# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_mjh71_compound_8b _database_code_depnum_ccdc_archive 'CCDC 860567' #TrackingRef 'web_deposit_cif_file_0_BillClegg_1325609978.angew.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H26 N4 O3' _chemical_formula_sum 'C29 H26 N4 O3' _chemical_formula_weight 478.54 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.055(3) _cell_length_b 7.5478(12) _cell_length_c 19.591(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.937(2) _cell_angle_gamma 90.00 _cell_volume 2476.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9917 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.55 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.993 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Diamond Light Source Station I19' _diffrn_radiation_monochromator 'double crystal silicon' _diffrn_measurement_device_type 'Crystal Logic diffractometer and Rigaku Saturn 724+ CCD' _diffrn_measurement_method 'thick-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24824 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 27.56 _reflns_number_total 6127 _reflns_number_gt 4800 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Rigaku CrystalClear' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0936P)^2^+1.0836P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.054(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6127 _refine_ls_number_parameters 523 _refine_ls_number_restraints 818 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1871 _refine_ls_wR_factor_gt 0.1782 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.008 _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 0.40975(9) 0.5744(2) 0.79812(7) 0.0543(4) Uani 1 1 d . . . O2 O 0.28622(8) 1.06181(18) 0.68967(7) 0.0460(3) Uani 1 1 d . . . O3 O 0.43541(8) 0.33531(17) 0.54030(7) 0.0434(3) Uani 1 1 d . A . H3 H 0.4615(16) 0.320(4) 0.5030(14) 0.069(8) Uiso 1 1 d . . . N1 N 0.35310(9) 0.8412(2) 0.75873(7) 0.0392(3) Uani 1 1 d . . . N2 N 0.45331(9) 0.7679(2) 0.53445(7) 0.0391(3) Uani 1 1 d . . . C1 C 0.41808(10) 0.6998(2) 0.58650(8) 0.0364(4) Uani 1 1 d . . . C2 C 0.44612(10) 0.5423(2) 0.63046(9) 0.0379(4) Uani 1 1 d . A . H2 H 0.4824 0.5850 0.6735 0.045 Uiso 1 1 calc R . . C3 C 0.37229(11) 0.4582(2) 0.65205(10) 0.0435(4) Uani 1 1 d . . . H3A H 0.3381 0.4048 0.6107 0.052 Uiso 1 1 calc R . . H3B H 0.3897 0.3624 0.6861 0.052 Uiso 1 1 calc R . . C4 C 0.32391(11) 0.5936(2) 0.68412(9) 0.0409(4) Uani 1 1 d . . . H4 H 0.2744 0.5329 0.6923 0.049 Uiso 1 1 calc R . . C5 C 0.36797(11) 0.6597(2) 0.75365(9) 0.0418(4) Uani 1 1 d . . . C6 C 0.30933(10) 0.9108(2) 0.69736(9) 0.0391(4) Uani 1 1 d . . . C7 C 0.29769(10) 0.7642(2) 0.64231(9) 0.0397(4) Uani 1 1 d . . . H7 H 0.2405 0.7563 0.6185 0.048 Uiso 1 1 calc R . . C8 C 0.35066(10) 0.7934(2) 0.59093(8) 0.0370(4) Uani 1 1 d . B . C9 C 0.40663(11) 0.8996(3) 0.50768(9) 0.0411(4) Uani 1 1 d . B . H9 H 0.4159 0.9702 0.4699 0.049 Uiso 1 1 calc R . . C10 C 0.37778(11) 0.9399(2) 0.82172(9) 0.0403(4) Uani 1 1 d . . . C11 C 0.41692(13) 1.1004(3) 0.82085(11) 0.0519(5) Uani 1 1 d . . . H11 H 0.4280 1.1463 0.7785 0.062 Uiso 1 1 calc R . . C12 C 0.43972(15) 1.1932(3) 0.88246(12) 0.0606(6) Uani 1 1 d . . . H12 H 0.4664 1.3036 0.8823 0.073 Uiso 1 1 calc R . . C13 C 0.42392(14) 1.1261(3) 0.94402(11) 0.0581(5) Uani 1 1 d . . . H13 H 0.4397 1.1903 0.9861 0.070 Uiso 1 1 calc R . . C14 C 0.38538(14) 0.9665(3) 0.94424(10) 0.0555(5) Uani 1 1 d . . . H14 H 0.3750 0.9202 0.9868 0.067 Uiso 1 1 calc R . . C15 C 0.36141(12) 0.8719(3) 0.88317(10) 0.0472(4) Uani 1 1 d . . . H15 H 0.3342 0.7622 0.8835 0.057 Uiso 1 1 calc R . . N4 N 0.49173(9) 0.4224(2) 0.59410(8) 0.0416(4) Uani 1 1 d DU . . C16 C 0.5392(3) 0.2887(8) 0.6346(3) 0.0388(14) Uani 0.698(8) 1 d PDU A 1 C17 C 0.5073(5) 0.1276(9) 0.6494(4) 0.0422(17) Uani 0.698(8) 1 d PDU A 1 H17 H 0.4522 0.1033 0.6335 0.051 Uiso 0.698(8) 1 calc PR A 1 C18 C 0.5566(4) 0.0023(11) 0.6876(5) 0.0507(14) Uani 0.698(8) 1 d PDU A 1 H18 H 0.5357 -0.1089 0.6982 0.061 Uiso 0.698(8) 1 calc PR A 1 C19 C 0.6357(3) 0.0409(6) 0.7099(3) 0.0614(11) Uani 0.698(8) 1 d PDU A 1 H19 H 0.6698 -0.0441 0.7362 0.074 Uiso 0.698(8) 1 calc PR A 1 C20 C 0.6669(2) 0.2033(5) 0.6944(3) 0.0624(12) Uani 0.698(8) 1 d PDU A 1 H20 H 0.7222 0.2262 0.7097 0.075 Uiso 0.698(8) 1 calc PR A 1 C21 C 0.6188(2) 0.3329(5) 0.6570(2) 0.0497(9) Uani 0.698(8) 1 d PDU A 1 C22 C 0.6529(2) 0.5065(6) 0.6391(3) 0.0685(12) Uani 0.698(8) 1 d PDU A 1 H22A H 0.7104 0.5090 0.6579 0.082 Uiso 0.698(8) 1 calc PR A 1 H22B H 0.6267 0.6038 0.6592 0.082 Uiso 0.698(8) 1 calc PR A 1 H22C H 0.6439 0.5200 0.5885 0.082 Uiso 0.698(8) 1 calc PR A 1 C16A C 0.5336(7) 0.3012(17) 0.6496(7) 0.037(3) Uani 0.302(8) 1 d PDU A 2 C17A C 0.5114(12) 0.122(2) 0.6531(12) 0.048(5) Uani 0.302(8) 1 d PDU A 2 H17A H 0.4648 0.0811 0.6228 0.058 Uiso 0.302(8) 1 calc PR A 2 C18A C 0.5551(9) 0.004(3) 0.6989(10) 0.055(4) Uani 0.302(8) 1 d PDU A 2 H18A H 0.5367 -0.1142 0.7003 0.066 Uiso 0.302(8) 1 calc PR A 2 C19A C 0.6243(6) 0.0534(12) 0.7423(6) 0.058(2) Uani 0.302(8) 1 d PDU A 2 H19A H 0.6538 -0.0288 0.7739 0.070 Uiso 0.302(8) 1 calc PR A 2 C20A C 0.6497(5) 0.2256(10) 0.7388(7) 0.067(3) Uani 0.302(8) 1 d PDU A 2 H20A H 0.6978 0.2622 0.7683 0.080 Uiso 0.302(8) 1 calc PR A 2 C21A C 0.6069(4) 0.3477(9) 0.6931(7) 0.054(2) Uani 0.302(8) 1 d PDU A 2 C22A C 0.6374(5) 0.5341(10) 0.6939(11) 0.102(6) Uani 0.302(8) 1 d PDU A 2 H22D H 0.6885 0.5428 0.7265 0.153 Uiso 0.302(8) 1 calc PR A 2 H22E H 0.5986 0.6147 0.7085 0.153 Uiso 0.302(8) 1 calc PR A 2 H22F H 0.6451 0.5668 0.6472 0.153 Uiso 0.302(8) 1 calc PR A 2 N3 N 0.34419(9) 0.9229(2) 0.53991(7) 0.0401(3) Uani 1 1 d DU . . C23 C 0.2794(8) 1.0511(18) 0.5185(8) 0.048(2) Uani 0.534(3) 1 d PDU B 1 H23A H 0.3025 1.1669 0.5092 0.058 Uiso 0.534(3) 1 calc PR B 1 H23B H 0.2499 1.0677 0.5570 0.058 Uiso 0.534(3) 1 calc PR B 1 C24 C 0.2221(4) 0.9916(14) 0.4545(4) 0.055(2) Uani 0.534(3) 1 d PDU B 1 C25 C 0.2011(5) 0.8168(14) 0.4445(5) 0.079(2) Uani 0.534(3) 1 d PDU B 1 H25 H 0.2272 0.7321 0.4770 0.095 Uiso 0.534(3) 1 calc PR B 1 C26 C 0.1424(5) 0.7565(15) 0.3880(4) 0.103(2) Uani 0.534(3) 1 d PDU B 1 H26 H 0.1285 0.6348 0.3822 0.124 Uiso 0.534(3) 1 calc PR B 1 C27 C 0.1069(4) 0.8836(17) 0.3424(4) 0.108(3) Uani 0.534(3) 1 d PDU B 1 H27 H 0.0676 0.8487 0.3037 0.130 Uiso 0.534(3) 1 calc PR B 1 C28 C 0.1265(6) 1.0596(16) 0.3510(4) 0.120(3) Uani 0.534(3) 1 d PDU B 1 H28 H 0.1010 1.1453 0.3188 0.144 Uiso 0.534(3) 1 calc PR B 1 C29 C 0.1841(4) 1.1103(10) 0.4075(2) 0.0832(18) Uani 0.534(3) 1 d PDU B 1 H29 H 0.1974 1.2322 0.4135 0.100 Uiso 0.534(3) 1 calc PR B 1 C23A C 0.2742(14) 1.026(3) 0.5098(17) 0.052(4) Uani 0.303(5) 1 d PDU B 2 H23C H 0.2916 1.1276 0.4843 0.063 Uiso 0.303(5) 1 calc PR B 2 H23D H 0.2500 1.0744 0.5479 0.063 Uiso 0.303(5) 1 calc PR B 2 C24A C 0.2120(6) 0.9255(13) 0.4614(6) 0.041(2) Uani 0.303(5) 1 d PDU B 2 C25A C 0.2196(7) 0.7528(14) 0.4425(7) 0.054(2) Uani 0.303(5) 1 d PDU B 2 H25A H 0.2666 0.6902 0.4627 0.065 Uiso 0.303(5) 1 calc PR B 2 C26A C 0.1617(7) 0.6645(16) 0.3950(6) 0.066(2) Uani 0.303(5) 1 d PDU B 2 H26A H 0.1705 0.5461 0.3819 0.079 Uiso 0.303(5) 1 calc PR B 2 C27A C 0.0923(6) 0.7485(16) 0.3675(7) 0.090(3) Uani 0.303(5) 1 d PDU B 2 H27A H 0.0513 0.6895 0.3362 0.108 Uiso 0.303(5) 1 calc PR B 2 C28A C 0.0837(9) 0.922(2) 0.3865(11) 0.126(6) Uani 0.303(5) 1 d PDU B 2 H28A H 0.0346 0.9813 0.3704 0.151 Uiso 0.303(5) 1 calc PR B 2 C29A C 0.1458(8) 1.0102(19) 0.4288(8) 0.108(4) Uani 0.303(5) 1 d PDU B 2 H29A H 0.1416 1.1344 0.4351 0.130 Uiso 0.303(5) 1 calc PR B 2 C23B C 0.2825(15) 1.062(4) 0.5263(14) 0.054(6) Uani 0.163(4) 1 d PDU B 3 H23E H 0.3089 1.1769 0.5214 0.065 Uiso 0.163(4) 1 calc PR B 3 H23F H 0.2563 1.0712 0.5671 0.065 Uiso 0.163(4) 1 calc PR B 3 C24B C 0.2194(9) 1.032(3) 0.4627(8) 0.045(4) Uani 0.163(4) 1 d PDU B 3 C25B C 0.1428(6) 0.9921(16) 0.4686(6) 0.040(2) Uani 0.163(4) 1 d PDU B 3 H25C H 0.1295 1.0026 0.5134 0.048 Uiso 0.163(4) 1 calc PR B 3 C26B C 0.0834(9) 0.938(3) 0.4154(7) 0.069(4) Uani 0.163(4) 1 d PDU B 3 H26C H 0.0354 0.8827 0.4220 0.083 Uiso 0.163(4) 1 calc PR B 3 C27B C 0.1015(10) 0.973(3) 0.3509(8) 0.066(4) Uani 0.163(4) 1 d PDU B 3 H27C H 0.0588 0.9722 0.3119 0.079 Uiso 0.163(4) 1 calc PR B 3 C28B C 0.1769(10) 1.010(3) 0.3390(7) 0.091(5) Uani 0.163(4) 1 d PDU B 3 H28C H 0.1882 1.0115 0.2933 0.109 Uiso 0.163(4) 1 calc PR B 3 C29B C 0.2362(8) 1.044(2) 0.3974(6) 0.068(4) Uani 0.163(4) 1 d PDU B 3 H29C H 0.2884 1.0757 0.3915 0.082 Uiso 0.163(4) 1 calc PR B 3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0614(9) 0.0505(8) 0.0498(8) 0.0058(6) 0.0075(6) 0.0125(7) O2 0.0488(7) 0.0479(7) 0.0426(7) 0.0022(5) 0.0118(5) 0.0101(6) O3 0.0431(7) 0.0455(7) 0.0434(7) -0.0075(5) 0.0125(5) -0.0029(5) N1 0.0389(7) 0.0428(8) 0.0366(7) 0.0015(6) 0.0093(6) 0.0022(6) N2 0.0407(7) 0.0396(7) 0.0387(7) -0.0018(6) 0.0120(6) -0.0014(6) C1 0.0354(8) 0.0381(8) 0.0369(8) -0.0025(6) 0.0098(6) -0.0019(6) C2 0.0390(8) 0.0366(8) 0.0392(8) -0.0014(6) 0.0103(7) -0.0003(7) C3 0.0469(10) 0.0388(9) 0.0489(10) -0.0012(7) 0.0193(8) -0.0020(7) C4 0.0392(9) 0.0434(9) 0.0432(9) -0.0008(7) 0.0158(7) -0.0035(7) C5 0.0414(9) 0.0434(9) 0.0431(9) 0.0035(7) 0.0147(7) 0.0031(7) C6 0.0347(8) 0.0472(10) 0.0374(8) 0.0018(7) 0.0115(7) 0.0028(7) C7 0.0334(8) 0.0475(10) 0.0388(8) -0.0016(7) 0.0083(7) 0.0021(7) C8 0.0339(8) 0.0426(9) 0.0343(8) -0.0012(6) 0.0056(6) 0.0006(7) C9 0.0432(9) 0.0466(10) 0.0348(8) 0.0002(7) 0.0103(7) 0.0001(7) C10 0.0373(8) 0.0444(9) 0.0395(8) 0.0007(7) 0.0081(7) 0.0034(7) C11 0.0550(11) 0.0525(11) 0.0481(10) 0.0040(8) 0.0093(9) -0.0047(9) C12 0.0648(13) 0.0531(12) 0.0605(12) -0.0013(10) 0.0034(10) -0.0086(10) C13 0.0588(12) 0.0630(13) 0.0479(11) -0.0076(9) -0.0017(9) 0.0040(10) C14 0.0607(12) 0.0668(13) 0.0387(9) 0.0023(9) 0.0083(9) 0.0041(10) C15 0.0493(10) 0.0512(11) 0.0418(9) 0.0024(8) 0.0108(8) -0.0015(8) N4 0.0392(7) 0.0381(7) 0.0483(8) -0.0054(6) 0.0102(6) -0.0004(6) C16 0.042(2) 0.0373(19) 0.039(2) -0.0065(17) 0.0117(16) 0.0056(13) C17 0.047(3) 0.044(3) 0.037(3) -0.002(2) 0.009(2) 0.002(2) C18 0.061(3) 0.038(2) 0.051(2) -0.0010(18) 0.0057(19) -0.004(2) C19 0.059(2) 0.0499(18) 0.067(3) 0.008(2) -0.008(2) 0.0071(15) C20 0.0483(17) 0.0569(19) 0.074(3) 0.0075(18) -0.0080(17) -0.0032(14) C21 0.0479(17) 0.0464(16) 0.0527(19) 0.0016(14) 0.0041(15) -0.0023(12) C22 0.0487(18) 0.057(2) 0.093(3) 0.014(2) -0.0046(19) -0.0128(15) C16A 0.030(3) 0.033(3) 0.054(7) -0.019(3) 0.019(3) 0.002(2) C17A 0.043(8) 0.042(7) 0.057(9) 0.000(6) 0.004(6) -0.016(6) C18A 0.054(6) 0.047(6) 0.063(8) 0.006(5) 0.008(5) 0.003(5) C19A 0.056(5) 0.049(4) 0.064(6) 