data_vrt-928486 _refine_ls_number_constraints ? #Added by publCIF _symmetry_space_group_name_hall 'P 2yb' #Added by publCIF _cell_special_details ? #Added by publCIF _audit_update_record ; 2010-12-17 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 F N6 O3' _chemical_formula_weight 428.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.9016(2) _cell_length_b 10.9184(2) _cell_length_c 19.2975(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.8260(10) _cell_angle_gamma 90.00 _cell_volume 2034.19(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6639 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.856 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8824 _exptl_absorpt_correction_T_max 0.9193 _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX II' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14666 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 64.88 _reflns_number_total 6639 _reflns_number_gt 6210 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex II' _computing_cell_refinement 'Apex II' _computing_data_reduction 'Apex II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Mercury _computing_publication_material publCIF _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^)+(0.0546P)^2^+0.3977P] 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 0.00020(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 -0.08(12) _refine_ls_number_reflns 6639 _refine_ls_number_parameters 731 _refine_ls_number_restraints 33 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 3.400 _refine_ls_shift/su_mean 0.007 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.30546(18) 0.01802(17) 0.33753(9) 0.0194(4) Uani 1 1 d . . . C2 C 0.2562(2) -0.01433(19) 0.39301(10) 0.0173(4) Uani 1 1 d . . . N3 N 0.34895(17) -0.00102(17) 0.45582(10) 0.0179(4) Uani 1 1 d . . . H3 H 0.332(2) -0.0213(18) 0.4936(12) 0.003(5) Uiso 1 1 d . . . C4 C 0.4702(2) 0.04331(18) 0.44054(11) 0.0172(4) Uani 1 1 d . . . C5 C 0.5989(2) 0.07166(19) 0.48428(11) 0.0194(4) Uani 1 1 d . . . C6 C 0.6953(2) 0.1138(2) 0.44756(11) 0.0206(4) Uani 1 1 d . . . F6 F 0.82398(12) 0.14063(12) 0.48706(6) 0.0247(3) Uani 1 1 d . . . C7 C 0.6736(2) 0.1245(2) 0.37369(11) 0.0206(4) Uani 1 1 d . . . C8 C 0.5431(2) 0.0938(2) 0.33221(12) 0.0206(4) Uani 1 1 d . . . H8 H 0.523(2) 0.102(2) 0.2799(14) 0.021(6) Uiso 1 1 d . . . C9 C 0.4411(2) 0.0543(2) 0.36637(11) 0.0189(4) Uani 1 1 d . . . N10 N 0.12518(18) -0.05978(18) 0.38832(10) 0.0207(4) Uani 1 1 d . . . H10 H 0.085(2) -0.085(2) 0.3491(13) 0.012(6) Uiso 1 1 d . . . C11 C 0.0709(2) -0.08387(19) 0.44764(11) 0.0184(4) Uani 1 1 d . . . O11 O 0.13513(15) -0.05992(14) 0.50807(8) 0.0220(3) Uani 1 1 d . . . N12 N -0.05733(19) -0.13263(18) 0.43236(11) 0.0224(4) Uani 1 1 d . . . H12 H -0.090(3) -0.154(3) 0.3938(16) 0.027(8) Uiso 1 1 d . . . C13 C -0.1207(2) -0.1752(2) 0.48922(12) 0.0247(5) Uani 