14A 0.998(16) . ? C14 H14B 0.994(19) . ? C15 C16 1.526(2) . ? C15 H15A 0.979(16) . ? C15 H15B 0.958(19) . ? C16 H16A 0.969(18) . ? C16 H16B 0.966(17) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 C7 N1 C8 109.86(15) . . ? C7 N1 C1 113.26(15) . . ? C8 N1 C1 111.34(15) . . ? C9 N2 C2 125.02(15) . . ? C9 N2 H2 118.0(12) . . ? C2 N2 H2 116.3(12) . . ? C9 N3 C10 124.83(16) . . ? C9 N3 H3 117.1(14) . . ? C10 N3 H3 117.9(14) . . ? N1 C1 C2 112.01(14) . . ? N1 C1 C6 114.62(13) . . ? C2 C1 C6 110.11(15) . . ? N1 C1 H1A 107.2(10) . . ? C2 C1 H1A 107.9(10) . . ? C6 C1 H1A 104.4(10) . . ? N2 C2 C3 110.64(15) . . ? N2 C2 C1 110.75(14) . . ? C3 C2 C1 110.78(15) . . ? N2 C2 H2A 104.4(9) . . ? C3 C2 H2A 109.9(9) . . ? C1 C2 H2A 110.2(9) . . ? C4 C3 C2 113.27(16) . . ? C4 C3 H3A 113.6(13) . . ? C2 C3 H3A 104.1(13) . . ? C4 C3 H3B 110.5(12) . . ? C2 C3 H3B 107.8(11) . . ? H3A C3 H3B 107.1(17) . . ? C3 C4 C5 109.50(17) . . ? C3 C4 H4A 109.1(12) . . ? C5 C4 H4A 111.7(11) . . ? C3 C4 H4B 115.9(12) . . ? C5 C4 H4B 107.8(12) . . ? H4A C4 H4B 102.8(17) . . ? C6 C5 C4 110.69(18) . . ? C6 C5 H5A 108.4(11) . . ? C4 C5 H5A 108.7(11) . . ? C6 C5 H5B 110.2(11) . . ? C4 C5 H5B 112.6(10) . . ? H5A C5 H5B 106.0(15) . . ? C5 C6 C1 112.18(15) . . ? C5 C6 H6A 111.9(13) . . ? C1 C6 H6A 108.1(13) . . ? C5 C6 H6B 112.5(12) . . ? C1 C6 H6B 105.4(12) . . ? H6A C6 H6B 106.3(17) . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 N2 115.59(16) . . ? N3 C9 S1 121.14(14) . . ? N2 C9 S1 123.27(13) . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C17 N11 C18 109.22(13) . . ? C17 N11 C11 112.27(13) . . ? C18 N11 C11 113.13(13) . . ? C19 N12 C12 125.30(15) . . ? C19 N12 H12 114.7(11) . . ? C12 N12 H12 119.2(11) . . ? C19 N13 C20 124.07(17) . . ? C19 N13 H13 117.9(13) . . ? C20 N13 H13 115.3(13) . . ? N11 C11 C12 111.84(13) . . ? N11 C11 C16 115.64(13) . . ? C12 C11 C16 109.34(14) . . ? N11 C11 H11A 106.0(8) . . ? C12 C11 H11A 106.7(8) . . ? C16 C11 H11A 106.8(8) . . ? N12 C12 C13 110.59(14) . . ? N12 C12 C11 110.50(13) . . ? C13 C12 C11 111.32(14) . . ? N12 C12 H12A 106.5(8) . . ? C13 C12 H12A 109.0(8) . . ? C11 C12 H12A 108.8(8) . . ? C12 C13 C14 111.73(15) . . ? C12 C13 H13A 106.7(10) . . ? C14 C13 H13A 109.8(10) . . ? C12 C13 H13B 109.5(10) . . ? C14 C13 H13B 111.9(10) . . ? H13A C13 H13B 107.0(14) . . ? C15 C14 C13 110.15(15) . . ? C15 C14 H14A 109.2(9) . . ? C13 C14 H14A 111.1(9) . . ? C15 C14 H14B 112.0(11) . . ? C13 C14 H14B 111.6(11) . . ? H14A C14 H14B 102.6(14) . . ? C14 C15 C16 111.27(16) . . ? C14 C15 H15A 109.1(9) . . ? C16 C15 H15A 109.8(9) . . ? C14 C15 H15B 110.0(11) . . ? C16 C15 H15B 113.2(11) . . ? H15A C15 H15B 103.1(15) . . ? C15 C16 C11 111.33(14) . . ? C15 C16 H16A 110.1(10) . . ? C11 C16 H16A 109.3(10) . . ? C15 C16 H16B 108.7(10) . . ? C11 C16 H16B 108.4(9) . . ? H16A C16 H16B 109.0(13) . . ? N11 C17 H17A 109.5 . . ? N11 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N11 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N11 C18 H18A 109.5 . . ? N11 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N11 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N12 C19 N13 113.42(15) . . ? N12 C19 S2 123.75(14) . . ? N13 C19 S2 122.83(14) . . ? N13 C20 H20A 109.5 . . ? N13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.214 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.038 #===END data_26a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H27 N3 O' _chemical_formula_sum 'C17 H27 N3 O' _chemical_formula_weight 289.42 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.7335(2) _cell_length_b 22.1650(6) _cell_length_c 