0.008(4) -0.004(5) 0.003(3) C20A 0.042(4) 0.051(4) 0.096(8) -0.006(4) -0.017(4) 0.005(3) C21A 0.034(3) 0.033(3) 0.090(7) -0.003(4) 0.002(4) -0.001(2) C22A 0.042(4) 0.038(4) 0.205(17) 0.002(6) -0.031(7) -0.005(3) N3 0.0377(7) 0.0474(8) 0.0345(7) 0.0020(6) 0.0052(6) 0.0044(6) C23 0.046(5) 0.066(6) 0.033(3) 0.005(4) 0.008(3) 0.017(4) C24 0.040(3) 0.086(7) 0.039(3) 0.010(4) 0.011(2) 0.008(3) C25 0.073(4) 0.109(6) 0.051(3) 0.001(5) 0.000(3) -0.021(4) C26 0.074(5) 0.168(7) 0.064(4) -0.029(5) 0.004(3) -0.032(5) C27 0.045(3) 0.220(8) 0.055(3) -0.034(5) -0.006(2) 0.027(5) C28 0.095(6) 0.195(8) 0.061(3) -0.006(5) -0.011(4) 0.080(6) C29 0.086(4) 0.119(5) 0.044(2) 0.012(3) 0.010(2) 0.055(3) C23A 0.047(6) 0.054(6) 0.055(10) 0.002(5) 0.005(5) 0.009(4) C24A 0.039(4) 0.048(5) 0.036(4) -0.002(4) 0.005(3) 0.007(4) C25A 0.057(5) 0.058(5) 0.041(4) -0.009(4) -0.005(4) -0.001(4) C26A 0.057(5) 0.092(6) 0.049(4) -0.020(5) 0.009(4) -0.010(4) C27A 0.048(5) 0.119(8) 0.093(7) -0.031(6) -0.016(5) -0.009(5) C28A 0.089(8) 0.152(9) 0.111(11) -0.050(10) -0.045(8) 0.046(7) C29A 0.093(7) 0.107(7) 0.101(8) -0.042(7) -0.040(7) 0.050(6) C23B 0.038(9) 0.059(12) 0.058(9) 0.018(9) -0.009(9) 0.008(7) C24B 0.037(5) 0.054(8) 0.045(6) -0.008(6) 0.008(5) 0.013(5) C25B 0.038(5) 0.043(5) 0.039(5) 0.009(5) 0.007(4) 0.001(4) C26B 0.056(7) 0.101(11) 0.040(7) 0.002(7) -0.020(5) 0.022(7) C27B 0.053(7) 0.093(12) 0.045(7) -0.029(8) -0.009(6) 0.037(8) C28B 0.081(9) 0.142(13) 0.044(6) 0.006(8) -0.002(6) 0.008(10) C29B 0.045(6) 0.104(10) 0.055(6) 0.013(7) 0.006(5) 0.010(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.203(2) . ? O2 C6 1.206(2) . ? O3 H3 0.93(3) . ? O3 N4 1.4427(19) . ? N1 C5 1.400(2) . ? N1 C6 1.392(2) . ? N1 C10 1.435(2) . ? N2 C1 1.377(2) . ? N2 C9 1.318(2) . ? C1 C2 1.493(2) . ? C1 C8 1.366(2) . ? C2 H2 1.000 . ? C2 C3 1.539(2) . ? C2 N4 1.464(2) . ? C3 H3A 0.990 . ? C3 H3B 0.990 . ? C3 C4 1.522(3) . ? C4 H4 1.000 . ? C4 C5 1.510(3) . ? C4 C7 1.545(3) . ? C6 C7 1.532(3) . ? C7 H7 1.000 . ? C7 C8 1.491(2) . ? C8 N3 1.387(2) . ? C9 H9 0.950 . ? C9 N3 1.349(2) . ? C10 C11 1.384(3) . ? C10 C15 1.385(3) . ? C11 H11 0.950 . ? C11 C12 1.386(3) . ? C12 H12 0.950 . ? C12 C13 1.381(3) . ? C13 H13 0.950 . ? C13 C14 1.373(3) . ? C14 H14 0.950 . ? C14 C15 1.386(3) . ? C15 H15 0.950 . ? N4 C16 1.435(5) . ? N4 C16A 1.494(11) . ? C16 C17 1.385(7) . ? C16 C21 1.385(6) . ? C17 H17 0.950 . ? C17 C18 1.386(6) . ? C18 H18 0.950 . ? C18 C19 1.369(7) . ? C19 H19 0.950 . ? C19 C20 1.392(5) . ? C20 H20 0.950 . ? C20 C21 1.393(4) . ? C21 C22 1.502(5) . ? C22 H22A 0.980 . ? C22 H22B 0.980 . ? C22 H22C 0.980 . ? C16A C17A 1.409(12) . ? C16A C21A 1.417(11) . ? C17A H17A 0.950 . ? C17A C18A 1.377(13) . ? C18A H18A 0.950 . ? C18A C19A 1.369(13) . ? C19A H19A 0.950 . ? C19A C20A 1.377(11) . ? C20A H20A 0.950 . ? C20A C21A 1.391(10) . ? C21A C22A 1.500(9) . ? C22A H22D 0.980 . ? C22A H22E 0.980 . ? C22A H22F 0.980 . ? N3 C23 1.469(8) . ? N3 C23A 1.453(12) . ? N3 C23B 1.475(15) . ? C23 H23A 0.990 . ? C23 H23B 0.990 . ? C23 C24 1.504(9) . ? C24 C25 1.371(10) . ? C24 C29 1.359(8) . ? C25 H25 0.950 . ? C25 C26 1.420(8) . ? C26 H26 0.950 . ? C26 C27 1.371(11) . ? C27 H27 0.950 . ? C27 C28 1.372(11) . ? C28 H28 0.950 . ? C28 C29 1.386(9) . ? C29 H29 0.950 . ? C23A H23C 0.990 . ? C23A H23D 0.990 . ? C23A C24A 1.489(12) . ? C24A C25A 1.368(10) . ? C24A C29A 1.349(10) . ? C25A H25A 0.950 . ? C25A C26A 1.392(10) . ? C26A H26A 0.950 . ? C26A C27A 1.360(11) . ? C27A H27A 0.950 . ? C27A C28A 1.374(13) . ? C28A H28A 0.950 . ? C28A C29A 1.388(12) . ? C29A H29A 0.950 . ? C23B H23E 0.990 . ? C23B H23F 0.990 . ? C23B C24B 1.500(14) . ? C24B C25B 1.368(12) . ? C24B C29B 1.367(13) . ? C25B H25C 0.950 . ? C25B C26B 1.371(12) . ? C26B H26C 0.950 . ? C26B C27B 1.382(14) . ? C27B H27C 0.950 . ? C27B C28B 1.378(14) . ? C28B H28C 0.950 . ? C28B C29B 1.399(13) . ? C29B H29C 0.950 . ? 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 H3 O3 N4 106.3(16) . . ? C5 N1 C6 112.47(15) . . ? C5 N1 C10 122.81(14) . . ? C6 N1 C10 124.67(15) . . ? C1 N2 C9 105.09(15) . . ? N2 C1 C2 125.97(15) . . ? N2 C1 C8 110.18(15) . . ? C2 C1 C8 123.80(15) . . ? C1 C2 H2 108.0 . . ? C1 C2 C3 107.32(14) . . ? C1 C2 N4 110.70(14) . . ? H2 C2 C3 108.0 . . ? H2 C2 N4 108.0 . . ? C3 C2 N4 114.64(14) . . ? C2 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C2 C3 C4 111.88(15) . . ? H3A C3 H3B 107.9 . . ? H3A C3 C4 109.2 . . ? H3B C3 C4 109.2 . . ? C3 C4 H4 107.4 . . ? C3 C4 C5 112.21(15) . . ? C3 C4 C7 117.74(15) . . ? H4 C4 C5 107.4 . . ? H4 C4 C7 107.4 . . ? C5 C4 C7 104.32(14) . . ? O1 C5 N1 124.27(17) . . ? O1 C5 C4 126.97(18) . . ? N1 C5 C4 108.76(15) . . ? O2 C6 N1 124.98(17) . . ? O2 C6 C7 126.82(16) . . ? N1 C6 C7 108.20(15) . . ? C4 C7 C6 104.05(14) . . ? C4 C7 H7 110.9 . . ? C4 C7 C8 109.24(14) . . ? C6 C7 H7 110.9 . . ? C6 C7 C8 110.75(15) . . ? H7 C7 C8 110.9 . . ? C1 C8 C7 126.28(16) . . ? C1 C8 N3 105.73(15) . . ? C7 C8 N3 127.96(15) . . ? N2 C9 H9 123.7 . . ? N2 C9 N3 112.51(16) . . ? H9 C9 N3 123.7 . . ? N1 C10 C11 120.47(17) . . ? N1 C10 C15 118.73(17) . . ? C11 C10 C15 120.81(18) . . ? C10 C11 H11 120.4 . . ? C10 C11 C12 119.2(2) . . ? H11 C11 C12 120.4 . . ? C11 C12 H12 119.8 . . ? C11 C12 C13 120.4(2) . . ? H12 C12 C13 119.8 . . ? C12 C13 H13 120.1 . . ? C12 C13 C14 119.8(2) . . ? H13 C13 C14 120.1 . . ? C13 C14 H14 119.6 . . ? C13 C14 C15 120.8(2) . . ? H14 C14 C15 119.6 . . ? C10 C15 C14 119.0(2) . . ? C10 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? O3 N4 C2 107.19(13) . . ? O3 N4 C16 108.1(3) . . ? O3 N4 C16A 114.4(5) . . ? C2 N4 C16 117.5(3) . . ? C2 N4 C16A 104.4(6) . . ? N4 C16 C17 122.0(5) . . ? N4 C16 C21 115.0(4) . . ? C17 C16 C21 123.0(5) . . ? C16 C17 H17 120.3 . . ? C16 C17 C18 119.3(6) . . ? H17 C17 C18 120.3 . . ? C17 C18 H18 120.4 . . ? C17 C18 C19 119.1(6) . . ? H18 C18 C19 120.4 . . ? C18 C19 H19 119.6 . . ? C18 C19 C20 120.9(5) . . ? H19 C19 C20 119.6 . . ? C19 C20 H20 119.3 . . ? C19 C20 C21 121.4(3) . . ? H20 C20 C21 119.3 . . ? C16 C21 C20 116.2(3) . . ? C16 C21 C22 122.4(3) . . ? C20 C21 C22 121.3(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N4 C16A C17A 121.8(10) . . ? N4 C16A C21A 122.1(9) . . ? C17A C16A C21A 115.0(10) . . ? C16A C17A H17A 118.8 . . ? C16A C17A C18A 122.3(14) . . ? H17A C17A C18A 118.8 . . ? C17A C18A H18A 119.1 . . ? C17A C18A C19A 121.8(15) . . ? H18A C18A C19A 119.1 . . ? C18A C19A H19A 121.1 . . ? C18A C19A C20A 117.8(10) . . ? H19A C19A C20A 121.1 . . ? C19A C20A H20A 119.1 . . ? C19A C20A C21A 121.7(7) . . ? H20A C20A C21A 119.1 . . ? C16A C21A C20A 121.3(7) . . ? C16A C21A C22A 120.2(8) . . ? C20A C21A C22A 118.4(7) . . ? C21A C22A H22D 109.5 . . ? C21A C22A H22E 109.5 . . ? C21A C22A H22F 109.5 . . ? H22D C22A H22E 109.5 . . ? H22D C22A H22F 109.5 . . ? H22E C22A H22F 109.5 . . ? C8 N3 C9 106.47(14) . . ? C8 N3 C23 128.5(9) . . ? C8 N3 C23A 128.1(17) . . ? C8 N3 C23B 126.1(15) . . ? C9 N3 C23 124.8(9) . . ? C9 N3 C23A 122.7(17) . . ? C9 N3 C23B 127.4(16) . . ? N3 C23 H23A 109.2 . . ? N3 C23 H23B 109.2 . . ? N3 C23 C24 112.1(7) . . ? H23A C23 H23B 107.9 . . ? H23A C23 C24 109.2 . . ? H23B C23 C24 109.2 . . ? C23 C24 C25 121.1(8) . . ? C23 C24 C29 121.3(9) . . ? C25 C24 C29 117.4(7) . . ? C24 C25 H25 118.4 . . ? C24 C25 C26 123.1(8) . . ? H25 C25 C26 118.4 . . ? C25 C26 H26 121.9 . . ? C25 C26 C27 116.3(8) . . ? H26 C26 C27 121.9 . . ? C26 C27 H27 119.0 . . ? C26 C27 C28 122.0(7) . . ? H27 C27 C28 119.0 . . ? C27 C28 H28 120.5 . . ? C27 C28 C29 119.0(7) . . ? H28 C28 C29 120.5 . . ? C24 C29 C28 122.3(8) . . ? C24 C29 H29 118.9 . . ? C28 C29 H29 118.9 . . ? N3 C23A H23C 108.6 . . ? N3 C23A H23D 108.6 . . ? N3 C23A C24A 114.6(11) . . ? H23C C23A H23D 107.6 . . ? H23C C23A C24A 108.6 . . ? H23D C23A C24A 108.6 . . ? C23A C24A C25A 124.5(9) . . ? C23A C24A C29A 119.4(9) . . ? C25A C24A C29A 115.9(9) . . ? C24A C25A H25A 118.4 . . ? C24A C25A C26A 123.1(9) . . ? H25A C25A C26A 118.4 . . ? C25A C26A H26A 120.2 . . ? C25A C26A C27A 119.7(9) . . ? H26A C26A C27A 120.2 . . ? C26A C27A H27A 121.1 . . ? C26A C27A C28A 117.8(9) . . ? H27A C27A C28A 121.1 . . ? C27A C28A H28A 119.6 . . ? C27A C28A C29A 120.7(11) . . ? H28A C28A C29A 119.6 . . ? C24A C29A C28A 122.0(11) . . ? C24A C29A H29A 119.0 . . ? C28A C29A H29A 119.0 . . ? N3 C23B H23E 108.6 . . ? N3 C23B H23F 108.6 . . ? N3 C23B C24B 114.7(16) . . ? H23E C23B H23F 107.6 . . ? H23E C23B C24B 108.6 . . ? H23F C23B C24B 108.6 . . ? C23B C24B C25B 120.7(17) . . ? C23B C24B C29B 121.6(16) . . ? C25B C24B C29B 117.8(12) . . ? C24B C25B H25C 117.2 . . ? C24B C25B C26B 125.6(12) . . ? H25C C25B C26B 117.2 . . ? C25B C26B H26C 123.9 . . ? C25B C26B C27B 112.2(14) . . ? H26C C26B C27B 123.9 . . ? C26B C27B H27C 117.6 . . ? C26B C27B C28B 124.8(15) . . ? H27C C27B C28B 117.6 . . ? C27B C28B H28C 121.6 . . ? C27B C28B C29B 116.8(13) . . ? H28C C28B C29B 121.6 . . ? C24B C29B C28B 120.5(12) . . ? C24B C29B H29C 119.8 . . ? C28B C29B H29C 119.8 . . ? 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 N2 C1 C2 176.87(16) . . . . ? C9 N2 C1 C8 -0.69(19) . . . . ? N2 C1 C2 C3 -151.16(16) . . . . ? N2 C1 C2 N4 -25.4(2) . . . . ? C8 C1 C2 C3 26.1(2) . . . . ? C8 C1 C2 N4 151.86(16) . . . . ? C1 C2 C3 C4 -51.87(19) . . . . ? N4 C2 C3 C4 -175.27(15) . . . . ? C2 C3 C4 C5 -68.0(2) . . . . ? C2 C3 C4 C7 53.1(2) . . . . ? C6 N1 C5 O1 173.98(17) . . . . ? C6 N1 C5 C4 -5.6(2) . . . . ? C10 N1 C5 O1 -8.6(3) . . . . ? C10 N1 C5 C4 171.83(15) . . . . ? C3 C4 C5 O1 -38.2(3) . . . . ? C3 C4 C5 N1 141.33(16) . . . . ? C7 C4 C5 O1 -166.75(19) . . . . ? C7 C4 C5 N1 12.79(18) . . . . ? C5 N1 C6 O2 176.73(18) . . . . ? C5 N1 C6 C7 -4.3(2) . . . . ? C10 N1 C6 O2 -0.6(3) . . . . ? C10 N1 C6 C7 178.30(15) . . . . ? O2 C6 C7 C4 -169.10(18) . . . . ? O2 C6 C7 C8 73.6(2) . . . . ? N1 C6 C7 C4 12.00(18) . . . . ? N1 C6 C7 C8 -105.26(16) . . . . ? C3 C4 C7 C6 -139.69(16) . . . . ? C3 C4 C7 C8 -21.4(2) . . . . ? C5 C4 C7 C6 -14.59(17) . . . . ? C5 C4 C7 C8 103.72(16) . . . . ? N2 C1 C8 C7 -177.78(15) . . . . ? N2 C1 C8 N3 0.09(19) . . . . ? C2 C1 C8 C7 4.6(3) . . . . ? C2 C1 C8 N3 -177.53(15) . . . . ? C4 C7 C8 C1 -7.8(2) . . . . ? C4 C7 C8 N3 174.77(16) . . . . ? C6 C7 C8 C1 106.2(2) . . . . ? C6 C7 C8 N3 -71.2(2) . . . . ? C1 N2 C9 N3 1.1(2) . . . . ? C5 N1 C10 C11 132.1(2) . . . . ? C5 N1 C10 C15 -48.1(2) . . . . ? C6 N1 C10 C11 -50.8(3) . . . . ? C6 N1 C10 C15 128.97(19) . . . . ? N1 C10 C11 C12 179.71(19) . . . . ? C15 C10 C11 C12 -0.1(3) . . . . ? C10 C11 C12 C13 0.3(3) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? C12 C13 C14 C15 -0.5(4) . . . . ? N1 C10 C15 C14 