1 1 d . . . H13A H -0.067(3) -0.251(3) 0.5140(15) 0.038(7) Uiso 1 1 d . . . H13B H -0.114(3) -0.110(3) 0.5232(15) 0.036(7) Uiso 1 1 d . . . C14 C -0.2679(2) -0.2163(2) 0.45981(12) 0.0264(5) Uani 1 1 d . . . H14A H -0.3200 -0.1498 0.4318 0.040 Uiso 1 1 calc R . . H14B H -0.3115 -0.2374 0.4991 0.040 Uiso 1 1 calc R . . H14C H -0.2678 -0.2881 0.4294 0.040 Uiso 1 1 calc R . . C15 C 0.6331(2) 0.0515(2) 0.56345(11) 0.0206(4) Uani 1 1 d . . . H15 H 0.728(2) 0.029(2) 0.5789(11) 0.012(5) Uiso 1 1 d . . . O16 O 0.54542(16) -0.04280(14) 0.58073(8) 0.0246(3) Uani 1 1 d . . . C17 C 0.4900(2) -0.0061(2) 0.64046(12) 0.0280(5) Uani 1 1 d . . . H17A H 0.387(3) 0.012(2) 0.6219(13) 0.028(6) Uiso 1 1 d . . . H17E H 0.495(3) -0.075(3) 0.6721(14) 0.029(6) Uiso 1 1 d . . . C18 C 0.5733(3) 0.1037(2) 0.67247(12) 0.0309(5) Uani 1 1 d . . . H18A H 0.654(3) 0.078(2) 0.7066(13) 0.027(6) Uiso 1 1 d . . . H18E H 0.516(3) 0.163(3) 0.6969(16) 0.053(9) Uiso 1 1 d . . . C19 C 0.6127(2) 0.1632(2) 0.60810(12) 0.0250(5) Uani 1 1 d . . . H19A H 0.539(3) 0.217(2) 0.5821(13) 0.025(6) Uiso 1 1 d . . . H19E H 0.693(3) 0.208(2) 0.6197(13) 0.026(6) Uiso 1 1 d . . . C20 C 0.7869(2) 0.1568(2) 0.33796(11) 0.0204(4) Uani 1 1 d . . . C21 C 0.8091(2) 0.0845(2) 0.28227(11) 0.0216(5) Uani 1 1 d . . . H21 H 0.751(3) 0.017(3) 0.2677(13) 0.024(6) Uiso 1 1 d . . . N22 N 0.90847(18) 0.10722(17) 0.24691(9) 0.0220(4) Uani 1 1 d . . . C23 C 0.9886(2) 0.2050(2) 0.26815(11) 0.0197(4) Uani 1 1 d . . . N24 N 0.97513(18) 0.28172(17) 0.32033(9) 0.0216(4) Uani 1 1 d . . . C25 C 0.8745(2) 0.2575(2) 0.35458(11) 0.0212(5) Uani 1 1 d . . . H25 H 0.865(2) 0.314(2) 0.3901(13) 0.015(5) Uiso 1 1 d . . . C26 C 1.0996(2) 0.2339(2) 0.22642(11) 0.0202(4) Uani 1 1 d . . . C27 C 1.0286(2) 0.2909(2) 0.15554(12) 0.0246(5) Uani 1 1 d . . . H27A H 1.095(3) 0.304(2) 0.1251(14) 0.028(7) Uiso 1 1 d . . . H27B H 0.989(3) 0.370(3) 0.1622(14) 0.033(7) Uiso 1 1 d . . . H27C H 0.951(3) 0.233(3) 0.1278(16) 0.046(8) Uiso 1 1 d . . . C28 C 1.2116(2) 0.3182(2) 0.26772(13) 0.0244(5) Uani 1 1 d . . . H28A H 1.2560(19) 0.2851(17) 0.3132(11) 0.001(4) Uiso 1 1 d . . . H28B H 1.282(2) 0.335(2) 0.2372(13) 0.021(6) Uiso 1 1 d . . . H28C H 1.174(3) 0.400(3) 0.2762(14) 0.036(7) Uiso 1 1 d . . . O29 O 1.16079(15) 0.12109(14) 0.20979(8) 0.0208(3) Uani 1 1 d . . . H29 H 1.207(3) 0.084(3) 0.2475(14) 0.024(7) Uiso 1 1 d . . . N31 N 0.68673(18) 0.88416(17) 0.16552(9) 0.0203(4) Uani 1 1 d . . . C32 C 0.7449(2) 0.8932(2) 0.11056(11) 0.0229(5) Uani 1 1 d . . . N33 N 0.6651(2) 0.8472(2) 0.04925(11) 0.0320(5) Uani 1 1 d . . . H33 H 0.698(3) 0.836(3) 0.0138(16) 0.039(8) Uiso 1 1 d . . . C34 C 0.5443(2) 0.8055(2) 0.06552(12) 0.0270(5) Uani 1 1 d . . . C35 C 0.4263(2) 0.7515(3) 0.02396(12) 0.0347(6) Uani 1 1 d . . . C36 C 0.3229(2) 0.7263(2) 0.05972(12) 0.0281(5) Uani 1 1 d . . . F36 F 0.20187(14) 0.68017(17) 0.02066(7) 