9.9252(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.7740(10) _cell_angle_gamma 90.00 _cell_volume 1880.88(9) _cell_formula_units_Z 4 _cell_measurement_temperature 446(2) _cell_measurement_reflns_used 9471 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 27.00 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max .48 _exptl_crystal_size_mid .38 _exptl_crystal_size_min .38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.022 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 446(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 'Nonius KappaCCD' _diffrn_measurement_method 'Phi/Omega-Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9471 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0633 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3892 _reflns_number_gt 3012 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0470P)^2^+0.1360P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0100(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(13) _refine_ls_number_reflns 3892 _refine_ls_number_parameters 513 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.011 _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 0.8447(3) 0.18991(11) 0.4142(3) 0.0218(6) Uani 1 1 d . . . H1 H 0.891(3) 0.1902(11) 0.524(3) 0.014(6) Uiso 1 1 d . . . C2 C 0.9368(3) 0.14467(11) 0.3369(3) 0.0221(6) Uani 1 1 d . . . H2 H 0.897(3) 0.1465(11) 0.224(3) 0.013(6) Uiso 1 1 d . . . C3 C 1.1105(3) 0.16175(12) 0.3714(4) 0.0295(7) Uani 1 1 d . . . H3A H 1.155(3) 0.1581(10) 0.481(3) 0.015(6) Uiso 1 1 d . . . H3B H 1.166(3) 0.1312(14) 0.320(3) 0.033(8) Uiso 1 1 d . . . C4 C 1.1367(3) 0.22583(12) 0.3179(4) 0.0321(7) Uani 1 1 d . . . H4A H 1.109(3) 0.2271(12) 0.206(3) 0.019(6) Uiso 1 1 d . . . H4B H 1.254(4) 0.2380(15) 0.339(3) 0.052(9) Uiso 1 1 d . . . C5 C 1.0412(3) 0.27123(12) 0.3882(3) 0.0296(7) Uani 1 1 d . . . H5A H 1.076(3) 0.2739(13) 0.497(3) 0.031(7) Uiso 1 1 d . . . H5B H 1.056(3) 0.3126(14) 0.350(3) 0.032(8) Uiso 1 1 d . . . C6 C 0.8685(3) 0.25358(11) 0.3541(3) 0.0271(7) Uani 1 1 d . . . H6A H 0.829(3) 0.2542(13) 0.230(3) 0.036(8) Uiso 1 1 d . . . H6B H 0.807(3) 0.2840(14) 0.400(3) 0.038(8) Uiso 1 1 d . . . C7 C 0.5855(3) 0.17401(13) 0.2479(3) 0.0370(8) Uani 1 1 d . . . H7A H 0.5773 0.2151 0.2166 0.044 Uiso 1 1 calc R . . H7B H 0.4827 0.1578 0.2434 0.044 Uiso 1 1 calc R . . H7C H 0.6389 0.1506 0.1903 0.044 Uiso 1 1 calc R . . C8 C 0.6062(3) 0.20290(13) 0.5105(3) 0.0375(8) Uani 1 1 d . . . H8A H 0.6742 0.1994 0.5993 0.045 Uiso 1 1 calc R . . H8B H 0.5076 0.1842 0.5127 0.045 Uiso 1 1 calc R . . H8C H 0.5898 0.2448 0.4871 0.045 Uiso 1 1 calc R . . C9 C 0.8509(3) 0.03929(11) 0.2868(3) 0.0187(6) Uani 1 1 d . . . C10 C 0.7828(3) -0.06816(11) 0.2596(3) 0.0218(6) Uani 1 1 d . . . H10 H 0.719(3) -0.0560(11) 0.161(3) 0.014(6) Uiso 1 1 d . . . C11 C 0.6872(3) -0.11012(12) 0.3410(3) 0.0302(7) Uani 1 1 d . . . H11A H 0.7518 -0.1210 0.4279 0.036 Uiso 1 1 calc R . . H11B H 0.6553 -0.1459 0.2883 0.036 Uiso 1 1 calc R . . H11C H 0.5964 -0.0889 0.3563 0.036 Uiso 1 1 calc R . . C12 C 0.9245(3) -0.10046(10) 0.2224(3) 0.0212(6) Uani 1 1 d . . . C13 C 1.0521(3) -0.11542(12) 0.3365(3) 0.0257(6) Uani 1 1 d . . . H13 H 1.0498 -0.1052 0.4270 0.031 Uiso 1 1 calc R . . C14 C 1.1796(3) -0.14645(13) 0.3013(3) 0.0309(7) Uani 1 1 d . . . H14 H 1.270(3) -0.1589(12) 0.392(3) 0.027(7) Uiso 1 1 d . . . C15 C 1.1799(3) -0.16138(12) 0.1520(4) 0.0348(7) Uani 1 1 d . . . H15 H 1.261(4) -0.1835(19) 0.122(4) 0.072(12) Uiso 1 1 d . . . C16 C 1.0544(3) -0.14648(14) 0.0367(4) 0.0350(7) Uani 1 1 d . . . H16 H 1.043(3) -0.1577(15) -0.070(3) 0.050(9) Uiso 1 1 d . . . C17 C 0.9262(3) -0.11608(12) 0.0730(3) 