# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl #TrackingRef '9a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 N O3' _chemical_formula_weight 357.39 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_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 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 11.245(2) _cell_length_b 12.063(3) _cell_length_c 13.951(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.496(10) _cell_angle_gamma 90.00 _cell_volume 1876.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.2371 _cell_measurement_theta_max 19.8449 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9834 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27778 _diffrn_reflns_av_R_equivalents 0.1752 _diffrn_reflns_av_sigmaI/netI 0.0966 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 27.97 _reflns_number_total 4382 _reflns_number_gt 1743 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^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 0.0091(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4382 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1416 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 0.839 _refine_ls_restrained_S_all 0.839 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instruction_details ; TITL S7 in P2(1)/n CELL 0.71073 11.2454 12.0634 13.9512 90.000 97.496 90.000 ZERR 4.00 0.0023 0.0025 0.0033 0.000 0.010 0.000 LATT 1 SYMM 0.500-X,0.500+Y,0.500-Z SFAC C H N O UNIT 92 76 4 12 L.S. 12 ACTA BOND $H CONF HTAB SIZE 0.2 0.2 0.1 TEMP 25 FMAP 2 MERG 2 PLAN 10 WGHT 0.045500 EXTI 0.009090 FVAR 0.19823 O2 4 0.074656 0.133278 0.510127 11.00000 0.07281 0.06801 = 0.07711 -0.01759 0.02937 -0.01699 C9 1 0.298862 0.161311 0.404951 11.00000 0.04909 0.04998 = 0.05831 -0.00062 0.01316 -0.00388 N1 3 0.052873 0.011519 0.382655 11.00000 0.06572 0.04958 = 0.07993 -0.00738 0.01867 -0.01167 AFIX 43 H1 2 0.016984 -0.041129 0.408963 11.00000 -1.20000 AFIX 0 O3 4 -0.071593 0.234269 0.307269 11.00000 0.05500 0.05977 = 0.14322 -0.01606 0.00862 -0.00655 C7 1 0.166470 0.170566 0.361995 11.00000 0.04884 0.04855 = 0.06770 -0.00452 0.01428 -0.00258 C6 1 0.138736 0.105542 0.268282 11.00000 0.04605 0.05879 = 0.06443 -0.00505 0.00669 0.00821 C17 1 -0.053196 0.425607 0.335034 11.00000 0.05639 0.05432 = 0.07359 0.00121 0.01888 0.00444 O1 4 0.657547 0.158364 0.526426 11.00000 0.06064 0.10499 = 0.08750 -0.00185 -0.01028 0.00090 C1 1 0.077559 0.009939 0.286790 11.00000 0.05125 0.05678 = 0.06683 -0.01190 0.00584 0.00624 C8 1 0.092257 0.105800 0.428903 11.00000 0.04819 0.05477 = 0.07535 -0.00705 0.01224 -0.00605 C12 1 0.541040 0.155652 0.483078 11.00000 0.05342 0.06561 = 0.06843 0.00419 -0.00061 -0.00055 C15 1 0.128143 0.292831 0.357481 11.00000 0.05212 0.05442 = 0.08255 -0.00212 0.01659 -0.00288 