0.0427(4) Uani 1 1 d . . . C37 C 0.3291(2) 0.7509(2) 0.13130(12) 0.0216(5) Uani 1 1 d . . . C38 C 0.4505(2) 0.8049(2) 0.17056(12) 0.0209(5) Uani 1 1 d . . . H38 H 0.459(2) 0.825(2) 0.2186(13) 0.014(5) Uiso 1 1 d . . . C39 C 0.5568(2) 0.8312(2) 0.13732(11) 0.0197(4) Uani 1 1 d . . . N40 N 0.87197(19) 0.94480(19) 0.11460(10) 0.0236(4) Uani 1 1 d . . . H40 H 0.904(3) 0.983(3) 0.1542(16) 0.043(9) Uiso 1 1 d . . . C41 C 0.9361(3) 0.9543(3) 0.05674(13) 0.0379(6) Uani 1 1 d . A . O41 O 0.8802(2) 0.9146(3) -0.00212(9) 0.0588(7) Uani 1 1 d . . . N42 N 1.0599(2) 1.0086(3) 0.07354(12) 0.0458(7) Uani 1 1 d . . . H42 H 1.087(3) 1.038(2) 0.1126(15) 0.022(7) Uiso 1 1 d . . . C43A C 1.1543(6) 1.0065(6) 0.0213(3) 0.0249(15) Uani 0.520(11) 1 d PU A 1 H43A H 1.2502 0.9847 0.0455 0.030 Uiso 0.520(11) 1 calc PR A 1 H43B H 1.1207 0.9469 -0.0174 0.030 Uiso 0.520(11) 1 calc PR A 1 C44A C 1.1474(5) 1.1358(6) -0.0075(3) 0.0287(16) Uani 0.520(11) 1 d PU A 1 H44A H 1.0504 1.1590 -0.0255 0.043 Uiso 0.520(11) 1 calc PR A 1 H44B H 1.1969 1.1400 -0.0461 0.043 Uiso 0.520(11) 1 calc PR A 1 H44C H 1.1905 1.1920 0.0306 0.043 Uiso 0.520(11) 1 calc PR A 1 C43B C 1.1128(5) 1.0798(7) 0.0183(3) 0.0250(18) Uani 0.480(11) 1 d PU A 2 H43C H 1.1712 1.1495 0.0400 0.030 Uiso 0.480(11) 1 calc PR A 2 H43D H 1.0353 1.1113 -0.0191 0.030 Uiso 0.480(11) 1 calc PR A 2 C44B C 1.1970(7) 0.9865(5) -0.0117(4) 0.0322(18) Uani 0.480(11) 1 d PU A 2 H44D H 1.2799 0.9653 0.0245 0.048 Uiso 0.480(11) 1 calc PR A 2 H44E H 1.2246 1.0209 -0.0533 0.048 Uiso 0.480(11) 1 calc PR A 2 H44F H 1.1412 0.9127 -0.0255 0.048 Uiso 0.480(11) 1 calc PR A 2 C45 C 0.4113(3) 0.7270(3) -0.05422(13) 0.0469(8) Uani 1 1 d . . . H45 H 0.341(3) 0.668(3) -0.0709(15) 0.045(8) Uiso 1 1 d . . . O46 O 0.53821(18) 0.6778(2) -0.06517(9) 0.0434(5) Uani 1 1 d . . . C47 C 0.5266(3) 0.6851(3) -0.14016(13) 0.0494(8) Uani 1 1 d . . . H47A H 0.458(3) 0.612(3) -0.1645(16) 0.051(8) Uiso 1 1 d . . . H47E H 0.616(3) 0.677(3) -0.1510(14) 0.039(7) Uiso 1 1 d . . . C48 C 0.4592(4) 0.8063(4) -0.16229(16) 0.0612(10) Uani 1 1 d . . . H48A H 0.3917 0.7991 -0.2084 0.073 Uiso 1 1 calc R . . H48B H 0.5293 0.8687 -0.1667 0.073 Uiso 1 1 calc R . . C49 C 0.3850(3) 0.8408(4) -0.10213(16) 0.0566(10) Uani 1 1 d . . . H49A H 0.285(4) 0.860(3) -0.1167(17) 0.054(9) Uiso 1 1 d . . . H49E H 0.433(5) 0.921(5) -0.073(3) 0.101(15) Uiso 1 1 d . . . C50 C 0.2115(2) 0.72619(19) 0.16536(11) 0.0194(4) Uani 1 1 d . . . C51 C 0.1803(2) 0.8075(2) 0.21528(12) 0.0221(5) Uani 1 1 d . . . H51 H 0.236(2) 0.888(2) 0.2275(12) 0.020(6) Uiso 1 1 d . . . N52 N 0.07967(18) 0.78862(17) 0.25021(10) 0.0227(4) Uani 1 1 d . . . C53 C 0.0059(2) 0.6860(2) 0.23383(11) 0.0189(4) Uani 1 1 d . . . N54 N 0.02594(18) 0.60198(16) 0.18689(9) 0.0197(4) Uani 1 1 d . . . C55 C 0.1291(2) 0.6226(2) 0.15365(11) 0.0196(4) Uani 1 1 d . . . H55 H 0.146(2) 0.564(2) 0.1193(14) 0.021(6) Uiso 