0.0273(6) Uani 1 1 d . . . H17 H 0.838(3) -0.1045(14) -0.007(3) 0.042(8) Uiso 1 1 d . . . N1 N 0.6811(2) 0.17160(10) 0.4026(2) 0.0279(6) Uani 1 1 d . . . N2 N 0.9164(2) 0.08253(9) 0.3844(2) 0.0214(5) Uani 1 1 d . . . H2N H 0.935(3) 0.0749(13) 0.475(3) 0.026 Uiso 1 1 d . . . N3 N 0.8248(3) -0.01427(9) 0.3523(3) 0.0230(5) Uani 1 1 d . . . H3N H 0.850(3) -0.0171(12) 0.447(3) 0.022(7) Uiso 1 1 d . . . O1 O 0.81646(19) 0.04696(8) 0.14578(18) 0.0241(4) Uani 1 1 d . . . C18 C 0.5037(3) -0.04035(11) 0.7523(3) 0.0202(6) Uani 1 1 d . . . H18 H 0.474(3) -0.0120(12) 0.830(3) 0.024 Uiso 1 1 d . . . C19 C 0.6382(3) -0.00885(11) 0.6963(3) 0.0198(6) Uani 1 1 d . . . H19 H 0.674(3) -0.0354(12) 0.625(3) 0.024 Uiso 1 1 d . . . C20 C 0.5836(3) 0.05023(12) 0.6162(3) 0.0238(6) Uani 1 1 d . . . H20A H 0.665(3) 0.0683(12) 0.585(3) 0.024(7) Uiso 1 1 d . . . H20B H 0.555(3) 0.0751(13) 0.695(3) 0.027(7) Uiso 1 1 d . . . C21 C 0.4466(3) 0.04144(12) 0.4831(3) 0.0263(6) Uani 1 1 d . . . H21A H 0.4140 0.0800 0.4408 0.032 Uiso 1 1 calc R . . H21B H 0.4812 0.0159 0.4158 0.032 Uiso 1 1 calc R . . C22 C 0.3107(3) 0.01122(13) 0.5372(3) 0.0268(6) Uani 1 1 d . . . H22A H 0.221(3) 0.0039(14) 0.448(3) 0.041(8) Uiso 1 1 d . . . H22B H 0.275(3) 0.0358(14) 0.607(3) 0.036(8) Uiso 1 1 d . . . C23 C 0.3633(3) -0.04795(12) 0.6192(3) 0.0261(6) Uani 1 1 d . . . H23A H 0.388(3) -0.0776(13) 0.542(3) 0.027(7) Uiso 1 1 d . . . H23B H 0.287(4) -0.0674(15) 0.663(3) 0.044(9) Uiso 1 1 d . . . C24 C 0.6148(3) -0.14275(12) 0.7498(3) 0.0334(7) Uani 1 1 d . . . H24A H 0.6511 -0.1776 0.8046 0.040 Uiso 1 1 calc R . . H24B H 0.6991 -0.1263 0.7126 0.040 Uiso 1 1 calc R . . H24C H 0.5307 -0.1542 0.6759 0.040 Uiso 1 1 calc R . . C25 C 0.4431(3) -0.12020(13) 0.9189(3) 0.0344(7) Uani 1 1 d . . . H25A H 0.4069 -0.0880 0.9690 0.041 Uiso 1 1 calc R . . H25B H 0.4933 -0.1504 0.9822 0.041 Uiso 1 1 calc R . . H25 H 0.3558 -0.1378 0.8568 0.041 Uiso 1 1 calc R . . C26 C 0.9172(3) 0.00903(11) 0.8027(3) 0.0208(6) Uani 1 1 d . . . C27 C 1.1803(3) 0.04013(11) 0.9380(3) 0.0213(6) Uani 1 1 d . . . H27 H 1.216(3) 0.0177(13) 0.862(3) 0.026 Uiso 1 1 d . . . C28 C 1.2776(3) 0.02389(13) 1.0941(3) 0.0302(7) Uani 1 1 d . . . H28A H 1.2378 0.0476 1.1602 0.036 Uiso 1 1 calc R . . H28B H 1.3865 0.0327 1.1007 0.036 Uiso 1 1 calc R . . H28C H 1.2652 -0.0182 1.1124 0.036 Uiso 1 1 calc R . . C29 C 1.1977(3) 0.10633(11) 0.9017(3) 0.0283(6) Uani 1 1 d . . . C30 C 1.3443(5) 0.12899(15) 0.8927(4) 0.0515(10) Uani 1 1 d . . . H30 H 1.434(4) 0.1034(18) 0.897(4) 0.064(12) Uiso 1 1 d . . . C31 C 1.3638(7) 0.1893(2) 0.8625(5) 0.0792(15) Uani 1 1 d . . . H31 H 1.474(6) 0.204(2) 0.856(4) 0.101(16) Uiso 1 1 d . . . C32 C 1.2391(10) 0.2281(2) 0.8423(5) 0.095(2) Uani 1 1 d . . . H32 H 1.261(5) 0.269(3) 0.812(5) 0.114 Uiso 1 1 d . . . C33 C 1.0945(8) 0.20672(18) 0.8508(5) 0.0887(19) Uani 1 1 d . . . H33 H 1.010(6) 0.228(3) 0.846(5) 0.106 Uiso 1 1 d . . . C34 C 1.0727(5) 0.14582(15) 0.8802(4) 0.0505(10) Uani 1 1 d . . . H34 H 0.971(4) 0.1315(18) 0.880(4) 0.071(13) Uiso 1 1 d . . . O2 O 0.95586(18) 0.00400(8) 0.67735(18) 0.0237(4) Uani 1 1 d . . . N4 N 0.5575(2) -0.09586(9) 0.8385(2) 0.0229(5) Uani 1 1 d . . . N5 N 0.7692(2) 0.00011(10) 0.8229(2) 0.0217(5) Uani 1 1 d . . . H5N H 0.752(3) 0.0050(12) 0.912(3) 0.019(7) Uiso 1 1 d . . . N6 N 1.0201(2) 0.02266(11) 0.9345(3) 0.0281(6) Uani 1 1 d . . . H6N H 0.979(3) 0.0294(12) 1.020(3) 0.029(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 C1 0.0213(13) 0.0180(12) 0.0255(17) 0.0007(12) 0.0038(11) -0.0026(10) C2 0.0236(14) 0.0151(12) 0.0275(17) 0.0017(11) 0.0051(12) -0.0007(10) C3 0.0219(14) 0.0201(14) 0.047(2) 0.0017(14) 