179.77(18) . . . . ? C11 C10 C15 C14 -0.5(3) . . . . ? C13 C14 C15 C10 0.8(3) . . . . ? C1 C2 N4 O3 -73.14(17) . . . . ? C1 C2 N4 C16 164.9(3) . . . . ? C1 C2 N4 C16A 165.2(5) . . . . ? C3 C2 N4 O3 48.43(19) . . . . ? C3 C2 N4 C16 -73.5(3) . . . . ? C3 C2 N4 C16A -73.3(5) . . . . ? O3 N4 C16 C17 -36.8(7) . . . . ? O3 N4 C16 C21 142.8(4) . . . . ? C2 N4 C16 C17 84.6(6) . . . . ? C2 N4 C16 C21 -95.8(5) . . . . ? N4 C16 C17 C18 178.7(5) . . . . ? C21 C16 C17 C18 -0.9(8) . . . . ? C16 C17 C18 C19 0.1(8) . . . . ? C17 C18 C19 C20 -0.2(9) . . . . ? C18 C19 C20 C21 1.1(9) . . . . ? N4 C16 C21 C20 -177.9(4) . . . . ? N4 C16 C21 C22 -1.0(7) . . . . ? C17 C16 C21 C20 1.7(8) . . . . ? C17 C16 C21 C22 178.6(6) . . . . ? C19 C20 C21 C16 -1.8(7) . . . . ? C19 C20 C21 C22 -178.7(4) . . . . ? O3 N4 C16A C17A -7.9(19) . . . . ? O3 N4 C16A C21A 159.2(10) . . . . ? C2 N4 C16A C17A 108.9(16) . . . . ? C2 N4 C16A C21A -83.9(13) . . . . ? N4 C16A C17A C18A 172.3(11) . . . . ? C21A C16A C17A C18A 4(2) . . . . ? C16A C17A C18A C19A -2.1(16) . . . . ? C17A C18A C19A C20A -0.4(11) . . . . ? C18A C19A C20A C21A 0.4(17) . . . . ? C19A C20A C21A C16A 2.1(18) . . . . ? C19A C20A C21A C22A 178.2(11) . . . . ? N4 C16A C21A C20A -172.3(11) . . . . ? N4 C16A C21A C22A 11.7(19) . . . . ? C17A C16A C21A C20A -4(2) . . . . ? C17A C16A C21A C22A 179.7(16) . . . . ? N2 C9 N3 C8 -1.0(2) . . . . ? N2 C9 N3 C23 -175.6(5) . . . . ? N2 C9 N3 C23A -163.7(8) . . . . ? N2 C9 N3 C23B 176.7(11) . . . . ? C1 C8 N3 C9 0.53(19) . . . . ? C1 C8 N3 C23 174.9(5) . . . . ? C1 C8 N3 C23A 161.9(9) . . . . ? C1 C8 N3 C23B -177.2(11) . . . . ? C7 C8 N3 C9 178.36(17) . . . . ? C7 C8 N3 C23 -7.3(6) . . . . ? C7 C8 N3 C23A -20.2(9) . . . . ? C7 C8 N3 C23B 0.6(11) . . . . ? C8 N3 C23 C24 -98.4(13) . . . . ? C9 N3 C23 C24 75.0(15) . . . . ? N3 C23 C24 C25 37.9(19) . . . . ? N3 C23 C24 C29 -147.7(10) . . . . ? C23 C24 C25 C26 174.6(11) . . . . ? C29 C24 C25 C26 0.0(14) . . . . ? C24 C25 C26 C27 0.4(14) . . . . ? C25 C26 C27 C28 -0.5(14) . . . . ? C26 C27 C28 C29 0.2(15) . . . . ? C23 C24 C29 C28 -174.9(11) . . . . ? C25 C24 C29 C28 -0.3(12) . . . . ? C27 C28 C29 C24 0.2(13) . . . . ? C8 N3 C23A C24A -73(3) . . . . ? C9 N3 C23A C24A 86(3) . . . . ? N3 C23A C24A C25A -4(4) . . . . ? N3 C23A C24A C29A -178(2) . . . . ? C23A C24A C25A C26A -177(2) . . . . ? C29A C24A C25A C26A -3(2) . . . . ? C24A C25A C26A C27A -3(2) . . . . ? C25A C26A C27A C28A 2(2) . . . . ? C26A C27A C28A C29A 4(3) . . . . ? C23A C24A C29A C28A -176(3) . . . . ? C25A C24A C29A C28A 9(3) . . . . ? C27A C28A C29A C24A -10(3) . . . . ? C8 N3 C23B C24B -105(2) . . . . ? C9 N3 C23B C24B 77(3) . . . . ? N3 C23B C24B C25B 111(3) . . . . ? N3 C23B C24B C29B -69(4) . . . . ? C23B C24B C25B C26B -170.2(19) . . . . ? C29B C24B C25B C26B 10(3) . . . . ? C24B C25B C26B C27B -17(3) . . . . ? C25B C26B C27B C28B 18(4) . . . . ? C26B C27B C28B C29B -12(4) . . . . ? C23B C24B C29B C28B 178(2) . . . . ? C25B C24B C29B C28B -2(3) . . . . ? C27B C28B C29B C24B 3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 N2 0.93(3) 1.87(3) 2.722(2) 151(2) 3_666 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.045 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.049 data_mjh68_compound_9c _database_code_depnum_ccdc_archive 'CCDC 860568' #TrackingRef 'MJH68.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H24 F3 N3 O5' _chemical_formula_sum 'C27 H24 F3 N3 O5' _chemical_formula_weight 527.49 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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.988(10) _cell_length_b 7.353(7) _cell_length_c 29.70(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.027(8) _cell_angle_gamma 90.00 _cell_volume 2390(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4077 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 25.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.988 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Diamond Light Source Station I19' _diffrn_radiation_monochromator 'double crystal silicon' _diffrn_measurement_device_type 'Crystal Logic diffractometer and Rigaku Saturn 724+ CCD' _diffrn_measurement_method 'thick-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21186 _diffrn_reflns_av_R_equivalents 0.1064 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 21.25 _reflns_number_total 2913 _reflns_number_gt 1923 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Rigaku CrystalClear' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.20(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2913 _refine_ls_number_parameters 344 _refine_ls_number_restraints 396 _refine_ls_R_factor_all 0.2693 _refine_ls_R_factor_gt 0.2297 _refine_ls_wR_factor_ref 0.6335 _refine_ls_wR_factor_gt 0.6078 _refine_ls_goodness_of_fit_ref 2.681 _refine_ls_restrained_S_all 2.564 _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 N1 N 0.3776(10) 0.8800(19) 0.7086(5) 0.107(4) Uani 1 1 d U . . N2 N 0.4579(9) 0.814(2) 0.5474(4) 0.113(4) Uani 1 1 d U . . N3 N 0.5809(9) 0.978(2) 0.5979(5) 0.116(4) Uani 1 1 d U . . O1 O 0.2629(11) 0.6228(17) 0.7001(5) 0.139(5) Uani 1 1 d U . . O2 O 0.5236(11) 1.095(2) 0.7045(4) 0.152(5) Uani 1 1 d U . . O3 O 0.4704(15) 0.3741(18) 0.5501(7) 0.183(6) Uani 1 1 d U . . H3 H 0.5172 0.4573 0.5427 0.274 Uiso 1 1 calc R . . O4 O 0.3248(17) 0.548(3) 0.4815(6) 0.191(7) Uani 1 1 d U . . O5 O 0.2001(8) 0.656(2) 0.5316(3) 0.140(5) Uani 1 1 d U . . C1 C 0.3567(15) 0.707(3) 0.6981(6) 0.108(4) Uani 1 1 d U . . C2 C 0.4733(15) 0.635(3) 0.6806(6) 0.127(4) Uani 1 1 d U . . H2 H 0.5210 0.5691 0.7058 0.152 Uiso 1 1 calc R . . C3 C 0.4462(17) 0.508(2) 0.6432(7) 0.130(5) Uani 1 1 d U . . H3A H 0.3951 0.4091 0.6539 0.156 Uiso 1 1 calc R . . H3B H 0.5241 0.4531 0.6357 0.156 Uiso 1 1 calc R . . C4 C 0.3808(10) 0.585(2) 0.5991(6) 0.102(4) Uani 1 1 d U . . H4 H 0.3000 0.6315 0.6072 0.122 Uiso 1 1 calc R . . C5 C 0.4510(10) 0.744(2) 0.5891(5) 0.103(4) Uani 1 1 d U . . C6 C 0.5227(9) 0.830(3) 0.6205(5) 0.111(4) Uani 1 1 d U . . C7 C 0.5412(13) 0.802(3) 0.6702(6) 0.123(4) Uani 1 1 d U . . H7 H 0.6301 0.7850 0.6796 0.147 Uiso 1 1 calc R . . C8 C 0.4902(14) 0.943(3) 0.6982(6) 0.117(4) Uani 1 1 d U . . C9 C 0.5377(12) 0.954(2) 0.5531(6) 0.112(5) Uani 1 1 d U . . H9 H 0.5615 1.0271 0.5290 0.134 Uiso 1 1 calc R . . C10 C 0.3523(18) 0.452(3) 0.5590(8) 0.139(4) Uani 1 1 d U . . C11 C 0.2925(19) 0.561(3) 0.5168(8) 0.138(5) Uani 1 1 d U . . C12 C 0.1464(15) 0.795(4) 0.4951(7) 0.182(8) Uani 1 1 d U . . H12A H 0.1505 0.9168 0.5095 0.219 Uiso 1 1 calc R . . H12B H 0.2031 0.7979 0.4709 0.219 Uiso 1 1 calc R . . C13 C 0.0342(16) 0.777(5) 0.4748(12) 0.258(16) Uani 1 1 d U . . H13A H 0.0171 0.8779 0.4536 0.386 Uiso 1 1 calc R . . H13B H -0.0252 0.7785 0.4976 0.386 Uiso 1 1 calc R . . H13C H 0.0281 0.6616 0.4583 0.386 Uiso 1 1 calc R . . C14 C 0.2773(19) 0.300(3) 0.5721(6) 0.192(6) Uani 1 1 d DU . . F1 F 0.3338(17) 0.1743(17) 0.6008(6) 0.231(6) Uani 1 1 d DU . . F2 F 0.1757(12) 0.3553(19) 0.5918(5) 0.190(5) Uani 1 1 d DU . . F3 F 0.2404(17) 0.210(2) 0.5335(6) 0.248(8) Uani 1 1 d DU . . C15 C 0.6801(11) 1.086(3) 0.6128(6) 0.116(5) Uani 1 1 d U . . H15A H 0.6666 1.1339 0.6431 0.139 Uiso 1 1 calc R . . H15B H 0.6836 1.1905 0.5921 0.139 Uiso 1 1 calc R . . C16 C 0.7972(10) 0.993(2) 0.6157(5) 0.117(5) Uani 1 1 d DU . . C17 C 0.8140(13) 0.826(3) 0.5992(6) 0.130(5) Uani 1 1 d DU . . H17 H 0.7444 0.7604 0.5866 0.156 Uiso 1 1 calc R . . C18 C 0.9285(13) 0.742(3) 0.5995(6) 0.144(6) Uani 1 1 d DU . . H18 H 0.9365 0.6290 0.5846 0.172 Uiso 1 1 calc R . . C19 C 1.0243(14) 0.820(3) 0.6205(7) 0.164(7) Uani 1 1 d DU . . H19 H 1.1014 0.7604 0.6224 0.197 Uiso 1 1 calc R . . C20 C 1.0131(11) 0.978(3) 0.6386(8) 0.163(7) Uani 1 1 d DU . . H20 H 1.0829 1.0357 0.6533 0.196 Uiso 1 1 calc R . . C21 C 0.9001(11) 1.064(3) 0.6370(6) 0.144(6) Uani 1 1 d DU . . H21 H 0.8951 1.1781 0.6517 0.172 Uiso 1 1 calc R . . C22 C 0.2922(12) 0.975(2) 0.7315(5) 0.101(4) Uani 1 1 d DU . . C23 C 0.2620(14) 1.147(2) 0.7206(5) 0.112(4) Uani 1 1 d DU . . H23 H 0.3006 1.2022 0.6966 0.134 Uiso 1 1 calc R . . C24 C 0.1771(15) 1.252(2) 0.7422(6) 0.127(5) Uani 1 1 d DU . . H24 H 0.1604 1.3743 0.7335 0.152 Uiso 1 1 calc R . . C25 C 0.1218(19) 1.176(3) 0.7748(7) 0.144(6) Uani 1 1 d DU . . H25 H 0.0636 1.2438 0.7896 0.172 Uiso 1 1 calc R . . C26 C 0.1450(17) 1.008(3) 0.7873(6) 0.136(5) Uani 1 1 d DU . . H26 H 0.1002 0.9516 0.8094 0.163 Uiso 1 1 calc R . . C27 C 0.2376(14) 0.913(2) 0.7674(6) 0.117(5) Uani 1 1 d DU . . H27 H 0.2631 0.7989 0.7800 0.141 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.067(6) 0.118(7) 0.129(9) 0.022(7) -0.029(5) -0.012(5) N2 0.052(5) 0.175(11) 0.108(7) 0.022(7) -0.009(5) -0.027(6) N3 0.051(5) 0.166(10) 0.128(8) 0.020(7) -0.006(6) -0.016(5) O1 0.111(7) 0.116(8) 0.187(12) 0.026(8) 0.003(7) -0.018(6) O2 0.120(8) 0.216(12) 0.120(9) -0.028(9) 0.003(7) -0.092(9) O3 0.197(11) 0.089(8) 0.278(17) 0.027(9) 0.112(11) 0.020(8) O4 0.214(15) 0.227(16) 0.150(10) -0.014(11) 0.107(10) -0.042(12) O5 0.060(5) 0.273(14) 0.086(7) -0.012(7) 0.000(4) -0.019(6) C1 0.102(8) 0.101(8) 0.121(11) 0.037(8) 0.003(8) 0.004(6) C2 0.096(8) 0.142(9) 0.139(10) 0.043(7) -0.009(7) 0.020(7) C3 0.118(11) 0.096(9) 0.173(10) 0.038(6) 0.000(8) 0.039(8) C4 0.043(6) 0.111(9) 0.150(9) 0.023(6) -0.001(6) 0.005(5) C5 0.046(6) 0.153(10) 0.108(8) 0.027(7) -0.007(6) -0.018(6) C6 0.026(5) 0.190(12) 0.111(7) 0.031(7) -0.023(5) -0.018(6) C7 0.065(6) 0.176(11) 0.120(8) 0.031(7) -0.031(6) -0.008(7) C8 0.085(7) 0.164(10) 0.098(9) 0.032(8) -0.016(7) -0.028(8) C9 0.064(7) 0.151(12) 0.119(8) 0.032(8) -0.003(7) -0.019(7) C10 0.125(9) 0.125(10) 0.170(10) 0.005(6) 0.040(8) -0.030(6) C11 0.122(11) 0.179(14) 0.117(9) -0.024(9) 0.040(8) -0.029(8) C12 0.072(8) 0.33(2) 0.132(13) 0.011(13) -0.044(9) 0.008(12) C13 0.073(11) 0.35(4) 0.34(4) 0.10(3) -0.067(15) -0.036(16) C14 0.230(16) 0.130(14) 0.229(17) -0.026(8) 0.100(13) -0.079(10) F1 0.350(17) 0.091(8) 0.277(14) -0.004(8) 0.164(13) -0.034(9) F2 0.175(9) 0.197(11) 0.206(12) -0.045(9) 0.067(8) -0.115(8) F3 0.300(19) 0.180(13) 0.283(14) -0.088(10) 0.131(12) -0.130(12) C15 0.064(6) 0.168(12) 0.115(10) 0.015(9) 0.008(6) -0.020(6) C16 0.053(5) 0.191(13) 0.105(11) -0.012(10) -0.004(6) -0.023(7) C17 0.083(7) 0.169(13) 0.132(13) 0.001(10) -0.017(9) -0.016(8) C18 0.087(8) 0.219(16) 0.123(13) -0.032(12) 0.004(9) -0.005(9) C19 0.068(7) 0.28(2) 0.140(16) -0.029(14) 0.001(9) -0.007(11) C20 0.048(6) 0.27(2) 0.169(16) -0.031(14) -0.028(9) -0.058(9) C21 0.078(7) 0.242(16) 0.106(11) -0.045(12) -0.019(8) -0.032(9) C22 0.072(7) 0.105(8) 0.121(10) -0.004(7) -0.029(6) -0.025(6) C23 0.119(11) 