1 1 d . . . C56 C -0.1065(2) 0.6591(2) 0.27506(11) 0.0220(5) Uani 1 1 d . . . C57 C -0.2204(2) 0.5772(2) 0.23276(13) 0.0279(5) Uani 1 1 d . . . H57A H -0.2933 0.5664 0.2593 0.042 Uiso 1 1 calc R . . H57B H -0.1813 0.4972 0.2251 0.042 Uiso 1 1 calc R . . H57C H -0.2597 0.6154 0.1867 0.042 Uiso 1 1 calc R . . C58 C -0.0364(2) 0.5977(2) 0.34497(12) 0.0265(5) Uani 1 1 d . . . H58A H 0.005(3) 0.518(3) 0.3330(13) 0.023(6) Uiso 1 1 d . . . H58B H -0.105(3) 0.579(3) 0.3724(15) 0.034(7) Uiso 1 1 d . . . H58C H 0.036(3) 0.652(3) 0.3723(14) 0.030(7) Uiso 1 1 d . . . O59 O -0.16472(16) 0.77145(15) 0.29306(8) 0.0244(3) Uani 1 1 d . . . H59 H -0.210(3) 0.812(3) 0.2537(19) 0.053(10) 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 N1 0.0179(8) 0.0242(9) 0.0157(9) 0.0007(7) 0.0027(7) -0.0019(7) C2 0.0159(10) 0.0180(10) 0.0174(11) -0.0009(8) 0.0025(8) -0.0002(8) N3 0.0170(9) 0.0233(9) 0.0145(9) 0.0015(7) 0.0059(7) -0.0022(7) C4 0.0184(10) 0.0178(10) 0.0156(10) 0.0006(8) 0.0046(8) 0.0005(8) C5 0.0193(10) 0.0214(10) 0.0174(11) -0.0002(8) 0.0036(8) 0.0007(8) C6 0.0156(9) 0.0237(11) 0.0211(11) -0.0019(9) 0.0012(8) -0.0026(8) F6 0.0167(6) 0.0376(7) 0.0187(6) 0.0002(5) 0.0016(4) -0.0076(5) C7 0.0208(10) 0.0211(10) 0.0207(11) 0.0013(9) 0.0064(8) -0.0021(9) C8 0.0214(10) 0.0254(11) 0.0153(11) 0.0013(8) 0.0044(8) -0.0018(8) C9 0.0175(10) 0.0205(10) 0.0187(11) 0.0003(8) 0.0041(8) 0.0007(8) N10 0.0180(9) 0.0303(10) 0.0130(9) -0.0031(8) 0.0016(7) -0.0044(8) C11 0.0184(10) 0.0209(10) 0.0164(11) 0.0002(8) 0.0048(8) 0.0014(8) O11 0.0195(7) 0.0312(8) 0.0154(8) -0.0019(6) 0.0039(6) -0.0047(6) N12 0.0201(9) 0.0319(11) 0.0150(10) -0.0021(8) 0.0034(8) -0.0057(7) C13 0.0228(11) 0.0340(13) 0.0181(11) -0.0014(10) 0.0064(9) -0.0046(10) C14 0.0227(11) 0.0295(12) 0.0290(12) -0.0005(10) 0.0101(9) -0.0035(9) C15 0.0149(10) 0.0265(11) 0.0196(11) 0.0028(9) 0.0021(8) -0.0029(8) O16 0.0268(8) 0.0296(8) 0.0178(7) 0.0015(6) 0.0061(6) -0.0070(6) C17 0.0243(12) 0.0421(14) 0.0195(11) 0.0073(10) 0.0091(9) 0.0011(10) C18 0.0313(12) 0.0421(14) 0.0198(12) -0.0029(10) 0.0068(10) 0.0045(11) C19 0.0222(11) 0.0309(12) 0.0201(11) -0.0025(9) 0.0011(8) -0.0014(9) C20 0.0173(10) 0.0276(12) 0.0148(10) 0.0045(8) 0.0005(8) -0.0016(8) C21 0.0198(10) 0.0246(12) 0.0201(11) 0.0012(9) 0.0035(8) -0.0056(9) N22 0.0186(8) 0.0264(10) 0.0210(9) 0.0000(8) 0.0047(7) -0.0029(7) C23 0.0169(10) 0.0236(11) 0.0176(11) 0.0044(9) 0.0017(8) -0.0002(8) N24 0.0202(9) 0.0270(10) 0.0184(9) 0.0002(8) 0.0055(7) -0.0033(8) C25 0.0209(11) 0.0263(11) 0.0165(11) 0.0000(9) 0.0046(8) -0.0028(9) C26 0.0175(10) 0.0232(11) 0.0203(11) 0.0008(9) 0.0053(8) -0.0011(9) C27 0.0255(12) 0.0279(12) 0.0224(12) 0.0072(10) 0.0095(10) 0.0029(10) C28 0.0205(11) 0.0287(13) 0.0258(13) -0.0003(10) 0.0091(9) -0.0035(9) O29 0.0210(7) 0.0235(8) 0.0171(8) 0.0024(7) 0.0024(6) 0.0025(6) N31 0.0182(9) 0.0253(9) 0.0169(9) -0.0005(7) 