0.0091(13) -0.0011(11) C4 0.0283(16) 0.0224(14) 0.047(2) 0.0003(14) 0.0105(14) -0.0048(12) C5 0.0299(15) 0.0175(13) 0.041(2) 0.0014(13) 0.0053(13) -0.0042(11) C6 0.0274(15) 0.0152(13) 0.039(2) -0.0017(13) 0.0081(13) -0.0021(11) C7 0.0222(14) 0.0295(15) 0.057(2) -0.0023(15) 0.0016(13) -0.0028(12) C8 0.0266(15) 0.0252(14) 0.063(2) 0.0012(15) 0.0146(14) 0.0001(12) C9 0.0150(12) 0.0169(12) 0.0259(16) -0.0010(11) 0.0079(10) 0.0027(9) C10 0.0232(13) 0.0170(12) 0.0252(16) -0.0028(12) 0.0052(11) -0.0023(10) C11 0.0297(14) 0.0181(13) 0.044(2) -0.0031(12) 0.0105(13) -0.0032(11) C12 0.0234(13) 0.0105(11) 0.0302(16) 0.0005(11) 0.0067(11) -0.0023(10) C13 0.0284(14) 0.0216(13) 0.0273(17) -0.0041(12) 0.0062(12) -0.0035(11) C14 0.0239(14) 0.0256(14) 0.042(2) 0.0042(14) 0.0038(13) -0.0016(11) C15 0.0293(16) 0.0229(15) 0.056(2) 0.0020(15) 0.0181(15) 0.0001(12) C16 0.0398(17) 0.0349(16) 0.033(2) -0.0046(14) 0.0146(14) 0.0032(13) C17 0.0302(15) 0.0232(13) 0.0275(17) 0.0008(12) 0.0035(13) 0.0017(12) N1 0.0206(11) 0.0204(11) 0.0431(16) -0.0005(11) 0.0072(10) -0.0009(9) N2 0.0264(11) 0.0149(10) 0.0216(14) 0.0002(10) 0.0016(10) -0.0007(8) N3 0.0335(12) 0.0157(10) 0.0194(14) -0.0018(10) 0.0043(10) -0.0018(9) O1 0.0284(9) 0.0214(9) 0.0229(11) -0.0010(8) 0.0063(7) -0.0006(7) C18 0.0174(13) 0.0199(13) 0.0239(16) -0.0010(11) 0.0057(10) -0.0018(10) C19 0.0158(12) 0.0232(13) 0.0202(15) -0.0015(12) 0.0035(10) -0.0001(10) C20 0.0226(14) 0.0231(14) 0.0268(17) 0.0015(13) 0.0075(11) -0.0033(11) C21 0.0253(14) 0.0257(13) 0.0280(16) 0.0049(13) 0.0056(11) 0.0058(11) C22 0.0205(14) 0.0307(15) 0.0271(18) 0.0022(13) 0.0002(12) 0.0028(12) C23 0.0191(14) 0.0253(14) 0.0335(18) 0.0006(13) 0.0043(12) -0.0040(11) C24 0.0357(16) 0.0213(14) 0.0430(19) -0.0021(13) 0.0074(13) 0.0042(12) C25 0.0291(15) 0.0244(14) 0.052(2) 0.0082(14) 0.0139(13) -0.0015(12) C26 0.0183(13) 0.0196(12) 0.0238(17) 0.0031(12) 0.0025(10) -0.0014(10) C27 0.0185(13) 0.0213(13) 0.0251(16) -0.0034(12) 0.0071(11) -0.0010(10) C28 0.0251(14) 0.0265(14) 0.0356(18) -0.0026(12) -0.0018(12) 0.0026(11) C29 0.0407(16) 0.0200(13) 0.0242(17) -0.0032(12) 0.0065(12) -0.0039(12) C30 0.064(2) 0.0367(19) 0.062(3) -0.0170(18) 0.0333(19) -0.0256(18) C31 0.132(4) 0.049(3) 0.070(3) -0.014(2) 0.051(3) -0.049(3) C32 0.201(7) 0.028(2) 0.049(3) 0.003(2) 0.005(3) -0.033(4) C33 0.148(5) 0.029(2) 0.066(3) -0.005(2) -0.034(3) 0.029(3) C34 0.062(2) 0.0272(16) 0.051(2) -0.0042(16) -0.0148(18) 0.0147(16) O2 0.0201(9) 0.0272(9) 0.0243(11) -0.0018(8) 0.0058(7) -0.0021(7) N4 0.0212(11) 0.0188(10) 0.0298(14) -0.0004(10) 0.0082(9) -0.0004(9) N5 0.0177(11) 0.0302(12) 0.0173(14) -0.0028(10) 0.0041(9) -0.0033(9) N6 0.0179(11) 0.0444(14) 0.0221(14) -0.0041(11) 0.0041(10) -0.0088(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 C1 N1 1.467(3) . ? C1 C6 1.562(4) . ? C1 C2 1.580(4) . ? C1 H1 1.08(2) . ? C2 N2 1.478(3) . ? C2 C3 1.533(4) . ? C2 H2 1.10(2) . ? C3 C4 1.549(4) . ? C3 H3A 1.08(3) . ? C3 H3B 1.02(3) . ? C4 C5 1.560(4) . ? C4 H4A 1.09(3) . ? C4 H4B 1.04(3) . ? C5 C6 1.528(4) . ? C5 H5A 1.06(3) . ? C5 H5B 1.01(3) . ? C6 H6A 1.21(3) . ? C6 H6B 1.03(3) . ? C7 N1 1.592(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N1 1.530(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 O1 1.380(3) . ? C9 N3 1.395(3) . ? C9 N2 1.400(3) . ? C10 N3 1.507(3) . ? C10 C12 1.538(3) . ? C10 C11 1.577(4) . ? C10 H10 1.06(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.456(4) . ? C12 C17 1.526(4) . ? C13 C14 1.412(4) . ? C13 H13 0.9300 . ? C14 C15 1.519(5) . ? C14 H14 1.10(3) . ? C15 C16 1.452(4) . ? C15 H15 0.96(4) . ? C16 C17 1.415(4) . ? C16 H16 1.07(3) . ? C17 H17 