0.083(8) 0.129(11) -0.004(7) -0.015(8) -0.039(7) C24 0.120(12) 0.110(11) 0.142(14) -0.004(9) -0.035(9) -0.009(8) C25 0.148(14) 0.144(13) 0.138(15) -0.012(11) 0.003(10) 0.033(12) C26 0.136(12) 0.136(12) 0.136(13) 0.002(11) 0.011(9) 0.004(10) C27 0.095(9) 0.105(10) 0.147(13) 0.033(8) -0.013(7) 0.011(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 C1 1.33(2) . ? N1 C8 1.38(2) . ? N1 C22 1.391(19) . ? N2 C5 1.349(18) . ? N2 C9 1.35(2) . ? N3 C6 1.45(2) . ? N3 C9 1.38(2) . ? N3 C15 1.390(19) . ? O1 C1 1.208(18) . ? O2 C8 1.18(2) . ? O3 H3 0.840 . ? O3 C10 1.46(2) . ? O4 C11 1.14(2) . ? O5 C11 1.34(2) . ? O5 C12 1.57(3) . ? C1 C2 1.52(2) . ? C2 H2 1.000 . ? C2 C3 1.46(3) . ? C2 C7 1.48(2) . ? C3 H3A 0.990 . ? C3 H3B 0.990 . ? C3 C4 1.55(2) . ? C4 H4 1.000 . ? C4 C5 1.44(2) . ? C4 C10 1.55(3) . ? C5 C6 1.33(2) . ? C6 C7 1.49(2) . ? C7 H7 1.000 . ? C7 C8 1.47(3) . ? C9 H9 0.950 . ? C10 C11 1.58(3) . ? C10 C14 1.46(3) . ? C12 H12A 0.990 . ? C12 H12B 0.990 . ? C12 C13 1.33(2) . ? C13 H13A 0.980 . ? C13 H13B 0.980 . ? C13 H13C 0.980 . ? C14 F1 1.369(15) . ? C14 F2 1.365(15) . ? C14 F3 1.355(15) . ? C15 H15A 0.990 . ? C15 H15B 0.990 . ? C15 C16 1.45(2) . ? C16 C17 1.345(15) . ? C16 C21 1.350(14) . ? C17 H17 0.950 . ? C17 C18 1.399(16) . ? C18 H18 0.950 . ? C18 C19 1.307(16) . ? C19 H19 0.950 . ? C19 C20 1.290(17) . ? C20 H20 0.950 . ? C20 C21 1.391(17) . ? C21 H21 0.950 . ? C22 C23 1.343(15) . ? C22 C27 1.349(15) . ? C23 H23 0.950 . ? C23 C24 1.407(16) . ? C24 H24 0.950 . ? C24 C25 1.312(16) . ? C25 H25 0.950 . ? C25 C26 1.305(16) . ? C26 H26 0.950 . ? C26 C27 1.407(16) . ? C27 H27 0.950 . ? 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 C1 N1 C8 114.2(17) . . ? C1 N1 C22 119.0(13) . . ? C8 N1 C22 126.6(16) . . ? C5 N2 C9 105.2(13) . . ? C6 N3 C9 102.8(12) . . ? C6 N3 C15 130.1(13) . . ? C9 N3 C15 125.0(13) . . ? H3 O3 C10 109.5 . . ? C11 O5 C12 111.5(15) . . ? N1 C1 O1 127.6(17) . . ? N1 C1 C2 106.3(16) . . ? O1 C1 C2 126.1(18) . . ? C1 C2 H2 108.5 . . ? C1 C2 C3 111.0(16) . . ? C1 C2 C7 103.9(16) . . ? H2 C2 C3 108.5 . . ? H2 C2 C7 108.5 . . ? C3 C2 C7 116.2(17) . . ? C2 C3 H3A 108.0 . . ? C2 C3 H3B 108.0 . . ? C2 C3 C4 117.4(14) . . ? H3A C3 H3B 107.2 . . ? H3A C3 C4 108.0 . . ? H3B C3 C4 108.0 . . ? C3 C4 H4 106.0 . . ? C3 C4 C5 104.6(12) . . ? C3 C4 C10 117.8(15) . . ? H4 C4 C5 106.0 . . ? H4 C4 C10 106.0 . . ? C5 C4 C10 115.4(14) . . ? N2 C5 C4 124.6(14) . . ? N2 C5 C6 112.8(14) . . ? C4 C5 C6 122.4(15) . . ? N3 C6 C5 106.8(13) . . ? N3 C6 C7 122.4(14) . . ? C5 C6 C7 130.7(15) . . ? C2 C7 C6 107.2(15) . . ? C2 C7 H7 109.8 . . ? C2 C7 C8 104.0(16) . . ? C6 C7 H7 109.8 . . ? C6 C7 C8 115.9(15) . . ? H7 C7 C8 109.8 . . ? N1 C8 O2 124(2) . . ? N1 C8 C7 106.3(18) . . ? O2 C8 C7 128.8(17) . . ? N2 C9 N3 112.4(14) . . ? N2 C9 H9 123.8 . . ? N3 C9 H9 123.8 . . ? O3 C10 C4 105.3(15) . . ? O3 C10 C11 111.6(17) . . ? O3 C10 C14 106.1(16) . . ? C4 C10 C11 109.4(16) . . ? C4 C10 C14 111.0(16) . . ? C11 C10 C14 113.2(17) . . ? O4 C11 O5 131(2) . . ? O4 C11 C10 123(2) . . ? O5 C11 C10 106.2(17) . . ? O5 C12 H12A 106.9 . . ? O5 C12 H12B 106.9 . . ? O5 C12 C13 122(3) . . ? H12A C12 H12B 106.7 . . ? H12A C12 C13 106.9 . . ? H12B C12 C13 106.9 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 F1 116.6(17) . . ? C10 C14 F2 112.9(17) . . ? C10 C14 F3 106.3(17) . . ? F1 C14 F2 106.2(16) . . ? F1 C14 F3 106.3(17) . . ? F2 C14 F3 108.1(16) . . ? N3 C15 H15A 108.6 . . ? N3 C15 H15B 108.6 . . ? N3 C15 C16 114.7(15) . . ? H15A C15 H15B 107.6 . . ? H15A C15 C16 108.6 . . ? H15B C15 C16 108.6 . . ? C15 C16 C17 123.9(12) . . ? C15 C16 C21 123.3(15) . . ? C17 C16 C21 112.8(15) . . ? C16 C17 H17 118.3 . . ? C16 C17 C18 123.5(14) . . ? H17 C17 C18 118.3 . . ? C17 C18 H18 120.1 . . ? C17 C18 C19 119.8(16) . . ? H18 C18 C19 120.1 . . ? C18 C19 H19 120.3 . . ? C18 C19 C20 119.3(17) . . ? H19 C19 C20 120.3 . . ? C19 C20 H20 119.5 . . ? C19 C20 C21 120.9(14) . . ? H20 C20 C21 119.5 . . ? C16 C21 C20 123.3(14) . . ? C16 C21 H21 118.4 . . ? C20 C21 H21 118.4 . . ? N1 C22 C23 121.2(14) . . ? N1 C22 C27 125.7(14) . . ? C23 C22 C27 113.0(15) . . ? C22 C23 H23 117.7 . . ? C22 C23 C24 124.6(15) . . ? H23 C23 C24 117.7 . . ? C23 C24 H24 121.0 . . ? C23 C24 C25 118.1(16) . . ? H24 C24 C25 121.0 . . ? C24 C25 H25 119.3 . . ? C24 C25 C26 121.4(19) . . ? H25 C25 C26 119.3 . . ? C25 C26 H26 120.6 . . ? C25 C26 C27 118.8(16) . . ? H26 C26 C27 120.6 . . ? C22 C27 C26 123.5(14) . . ? C22 C27 H27 118.2 . . ? C26 C27 H27 118.2 . . ? 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 C8 N1 C1 O1 -173.5(16) . . . . ? C8 N1 C1 C2 4.0(17) . . . . ? C22 N1 C1 O1 11(2) . . . . ? C22 N1 C1 C2 -171.1(12) . . . . ? N1 C1 C2 C3 -142.5(15) . . . . ? N1 C1 C2 C7 -16.9(17) . . . . ? O1 C1 C2 C3 35(2) . . . . ? O1 C1 C2 C7 160.6(17) . . . . ? C1 C2 C3 C4 65(2) . . . . ? C7 C2 C3 C4 -53(2) . . . . ? C2 C3 C4 C5 50(2) . . . . ? C2 C3 C4 C10 179.6(15) . . . . ? C9 N2 C5 C4 -176.6(14) . . . . ? C9 N2 C5 C6 -0.9(18) . . . . ? C3 C4 C5 N2 154.0(15) . . . . ? C3 C4 C5 C6 -21(2) . . . . ? C10 C4 C5 N2 23(2) . . . . ? C10 C4 C5 C6 -152.5(16) . . . . ? N2 C5 C6 N3 2.3(18) . . . . ? N2 C5 C6 C7 178.3(17) . . . . ? C4 C5 C6 N3 178.2(13) . . . . ? C4 C5 C6 C7 -6(3) . . . . ? C9 N3 C6 C5 -2.8(16) . . . . ? C9 N3 C6 C7 -179.2(15) . . . . ? C15 N3 C6 C5 -166.1(16) . . . . ? C15 N3 C6 C7 17(3) . . . . ? C1 C2 C7 C6 -100.8(17) . . . . ? C1 C2 C7 C8 22.5(16) . . . . ? C3 C2 C7 C6 21(2) . . . . ? C3 C2 C7 C8 144.8(14) . . . . ? N3 C6 C7 C2 -177.4(13) . . . . ? N3 C6 C7 C8 67.0(19) . . . . ? C5 C6 C7 C2 7(3) . . . . ? C5 C6 C7 C8 -108(2) . . . . ? C1 N1 C8 O2 178.7(16) . . . . ? C1 N1 C8 C7 10.8(17) . . . . ? C22 N1 C8 O2 -7(2) . . . . ? C22 N1 C8 C7 -174.5(13) . . . . ? C2 C7 C8 N1 -20.9(16) . . . . ? C2 C7 C8 O2 172.1(17) . . . . ? C6 C7 C8 N1 96.6(16) . . . . ? C6 C7 C8 O2 -70(2) . . . . ? C5 N2 C9 N3 -1.1(18) . . . . ? C6 N3 C9 N2 2.4(17) . . . . ? C15 N3 C9 N2 166.9(15) . . . . ? C3 C4 C10 O3 -56.8(19) . . . . ? C3 C4 C10 C11 -176.9(14) . . . . ? C3 C4 C10 C14 58(2) . . . . ? C5 C4 C10 O3 67.7(18) . . . . ? C5 C4 C10 C11 -52.3(18) . . . . ? C5 C4 C10 C14 -177.9(14) . . . . ? C12 O5 C11 O4 -12(3) . . . . ? C12 O5 C11 C10 170.5(15) . . . . ? O3 C10 C11 O4 15(3) . . . . ? O3 C10 C11 O5 -167.3(15) . . . . ? C4 C10 C11 O4 131(2) . . . . ? C4 C10 C11 O5 -51.2(18) . . . . ? C14 C10 C11 O4 -105(2) . . . . ? C14 C10 C11 O5 73(2) . . . . ? C11 O5 C12 C13 113(3) . . . . ? O3 C10 C14 F1 42(2) . . . . ? O3 C10 C14 F2 165.3(16) . . . . ? O3 C10 C14 F3 -76(2) . . . . ? C4 C10 C14 F1 -72(2) . . . . ? C4 C10 C14 F2 51(2) . . . . ? C4 C10 C14 F3 169.8(15) . . . . ? C11 C10 C14 F1 164.7(16) . . . . ? C11 C10 C14 F2 -72(2) . . . . ? C11 C10 C14 F3 46(2) . . . . ? C6 N3 C15 C16 71(2) . . . . ? C9 N3 C15 C16 -89(2) . . . . ? N3 C15 C16 C17 10(3) . . . . ? N3 C15 C16 C21 -167.4(17) . . . . ? C15 C16 C17 C18 175.9(17) . . . . ? C21 C16 C17 C18 -7(3) . . . . ? C16 C17 C18 C19 7(3) . . . . ? C17 C18 C19 C20 -4(4) . . . . ? C18 C19 C20 C21 2(4) . . . . ? C15 C16 C21 C20 -178.1(18) . . . . ? C17 C16 C21 C20 5(3) . . . . ? C19 C20 C21 C16 -2(4) . . . . ? C1 N1 C22 C23 -139.0(15) . . . . ? C1 N1 C22 C27 45(2) . . . . ? C8 N1 C22 C23 46.5(19) . . . . ? C8 N1 C22 C27 -129.1(17) . . . . ? N1 C22 C23 C24 -179.7(13) . . . . ? C27 C22 C23 C24 -4(2) . . . . ? C22 C23 C24 C25 -1(3) . . . . ? C23 C24 C25 C26 1(3) . . . . ? C24 C25 C26 C27 5(3) . . . . ? N1 C22 C27 C26 -175.0(15) . . . . ? C23 C22 C27 C26 9(2) . . . . ? C25 C26 C27 C22 -10(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O4 0.84 1.94 2.58(2) 132 3_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 21.25 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.594 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.142 #===END data_mjh74_compound_9d _database_code_depnum_ccdc_archive 'CCDC 860569' #TrackingRef 'web_deposit_cif_file_0_BillClegg_1325609978.angew.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H40 F3 N3 O6 Si' _chemical_formula_sum 'C34 H40 F3 N3 O6 Si' _chemical_formula_weight 671.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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' 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 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8328(6) _cell_length_b 12.7806(8) _cell_length_c 13.3203(6) _cell_angle_alpha 72.909(5) _cell_angle_beta 79.316(4) _cell_angle_gamma 71.622(6) _cell_volume 1664.08(16) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6507 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 28.53 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.955 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube with Enhance optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_reflns_number 15021 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 28.60 _reflns_number_total 6980 _reflns_number_gt 5675 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0375P)^2^+0.8194P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0030(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6980 _refine_ls_number_parameters 435 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Si Si 0.46376(4) 0.72089(4) 0.33596(4) 0.02048(12) Uani 1 1 d . . . O1 O 0.54370(10) 0.64593(9) 0.25011(9) 0.0211(2) Uani 1 1 d . . . O2 O 0.76419(11) 0.32632(10) 0.13681(9) 0.0241(3) Uani 1 1 d . . . O3 O 0.95412(12) 0.28005(10) 0.43125(9) 0.0248(3) Uani 1 1 d . . . O4 O 1.00640(11) 0.62439(10) 0.04882(9) 0.0213(3) Uani 1 1 d . . . H4 H 1.064(2) 0.655(2) 0.0418(19) 0.049(7) Uiso 1 1 d . . . O5 O 0.81535(11) 0.89293(9) 0.09192(9) 0.0249(3) Uani 1 1 d . . . O6 O 1.03256(12) 0.81561(11) 0.06265(10) 0.0307(3) Uani 1 1 d . . . N1 N 0.85112(13) 0.27898(11) 0.29516(10) 0.0177(3) Uani 1 1 d . . . N2 N 1.04327(13) 0.52117(12) 0.36289(10) 0.0194(3) Uani 1 1 d . . . N3 N 0.92285(13) 0.69950(12) 0.30146(10) 0.0208(3) Uani 1 1 d . . . F1 F 0.81760(10) 0.64444(8) -0.05902(7) 0.0268(2) Uani 1 1 d . . . F2 F 0.69170(10) 0.79672(9) -0.01814(8) 0.0312(2) Uani 1 1 d . . . F3 F 0.87430(11) 0.79961(9) -0.11503(8) 0.0360(3) Uani 1 1 d . . . C1 C 0.75654(14) 0.56036(13) 0.17346(12) 0.0158(3) Uani 1 1 d . . . H1 H 0.7137 0.5801 0.1074 0.019 Uiso 1 1 calc R . . C2 C 0.87097(15) 0.45085(13) 0.17334(12) 0.0160(3) Uani 1 1 d . . . H2 H 0.9230 0.4605 0.1026 0.019 Uiso 1 1 calc R . . C3 C 0.96415(15) 0.41735(13) 0.25930(12) 0.0164(3) Uani 1 1 d . . . H3 H 1.0548 0.3860 0.2276 0.020 Uiso 1 1 calc R . . C4 C 0.96349(15) 0.51725(14) 0.29479(12) 0.0168(3) Uani 1 1 d . . . C5 C 0.89232(15) 0.62605(13) 0.25814(12) 0.0166(3) Uani 1 1 d . . . C6 C 0.80683(15) 