0.0027(7) -0.0044(7) C32 0.0204(11) 0.0293(12) 0.0176(11) 0.0019(9) 0.0011(8) -0.0036(9) N33 0.0268(10) 0.0557(14) 0.0138(10) -0.0011(9) 0.0052(8) -0.0178(9) C34 0.0208(11) 0.0390(14) 0.0209(11) 0.0039(10) 0.0043(9) -0.0080(9) C35 0.0290(12) 0.0600(17) 0.0142(12) 0.0010(11) 0.0026(9) -0.0174(12) C36 0.0206(11) 0.0416(14) 0.0202(12) 0.0002(10) 0.0006(8) -0.0119(10) F36 0.0270(7) 0.0810(12) 0.0183(7) -0.0029(7) 0.0013(5) -0.0275(7) C37 0.0203(10) 0.0224(10) 0.0207(12) 0.0046(9) 0.0015(8) -0.0015(9) C38 0.0234(11) 0.0240(11) 0.0146(11) 0.0003(9) 0.0026(8) -0.0018(9) C39 0.0174(10) 0.0236(11) 0.0163(11) 0.0017(9) 0.0002(8) -0.0028(9) N40 0.0218(9) 0.0342(11) 0.0144(9) -0.0012(8) 0.0031(7) -0.0089(8) C41 0.0309(13) 0.0642(18) 0.0170(12) 0.0013(12) 0.0015(9) -0.0207(13) O41 0.0426(11) 0.117(2) 0.0185(9) -0.0124(11) 0.0102(8) -0.0489(13) N42 0.0351(13) 0.0858(19) 0.0174(11) -0.0063(12) 0.0076(9) -0.0355(13) C43A 0.024(3) 0.030(3) 0.024(3) -0.008(2) 0.013(2) -0.002(2) C44A 0.022(2) 0.036(3) 0.029(3) 0.004(2) 0.0075(18) -0.005(2) C43B 0.011(2) 0.033(4) 0.030(3) 0.002(3) 0.004(2) 0.000(2) C44B 0.033(3) 0.031(3) 0.033(4) -0.004(2) 0.007(3) 0.002(2) C45 0.0277(13) 0.093(2) 0.0191(13) -0.0065(13) 0.0041(10) -0.0325(15) O46 0.0429(10) 0.0697(13) 0.0178(8) -0.0081(8) 0.0076(7) -0.0170(9) C47 0.0441(16) 0.087(2) 0.0183(13) -0.0059(14) 0.0102(11) -0.0248(16) C48 0.063(2) 0.098(3) 0.0268(15) 0.0028(17) 0.0189(14) -0.023(2) C49 0.0292(14) 0.115(3) 0.0248(15) 0.0179(17) 0.0047(11) -0.0069(16) C50 0.0200(10) 0.0211(11) 0.0157(11) 0.0033(8) 0.0010(8) 0.0005(8) C51 0.0177(10) 0.0233(11) 0.0239(12) -0.0010(9) 0.0016(8) -0.0007(9) N52 0.0198(9) 0.0255(10) 0.0221(10) -0.0055(8) 0.0036(7) 0.0010(7) C53 0.0186(10) 0.0215(11) 0.0152(10) 0.0002(8) 0.0009(8) 0.0022(8) N54 0.0198(8) 0.0213(9) 0.0189(9) -0.0016(7) 0.0063(7) -0.0010(7) C55 0.0218(10) 0.0221(11) 0.0155(10) -0.0021(9) 0.0054(8) 0.0003(9) C56 0.0216(10) 0.0262(11) 0.0192(11) -0.0027(9) 0.0067(8) 0.0032(9) C57 0.0225(11) 0.0359(13) 0.0271(12) -0.0012(10) 0.0091(9) -0.0018(10) C58 0.0259(12) 0.0333(13) 0.0222(12) 0.0020(10) 0.0093(9) 0.0056(10) O59 0.0249(8) 0.0328(9) 0.0152(8) -0.0002(7) 0.0037(6) 0.0089(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.319(3) . ? N1 C9 1.392(3) . ? C2 N3 1.356(3) . ? C2 N10 1.373(3) . ? N3 C4 1.386(3) . ? C4 C5 1.398(3) . ? C4 C9 1.401(3) . ? C5 C6 1.388(3) . ? C5 C15 1.506(3) . ? C6 F6 1.363(2) . ? C6 C7 1.398(3) . ? C7 C8 1.401(3) . ? C7 C20 1.485(3) . ? C8 C9 1.391(3) . ? N10 C11 1.393(3) . ? C11 O11 1.226(3) . ? C11 N12 1.348(3) . ? N12 C13 1.456(3) . ? C13 C14 1.510(3) . ? C15 O16 1.433(3) . ? C15 C19 1.533(3) . ? O16 C17 1.439(3) . ? C17 C18 1.508(4) . ? C18 C19 1.527(3) . ? C20 C21 1.390(3) . ? C20 C25 1.392(3) . ? C21 N22 1.339(3) . ? N22 C23 1.339(3) . ? C23 N24 1.339(3) . ? C23 C26 1.532(3) . ? N24 C25 1.339(3) . ? C26 O29 