1.03(3) . ? N2 H2N 0.90(3) . ? N3 H3N 0.92(3) . ? C18 N4 1.517(3) . ? C18 C19 1.563(3) . ? C18 C23 1.617(4) . ? C18 H18 1.06(3) . ? C19 N5 1.530(3) . ? C19 C20 1.556(3) . ? C19 H19 1.01(3) . ? C20 C21 1.603(4) . ? C20 H20A 0.92(3) . ? C20 H20B 1.03(3) . ? C21 C22 1.551(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.563(4) . ? C22 H22A 1.07(3) . ? C22 H22B 0.98(3) . ? C23 H23A 1.06(3) . ? C23 H23B 0.97(3) . ? C24 N4 1.512(3) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 N4 1.501(3) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25 0.9600 . ? C26 O2 1.359(3) . ? C26 N5 1.362(3) . ? C26 N6 1.459(3) . ? C27 N6 1.445(3) . ? C27 C29 1.526(4) . ? C27 C28 1.648(4) . ? C27 H27 1.00(3) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C34 1.382(4) . ? C29 C30 1.395(4) . ? C30 C31 1.389(6) . ? C30 H30 0.96(4) . ? C31 C32 1.369(8) . ? C31 H31 1.03(5) . ? C32 C33 1.367(8) . ? C32 H32 0.99(6) . ? C33 C34 1.403(6) . ? C33 H33 0.87(5) . ? C34 H34 0.94(4) . ? N5 H5N 0.93(3) . ? N6 H6N 1.00(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C6 115.0(2) . . ? N1 C1 C2 111.8(2) . . ? C6 C1 C2 105.5(2) . . ? N1 C1 H1 104.0(12) . . ? C6 C1 H1 109.1(13) . . ? C2 C1 H1 111.6(12) . . ? N2 C2 C3 109.7(2) . . ? N2 C2 C1 109.2(2) . . ? C3 C2 C1 108.3(2) . . ? N2 C2 H2 109.0(12) . . ? C3 C2 H2 107.9(12) . . ? C1 C2 H2 112.6(12) . . ? C2 C3 C4 111.0(2) . . ? C2 C3 H3A 109.9(12) . . ? C4 C3 H3A 111.4(13) . . ? C2 C3 H3B 105.8(15) . . ? C4 C3 H3B 108.6(16) . . ? H3A C3 H3B 110(2) . . ? C3 C4 C5 108.0(2) . . ? C3 C4 H4A 110.8(14) . . ? C5 C4 H4A 114.3(13) . . ? C3 C4 H4B 112.2(19) . . ? C5 C4 H4B 109.8(18) . . ? H4A C4 H4B 102(2) . . ? C6 C5 C4 109.2(2) . . ? C6 C5 H5A 107.6(14) . . ? C4 C5 H5A 115.1(15) . . ? C6 C5 H5B 110.2(15) . . ? C4 C5 H5B 107.2(16) . . ? H5A C5 H5B 107(2) . . ? C5 C6 C1 110.4(2) . . ? C5 C6 H6A 106.7(13) . . ? C1 C6 H6A 111.5(14) . . ? C5 C6 H6B 108.3(16) . . ? C1 C6 H6B 107.4(17) . . ? H6A C6 H6B 112(2) . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O1 C9 N3 123.7(2) . . ? O1 C9 N2 126.3(2) . . ? N3 C9 N2 110.0(2) . . ? N3 C10 C12 114.1(2) . . ? N3 C10 C11 104.1(2) . . ? C12 C10 C11 112.6(2) . . ? N3 C10 H10 112.3(13) . . ? C12 C10 H10 101.2(13) . . ? C11 C10 H10 112.9(12) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 123.1(2) . . ? C13 C12 C10 116.4(2) . . ? C17 C12 C10 120.5(2) . . ? C14 C13 C12 115.8(3) . . ? C14 C13 H13 122.1 . . ? C12 C13 H13 122.1 . . ? C13 C14 C15 120.4(3) . . ? C13 C14 H14 113.0(14) . . ? C15 C14 H14 126.6(14) . . ? C16 C15 C14 124.6(3) . . ? C16 C15 H15 111(2) . . ? C14 C15 H15 124(2) . . ? C17 C16 C15 114.6(3) . . ? C17 C16 H16 116.2(17) . . ? C15 C16 H16 129.0(17) . . ? C16 C17 C12 121.4(2) . . ? C16 C17 H17 115.6(17) . . ? C12 C17 H17 123.0(17) . . ? C1 N1 C8 111.6(2) . . ? C1 N1 C7 112.2(2) . . ? C8 N1 C7 116.4(2) . . ? C9 N2 C2 118.4(2) . . ? C9 N2 H2N 122.1(18) . . ? C2 N2 H2N 119.1(18) . . ? C9 N3 C10 115.6(2) . . ? C9 N3 H3N 120.4(16) . . ? C10 N3 H3N 123.1(16) . . ? N4 C18 C19 113.19(19) . . ? N4 C18 C23 118.15(19) . . ? C19 C18 C23 104.8(2) . . ? N4 C18 H18 99.5(14) . . ? C19 C18 H18 107.6(14) . . ? C23 C18 H18 113.4(13) . . ? N5 C19 C20 114.2(2) . . ? N5 C19 C18 104.8(2) . . ? C20 C19 C18 112.6(2) . . ? N5 C19 H19 111.2(14) . . ? C20 C19 H19 103.8(15) . . ? C18 C19 H19 110.3(14) . . ? C19 C20 C21 114.7(2) . . ? C19 C20 H20A 111.0(17) . . ? C21 C20 H20A 106.1(16) . . ? C19 C20 H20B 99.3(15) . . ? C21 C20 H20B 115.6(14) . . ? H20A C20 H20B 110(2) . . ? C22 C21 C20 105.2(2) . . ? C22 C21 H21A 110.7 . . ? C20 C21 H21A 110.7 . . ? C22 C21 H21B 110.7 . . ? C20 C21 H21B 110.7 . . ? H21A C21 H21B 