0.66148(13) 0.17064(12) 0.0162(3) Uani 1 1 d . . . H6 H 0.7300 0.7260 0.1836 0.019 Uiso 1 1 calc R . . C7 C 0.82092(15) 0.34792(13) 0.19419(12) 0.0174(3) Uani 1 1 d . . . C8 C 0.92463(15) 0.31994(13) 0.34191(12) 0.0177(3) Uani 1 1 d . . . C9 C 1.01428(16) 0.63305(14) 0.36254(13) 0.0215(3) Uani 1 1 d . . . H9 H 1.0559 0.6602 0.4024 0.026 Uiso 1 1 calc R . . C10 C 0.88853(15) 0.70596(13) 0.06652(12) 0.0184(3) Uani 1 1 d . . . C11 C 0.92108(16) 0.81224(14) 0.07384(12) 0.0218(3) Uani 1 1 d . . . C12 C 0.8370(2) 0.99466(16) 0.10680(17) 0.0362(5) Uani 1 1 d . . . H12A H 0.8950 1.0259 0.0466 0.043 Uiso 1 1 calc R . . H12B H 0.8789 0.9753 0.1724 0.043 Uiso 1 1 calc R . . C13 C 0.7083(2) 1.07910(17) 0.11360(19) 0.0424(5) Uani 1 1 d . . . H13A H 0.7201 1.1498 0.1198 0.064 Uiso 1 1 calc R . . H13B H 0.6535 1.0489 0.1757 0.064 Uiso 1 1 calc R . . H13C H 0.6659 1.0947 0.0498 0.064 Uiso 1 1 calc R . . C14 C 0.81621(17) 0.73710(14) -0.03107(13) 0.0231(4) Uani 1 1 d . . . C15 C 0.65124(15) 0.54693(13) 0.26696(12) 0.0184(3) Uani 1 1 d . . . H15A H 0.6227 0.4788 0.2728 0.022 Uiso 1 1 calc R . . H15B H 0.6870 0.5370 0.3334 0.022 Uiso 1 1 calc R . . C16 C 0.3627(2) 0.64033(18) 0.43861(16) 0.0389(5) Uani 1 1 d . . . H16A H 0.4192 0.5796 0.4880 0.058 Uiso 1 1 calc R . . H16B H 0.3170 0.6068 0.4049 0.058 Uiso 1 1 calc R . . H16C H 0.2985 0.6921 0.4770 0.058 Uiso 1 1 calc R . . C17 C 0.58114(19) 0.75052(19) 0.40213(17) 0.0399(5) Uani 1 1 d . . . H17A H 0.6347 0.7937 0.3491 0.060 Uiso 1 1 calc R . . H17B H 0.6378 0.6784 0.4394 0.060 Uiso 1 1 calc R . . H17C H 0.5328 0.7951 0.4528 0.060 Uiso 1 1 calc R . . C18 C 0.35983(17) 0.85523(15) 0.25541(14) 0.0268(4) Uani 1 1 d . . . C19 C 0.4445(2) 0.90885(19) 0.16183(19) 0.0511(6) Uani 1 1 d . . . H19A H 0.3900 0.9796 0.1205 0.077 Uiso 1 1 calc R . . H19B H 0.4845 0.8557 0.1171 0.077 Uiso 1 1 calc R . . H19C H 0.5133 0.9256 0.1878 0.077 Uiso 1 1 calc R . . C20 C 0.2527(2) 0.8316(2) 0.2127(2) 0.0502(6) Uani 1 1 d . . . H20A H 0.2032 0.9024 0.1676 0.075 Uiso 1 1 calc R . . H20B H 0.1936 0.8022 0.2717 0.075 Uiso 1 1 calc R . . H20C H 0.2924 0.7752 0.1713 0.075 Uiso 1 1 calc R . . C21 C 0.2961(2) 0.9397(2) 0.3237(2) 0.0548(6) Uani 1 1 d . . . H21A H 0.2414 1.0097 0.2816 0.082 Uiso 1 1 calc R . . H21B H 0.3643 0.9578 0.3492 0.082 Uiso 1 1 calc R . . H21C H 0.2419 0.9058 0.3841 0.082 Uiso 1 1 calc R . . C22 C 0.81766(16) 0.17360(14) 0.34113(12) 0.0208(3) Uani 1 1 d . . . C23 C 0.68860(18) 0.17280(16) 0.35543(14) 0.0276(4) Uani 1 1 d . . . H23 H 0.6211 0.2418 0.3380 0.033 Uiso 1 1 calc R . . C24 C 0.6591(2) 0.06897(18) 0.39588(15) 0.0369(5) Uani 1 1 d . . . H24 H 0.5706 0.0670 0.4056 0.044 Uiso 1 1 calc R . . C25 C 0.7569(2) -0.03087(17) 0.42191(15) 0.0390(5) Uani 1 1 d . . . H25 H 0.7359 -0.1015 0.4486 0.047 Uiso 1 1 calc R . . C26 C 0.8847(2) -0.02833(16) 0.40928(17) 0.0412(5) Uani 1 1 d . . . H26 H 0.9520 -0.0971 0.4287 0.049 Uiso 1 1 calc R . . C27 C 0.91612(19) 0.07421(15) 0.36832(15) 0.0320(4) Uani 1 1 d . . . H27 H 1.0046 0.0760 0.3591 0.038 Uiso 1 1 calc R . . C28 C 1.15666(16) 0.43074(15) 0.40436(13) 0.0232(4) Uani 1 1 d . . . H28A H 1.1289 0.3621 0.4448 0.028 Uiso 1 1 calc R . . H28B H 1.1934 0.4556 0.4532 0.028 Uiso 1 1 calc R . . C29 C 1.26106(16) 0.40112(16) 0.31667(14) 0.0255(4) Uani 1 1 d . . . C30 C 1.30784(19) 0.28987(17) 0.30749(15) 0.0343(4) Uani 1 1 d . . . H30 H 1.2757 0.2319 0.3577 0.041 Uiso 1 1 calc R . . C31 C 1.4011(2) 0.2622(2) 0.22587(17) 0.0443(5) Uani 1 1 d . . . H31 H 1.4315 0.1858 0.2198 0.053 Uiso 1 1 calc R . . C32 C 1.4493(2) 0.3447(2) 0.15413(18) 0.0476(6) Uani 1 1 d . . . H32 H 1.5140 0.3256 0.0987 0.057 Uiso 1 1 calc R . . C33 C 1.4043(2) 0.4547(2) 0.16247(19) 0.0541(6) Uani 1 1 d . . . H33 H 1.4380 0.5119 0.1127 0.065 Uiso 1 1 calc R . . C34 C 1.3095(2) 0.4834(2) 0.24308(17) 0.0431(5) Uani 1 1 d . . . H34 H 1.2779 0.5604 0.2475 0.052 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 Si 0.0156(2) 0.0212(2) 0.0230(2) -0.00662(19) -0.00033(17) -0.00267(18) O1 0.0168(6) 0.0196(6) 0.0245(6) -0.0060(5) -0.0016(4) -0.0018(5) O2 0.0310(7) 0.0213(6) 0.0251(6) -0.0062(5) -0.0083(5) -0.0110(5) O3 0.0333(7) 0.0219(6) 0.0202(6) -0.0021(5) -0.0078(5) -0.0088(5) O4 0.0168(6) 0.0199(6) 0.0254(6) -0.0076(5) 0.0036(5) -0.0042(5) O5 0.0281(7) 0.0149(6) 0.0319(7) -0.0082(5) 0.0041(5) -0.0079(5) O6 0.0267(7) 0.0282(7) 0.0393(7) -0.0103(6) 0.0072(5) -0.0149(6) N1 0.0210(7) 0.0139(7) 0.0193(7) -0.0035(5) -0.0028(5) -0.0065(5) N2 0.0197(7) 0.0232(7) 0.0176(6) -0.0060(6) -0.0021(5) -0.0084(6) N3 0.0240(7) 0.0214(7) 0.0214(7) -0.0094(6) 0.0017(5) -0.0109(6) F1 0.0321(6) 0.0290(6) 0.0215(5) -0.0104(4) -0.0034(4) -0.0075(4) F2 0.0272(6) 0.0294(6) 0.0300(5) -0.0067(5) -0.0080(4) 0.0036(5) F3 0.0478(7) 0.0365(6) 0.0189(5) 0.0048(5) 0.0005(5) -0.0182(5) C1 0.0169(8) 0.0136(8) 0.0167(7) -0.0036(6) -0.0023(6) -0.0039(6) C2 0.0174(8) 0.0153(8) 0.0159(7) -0.0051(6) -0.0001(6) -0.0052(6) C3 0.0150(8) 0.0170(8) 0.0172(7) -0.0053(6) -0.0012(6) -0.0038(6) C4 0.0165(8) 0.0201(8) 0.0151(7) -0.0051(6) 0.0000(6) -0.0074(6) C5 0.0176(8) 0.0179(8) 0.0158(7) -0.0061(6) 0.0029(6) -0.0078(6) C6 0.0173(8) 0.0141(8) 0.0164(7) -0.0047(6) 0.0012(6) -0.0043(6) C7 0.0174(8) 0.0146(8) 0.0191(8) -0.0061(6) -0.0002(6) -0.0023(6) C8 0.0165(8) 0.0150(8) 0.0209(8) -0.0069(6) -0.0011(6) -0.0014(6) C9 0.0234(9) 0.0256(9) 0.0213(8) -0.0110(7) 0.0007(6) -0.0118(7) C10 0.0183(8) 0.0157(8) 0.0193(8) -0.0042(6) 0.0013(6) -0.0043(6) C11 0.0266(9) 0.0179(8) 0.0190(8) -0.0017(7) 0.0030(6) -0.0093(7) C12 0.0404(11) 0.0230(10) 0.0523(12) -0.0163(9) 0.0062(9) -0.0185(9) C13 0.0489(13) 0.0268(11) 0.0572(13) -0.0242(10) -0.0019(10) -0.0079(9) C14 0.0256(9) 0.0207(9) 0.0191(8) -0.0027(7) 0.0008(6) -0.0048(7) C15 0.0166(8) 0.0149(8) 0.0225(8) -0.0043(6) -0.0004(6) -0.0041(6) C16 0.0316(11) 0.0366(12) 0.0359(11) -0.0020(9) 0.0077(8) -0.0052(9) C17 0.0282(11) 0.0500(13) 0.0477(12) -0.0296(10) -0.0076(9) -0.0014(9) C18 0.0222(9) 0.0220(9) 0.0314(9) -0.0059(7) -0.0011(7) -0.0012(7) C19 0.0440(13) 0.0306(12) 0.0557(14) 0.0105(10) 0.0047(11) -0.0043(10) C20 0.0407(13) 0.0449(13) 0.0597(15) 0.0032(11) -0.0260(11) -0.0080(11) C21 0.0561(15) 0.0370(13) 0.0536(14) -0.0173(11) -0.0109(11) 0.0200(11) C22 0.0295(9) 0.0169(8) 0.0181(8) -0.0047(7) -0.0029(6) -0.0087(7) C23 0.0316(10) 0.0254(10) 0.0271(9) -0.0025(7) -0.0053(7) -0.0124(8) C24 0.0473(12) 0.0406(12) 0.0314(10) -0.0011(9) -0.0067(9) -0.0298(10) C25 0.0701(15) 0.0254(10) 0.0304(10) 0.0021(8) -0.0121(10) -0.0298(11) C26 0.0597(14) 0.0159(10) 0.0445(12) -0.0001(8) -0.0150(10) -0.0073(9) C27 0.0340(11) 0.0203(9) 0.0401(11) -0.0051(8) -0.0069(8) -0.0061(8) C28 0.0205(8) 0.0280(9) 0.0220(8) -0.0049(7) -0.0050(6) -0.0078(7) C29 0.0179(9) 0.0344(10) 0.0275(9) -0.0104(8) -0.0058(7) -0.0073(7) C30 0.0293(10) 0.0351(11) 0.0332(10) -0.0077(9) -0.0112(8) 0.0020(8) C31 0.0322(11) 0.0501(14) 0.0442(12) -0.0215(11) -0.0122(9) 0.0108(10) C32 0.0225(11) 0.0782(18) 0.0444(12) -0.0325(13) 0.0014(9) -0.0039(11) C33 0.0500(14) 0.0737(18) 0.0472(13) -0.0212(13) 0.0187(11) -0.0370(13) C34 0.0464(13) 0.0463(13) 0.0444(12) -0.0201(10) 0.0143(10) -0.0264(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 Si O1 1.6519(12) . ? Si C16 1.8595(19) . ? Si C17 1.8581(19) . ? Si C18 1.8743(18) . ? O1 C15 1.4174(19) . ? O2 C7 1.2013(18) . ? O3 C8 1.2082(19) . ? O4 H4 0.81(2) . ? O4 C10 1.4023(19) . ? O5 C11 1.316(2) . ? O5 C12 1.465(2) . ? O6 C11 1.202(2) . ? N1 C7 1.406(2) . ? N1 C8 1.391(2) . ? N1 C22 1.436(2) . ? N2 C4 1.3846(19) . ? N2 C9 1.363(2) . ? N2 C28 1.460(2) . ? N3 C5 1.381(2) . ? N3 C9 1.314(2) . ? F1 C14 1.3368(19) . ? F2 C14 1.331(2) . ? F3 C14 1.3475(19) . ? C1 H1 1.000 . ? C1 C2 1.550(2) . ? C1 C6 1.541(2) . ? C1 C15 1.534(2) . ? C2 H2 1.000 . ? C2 C3 1.543(2) . ? C2 C7 1.510(2) . ? C3 H3 1.000 . ? C3 C4 1.484(2) . ? C3 C8 1.517(2) . ? C4 C5 1.353(2) . ? C5 C6 1.499(2) . ? C6 H6 1.000 . ? C6 C10 1.558(2) . ? C9 H9 0.950 . ? C10 C11 1.540(2) . ? C10 C14 1.529(2) . ? C12 H12A 0.990 . ? C12 H12B 0.990 . ? C12 C13 1.476(3) . ? C13 H13A 0.980 . ? C13 H13B 0.980 . ? C13 H13C 0.980 . ? C15 H15A 0.990 . ? C15 H15B 0.990 . ? C16 H16A 0.980 . ? C16 H16B 0.980 . ? C16 H16C 0.980 . ? C17 H17A 0.980 . ? C17 H17B 0.980 . ? C17 H17C 0.980 . ? C18 C19 1.528(3) . ? C18 C20 1.526(3) . ? C18 C21 1.532(3) . ? C19 H19A 0.980 . ? C19 H19B 0.980 . ? C19 H19C 0.980 . ? C20 H20A 0.980 . ? C20 H20B 0.980 . ? C20 H20C 0.980 . ? C21 H21A 0.980 . ? C21 H21B 0.980 . ? C21 H21C 0.980 . ? C22 C23 1.378(2) . ? C22 C27 1.379(2) . ? C23 H23 0.950 . ? C23 C24 1.392(3) . ? C24 H24 0.950 . ? C24 C25 1.376(3) . ? C25 H25 0.950 . ? C25 C26 1.374(3) . ? C26 H26 0.950 . ? C26 C27 1.387(3) . ? C27 H27 0.950 . ? C28 H28A 0.990 . ? C28 H28B 0.990 . ? C28 C29 1.512(2) . ? C29 C30 1.385(3) . ? C29 C34 1.376(3) . ? C30 H30 0.950 . ? C30 C31 1.386(3) . ? C31 H31 0.950 . ? C31 C32 1.367(3) . ? C32 H32 0.950 . ? C32 C33 1.365(3) . ? C33 H33 0.950 . ? C33 C34 1.388(3) . ? C34 H34 0.950 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Si C16 110.25(8) . . ? O1 Si C17 110.08(8) . . ? O1 Si C18 104.83(7) . . ? C16 Si C17 108.42(10) . . ? C16 Si C18 111.58(9) . . ? C17 Si C18 111.65(9) . . ? Si O1 C15 127.28(10) . . ? H4 O4 C10 106.3(17) . . ? C11 O5 C12 116.05(13) . . ? C7 N1 C8 112.60(12) . . ? C7 N1 C22 123.34(12) . . ? C8 N1 C22 123.91(13) . . ? C4 N2 C9 105.62(13) . . ? C4 N2 C28 126.58(13) . . ? C9 N2 C28 126.11(13) . . ? C5 N3 C9 104.05(13) . . ? H1 C1 C2 107.4 . . ? H1 C1 C6 107.4 . . ? H1 C1 C15 107.4 . . ? C2 C1 C6 111.17(12) . . ? C2 C1 C15 113.95(12) . . ? C6 C1 C15 109.15(12) . . ? C1 C2 H2 108.8 . . ? C1 C2 C3 115.46(12) . . ? C1 C2 C7 111.14(12) . . ? H2 C2 C3 108.8 . . ? H2 C2 C7 108.8 . . ? C3 C2 C7 103.71(12) . . ? C2 C3 H3 107.6 . . ? C2 C3 C4 111.84(13) . . ? C2 C3 C8 104.35(12) . . ? H3 C3 C4 107.6 . . ? H3 C3 C8 107.6 . . ? C4 C3 C8 117.38(13) . . ? N2 C4 C3 127.69(14) . . ? N2 C4 C5 106.03(13) . . ? C3 C4 C5 125.99(14) . . ? N3 C5 C4 111.14(14) . . ? N3 C5 C6 125.28(14) . . ? C4 C5 C6 123.04(14) . . ? C1 C6 C5 108.52(12) . . ? C1 C6 H6 108.4 . . ? C1 C6 C10 115.86(12) . . ? C5 C6 H6 108.4 . . ? C5 C6 C10 106.98(12) . . ? H6 C6 C10 108.4 . . ? O2 C7 N1 124.40(14) . . ? O2 C7 C2 127.49(14) . . ? N1 C7 C2 108.11(12) . . ? O3 C8 N1 124.66(14) . . ? O3 C8 C3 127.73(14) . . ? N1 C8 C3 107.55(13) . . ? N2 C9 N3 113.15(14) . . ? N2 C9 H9 123.4 . . ? N3 C9 H9 123.4 . . ? O4 C10 C6 112.07(13) . . ? O4 C10 C11 108.19(13) . . ? O4 C10 C14 106.07(13) . . ? C6 C10 C11 108.95(12) . . ? C6 C10 C14 112.58(13) . . ? C11 C10 C14 108.83(13) . . ? O5 C11 O6 127.09(15) . . ? O5 C11 