1.440(3) . ? C26 C28 1.523(3) . ? C26 C27 1.525(3) . ? N31 C32 1.318(3) . ? N31 C39 1.406(3) . ? C32 N33 1.364(3) . ? C32 N40 1.365(3) . ? N33 C34 1.380(3) . ? C34 C35 1.393(3) . ? C34 C39 1.392(3) . ? C35 C36 1.383(3) . ? C35 C45 1.507(3) . ? C36 F36 1.363(3) . ? C36 C37 1.395(3) . ? C37 C38 1.401(3) . ? C37 C50 1.484(3) . ? C38 C39 1.379(3) . ? N40 C41 1.405(3) . ? C41 O41 1.227(3) . ? C41 N42 1.335(3) . ? N42 C43B 1.505(8) . ? N42 C43A 1.520(7) . ? C43A C44A 1.513(9) . ? C43B C44B 1.510(10) . ? C45 O46 1.425(4) . ? C45 C49 1.536(5) . ? O46 C47 1.428(3) . ? C47 C48 1.501(5) . ? C48 C49 1.552(4) . ? C50 C55 1.384(3) . ? C50 C51 1.394(3) . ? C51 N52 1.337(3) . ? N52 C53 1.337(3) . ? C53 N54 1.335(3) . ? C53 C56 1.533(3) . ? N54 C55 1.340(3) . ? C56 O59 1.431(3) . ? C56 C57 1.526(3) . ? C56 C58 1.528(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 C2 N1 C9 104.43(17) . . ? N1 C2 N3 113.45(18) . . ? N1 C2 N10 123.86(18) . . ? N3 C2 N10 122.67(19) . . ? C2 N3 C4 107.08(18) . . ? N3 C4 C5 131.7(2) . . ? N3 C4 C9 104.83(18) . . ? C5 C4 C9 123.4(2) . . ? C6 C5 C4 113.78(19) . . ? C6 C5 C15 122.76(18) . . ? C4 C5 C15 123.36(18) . . ? F6 C6 C5 116.70(18) . . ? F6 C6 C7 117.74(17) . . ? C5 C6 C7 125.47(19) . . ? C6 C7 C8 118.45(19) . . ? C6 C7 C20 122.14(18) . . ? C8 C7 C20 119.21(19) . . ? C9 C8 C7 118.5(2) . . ? C8 C9 N1 129.5(2) . . ? C8 C9 C4 120.3(2) . . ? N1 C9 C4 110.21(18) . . ? C2 N10 C11 123.04(18) . . ? O11 C11 N12 123.84(19) . . ? O11 C11 N10 121.85(19) . . ? N12 C11 N10 114.29(19) . . ? C11 N12 C13 120.3(2) . . ? N12 C13 C14 110.68(19) . . ? O16 C15 C5 109.26(17) . . ? O16 C15 C19 106.19(16) . . ? C5 C15 C19 115.21(18) . . ? C15 O16 C17 110.16(17) . . ? O16 C17 C18 106.18(18) . . ? C17 C18 C19 102.72(19) . . ? C18 C19 C15 102.00(19) . . ? C21 C20 C25 115.43(19) . . ? C21 C20 C7 119.3(2) . . ? C25 C20 C7 125.3(2) . . ? N22 C21 C20 123.3(2) . . ? C21 N22 C23 116.38(19) . . ? N22 C23 N24 125.29(19) . . ? N22 C23 C26 116.63(19) . . ? N24 C23 C26 118.01(19) . . ? C25 N24 C23 117.19(18) . . ? N24 C25 C20 122.4(2) . . ? O29 C26 C28 109.88(17) . . ? O29 C26 C27 106.41(17) . . ? C28 C26 C27 111.09(19) . . ? O29 C26 C23 109.13(17) . . ? C28 C26 C23 111.88(18) . . ? C27 C26 C23 108.27(17) . . ? C32 N31 C39 104.19(17) . . ? N31 C32 N33 113.46(19) . . ? N31 C32 N40 123.15(19) . . ? N33 C32 N40 123.4(2) . . ? C32 N33 C34 106.8(2) . . ? N33 C34 C35 131.9(2) . . ? N33 C34 C39 105.66(19) . . ? C35 C34 C39 122.4(2) . . ? C36 C35 C34 114.6(2) . . ? C36 C35 C45 123.0(2) . . ? C34 C35 C45 122.4(2) . . ? F36 C36 C35 117.1(2) . . ? F36 C36 C37 117.29(19) . . ? C35 C36 C37 125.5(2) . . ? C36 C37 C38 117.4(2) . . ? C36 C37 C50 122.51(19) . . ? C38 C37 C50 120.0(2) . . ? C39 C38 C37 119.2(2) . . ? C38 C39 C34 120.8(2) . . ? C38 C39 N31 129.3(2) . . ? C34 C39 N31 109.87(18) . . ? C32 N40 C41 123.95(19) . . ? O41 C41 N42 