108.8 . . ? C21 C22 C23 112.2(2) . . ? C21 C22 H22A 105.4(16) . . ? C23 C22 H22A 113.1(17) . . ? C21 C22 H22B 112.3(17) . . ? C23 C22 H22B 101.5(17) . . ? H22A C22 H22B 113(2) . . ? C22 C23 C18 115.6(2) . . ? C22 C23 H23A 102.9(14) . . ? C18 C23 H23A 114.9(13) . . ? C22 C23 H23B 116.7(18) . . ? C18 C23 H23B 99.2(18) . . ? H23A C23 H23B 108(2) . . ? N4 C24 H24A 109.5 . . ? N4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N4 C25 H25A 109.5 . . ? N4 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N4 C25 H25 109.5 . . ? H25A C25 H25 109.5 . . ? H25B C25 H25 109.5 . . ? O2 C26 N5 122.9(2) . . ? O2 C26 N6 127.9(2) . . ? N5 C26 N6 109.1(2) . . ? N6 C27 C29 113.3(2) . . ? N6 C27 C28 106.0(2) . . ? C29 C27 C28 112.0(2) . . ? N6 C27 H27 107.4(14) . . ? C29 C27 H27 103.7(16) . . ? C28 C27 H27 114.6(15) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C34 C29 C30 118.0(3) . . ? C34 C29 C27 122.1(3) . . ? C30 C29 C27 119.9(3) . . ? C31 C30 C29 121.0(4) . . ? C31 C30 H30 116(2) . . ? C29 C30 H30 122(2) . . ? C32 C31 C30 120.5(5) . . ? C32 C31 H31 121(3) . . ? C30 C31 H31 118(3) . . ? C31 C32 C33 119.4(4) . . ? C31 C32 H32 115(3) . . ? C33 C32 H32 125(3) . . ? C32 C33 C34 120.9(5) . . ? C32 C33 H33 127(4) . . ? C34 C33 H33 112(4) . . ? C29 C34 C33 120.3(4) . . ? C29 C34 H34 120(2) . . ? C33 C34 H34 119(2) . . ? C25 N4 C24 113.5(2) . . ? C25 N4 C18 115.34(19) . . ? C24 N4 C18 109.3(2) . . ? C26 N5 C19 118.1(2) . . ? C26 N5 H5N 117.6(15) . . ? C19 N5 H5N 123.8(15) . . ? C27 N6 C26 119.6(2) . . ? C27 N6 H6N 116.9(15) . . ? C26 N6 H6N 122.1(15) . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.210 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.038 #===END data_26b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H27 N3 O' _chemical_formula_weight 289.42 _chemical_absolute_configuration syn 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.1661(4) _cell_length_b 11.3191(6) _cell_length_c 15.5757(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1616.01(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7841 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 26.99 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .1 __exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Phi/Omega-Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7841 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2021 _reflns_number_gt 1677 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0415P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.3(15) _refine_ls_number_reflns 2021 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0724 _refine_ls_wR_factor_gt 0.0683 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.20537(12) 0.27340(11) 0.02288(9) 0.0222(3) Uani 1 1 d . . . N1 N 0.47777(16) -0.06805(14) 0.05998(10) 0.0193(4) Uani 1 1 d . . . N2 N 0.41723(17) 0.17663(14) 0.05144(10) 0.0194(4) Uani 1 1 d . . . H2 H 0.508(2) 0.1724(17) 0.0408(13) 0.016(5) Uiso 1 1 d . . . N3 N 0.41206(17) 0.32491(14) -0.04976(10) 0.0193(4) Uani 1 1 d . . . H3 H 0.502(2) 0.3177(17) -0.0487(13) 0.022(6) Uiso 1 1 d . . . C1 C 0.43950(19) -0.00419(17) 0.13915(11) 0.0178(4) Uani 1 1 d . . . H1A H 0.5380(18) 0.0200(16) 0.1645(10) 0.008(4) Uiso 1 1 d . . . C2 C 0.35338(19) 0.10875(15) 0.12111(11) 0.0172(4) Uani 1 1 d . . . H2A H 0.2544(18) 0.0863(14) 0.1036(10) 0.005(4) Uiso 1 1 d . . . C3 C 0.3427(2) 0.18141(17) 0.20390(12) 0.0240(4) Uani 1 1 d . . . H3A H 0.446(2) 0.2012(18) 0.2231(12) 0.022(5) Uiso 1 1 d . . . H3B H 0.296(2) 0.2589(18) 0.1896(14) 0.029(5) Uiso 1 1 d . . . C4 C 0.2640(2) 0.1128(2) 0.27398(14) 0.0272(5) Uani 1 1 d . . . H4A H 0.1596(19) 0.1005(15) 0.2582(10) 