C10 112.19(13) . . ? O6 C11 C10 120.72(15) . . ? O5 C12 H12A 110.2 . . ? O5 C12 H12B 110.2 . . ? O5 C12 C13 107.55(15) . . ? H12A C12 H12B 108.5 . . ? H12A C12 C13 110.2 . . ? H12B C12 C13 110.2 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? F1 C14 F2 107.30(13) . . ? F1 C14 F3 105.99(13) . . ? F1 C14 C10 111.66(13) . . ? F2 C14 F3 107.23(13) . . ? F2 C14 C10 113.37(13) . . ? F3 C14 C10 110.90(13) . . ? O1 C15 C1 108.59(12) . . ? O1 C15 H15A 110.0 . . ? O1 C15 H15B 110.0 . . ? C1 C15 H15A 110.0 . . ? C1 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? Si C16 H16A 109.5 . . ? Si C16 H16B 109.5 . . ? Si C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Si C17 H17A 109.5 . . ? Si C17 H17B 109.5 . . ? Si C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? Si C18 C19 109.74(13) . . ? Si C18 C20 111.24(13) . . ? Si C18 C21 109.62(13) . . ? C19 C18 C20 108.31(18) . . ? C19 C18 C21 109.01(18) . . ? C20 C18 C21 108.87(18) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N1 C22 C23 119.79(15) . . ? N1 C22 C27 119.11(15) . . ? C23 C22 C27 121.09(16) . . ? C22 C23 H23 120.6 . . ? C22 C23 C24 118.74(18) . . ? H23 C23 C24 120.6 . . ? C23 C24 H24 119.7 . . ? C23 C24 C25 120.60(18) . . ? H24 C24 C25 119.7 . . ? C24 C25 H25 120.0 . . ? C24 C25 C26 119.93(17) . . ? H25 C25 C26 120.0 . . ? C25 C26 H26 119.9 . . ? C25 C26 C27 120.28(19) . . ? H26 C26 C27 119.9 . . ? C22 C27 C26 119.35(18) . . ? C22 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? N2 C28 H28A 109.3 . . ? N2 C28 H28B 109.3 . . ? N2 C28 C29 111.47(13) . . ? H28A C28 H28B 108.0 . . ? H28A C28 C29 109.3 . . ? H28B C28 C29 109.3 . . ? C28 C29 C30 120.18(16) . . ? C28 C29 C34 121.30(17) . . ? C30 C29 C34 118.50(18) . . ? C29 C30 H30 119.7 . . ? C29 C30 C31 120.7(2) . . ? H30 C30 C31 119.7 . . ? C30 C31 H31 119.9 . . ? C30 C31 C32 120.1(2) . . ? H31 C31 C32 119.9 . . ? C31 C32 H32 120.1 . . ? C31 C32 C33 119.8(2) . . ? H32 C32 C33 120.1 . . ? C32 C33 H33 119.7 . . ? C32 C33 C34 120.5(2) . . ? H33 C33 C34 119.7 . . ? C29 C34 C33 120.4(2) . . ? C29 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? 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 C16 Si O1 C15 -71.69(14) . . . . ? C17 Si O1 C15 47.89(15) . . . . ? C18 Si O1 C15 168.09(12) . . . . ? C6 C1 C2 C3 52.88(17) . . . . ? C6 C1 C2 C7 170.62(12) . . . . ? C15 C1 C2 C3 -70.97(16) . . . . ? C15 C1 C2 C7 46.77(17) . . . . ? C1 C2 C3 C4 -24.87(18) . . . . ? C1 C2 C3 C8 103.01(14) . . . . ? C7 C2 C3 C4 -146.69(13) . . . . ? C7 C2 C3 C8 -18.81(15) . . . . ? C9 N2 C4 C3 174.12(15) . . . . ? C9 N2 C4 C5 0.03(16) . . . . ? C28 N2 C4 C3 8.3(2) . . . . ? C28 N2 C4 C5 -165.81(14) . . . . ? C2 C3 C4 N2 -173.40(14) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? C8 C3 C4 N2 66.1(2) . . . . ? C8 C3 C4 C5 -120.98(17) . . . . ? N2 C4 C5 N3 -0.67(17) . . . . ? N2 C4 C5 C6 171.27(13) . . . . ? C3 C4 C5 N3 -174.89(14) . . . . ? C3 C4 C5 C6 -3.0(2) . . . . ? C9 N3 C5 C4 1.04(17) . . . . ? C9 N3 C5 C6 -170.67(14) . . . . ? N3 C5 C6 C1 -159.28(14) . . . . ? N3 C5 C6 C10 75.04(18) . . . . ? C4 C5 C6 C1 29.9(2) . . . . ? C4 C5 C6 C10 -95.74(17) . . . . ? C2 C1 C6 C5 -52.55(16) . . . . ? C2 C1 C6 C10 67.76(16) . . . . ? C15 C1 C6 C5 73.99(15) . . . . ? C15 C1 C6 C10 -165.70(13) . . . . ? C8 N1 C7 O2 176.05(15) . . . . ? C8 N1 C7 C2 -4.38(17) . . . . ? C22 N1 C7 O2 0.3(2) . . . . ? C22 N1 C7 C2 179.91(13) . . . . ? C1 C2 C7 O2 69.6(2) . . . . ? C1 C2 C7 N1 -109.97(14) . . . . ? C3 C2 C7 O2 -165.76(15) . . . . ? C3 C2 C7 N1 14.69(16) . . . . ? C7 N1 C8 O3 174.33(15) . . . . ? C7 N1 C8 C3 -8.29(17) . . . . ? C22 N1 C8 O3 -10.0(2) . . . . ? C22 N1 C8 C3 167.39(14) . . . . ? C2 C3 C8 O3 -165.72(16) . . . . ? C2 C3 C8 N1 17.01(16) . . . . ? C4 C3 C8 O3 -41.3(2) . . . . ? C4 C3 C8 N1 141.41(13) . . . . ? C5 N3 C9 N2 -1.04(18) . . . . ? C4 N2 C9 N3 0.66(18) . . . . ? C28 N2 C9 N3 166.58(14) . . . . ? C1 C6 C10 O4 -64.84(17) . . . . ? C1 C6 C10 C11 175.47(13) . . . . ? C1 C6 C10 C14 54.65(18) . . . . ? C5 C6 C10 O4 56.31(16) . . . . ? C5 C6 C10 C11 -63.38(16) . . . . ? C5 C6 C10 C14 175.79(13) . . . . ? C12 O5 C11 O6 -4.3(3) . . . . ? C12 O5 C11 C10 176.27(14) . . . . ? O4 C10 C11 O5 -179.14(13) . . . . ? O4 C10 C11 O6 1.4(2) . . . . ? C6 C10 C11 O5 -57.07(17) . . . . ? C6 C10 C11 O6 123.49(16) . . . . ? C14 C10 C11 O5 66.03(17) . . . . ? C14 C10 C11 O6 -113.42(17) . . . . ? C11 O5 C12 C13 173.60(16) . . . . ? O4 C10 C14 F1 46.20(17) . . . . ? O4 C10 C14 F2 167.55(13) . . . . ? O4 C10 C14 F3 -71.76(16) . . . . ? C6 C10 C14 F1 -76.71(16) . . . . ? C6 C10 C14 F2 44.64(18) . . . . ? C6 C10 C14 F3 165.33(13) . . . . ? C11 C10 C14 F1 162.40(13) . . . . ? C11 C10 C14 F2 -76.25(17) . . . . ? C11 C10 C14 F3 44.44(18) . . . . ? Si O1 C15 C1 -133.34(11) . . . . ? C2 C1 C15 O1 -171.36(11) . . . . ? C6 C1 C15 O1 63.71(15) . . . . ? O1 Si C18 C19 -51.88(15) . . . . ? O1 Si C18 C20 67.95(15) . . . . ? O1 Si C18 C21 -171.58(14) . . . . ? C16 Si C18 C19 -171.21(15) . . . . ? C16 Si C18 C20 -51.38(17) . . . . ? C16 Si C18 C21 69.09(17) . . . . ? C17 Si C18 C19 67.27(17) . . . . ? C17 Si C18 C20 -172.89(15) . . . . ? C17 Si C18 C21 -52.42(17) . . . . ? C7 N1 C22 C23 -59.0(2) . . . . ? C7 N1 C22 C27 119.73(17) . . . . ? C8 N1 C22 C23 125.81(17) . . . . ? C8 N1 C22 C27 -55.5(2) . . . . ? N1 C22 C23 C24 177.24(15) . . . . ? C27 C22 C23 C24 -1.4(3) . . . . ? C22 C23 C24 C25 0.5(3) . . . . ? C23 C24 C25 C26 0.9(3) . . . . ? C24 C25 C26 C27 -1.3(3) . . . . ? N1 C22 C27 C26 -177.73(16) . . . . ? C23 C22 C27 C26 0.9(3) . . . . ? C25 C26 C27 C22 0.5(3) . . . . ? C4 N2 C28 C29 61.0(2) . . . . ? C9 N2 C28 C29 -102.01(18) . . . . ? N2 C28 C29 C30 -124.69(17) . . . . ? N2 C28 C29 C34 53.8(2) . . . . ? C28 C29 C30 C31 178.34(16) . . . . ? C34 C29 C30 C31 -0.2(3) . . . . ? C29 C30 C31 C32 0.9(3) . . . . ? C30 C31 C32 C33 -0.7(3) . . . . ? C31 C32 C33 C34 -0.2(4) . . . . ? C28 C29 C34 C33 -179.25(19) . . . . ? C30 C29 C34 C33 -0.8(3) . . . . ? C32 C33 C34 C29 0.9(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O6 0.81(2) 2.07(2) 2.6092(17) 124(2) . _diffrn_measured_fraction_theta_max 0.820 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.335 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.047 data_mjh55_compound_10a _database_code_depnum_ccdc_archive 'CCDC 860570' #TrackingRef 'web_deposit_cif_file_0_BillClegg_1325609978.angew.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H25 N3 O5' _chemical_formula_sum 'C26 H25 N3 O5' _chemical_formula_weight 459.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0807(3) _cell_length_b 11.5619(5) _cell_length_c 12.7860(5) _cell_angle_alpha 79.423(3) _cell_angle_beta 86.322(3) _cell_angle_gamma 82.872(3) _cell_volume 1164.15(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6804 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 28.41 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube with Enhance optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9971 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 28.48 _reflns_number_total 4854 _reflns_number_gt 3963 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0619P)^2^+0.0759P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4854 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _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 O1 O 0.35081(10) 0.62199(8) 0.52514(7) 0.0244(2) Uani 1 1 d . . . O2 O 0.87150(10) 0.65515(8) 0.37274(7) 0.0273(2) Uani 1 1 d . . . O3 O 0.55964(10) 0.85006(8) -0.00848(7) 0.0219(2) Uani 1 1 d . . . H3 H 0.564(2) 0.8963(16) -0.0700(15) 0.041(5) Uiso 1 1 d . . . O4 O 0.88771(11) 0.80721(9) -0.07200(7) 0.0302(2) Uani 1 1 d . . . O5 O 0.97207(10) 0.86043(9) 0.07361(7) 0.0294(2) Uani 1 1 d . . . N1 N 0.62446(12) 0.64929(9) 0.47365(8) 0.0194(2) Uani 1 1 d . . . N2 N 0.41347(12) 0.97891(9) 0.19175(7) 0.0192(2) Uani 1 1 d . . . N3 N 0.25992(11) 0.87430(9) 0.31599(8) 0.0192(2) Uani 1 1 d . . . C1 C 0.45704(14) 0.64417(10) 0.45619(9) 0.0187(3) Uani 1 1 d . . . C2 C 0.43708(14) 0.66949(11) 0.33641(9) 0.0184(3) Uani 1 1 d . . . H2 H 0.3520 0.6230 0.3157 0.022 Uiso 1 1 calc R . . C3 C 0.39900(13) 0.79893(11) 0.29330(9) 0.0172(2) Uani 1 1 d . . . C4 C 0.49117(14) 0.86484(11) 0.21693(9) 0.0167(2) Uani 1 1 d . . . C5 C 0.65584(14) 0.81996(10) 0.16936(9) 0.0171(2) Uani 1 1 d . . . H5 H 0.7462 0.8398 0.2107 0.020 Uiso 1 1 calc R . . C6 C 0.66712(15) 0.68510(11) 0.18284(9) 0.0200(3) Uani 1 1 d . . . H6A H 0.5951 0.6640 0.1311 0.024 Uiso 1 1 calc R . . H6B H 0.7835 0.6533 0.1666 0.024 Uiso 1 1 calc R . . C7 C 0.61412(14) 0.62745(11) 0.29491(9) 0.0193(3) Uani 1 1 d . . . H7 H 0.6207 0.5402 0.2965 0.023 Uiso 1 1 calc R . . C8 C 0.72401(15) 0.64666(10) 0.38056(9) 0.0195(3) Uani 1 1 d . . . C9 C 0.27548(15) 0.98026(11) 0.25318(9) 0.0205(3) Uani 1 1 d . . . H9 H 0.1961 1.0482 0.2532 0.025 Uiso 1 1 calc R . . C10 C 0.12895(14) 0.85257(12) 0.39962(9) 0.0217(3) Uani 1 1 d . . . H10A H 0.1093 0.7683 0.4099 0.026 Uiso 1 1 calc R . . H10B H 0.0241 0.9013 0.3758 0.026 Uiso 1 1 calc R . . C11 C 0.17085(14) 0.88075(11) 0.50569(9) 0.0197(3) Uani 1 1 d . . . C12 C 0.10348(15) 0.81836(12) 0.59877(10) 0.0243(3) Uani 1 1 d . . . H12 H 0.0335 0.7592 0.5948 0.029 Uiso 1 1 calc R . . C13 C 0.13734(16) 0.84149(13) 0.69735(10) 0.0284(3) Uani 1 1 d . . . H13 H 0.0911 0.7981 0.7605 0.034 Uiso 1 1 calc R . . C14 C 0.23883(16) 0.92802(13) 0.70371(10) 0.0274(3) Uani 1 1 d . . . H14 H 0.2634 0.9433 0.7712 0.033 Uiso 1 1 calc R . . C15 C 0.30407(15) 0.99192(12) 0.61155(10) 0.0261(3) Uani 1 1 d . . . H15 H 0.3724 1.0520 0.6157 0.031 Uiso 1 1 calc R . . C16 C 0.27003(14) 0.96865(12) 0.51286(10) 0.0229(3) Uani 1 1 d . . . H16 H 0.3149 1.0131 0.4498 0.028 Uiso 1 1 calc R . . C17 C 0.68632(15) 0.64352(11) 0.57749(9) 0.0213(3) Uani 1 1 d . . . C18 C 0.60534(18) 0.71629(13) 0.64378(11) 0.0310(3) Uani 1 1 d . . . H18 H 0.5114 0.7706 0.6204 0.037 Uiso 1 1 calc R . . C19 C 0.6629(2) 0.70898(14) 0.74478(11) 0.0385(4) Uani 1 1 d . . . H19 H 0.6074 0.7581 0.7912 0.046 Uiso 1 1 calc R . . C20 C 0.8006(2) 0.63066(13) 0.77835(11) 0.0349(3) Uani 1 1 d . . . H20 H 0.8400 0.6263 0.8476 0.042 Uiso 1 1 calc R . . C21 C 0.88048(17) 0.55905(12) 0.71140(10) 0.0287(3) Uani 1 1 d . . . H21 H 0.9752 0.5055 0.7347 0.034 Uiso 1 1 calc R . . C22 C 0.82407(15) 0.56420(11) 0.60991(10) 0.0226(3) Uani 1 1 d . . . H22 H 0.8789 0.5144 0.5638 0.027 Uiso 1 1 calc R . . C23 C 0.68103(14) 0.87895(11) 0.05319(9) 0.0182(3) Uani 1 1 d . . . H23 H 0.6664 0.9667 0.0496 0.022 Uiso 1 1 calc R . . C24 C 0.85661(14) 0.84302(11) 0.00981(9) 0.0190(3) Uani 1 1 d . . . C25 C 1.14549(15) 0.82714(13) 0.04207(11) 