125.6(2) . . ? O41 C41 N40 121.3(2) . . ? N42 C41 N40 113.1(2) . . ? C41 N42 C43B 120.2(3) . . ? C41 N42 C43A 119.9(3) . . ? C43B N42 C43A 34.5(2) . . ? C44A C43A N42 104.2(5) . . ? N42 C43B C44B 103.3(6) . . ? O46 C45 C35 108.7(2) . . ? O46 C45 C49 104.6(2) . . ? C35 C45 C49 115.2(3) . . ? C45 O46 C47 104.7(2) . . ? O46 C47 C48 105.5(3) . . ? C47 C48 C49 104.8(3) . . ? C45 C49 C48 102.1(3) . . ? C55 C50 C51 114.82(19) . . ? C55 C50 C37 124.7(2) . . ? C51 C50 C37 120.47(19) . . ? N52 C51 C50 123.7(2) . . ? C53 N52 C51 116.05(19) . . ? N54 C53 N52 125.51(19) . . ? N54 C53 C56 117.06(18) . . ? N52 C53 C56 117.35(19) . . ? C53 N54 C55 116.96(18) . . ? N54 C55 C50 122.9(2) . . ? O59 C56 C57 110.04(17) . . ? O59 C56 C58 106.87(17) . . ? C57 C56 C58 110.6(2) . . ? O59 C56 C53 109.85(18) . . ? C57 C56 C53 111.71(17) . . ? C58 C56 C53 107.59(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 C2 N3 0.5(2) . . . . ? C9 N1 C2 N10 -178.1(2) . . . . ? N1 C2 N3 C4 -0.4(2) . . . . ? N10 C2 N3 C4 178.27(19) . . . . ? C2 N3 C4 C5 -178.8(2) . . . . ? C2 N3 C4 C9 0.0(2) . . . . ? N3 C4 C5 C6 179.6(2) . . . . ? C9 C4 C5 C6 0.9(3) . . . . ? N3 C4 C5 C15 3.1(4) . . . . ? C9 C4 C5 C15 -175.6(2) . . . . ? C4 C5 C6 F6 -178.68(18) . . . . ? C15 C5 C6 F6 -2.1(3) . . . . ? C4 C5 C6 C7 -2.3(3) . . . . ? C15 C5 C6 C7 174.3(2) . . . . ? F6 C6 C7 C8 178.21(19) . . . . ? C5 C6 C7 C8 1.8(3) . . . . ? F6 C6 C7 C20 3.5(3) . . . . ? C5 C6 C7 C20 -172.9(2) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C20 C7 C8 C9 174.9(2) . . . . ? C7 C8 C9 N1 -179.4(2) . . . . ? C7 C8 C9 C4 -1.3(3) . . . . ? C2 N1 C9 C8 177.9(2) . . . . ? C2 N1 C9 C4 -0.5(2) . . . . ? N3 C4 C9 C8 -178.23(19) . . . . ? C5 C4 C9 C8 0.7(3) . . . . ? N3 C4 C9 N1 0.3(2) . . . . ? C5 C4 C9 N1 179.23(19) . . . . ? N1 C2 N10 C11 -174.5(2) . . . . ? N3 C2 N10 C11 7.0(3) . . . . ? C2 N10 C11 O11 3.7(3) . . . . ? C2 N10 C11 N12 -177.53(19) . . . . ? O11 C11 N12 C13 -8.2(3) . . . . ? N10 C11 N12 C13 173.07(19) . . . . ? C11 N12 C13 C14 175.3(2) . . . . ? C6 C5 C15 O16 -151.77(19) . . . . ? C4 C5 C15 O16 24.4(3) . . . . ? C6 C5 C15 C19 88.8(2) . . . . ? C4 C5 C15 C19 -95.0(2) . . . . ? C5 C15 O16 C17 -134.24(17) . . . . ? C19 C15 O16 C17 -9.4(2) . . . . ? C15 O16 C17 C18 -13.5(2) . . . . ? O16 C17 C18 C19 30.7(2) . . . . ? C17 C18 C19 C15 -35.1(2) . . . . ? O16 C15 C19 C18 27.9(2) . . . . ? C5 C15 C19 C18 148.97(18) . . . . ? C6 C7 C20 C21 129.0(2) . . . . ? C8 C7 C20 C21 -45.6(3) . . . . ? C6 C7 C20 C25 -52.3(3) . . . . ? C8 C7 C20 C25 133.1(2) . . . . ? C25 C20 C21 N22 0.9(3) . . . . ? C7 C20 C21 N22 179.7(2) . . . . ? C20 C21 N22 C23 0.4(3) . . . . ? C21 N22 C23 N24 -1.4(3) . . . . ? C21 N22 C23 C26 -178.18(18) . . . . ? N22 C23 N24 C25 1.0(3) . . . . ? C26 C23 N24 C25 177.74(19) . . . . ? C23 N24 C25 C20 0.4(3) . . . . ? C21 C20 C25 N24 -1.3(3) . . . . ? C7 C20 C25 N24 