0.013(4) Uiso 1 1 d . . . H4B H 0.256(2) 0.1608(18) 0.3264(13) 0.028(5) Uiso 1 1 d . . . C5 C 0.3390(2) -0.0052(2) 0.29090(13) 0.0285(5) Uani 1 1 d . . . H5A H 0.288(2) -0.0503(18) 0.3307(13) 0.030(6) Uiso 1 1 d . . . H5B H 0.439(2) 0.0062(19) 0.3174(12) 0.026(5) Uiso 1 1 d . . . C6 C 0.3559(2) -0.07562(17) 0.20760(12) 0.0223(4) Uani 1 1 d . . . H6A H 0.257(2) -0.0999(16) 0.1881(12) 0.020(5) Uiso 1 1 d . . . H6B H 0.4013(19) -0.1544(19) 0.2194(13) 0.023(5) Uiso 1 1 d . . . C7 C 0.5680(2) -0.17108(18) 0.07714(15) 0.0255(5) Uani 1 1 d . . . H7A H 0.5097(19) -0.2414(17) 0.1034(11) 0.018(5) Uiso 1 1 d . . . H7B H 0.609(2) -0.1952(19) 0.0224(14) 0.028(6) Uiso 1 1 d . . . H7C H 0.650(2) -0.1491(16) 0.1183(12) 0.024(5) Uiso 1 1 d . . . C8 C 0.3537(2) -0.10029(19) 0.00671(13) 0.0250(4) Uani 1 1 d . . . H8A H 0.284(2) -0.161(2) 0.0374(14) 0.034(6) Uiso 1 1 d . . . H8B H 0.302(2) -0.0244(18) -0.0107(12) 0.021(5) Uiso 1 1 d . . . H8C H 0.391(2) -0.138(2) -0.0451(14) 0.030(6) Uiso 1 1 d . . . C9 C 0.33821(19) 0.25958(15) 0.00949(11) 0.0176(4) Uani 1 1 d . . . C10 C 0.3579(2) 0.44186(16) -0.07457(11) 0.0184(4) Uani 1 1 d . . . H10 H 0.252(2) 0.4403(16) -0.0635(11) 0.019(5) Uiso 1 1 d . . . C11 C 0.4282(2) 0.53697(19) -0.01956(14) 0.0250(4) Uani 1 1 d . . . H11A H 0.537(2) 0.5378(18) -0.0309(13) 0.025(5) Uiso 1 1 d . . . H11B H 0.4120(19) 0.5190(18) 0.0417(13) 0.019(5) Uiso 1 1 d . . . H11C H 0.386(2) 0.615(2) -0.0332(13) 0.027(5) Uiso 1 1 d . . . C12 C 0.37264(19) 0.45969(16) -0.17109(12) 0.0189(4) Uani 1 1 d . . . C13 C 0.3264(2) 0.37071(18) -0.22670(13) 0.0240(4) Uani 1 1 d . . . H13 H 0.297(2) 0.2984(18) -0.2018(13) 0.025(5) Uiso 1 1 d . . . C14 C 0.3321(2) 0.38527(19) -0.31480(13) 0.0300(5) Uani 1 1 d . . . H14 H 0.299(2) 0.3192(18) -0.3515(13) 0.027(5) Uiso 1 1 d . . . C15 C 0.3851(2) 0.4892(2) -0.35014(14) 0.0291(5) Uani 1 1 d . . . H15 H 0.390(2) 0.4940(19) -0.4099(13) 0.027(6) Uiso 1 1 d . . . C16 C 0.4324(2) 0.57787(19) -0.29626(13) 0.0266(5) Uani 1 1 d . . . H16 H 0.472(2) 0.649(2) -0.3203(14) 0.039(6) Uiso 1 1 d . . . C17 C 0.4262(2) 0.56372(18) -0.20728(13) 0.0225(4) Uani 1 1 d . . . H17 H 0.457(2) 0.6277(19) -0.1716(12) 0.024(5) 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 O1 0.0136(6) 0.0230(7) 0.0300(8) 0.0046(6) 0.0003(5) 0.0001(5) N1 0.0172(7) 0.0192(8) 0.0215(8) -0.0024(7) -0.0013(6) 0.0013(7) N2 0.0137(8) 0.0188(8) 0.0255(9) 0.0067(7) 0.0034(7) 0.0014(7) N3 0.0131(8) 0.0204(9) 0.0243(9) 0.0058(7) 0.0012(7) 0.0029(7) C1 0.0173(9) 0.0191(10) 0.0171(9) -0.0005(8) -0.0012(8) -0.0014(8) C2 0.0155(9) 0.0159(9) 0.0203(9) 0.0003(8) 0.0013(8) -0.0030(8) C3 0.0239(10) 0.0220(10) 0.0261(10) -0.0049(9) 0.0035(9) -0.0019(10) C4 0.0279(11) 0.0303(11) 0.0233(11) -0.0074(10) 0.0061(9) -0.0062(10) C5 0.0321(11) 0.0353(12) 0.0182(10) 0.0032(9) 0.0013(10) -0.0061(11) C6 0.0250(10) 0.0196(10) 0.0224(10) 0.0056(9) 0.0004(9) 0.0008(10) C7 0.0223(10) 0.0207(10) 0.0336(12) -0.0026(10) 0.0022(10) 0.0046(9) C8 0.0257(10) 0.0267(11) 0.0225(10) -0.0048(9) -0.0012(9) 0.0000(10) C9 0.0175(8) 0.0162(9) 0.0190(9) -0.0025(8) -0.0022(8) -0.0020(8) C10 0.0164(9) 0.0166(9) 0.0223(10) 0.0029(8) 0.0005(8) 0.0017(8) C11 0.0270(11) 0.0239(11) 0.0242(11) -0.0008(10) -0.0021(9) 0.0024(9) C12 0.0150(9) 0.0190(9) 0.0228(10) 0.0028(8) -0.0002(7) 0.0042(8) C13 0.0255(10) 0.0198(10) 0.0267(11) 0.0022(9) -0.0026(9) -0.0004(9) C14 0.0362(11) 0.0285(11) 0.0251(11) -0.0033(10) -0.0053(10) 0.0040(11) C15 0.0296(11) 0.0364(13) 0.0213(11) 0.0035(10) -0.0002(9) 0.0084(10) C16 0.0264(10) 0.0234(11) 0.0301(12) 0.0105(10) 0.0051(9) 0.0055(9) C17 0.0203(9) 0.0191(10) 0.0281(11) -0.0001(10) 