AFIX 23 H15A 2 0.152963 0.326557 0.420010 11.00000 -1.20000 H15B 2 0.170177 0.330577 0.310517 11.00000 -1.20000 AFIX 0 C16 1 -0.004907 0.311115 0.330842 11.00000 0.05260 0.05816 = 0.07919 -0.00615 0.01829 -0.00261 C14 1 0.336218 0.191255 0.499684 11.00000 0.05754 0.10170 = 0.06683 -0.02157 0.01933 -0.01366 AFIX 43 H14 2 0.279349 0.214238 0.538238 11.00000 -1.20000 AFIX 0 C5 1 0.166845 0.125491 0.177130 11.00000 0.05828 0.08196 = 0.06744 0.00407 0.00245 0.00914 AFIX 43 H5 2 0.206735 0.189948 0.163406 11.00000 -1.20000 AFIX 0 C11 1 0.506026 0.123932 0.390402 11.00000 0.05330 0.09639 = 0.06705 -0.01171 0.00937 0.01634 AFIX 43 H11 2 0.562957 0.100125 0.352231 11.00000 -1.20000 AFIX 0 C2 1 0.046138 -0.068913 0.217847 11.00000 0.07240 0.06474 = 0.08647 -0.01942 0.00272 0.00474 AFIX 43 H2 2 0.006227 -0.133252 0.231853 11.00000 -1.20000 AFIX 0 C10 1 0.386481 0.126776 0.352438 11.00000 0.05693 0.08503 = 0.05827 -0.00941 0.00699 0.01009 AFIX 43 H10 2 0.364686 0.104378 0.288785 11.00000 -1.20000 AFIX 0 C18 1 -0.173157 0.443646 0.301712 11.00000 0.05978 0.07626 = 0.12632 0.00000 0.01472 0.00598 AFIX 43 H18 2 -0.221190 0.384639 0.277508 11.00000 -1.20000 AFIX 0 C13 1 0.454885 0.188098 0.538651 11.00000 0.06960 0.10790 = 0.05790 -0.01103 0.00677 -0.01723 AFIX 43 H13 2 0.476991 0.208003 0.602906 11.00000 -1.20000 AFIX 0 C22 1 0.015820 0.514113 0.371911 11.00000 0.07274 0.05787 = 0.07376 -0.00277 0.01292 0.00259 AFIX 43 H22 2 0.096330 0.503306 0.395095 11.00000 -1.20000 AFIX 0 C21 1 -0.033762 0.618783 0.374679 11.00000 0.10466 0.06427 = 0.08136 -0.00943 0.01883 0.00424 AFIX 43 H21 2 0.013185 0.678010 0.399946 11.00000 -1.20000 AFIX 0 C4 1 0.133982 0.046461 0.105490 11.00000 0.07155 0.10555 = 0.06270 -0.00695 -0.00481 0.02185 AFIX 43 H4 2 0.151421 0.058616 0.042989 11.00000 -1.20000 AFIX 0 C20 1 -0.151629 0.634969 0.340284 11.00000 0.10522 0.06752 = 0.10349 0.00207 0.03861 0.02465 AFIX 43 H20 2 -0.184295 0.705700 0.341508 11.00000 -1.20000 AFIX 0 C19 1 -0.222240 0.548922 0.304134 11.00000 0.07207 0.08967 = 0.14378 0.00947 0.02610 0.02390 AFIX 43 H19 2 -0.302679 0.560709 0.281277 11.00000 -1.20000 AFIX 0 C3 1 0.076129 -0.049101 0.126411 11.00000 0.07237 0.09311 = 0.08401 -0.02887 -0.01264 0.02484 AFIX 43 H3 2 0.056737 -0.101558 0.078046 11.00000 -1.20000 AFIX 0 C23 1 0.747635 0.145648 0.466248 11.00000 0.05217 0.17151 = 0.13429 -0.00786 0.00396 0.02199 AFIX 137 H23A 2 0.745056 0.071642 0.440761 11.00000 -1.50000 H23B 2 0.824630 0.158840 0.502959 11.00000 -1.50000 H23C 2 0.734735 0.197778 0.413933 11.00000 -1.50000 HKLF 4 END ; 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 O2 O 0.07466(12) 0.13328(12) 0.51013(11) 0.0709(5) Uani 1 1 d . . . C9 C 0.29886(17) 0.16131(16) 0.40495(15) 0.0519(5) Uani 1 1 d . . . N1 N 0.05287(14) 0.01152(14) 