180.0(2) . . . . ? N22 C23 C26 O29 -40.0(2) . . . . ? N24 C23 C26 O29 142.96(18) . . . . ? N22 C23 C26 C28 -161.81(19) . . . . ? N24 C23 C26 C28 21.1(3) . . . . ? N22 C23 C26 C27 75.4(2) . . . . ? N24 C23 C26 C27 -101.6(2) . . . . ? C39 N31 C32 N33 -1.8(3) . . . . ? C39 N31 C32 N40 177.5(2) . . . . ? N31 C32 N33 C34 0.5(3) . . . . ? N40 C32 N33 C34 -178.8(2) . . . . ? C32 N33 C34 C35 179.3(3) . . . . ? C32 N33 C34 C39 1.1(3) . . . . ? N33 C34 C35 C36 -177.6(3) . . . . ? C39 C34 C35 C36 0.4(4) . . . . ? N33 C34 C35 C45 0.3(5) . . . . ? C39 C34 C35 C45 178.2(3) . . . . ? C34 C35 C36 F36 176.2(2) . . . . ? C45 C35 C36 F36 -1.7(4) . . . . ? C34 C35 C36 C37 0.2(4) . . . . ? C45 C35 C36 C37 -177.7(3) . . . . ? F36 C36 C37 C38 -176.4(2) . . . . ? C35 C36 C37 C38 -0.4(4) . . . . ? F36 C36 C37 C50 1.3(3) . . . . ? C35 C36 C37 C50 177.3(2) . . . . ? C36 C37 C38 C39 0.1(3) . . . . ? C50 C37 C38 C39 -177.7(2) . . . . ? C37 C38 C39 C34 0.5(3) . . . . ? C37 C38 C39 N31 -179.7(2) . . . . ? N33 C34 C39 C38 177.7(2) . . . . ? C35 C34 C39 C38 -0.7(4) . . . . ? N33 C34 C39 N31 -2.2(3) . . . . ? C35 C34 C39 N31 179.4(2) . . . . ? C32 N31 C39 C38 -177.4(2) . . . . ? C32 N31 C39 C34 2.4(2) . . . . ? N31 C32 N40 C41 179.5(2) . . . . ? N33 C32 N40 C41 -1.3(4) . . . . ? C32 N40 C41 O41 -0.7(4) . . . . ? C32 N40 C41 N42 179.8(3) . . . . ? O41 C41 N42 C43B 29.8(6) . . . . ? N40 C41 N42 C43B -150.7(4) . . . . ? O41 C41 N42 C43A -10.2(6) . . . . ? N40 C41 N42 C43A 169.2(4) . . . . ? C41 N42 C43A C44A 106.5(4) . . . . ? C43B N42 C43A C44A 5.8(4) . . . . ? C41 N42 C43B C44B -93.2(4) . . . . ? C43A N42 C43B C44B 6.7(4) . . . . ? C36 C35 C45 O46 -139.0(3) . . . . ? C34 C35 C45 O46 43.4(4) . . . . ? C36 C35 C45 C49 104.0(3) . . . . ? C34 C35 C45 C49 -73.6(3) . . . . ? C35 C45 O46 C47 -166.6(2) . . . . ? C49 C45 O46 C47 -43.1(3) . . . . ? C45 O46 C47 C48 40.4(3) . . . . ? O46 C47 C48 C49 -21.2(3) . . . . ? O46 C45 C49 C48 28.1(3) . . . . ? C35 C45 C49 C48 147.4(2) . . . . ? C47 C48 C49 C45 -4.1(3) . . . . ? C36 C37 C50 C55 41.5(3) . . . . ? C38 C37 C50 C55 -140.8(2) . . . . ? C36 C37 C50 C51 -141.2(2) . . . . ? C38 C37 C50 C51 36.4(3) . . . . ? C55 C50 C51 N52 0.4(3) . . . . ? C37 C50 C51 N52 -177.1(2) . . . . ? C50 C51 N52 C53 -1.2(3) . . . . ? C51 N52 C53 N54 0.9(3) . . . . ? C51 N52 C53 C56 177.63(18) . . . . ? N52 C53 N54 C55 0.1(3) . . . . ? C56 C53 N54 C55 -176.57(18) . . . . ? C53 N54 C55 C50 -1.0(3) . . . . ? C51 C50 C55 N54 0.7(3) . . . . ? C37 C50 C55 N54 178.2(2) . . . . ? N54 C53 C56 O59 -150.41(18) . . . . ? N52 C53 C56 O59 32.6(2) . . . . ? N54 C53 C56 C57 -28.0(3) . . . . ? N52 C53 C56 C57 155.01(19) . . . . ? N54 C53 C56 C58 93.6(2) . . . . ? N52 C53 C56 C58 -83.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 64.88 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.183 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.035