0.0024(8) 0.0020(9) _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 C9 1.245(2) . ? N1 C8 1.454(2) . ? N1 C7 1.454(2) . ? N1 C1 1.472(2) . ? N2 C9 1.354(2) . ? N2 C2 1.453(2) . ? N2 H2 0.847(19) . ? N3 C9 1.363(2) . ? N3 C10 1.466(2) . ? N3 H3 0.826(19) . ? C1 C2 1.529(2) . ? C1 C6 1.542(3) . ? C1 H1A 1.023(17) . ? C2 C3 1.533(2) . ? C2 H2A 0.981(16) . ? C3 C4 1.522(3) . ? C3 H3A 1.020(18) . ? C3 H3B 1.00(2) . ? C4 C5 1.525(3) . ? C4 H4A 0.998(17) . ? C4 H4B 0.98(2) . ? C5 C6 1.531(3) . ? C5 H5A 0.93(2) . ? C5 H5B 1.012(19) . ? C6 H6A 0.994(18) . ? C6 H6B 1.00(2) . ? C7 H7A 1.042(19) . ? C7 H7B 0.97(2) . ? C7 H7C 1.022(19) . ? C8 H8A 1.06(2) . ? C8 H8B 1.02(2) . ? C8 H8C 0.98(2) . ? C10 C11 1.519(3) . ? C10 C12 1.523(3) . ? C10 H10 0.989(19) . ? C11 H11A 1.01(2) . ? C11 H11B 0.988(19) . ? C11 H11C 0.99(2) . ? C12 C13 1.394(3) . ? C12 C17 1.395(3) . ? C13 C14 1.383(3) . ? C13 H13 0.95(2) . ? C14 C15 1.386(3) . ? C14 H14 0.99(2) . ? C15 C16 1.378(3) . ? C15 H15 0.934(19) . ? C16 C17 1.396(3) . ? C16 H16 0.96(2) . ? C17 H17 0.95(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C7 110.38(16) . . ? C8 N1 C1 114.52(14) . . ? C7 N1 C1 112.05(15) . . ? C9 N2 C2 120.78(15) . . ? C9 N2 H2 117.9(13) . . ? C2 N2 H2 120.7(13) . . ? C9 N3 C10 120.02(15) . . ? C9 N3 H3 115.2(14) . . ? C10 N3 H3 115.6(14) . . ? N1 C1 C2 112.32(14) . . ? N1 C1 C6 116.11(15) . . ? C2 C1 C6 108.00(15) . . ? N1 C1 H1A 104.2(9) . . ? C2 C1 H1A 107.6(10) . . ? C6 C1 H1A 108.2(9) . . ? N2 C2 C1 111.81(14) . . ? N2 C2 C3 111.74(14) . . ? C1 C2 C3 109.09(15) . . ? N2 C2 H2A 107.6(9) . . ? C1 C2 H2A 108.2(9) . . ? C3 C2 H2A 108.3(9) . . ? C4 C3 C2 111.09(16) . . ? C4 C3 H3A 110.1(11) . . ? C2 C3 H3A 107.7(11) . . ? C4 C3 H3B 113.9(12) . . ? C2 C3 H3B 108.1(12) . . ? H3A C3 H3B 105.6(16) . . ? C3 C4 C5 110.92(17) . . ? C3 C4 H4A 110.4(10) . . ? C5 C4 H4A 110.7(10) . . ? C3 C4 H4B 110.5(11) . . ? C5 C4 H4B 112.0(12) . . ? H4A C4 H4B 102.0(15) . . ? C4 C5 C6 110.81(17) . . ? C4 C5 H5A 111.7(12) . . ? C6 C5 H5A 109.3(13) . . ? C4 C5 H5B 111.5(12) . . ? C6 C5 H5B 108.7(11) . . ? H5A C5 H5B 104.7(16) . . ? C5 C6 C1 111.30(16) . . ? C5 C6 H6A 108.1(11) . . ? C1 C6 H6A 112.7(11) . . ? C5 C6 H6B 110.5(11) . . ? C1 C6 H6B 112.8(11) . . ? H6A C6 H6B 100.9(15) . . ? N1 C7 H7A 113.1(10) . . ? N1 C7 H7B 106.4(13) . . ? H7A C7 H7B 109.2(16) . . ? N1 C7 H7C 109.9(11) . . ? H7A C7 H7C 108.6(14) . . ? H7B C7 H7C 109.6(15) . . ? N1 C8 H8A 112.4(11) . . ? N1 C8 H8B 107.8(10) . . ? H8A C8 H8B 112.7(16) . . ? N1 C8 H8C 108.0(12) . . ? H8A C8 H8C 107.4(17) . . ? H8B C8 H8C 108.3(16) . . ? O1 C9 N2 121.96(16) . . ? O1 C9 N3 122.08(16) . . ? N2 C9 N3 115.94(15) . . ? N3 C10 C11 110.33(15) . . ? N3 C10 C12 110.47(15) . . ? C11 C10 C12 115.16(16) . . ? N3 C10 H10 105.8(11) . . ? C11 C10 H10 109.4(10) . . ? C12 C10 H10 105.2(10) . . ? C10 C11 H11A 109.0(12) . . ? C10 C11 H11B 109.6(11) . . ? H11A C11 H11B 108.6(15) . . ? C10 C11 H11C 110.1(12) . . ? H11A C11 H11C 110.1(17) . . ? H11B C11 H11C 109.4(17) . . ? C13 C12 C17 117.75(18) . . ? C13 C12 C10 119.37(17) . . ? C17 C12 C10 122.83(17) . . ? C14 C13 C12 121.2(2) . . ? C14 C13 H13 121.4(12) . . ? C12 C13 H13 117.3(12) . . ? C13 C14 C15 120.6(2) . . ? C13 C14 H14 118.1(11) . . ? C15 C14 H14 121.3(11) . . ? C16 C15 C14 119.09(19) . . ? C16 C15 H15 123.4(13) . . ? C14 C15 H15 117.5(13) . . ? C15 C16 C17 120.5(2) . . ? C15 C16 H16 119.7(13) . . ? C17 C16 H16 119.8(13) . . ? C12 C17 C16 120.8(2) . . ? C12 C17 H17 120.5(12) . . ? C16 C17 H17 118.6(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.132 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.037 #===END