0.38266(13) 0.0643(5) Uani 1 1 d . . . H1 H 0.0170 -0.0411 0.4090 0.077 Uiso 1 1 calc R . . O3 O -0.07159(13) 0.23427(13) 0.30727(13) 0.0864(5) Uani 1 1 d . . . C7 C 0.16647(17) 0.17057(16) 0.36199(15) 0.0544(5) Uani 1 1 d . . . C6 C 0.13874(17) 0.10554(18) 0.26828(16) 0.0565(6) Uani 1 1 d . . . C17 C -0.05320(19) 0.42561(18) 0.33503(15) 0.0605(6) Uani 1 1 d . . . O1 O 0.65755(15) 0.15836(14) 0.52643(12) 0.0861(5) Uani 1 1 d . . . C1 C 0.07756(17) 0.00994(18) 0.28679(16) 0.0585(6) Uani 1 1 d . . . C8 C 0.09226(17) 0.10580(18) 0.42890(17) 0.0591(6) Uani 1 1 d . . . C12 C 0.54104(19) 0.15565(18) 0.48308(17) 0.0632(6) Uani 1 1 d . . . C15 C 0.12814(17) 0.29283(16) 0.35748(16) 0.0623(6) Uani 1 1 d . . . H15A H 0.1530 0.3266 0.4200 0.075 Uiso 1 1 calc R . . H15B H 0.1702 0.3306 0.3105 0.075 Uiso 1 1 calc R . . C16 C -0.00491(19) 0.31112(18) 0.33084(16) 0.0625(6) Uani 1 1 d . . . C14 C 0.3362(2) 0.1913(2) 0.49968(17) 0.0744(7) Uani 1 1 d . . . H14 H 0.2793 0.2142 0.5382 0.089 Uiso 1 1 calc R . . C5 C 0.16685(19) 0.1255(2) 0.17713(17) 0.0697(7) Uani 1 1 d . . . H5 H 0.2067 0.1899 0.1634 0.084 Uiso 1 1 calc R . . C11 C 0.5060(2) 0.12393(19) 0.39040(17) 0.0721(7) Uani 1 1 d . . . H11 H 0.5630 0.1001 0.3522 0.087 Uiso 1 1 calc R . . C2 C 0.0461(2) -0.0689(2) 0.21785(19) 0.0752(7) Uani 1 1 d . . . H2 H 0.0062 -0.1333 0.2319 0.090 Uiso 1 1 calc R . . C10 C 0.38648(18) 0.12678(18) 0.35244(15) 0.0668(7) Uani 1 1 d . . . H10 H 0.3647 0.1044 0.2888 0.080 Uiso 1 1 calc R . . C18 C -0.1732(2) 0.4436(2) 0.30171(19) 0.0872(8) Uani 1 1 d . . . H18 H -0.2212 0.3846 0.2775 0.105 Uiso 1 1 calc R . . C13 C 0.4549(2) 0.1881(2) 0.53865(16) 0.0786(7) Uani 1 1 d . . . H13 H 0.4770 0.2080 0.6029 0.094 Uiso 1 1 calc R . . C22 C 0.0158(2) 0.51411(19) 0.37191(15) 0.0678(6) Uani 1 1 d . . . H22 H 0.0963 0.5033 0.3951 0.081 Uiso 1 1 calc R . . C21 C -0.0338(3) 0.6188(2) 0.37468(17) 0.0828(8) Uani 1 1 d . . . H21 H 0.0132 0.6780 0.3999 0.099 Uiso 1 1 calc R . . C4 C 0.1340(2) 0.0465(3) 0.10549(18) 0.0811(7) Uani 1 1 d . . . H4 H 0.1514 0.0586 0.0430 0.097 Uiso 1 1 calc R . . C20 C -0.1516(3) 0.6350(2) 0.3403(2) 0.0899(9) Uani 1 1 d . . . H20 H -0.1843 0.7057 0.3415 0.108 Uiso 1 1 calc R . . C19 C -0.2222(2) 0.5489(3) 0.3041(2) 0.1008(9) Uani 1 1 d . . . H19 H -0.3027 0.5607 0.2813 0.121 Uiso 1 1 calc R . . C3 C 0.0761(2) -0.0491(2) 0.1264(2) 0.0852(8) Uani 1 1 d . . . H3 H 0.0567 -0.1016 0.0780 0.102 Uiso 1 1 calc R . . C23 C 0.7476(2) 0.1456(3) 0.4662(2) 0.1200(11) Uani 1 1 d . . . H23A H 0.7451 0.0716 0.4408 0.180 Uiso 1 1 calc R . . H23B H 0.8246 0.1588 0.5030 0.180 Uiso 1 1 calc R . . H23C H 0.7347 0.1978 0.4139 0.180 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 O2 0.0728(11) 0.0680(11) 0.0771(11) -0.0176(8) 0.0294(9) -0.0170(7) C9 0.0491(12) 0.0500(13) 