0.0301(3) Uani 1 1 d . . . H25A H 1.2191 0.8692 0.0773 0.036 Uiso 1 1 calc R . . H25B H 1.1619 0.8517 -0.0359 0.036 Uiso 1 1 calc R . . C26 C 1.1927(2) 0.69706(18) 0.0715(2) 0.0709(7) Uani 1 1 d . . . H26A H 1.3114 0.6780 0.0533 0.106 Uiso 1 1 calc R . . H26B H 1.1259 0.6555 0.0323 0.106 Uiso 1 1 calc R . . H26C H 1.1718 0.6720 0.1482 0.106 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0278(4) 0.0225(5) 0.0199(4) 0.0027(4) 0.0041(4) -0.0038(4) O2 0.0219(4) 0.0330(6) 0.0246(5) 0.0019(4) -0.0013(3) -0.0040(4) O3 0.0217(4) 0.0273(5) 0.0150(4) 0.0031(4) -0.0036(3) -0.0055(4) O4 0.0255(5) 0.0438(6) 0.0234(5) -0.0138(4) 0.0003(4) -0.0014(4) O5 0.0205(4) 0.0495(6) 0.0207(5) -0.0080(4) 0.0007(3) -0.0122(4) N1 0.0238(5) 0.0181(5) 0.0150(5) 0.0003(4) -0.0021(4) -0.0020(4) N2 0.0229(5) 0.0188(5) 0.0143(5) 0.0003(4) -0.0016(4) -0.0011(4) N3 0.0173(5) 0.0226(6) 0.0161(5) 0.0005(4) 0.0003(4) -0.0015(4) C1 0.0237(6) 0.0122(6) 0.0185(6) 0.0008(5) -0.0004(5) -0.0013(5) C2 0.0201(5) 0.0180(6) 0.0167(6) 0.0003(5) -0.0014(4) -0.0051(5) C3 0.0173(5) 0.0196(6) 0.0142(5) -0.0011(4) -0.0025(4) -0.0025(4) C4 0.0187(5) 0.0181(6) 0.0129(5) -0.0004(4) -0.0032(4) -0.0024(4) C5 0.0183(5) 0.0186(6) 0.0134(5) -0.0002(4) -0.0003(4) -0.0024(4) C6 0.0242(6) 0.0190(6) 0.0148(6) 0.0000(5) 0.0007(4) -0.0004(5) C7 0.0242(6) 0.0154(6) 0.0169(6) 0.0001(5) -0.0004(5) -0.0015(5) C8 0.0247(6) 0.0140(6) 0.0172(6) 0.0025(5) -0.0007(5) 0.0001(5) C9 0.0222(6) 0.0206(6) 0.0166(6) 0.0005(5) -0.0015(4) 0.0006(5) C10 0.0156(5) 0.0290(7) 0.0194(6) -0.0007(5) 0.0014(4) -0.0051(5) C11 0.0148(5) 0.0231(7) 0.0196(6) -0.0018(5) 0.0019(4) 0.0006(5) C12 0.0232(6) 0.0254(7) 0.0232(6) -0.0010(5) 0.0042(5) -0.0054(5) C13 0.0302(7) 0.0310(8) 0.0209(6) -0.0003(5) 0.0070(5) -0.0014(6) C14 0.0280(6) 0.0323(8) 0.0218(6) -0.0085(6) -0.0001(5) 0.0019(6) C15 0.0225(6) 0.0272(7) 0.0297(7) -0.0079(6) -0.0001(5) -0.0033(5) C16 0.0188(5) 0.0254(7) 0.0227(6) -0.0006(5) 0.0039(5) -0.0035(5) C17 0.0299(6) 0.0171(6) 0.0165(6) 0.0009(5) -0.0042(5) -0.0059(5) C18 0.0437(8) 0.0229(7) 0.0251(7) -0.0044(6) -0.0050(6) 0.0033(6) C19 0.0623(10) 0.0301(8) 0.0251(7) -0.0122(6) -0.0033(7) -0.0011(7) C20 0.0552(9) 0.0310(8) 0.0211(7) -0.0032(6) -0.0120(6) -0.0112(7) C21 0.0353(7) 0.0253(7) 0.0249(7) 0.0031(5) -0.0105(6) -0.0078(6) C22 0.0264(6) 0.0206(7) 0.0206(6) -0.0001(5) -0.0028(5) -0.0067(5) C23 0.0199(5) 0.0192(6) 0.0142(5) 0.0005(5) 0.0000(4) -0.0034(5) C24 0.0222(6) 0.0191(6) 0.0142(6) 0.0026(5) -0.0008(4) -0.0049(5) C25 0.0185(6) 0.0405(9) 0.0307(7) -0.0006(6) -0.0024(5) -0.0087(5) C26 0.0358(9) 0.0453(11) 0.124(2) 0.0128(12) -0.0307(11) -0.0042(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2060(14) . ? O2 C8 1.2043(14) . ? O3 H3 0.867(19) . ? O3 C23 1.4045(14) . ? O4 C24 1.1951(15) . ? O5 C24 1.3346(14) . ? O5 C25 1.4578(15) . ? N1 C1 1.3953(15) . ? N1 C8 1.3961(15) . ? N1 C17 1.4358(15) . ? N2 C4 1.3790(16) . ? N2 C9 1.3222(15) . ? N3 C3 1.3837(15) . ? N3 C9 1.3512(16) . ? N3 C10 1.4658(14) . ? C1 C2 1.5207(16) . ? C2 H2 1.000 . ? C2 C3 1.4977(17) . ? C2 C7 1.5457(16) . ? C3 C4 1.3650(16) . ? C4 C5 1.5001(15) . ? C5 H5 1.000 . ? C5 C6 1.5288(17) . ? C5 C23 1.5286(15) . ? C6 H6A 0.990 . ? C6 H6B 0.990 . ? C6 C7 1.5241(15) . ? C7 H7 1.000 . ? C7 C8 1.5166(16) . ? C9 H9 0.950 . ? C10 H10A 0.990 . ? C10 H10B 0.990 . ? C10 C11 1.5194(17) . ? C11 C12 1.3901(17) . ? C11 C16 1.3890(17) . ? C12 H12 0.950 . ? C12 C13 1.3860(19) . ? C13 H13 0.950 . ? C13 C14 1.3865(19) . ? C14 H14 0.950 . ? C14 C15 1.3819(19) . ? C15 H15 0.950 . ? C15 C16 1.3885(18) . ? C16 H16 0.950 . ? C17 C18 1.3815(19) . ? C17 C22 1.3850(18) . ? C18 H18 0.950 . ? C18 C19 1.385(2) . ? C19 H19 0.950 . ? C19 C20 1.382(2) . ? C20 H20 0.950 . ? C20 C21 1.375(2) . ? C21 H21 0.950 . ? C21 C22 1.3915(18) . ? C22 H22 0.950 . ? C23 H23 1.000 . ? C23 C24 1.5266(16) . ? C25 H25A 0.990 . ? C25 H25B 0.990 . ? C25 C26 1.489(2) . ? C26 H26A 0.980 . ? C26 H26B 0.980 . ? C26 H26C 0.980 . ? 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 H3 O3 C23 107.0(11) . . ? C24 O5 C25 116.50(10) . . ? C1 N1 C8 111.56(10) . . ? C1 N1 C17 123.14(10) . . ? C8 N1 C17 124.91(10) . . ? C4 N2 C9 104.77(10) . . ? C3 N3 C9 106.56(9) . . ? C3 N3 C10 128.49(10) . . ? C9 N3 C10 124.57(10) . . ? O1 C1 N1 125.02(11) . . ? O1 C1 C2 127.57(11) . . ? N1 C1 C2 107.40(9) . . ? C1 C2 H2 111.3 . . ? C1 C2 C3 112.63(10) . . ? C1 C2 C7 101.64(9) . . ? H2 C2 C3 111.3 . . ? H2 C2 C7 111.3 . . ? C3 C2 C7 108.32(9) . . ? N3 C3 C2 127.92(10) . . ? N3 C3 C4 105.77(10) . . ? C2 C3 C4 126.16(11) . . ? N2 C4 C3 110.42(10) . . ? N2 C4 C5 124.96(10) . . ? C3 C4 C5 124.60(11) . . ? C4 C5 H5 108.0 . . ? C4 C5 C6 108.59(9) . . ? C4 C5 C23 111.77(9) . . ? H5 C5 C6 108.0 . . ? H5 C5 C23 108.0 . . ? C6 C5 C23 112.45(9) . . ? C5 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C5 C6 C7 112.59(10) . . ? H6A C6 H6B 107.8 . . ? H6A C6 C7 109.1 . . ? H6B C6 C7 109.1 . . ? C2 C7 C6 116.70(10) . . ? C2 C7 H7 107.7 . . ? C2 C7 C8 102.77(9) . . ? C6 C7 H7 107.7 . . ? C6 C7 C8 113.77(10) . . ? H7 C7 C8 107.7 . . ? O2 C8 N1 124.95(11) . . ? O2 C8 C7 127.35(11) . . ? N1 C8 C7 107.67(10) . . ? N2 C9 N3 112.47(11) . . ? N2 C9 H9 123.8 . . ? N3 C9 H9 123.8 . . ? N3 C10 H10A 108.9 . . ? N3 C10 H10B 108.9 . . ? N3 C10 C11 113.53(9) . . ? H10A C10 H10B 107.7 . . ? H10A C10 C11 108.9 . . ? H10B C10 C11 108.9 . . ? C10 C11 C12 118.65(11) . . ? C10 C11 C16 122.44(11) . . ? C12 C11 C16 118.89(11) . . ? C11 C12 H12 119.6 . . ? C11 C12 C13 120.72(12) . . ? H12 C12 C13 119.6 . . ? C12 C13 H13 120.0 . . ? C12 C13 C14 119.93(12) . . ? H13 C13 C14 120.0 . . ? C13 C14 H14 120.1 . . ? C13 C14 C15 119.78(12) . . ? H14 C14 C15 120.1 . . ? C14 C15 H15 119.9 . . ? C14 C15 C16 120.21(12) . . ? H15 C15 C16 119.9 . . ? C11 C16 C15 120.45(11) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? N1 C17 C18 119.14(11) . . ? N1 C17 C22 119.57(11) . . ? C18 C17 C22 121.28(11) . . ? C17 C18 H18 120.4 . . ? C17 C18 C19 119.15(13) . . ? H18 C18 C19 120.4 . . ? C18 C19 H19 119.8 . . ? C18 C19 C20 120.37(13) . . ? H19 C19 C20 119.8 . . ? C19 C20 H20 120.1 . . ? C19 C20 C21 119.90(12) . . ? H20 C20 C21 120.1 . . ? C20 C21 H21 119.6 . . ? C20 C21 C22 120.73(13) . . ? H21 C21 C22 119.6 . . ? C17 C22 C21 118.57(12) . . ? C17 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? O3 C23 C5 109.81(9) . . ? O3 C23 H23 108.3 . . ? O3 C23 C24 110.95(9) . . ? C5 C23 H23 108.3 . . ? C5 C23 C24 111.11(9) . . ? H23 C23 C24 108.3 . . ? O4 C24 O5 124.09(11) . . ? O4 C24 C23 124.78(11) . . ? O5 C24 C23 111.10(10) . . ? O5 C25 H25A 109.4 . . ? O5 C25 H25B 109.4 . . ? O5 C25 C26 111.36(12) . . ? H25A C25 H25B 108.0 . . ? H25A C25 C26 109.4 . . ? H25B C25 C26 109.4 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? 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 C8 N1 C1 O1 164.76(12) . . . . ? C8 N1 C1 C2 -14.38(13) . . . . ? C17 N1 C1 O1 -8.33(19) . . . . ? C17 N1 C1 C2 172.53(10) . . . . ? O1 C1 C2 C3 92.18(15) . . . . ? O1 C1 C2 C7 -152.12(12) . . . . ? N1 C1 C2 C3 -88.70(11) . . . . ? N1 C1 C2 C7 27.00(12) . . . . ? C9 N3 C3 C2 -175.99(11) . . . . ? C9 N3 C3 C4 -0.12(12) . . . . ? C10 N3 C3 C2 10.95(18) . . . . ? C10 N3 C3 C4 -173.19(10) . . . . ? C1 C2 C3 N3 -63.40(15) . . . . ? C1 C2 C3 C4 121.53(12) . . . . ? C7 C2 C3 N3 -175.02(10) . . . . ? C7 C2 C3 C4 9.92(15) . . . . ? N3 C3 C4 N2 0.10(12) . . . . ? N3 C3 C4 C5 178.67(10) . . . . ? C2 C3 C4 N2 176.06(10) . . . . ? C2 C3 C4 C5 -5.37(18) . . . . ? C9 N2 C4 C3 -0.04(12) . . . . ? C9 N2 C4 C5 -178.61(10) . . . . ? N2 C4 C5 C6 -158.38(10) . . . . ? N2 C4 C5 C23 -33.76(15) . . . . ? C3 C4 C5 C6 23.25(14) . . . . ? C3 C4 C5 C23 147.87(11) . . . . ? C4 C5 C6 C7 -46.34(12) . . . . ? C23 C5 C6 C7 -170.57(9) . . . . ? C5 C6 C7 C2 56.65(13) . . . . ? C5 C6 C7 C8 -62.82(13) . . . . ? C1 C2 C7 C6 -153.90(10) . . . . ? C1 C2 C7 C8 -28.69(11) . . . . ? C3 C2 C7 C6 -35.08(13) . . . . ? C3 C2 C7 C8 90.13(10) . . . . ? C1 N1 C8 O2 176.60(12) . . . . ? C1 N1 C8 C7 -5.21(13) . . . . ? C17 N1 C8 O2 -10.45(19) . . . . ? C17 N1 C8 C7 167.74(10) . . . . ? C2 C7 C8 O2 -159.97(12) . . . . ? C2 C7 C8 N1 21.89(12) . . . . ? C6 C7 C8 O2 -32.88(17) . . . . ? C6 C7 C8 N1 148.99(10) . . . . ? C4 N2 C9 N3 -0.04(13) . . . . ? C3 N3 C9 N2 0.11(13) . . . . ? C10 N3 C9 N2 173.51(10) . . . . ? C3 N3 C10 C11 86.52(14) . . . . ? C9 N3 C10 C11 -85.40(14) . . . . ? N3 C10 C11 C12 -151.23(11) . . . . ? N3 C10 C11 C16 30.61(16) . . . . ? C10 C11 C12 C13 -179.60(12) . . . . ? C16 C11 C12 C13 -1.37(18) . . . . ? C11 C12 C13 C14 0.29(19) . . . . ? C12 C13 C14 C15 0.8(2) . . . . ? C13 C14 C15 C16 -0.83(19) . . . . ? C14 C15 C16 C11 -0.28(19) . . . . ? C10 C11 C16 C15 179.53(11) . . . . ? C12 C11 C16 C15 1.37(18) . . . . ? C1 N1 C17 C18 -49.52(17) . . . . ? C1 N1 C17 C22 129.53(13) . . . . ? C8 N1 C17 C18 138.32(13) . . . . ? C8 N1 C17 C22 -42.63(17) . . . . ? N1 C17 C18 C19 178.66(13) . . . . ? C22 C17 C18 C19 -0.4(2) . . . . ? C17 C18 C19 C20 0.6(2) . . . . ? C18 C19 C20 C21 -0.4(2) . . . . ? C19 C20 C21 C22 -0.1(2) . . . . ? N1 C17 C22 C21 -179.16(11) . . . . ? C18 C17 C22 C21 -0.13(19) . . . . ? C20 C21 C22 C17 0.39(19) . . . . ? C4 C5 C23 O3 -63.35(12) . . . . ? C4 C5 C23 C24 173.53(9) . . . . ? C6 C5 C23 O3 59.10(12) . . . . ? C6 C5 C23 C24 -64.03(12) . . . . ? C25 O5 C24 O4 -3.24(19) . . . . ? C25 O5 C24 C23 178.77(10) . . . . ? O3 C23 C24 O4 7.66(17) . . . . ? O3 C23 C24 O5 -174.36(10) . . . . ? C5 C23 C24 O4 130.13(13) . . . . ? C5 C23 C24 O5 -51.89(13) . . . . ? C24 O5 C25 C26 -79.68(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 N2 0.867(19) 1.935(19) 2.7909(13) 169.0(16) 2_675 _diffrn_measured_fraction_theta_max 0.825 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.352 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.040 data_mjh65_compound_7a_rearomatised _database_code_depnum_ccdc_archive 'CCDC 860571' #TrackingRef 'web_deposit_cif_file_0_BillClegg_1325609978.angew.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H19 N3 O2' _chemical_formula_sum 'C22 H19 N3 O2' _chemical_formula_weight 357.40 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.9615(6) _cell_length_b 6.7669(2) _cell_length_c 19.4128(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.967(4) _cell_angle_gamma 90.00 _cell_volume 1800.55(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3558 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 26.57 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube with Enhance optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_reflns_number 6118 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 26.63 _reflns_number_total 3455 _reflns_number_gt 2894 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0398P)^2^+0.8073P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0016(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3455 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.48027(8) 0.14815(19) 0.30648(6) 0.0394(3) Uani 1 1 d . . . O2 O 0.47539(7) 0.15322(15) 0.07170(5) 0.0289(3) Uani 1 1 d . . . N1 N 0.45460(8) 0.15176(18) 0.18616(6) 0.0256(3) Uani 1 1 d . . . N2 N 0.59702(9) 0.79713(18) 0.15899(7) 0.0294(3) Uani 1 1 d . . . N3 N 0.61224(8) 0.55160(17) 0.08533(6) 0.0247(3) Uani 1 1 d . . . C1 C 0.51091(11) 0.1703(2) 0.25292(8) 0.0262(3) Uani 1 1 d . . . C2 C 0.61388(10) 0.2230(2) 0.24618(7) 0.0238(3) Uani 1 1 d . . . H2 H 0.6564 0.1059 0.2614 0.029 Uiso 1 1 calc R . . C3 C 0.65250(11) 0.3969(2) 0.29401(8) 0.0291(3) Uani 1 1 d . . . H3A H 0.6436 0.3673 0.3423 0.035 Uiso 1 1 calc R . . H3B H 0.7233 0.4117 0.2951 0.035 Uiso 1 1 calc R . . C4 C 0.60145(12) 0.5923(2) 0.27024(8) 0.0314(4) Uani 1 1 d . . . H4A H 0.5334 0.5895 0.2779 0.038 Uiso 1 1 calc R . . H4B H 0.6358 0.7033 0.2976 0.038 Uiso 1 1 calc R . . C5 C 0.60265(10) 0.6193(2) 0.19426(8) 0.0252(3) Uani 1 1 d . . . C6 C 0.61196(10) 0.4679(2) 0.15016(7) 0.0226(3) Uani 1 1 d . . . C7 C 0.60861(10) 0.2523(2) 0.16660(7) 0.0223(3) Uani 1 1 d . . . H7 H 0.6613 0.1775 0.1495 0.027 Uiso 1 1 calc R . . C8 C 0.50775(10) 0.17637(19) 0.13332(7) 0.0233(3) Uani 1 1 d . . . C9 C 0.60343(11) 0.7489(2) 0.09434(8) 0.0286(3) Uani 1 1 d . . . H9 H 0.6020 0.8427 0.0578 0.034 Uiso 1 1 calc R . . C10 C 0.62813(11) 0.4530(2) 0.02132(7) 0.0287(3) Uani 1 1 d . . . H10A H 0.6182 0.5497 -0.0177 0.034 Uiso 1 1 calc R . . H10B H 0.5790 0.3469 0.0090 0.034 Uiso 1 1 calc R . . C11 C 0.72843(11) 0.3652(2) 0.02855(7) 0.0280(3) Uani 1 1 d . . . C12 C 0.81087(12) 0.4756(3) 0.05306(10) 0.0466(5) Uani 1 1 d . . . H12 H 0.8045 0.6090 0.0668 0.056 Uiso 1 1 calc R . . C13 C 0.90291(14) 0.3939(4) 0.05791(11) 0.0687(7) Uani 1 1 d . . . H13 H 0.9592 0.4717 0.0746 0.082 Uiso 1 1 calc R . . C14 C 0.91310(16) 0.2025(4) 0.03891(10) 0.0684(7) Uani 1 1 d . . . H14 H 0.9763 0.1473 0.0420 0.082 Uiso 1 1 calc R . . C15 C 0.83236(18) 0.0902(3) 0.01548(10) 0.0593(6) Uani 1 1 d . . . H15 H 0.8395 -0.0439 0.0029 0.071 Uiso 1 1 calc R . . C16 C 0.73977(14) 0.1708(3) 0.00986(9) 0.0399(4) Uani 1 1 d . . . H16 H 0.6839 0.0919 -0.0069 0.048 Uiso 1 1 calc R . . C17 C 0.35271(11) 0.1029(3) 0.17354(8) 0.0318(4) Uani 1 1 d . . . C18 C 0.32442(13) -0.0865(3) 0.18549(9) 0.0434(4) Uani 1 1 d . . . H18 H 0.3719 -0.1860 0.2002 0.052 Uiso 1 1 calc R . . C19 C 0.22599(14) -0.1308(4) 0.17587(10) 0.0546(5) Uani 1 1 d . . . H19 H 0.2057 -0.2616 0.1838 0.065 Uiso 1 1 calc R . . C20 C 0.15818(14) 0.0124(4) 0.15514(10) 0.0565(6) Uani 1 1 d . . . H20 H 0.0908 -0.0188 0.1491 0.068 Uiso 1 1 calc R . . C21 C 0.18633(14) 0.2020(4) 0.14275(11) 0.0585(6) Uani 1 1 d . . . H21 H 0.1384 0.3008 0.1281 0.070 Uiso 1 1 calc R . . C22 C 0.28566(12) 0.2493(3) 0.15174(10) 0.0456(5) Uani 1 1 d . . . H22 H 0.3061 0.3792 0.1430 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0348(6) 0.0573(8) 0.0272(6) 0.0056(5) 0.0081(5) -0.0007(5) O2 0.0337(6) 0.0262(6) 0.0247(6) 0.0007(4) 0.0004(4) -0.0018(4) N1 0.0224(6) 0.0279(6) 0.0255(6) 0.0022(5) 0.0022(5) 0.0017(5) N2 0.0326(7) 0.0195(6) 0.0336(7) 0.0019(5) 0.0004(5) -0.0001(5) N3 0.0248(6) 0.0229(6) 0.0257(6) 0.0034(5) 0.0032(5) 0.0001(5) C1 0.0279(7) 0.0248(7) 0.0251(7) 0.0041(6) 0.0028(6) 0.0044(6) C2 0.0229(7) 0.0218(7) 0.0254(7) 0.0048(6) 0.0011(6) 0.0041(6) C3 0.0322(8) 0.0290(8) 0.0241(7) 0.0009(6) 0.0000(6) 0.0009(6) C4 0.0396(9) 0.0249(8) 0.0290(8) -0.0039(6) 0.0043(7) 0.0019(7) C5 0.0230(7) 0.0209(7) 0.0302(8) 0.0008(6) 0.0009(6) 0.0012(6) C6 0.0208(7) 0.0209(7) 0.0253(7) 0.0027(6) 0.0021(5) 0.0007(5) C7 0.0240(7) 0.0178(7) 0.0248(7) 0.0016(6) 0.0038(6) 0.0036(5) C8 0.0274(7) 0.0153(7) 0.0262(8) 0.0030(6) 0.0026(6) 0.0038(5) C9 0.0305(8) 0.0202(7) 0.0334(8) 0.0063(6) 0.0021(6) -0.0014(6) C10 0.0301(8) 0.0322(8) 0.0227(7) 0.0018(6) 0.0024(6) -0.0024(6) C11 0.0320(8) 0.0318(8) 0.0201(7) 0.0011(6) 0.0048(6) -0.0002(6) C12 0.0346(9) 0.0583(12) 0.0466(10) -0.0224(9) 0.0066(8) -0.0061(8) C13 0.0313(10) 0.121(2) 0.0512(12) -0.0365(13) 0.0002(9) 0.0002(12) C14 0.0509(13) 0.116(2) 0.0360(10) -0.0163(12) 0.0032(9) 0.0391(14) C15 0.0862(17) 0.0563(13) 0.0399(11) 0.0020(10) 0.0235(11) 0.0336(12) C16 0.0550(11) 0.0344(9) 0.0332(9) -0.0010(7) 0.0157(8) 0.0013(8) C17 0.0247(8) 0.0444(9) 0.0258(8) -0.0014(7) 0.0035(6) -0.0010(7) C18 0.0364(9) 0.0501(11) 0.0434(10) 0.0074(9) 0.0066(8) -0.0077(8) C19 0.0409(11) 0.0745(15) 0.0485(11) 0.0073(10) 0.0090(9) -0.0192(10) C20 0.0303(10) 0.0973(18) 0.0431(11) -0.0039(11) 0.0095(8) -0.0129(11) C21 0.0321(10) 0.0875(17) 0.0512(12) -0.0085(11) -0.0043(8) 0.0161(11) C22 0.0328(9) 0.0543(12) 0.0462(10) -0.0034(9) -0.0011(8) 0.0077(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2065(18) . ? O2 C8 1.2058(17) . ? N1 C1 1.3877(18) . ? N1 C8 1.3858(18) . ? N1 C17 1.4354(19) . ? N2 C5 1.3794(18) . ? N2 C9 1.316(2) . ? N3 C6 1.3809(18) . ? N3 C9 1.3550(19) . ? N3 C10 1.4641(19) . ? C1 C2 1.511(2) . ? C2 H2 1.000 . ? C2 C3 1.532(2) . ? C2 C7 1.5455(19) . ? C3 H3A 0.990 . ? C3 H3B 0.990 . ? C3 C4 1.531(2) . ? C4 H4A 0.990 . ? C4 H4B 0.990 . ? C4 C5 1.490(2) . ? C5 C6 1.357(2) . ? C6 C7 1.4959(19) . ? C7 H7 1.000 . ? C7 C8 1.5225(19) . ? C9 H9 0.950 . ? C10 H10A 0.990 . ? C10 H10B 0.990 . ? C10 C11 1.503(2) . ? C11 C12 1.379(2) . ? C11 C16 1.382(2) . ? C12 H12 0.950 . ? C12 C13 1.386(3) . ? C13 H13 0.950 . ? C13 C14 1.361(3) . ? C14 H14 0.950 . ? C14 C15 1.364(3) . ? C15 H15 0.950 . ? C15 C16 1.388(3) . ? C16 H16 0.950 . ? C17 C18 1.374(2) . ? C17 C22 1.373(2) . ? C18 H18 0.950 . ? C18 C19 1.384(2) . ? C19 H19 0.950 . ? C19 C20 1.361(3) . ? C20 H20 0.950 . ? C20 C21 1.376(3) . ? C21 H21 0.950 . ? C21 C22 1.401(3) . ? C22 H22 0.950 . ? 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 C1 N1 C8 113.11(12) . . ? C1 N1 C17 123.17(12) . . ? C8 N1 C17 123.66(12) . . ? C5 N2 C9 104.43(12) . . ? C6 N3 C9 105.70(12) . . ? C6 N3 C10 127.86(12) . . ? C9 N3 C10 126.20(12) . . ? O1 C1 N1 124.25(14) . . ? O1 C1 C2 127.09(13) . . ? N1 C1 C2 108.66(12) . . ? C1 C2 H2 108.0 . . ? C1 C2 C3 111.09(12) . . ? C1 C2 C7 104.58(11) . . ? H2 C2 C3 108.0 . . ? H2 C2 C7 108.0 . . ? C3 C2 C7 116.83(12) . . ? C2 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C2 C3 C4 113.02(12) . . ? H3A C3 H3B 107.8 . . ? H3A C3 C4 109.0 . . ? H3B C3 C4 109.0 . . ? C3 C4 H4A 110.1 . . ? C3 C4 H4B 110.1 . . ? C3 C4 C5 108.17(12) . . ? H4A C4 H4B 108.4 . . ? H4A C4 C5 110.1 . . ? H4B C4 C5 110.1 . . ? N2 C5 C4 126.03(13) . . ? N2 C5 C6 110.41(13) . . ? C4 C5 C6 123.54(13) . . ? N3 C6 C5 106.39(12) . . ? N3 C6 C7 126.89(13) . . ? C5 C6 C7 126.23(13) . . ? C2 C7 C6 109.94(11) . . ? C2 C7 H7 111.6 . . ? C2 C7 C8 104.19(11) . . ? C6 C7 H7 111.6 . . ? C6 C7 C8 107.60(11) . . ? H7 C7 C8 111.6 . . ? O2 C8 N1 124.50(13) . . ? O2 C8 C7 127.34(13) . . ? N1 C8 C7 107.98(12) . . ? N2 C9 N3 113.06(13) . . ? N2 C9 H9 123.5 . . ? N3 C9 H9 123.5 . . ? N3 C10 H10A 109.0 . . ? N3 C10 H10B 109.0 . . ? N3 C10 C11 112.95(11) . . ? H10A C10 H10B 107.8 . . ? H10A C10 C11 109.0 . . ? H10B C10 C11 109.0 . . ? C10 C11 C12 121.31(15) . . ? C10 C11 C16 120.22(14) . . ? C12 C11 C16 118.47(16) . . ? C11 C12 H12 119.7 . . ? C11 C12 C13 120.65(19) . . ? H12 C12 C13 119.7 . . ? C12 C13 H13 119.8 . . ? C12 C13 C14 120.3(2) . . ? H13 C13 C14 119.8 . . ? C13 C14 H14 120.1 . . ? C13 C14 C15 119.87(19) . . ? H14 C14 C15 120.1 . . ? C14 C15 H15 119.8 . . ? C14 C15 C16 120.4(2) . . ? H15 C15 C16 119.8 . . ? C11 C16 C15 120.32(18) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? N1 C17 C18 119.56(14) . . ? N1 C17 C22 118.81(15) . . ? C18 C17 C22 121.60(16) . . ? C17 C18 H18 120.4 . . ? C17 C18 C19 119.29(18) . . ? H18 C18 C19 120.4 . . ? C18 C19 H19 119.9 . . ? C18 C19 C20 120.2(2) . . ? H19 C19 C20 119.9 . . ? C19 C20 H20 119.7 . . ? C19 C20 C21 120.66(18) . . ? H20 C20 C21 119.7 . . ? C20 C21 H21 120.0 . . ? C20 C21 C22 119.97(19) . . ? H21 C21 C22 120.0 . . ? C17 C22 C21 118.32(19) . . ? C17 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? 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 C8 N1 C1 O1 -177.50(14) . . . . ? C8 N1 C1 C2 2.89(16) . . . . ? C17 N1 C1 O1 -0.2(2) . . . . ? C17 N1 C1 C2 -179.86(13) . . . . ? O1 C1 C2 C3 -47.6(2) . . . . ? O1 C1 C2 C7 -174.45(15) . . . . ? N1 C1 C2 C3 132.02(12) . . . . ? N1 C1 C2 C7 5.14(15) . . . . ? C1 C2 C3 C4 -69.06(16) . . . . ? C7 C2 C3 C4 50.77(17) . . . . ? C2 C3 C4 C5 -50.28(17) . . . . ? C9 N2 C5 C4 178.33(14) . . . . ? C9 N2 C5 C6 -0.22(16) . . . . ? C3 C4 C5 N2 -155.44(14) . . . . ? C3 C4 C5 C6 22.9(2) . . . . ? N2 C5 C6 N3 0.00(16) . . . . ? N2 C5 C6 C7 -172.42(13) . . . . ? C4 C5 C6 N3 -178.60(13) . . . . ? C4 C5 C6 C7 9.0(2) . . . . ? C9 N3 C6 C5 0.22(15) . . . . ? C9 N3 C6 C7 172.57(13) . . . . ? C10 N3 C6 C5 174.84(13) . . . . ? C10 N3 C6 C7 -12.8(2) . . . . ? N3 C6 C7 C2 177.63(12) . . . . ? N3 C6 C7 C8 -69.50(17) . . . . ? C5 C6 C7 C2 -11.48(19) . . . . ? C5 C6 C7 C8 101.39(16) . . . . ? C1 C2 C7 C6 104.74(13) . . . . ? C1 C2 C7 C8 -10.32(14) . . . . ? C3 C2 C7 C6 -18.50(17) . . . . ? C3 C2 C7 C8 -133.56(12) . . . . ? C1 N1 C8 O2 174.66(13) . . . . ? C1 N1 C8 C7 -9.88(15) . . . . ? C17 N1 C8 O2 -2.6(2) . . . . ? C17 N1 C8 C7 172.88(13) . . . . ? C2 C7 C8 O2 -172.35(13) . . . . ? C2 C7 C8 N1 12.35(14) . . . . ? C6 C7 C8 O2 70.95(17) . . . . ? C6 C7 C8 N1 -104.35(13) . . . . ? C5 N2 C9 N3 0.37(16) . . . . ? C6 N3 C9 N2 -0.38(17) . . . . ? C10 N3 C9 N2 -175.12(12) . . . . ? C6 N3 C10 C11 -63.66(18) . . . . ? C9 N3 C10 C11 109.91(16) . . . . ? N3 C10 C11 C12 -51.4(2) . . . . ? N3 C10 C11 C16 129.30(15) . . . . ? C10 C11 C12 C13 -178.50(17) . . . . ? C16 C11 C12 C13 0.8(3) . . . . ? C11 C12 C13 C14 -0.4(3) . . . . ? C12 C13 C14 C15 -0.5(3) . . . . ? C13 C14 C15 C16 1.0(3) . . . . ? C10 C11 C16 C15 179.01(15) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C14 C15 C16 C11 -0.6(3) . . . . ? C1 N1 C17 C18 -73.0(2) . . . . ? C1 N1 C17 C22 105.08(18) . . . . ? C8 N1 C17 C18 104.00(18) . . . . ? C8 N1 C17 C22 -77.95(19) . . . . ? N1 C17 C18 C19 177.48(15) . . . . ? C22 C17 C18 C19 -0.5(3) . . . . ? C17 C18 C19 C20 -0.3(3) . . . . ? C18 C19 C20 C21 0.7(3) . . . . ? C19 C20 C21 C22 -0.2(3) . . . . ? N1 C17 C22 C21 -177.06(15) . . . . ? C18 C17 C22 C21 0.9(3) . . . . ? C20 C21 C22 C17 -0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.224 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.037 #===END