0.0583(14) -0.0006(10) 0.0132(11) -0.0039(10) N1 0.0657(12) 0.0496(12) 0.0799(13) -0.0074(10) 0.0187(10) -0.0117(9) O3 0.0550(10) 0.0598(10) 0.1432(16) -0.0161(10) 0.0086(9) -0.0065(8) C7 0.0488(13) 0.0485(13) 0.0677(14) -0.0045(11) 0.0143(11) -0.0026(10) C6 0.0461(13) 0.0588(15) 0.0644(15) -0.0050(12) 0.0067(11) 0.0082(11) C17 0.0564(14) 0.0543(14) 0.0736(15) 0.0012(12) 0.0189(11) 0.0044(11) O1 0.0606(11) 0.1050(14) 0.0875(12) -0.0019(10) -0.0103(9) 0.0009(9) C1 0.0512(13) 0.0568(15) 0.0668(15) -0.0119(12) 0.0058(11) 0.0062(11) C8 0.0482(13) 0.0548(15) 0.0754(16) -0.0070(13) 0.0122(12) -0.0060(10) C12 0.0534(14) 0.0656(16) 0.0684(17) 0.0042(12) -0.0006(12) -0.0005(11) C15 0.0521(13) 0.0544(14) 0.0826(16) -0.0021(11) 0.0166(11) -0.0029(10) C16 0.0526(14) 0.0582(15) 0.0792(16) -0.0061(12) 0.0183(12) -0.0026(11) C14 0.0575(15) 0.102(2) 0.0668(17) -0.0216(14) 0.0193(12) -0.0137(13) C5 0.0583(15) 0.0820(18) 0.0674(17) 0.0041(14) 0.0025(12) 0.0091(12) C11 0.0533(15) 0.0964(19) 0.0670(16) -0.0117(14) 0.0094(12) 0.0163(13) C2 0.0724(16) 0.0647(16) 0.0865(19) -0.0194(15) 0.0027(13) 0.0047(12) C10 0.0569(15) 0.0850(17) 0.0583(15) -0.0094(12) 0.0070(12) 0.0101(12) C18 0.0598(16) 0.0763(19) 0.126(2) 0.0000(16) 0.0147(14) 0.0060(13) C13 0.0696(17) 0.108(2) 0.0579(15) -0.0110(14) 0.0068(13) -0.0172(14) C22 0.0727(15) 0.0579(15) 0.0738(16) -0.0028(12) 0.0129(12) 0.0026(13) C21 0.105(2) 0.0643(18) 0.0814(19) -0.0094(13) 0.0188(16) 0.0042(15) C4 0.0716(17) 0.106(2) 0.0627(16) -0.0070(17) -0.0048(13) 0.0219(15) C20 0.105(2) 0.0675(19) 0.103(2) 0.0021(16) 0.0386(19) 0.0246(17) C19 0.0721(19) 0.090(2) 0.144(3) 0.009(2) 0.0261(17) 0.0239(17) C3 0.0724(17) 0.093(2) 0.084(2) -0.0289(17) -0.0126(14) 0.0248(16) C23 0.0522(17) 0.172(3) 0.134(3) -0.008(2) 0.0040(17) 0.0220(18) _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 O2 C8 1.221(2) . ? C9 C10 1.367(2) . ? C9 C14 1.382(3) . ? C9 C7 1.535(3) . ? N1 C8 1.353(2) . ? N1 C1 1.401(2) . ? N1 H1 0.8600 . ? O3 C16 1.211(2) . ? C7 C6 1.522(3) . ? C7 C15 1.536(3) . ? C7 C8 1.543(3) . ? C6 C5 1.371(3) . ? C6 C1 1.384(3) . ? C17 C22 1.379(3) . ? C17 C18 1.386(3) . ? C17 C16 1.488(3) . ? O1 C12 1.370(2) . ? O1 C23 1.406(3) . ? C1 C2 1.366(3) . ? C12 C11 1.357(3) . ? C12 C13 1.374(3) . ? C15 C16 1.510(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C14 C13 1.374(3) . ? C14 H14 0.9300 . ? C5 C4 1.396(3) . ? C5 H5 0.9300 . ? C11 C10 1.380(3) . ? C11 H11 0.9300 . ? C2 C3 1.382(3) . ? C2 H2 0.9300 . ? C10 H10 0.9300 . ? C18 C19 1.387(3) . ? C18 H18 0.9300 . ? C13 H13 0.9300 . ? C22 C21 1.383(3) . ? C22 H22 0.9300 . ? C21 C20 1.364(3) . ? C21 H21 0.9300 . ? C4 C3 1.374(3) . ? C4 H4 0.9300 . ? C20 C19 1.363(3) . ? C20 H20 0.9300 . ? C19 H19 0.9300 . ? C3 H3 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? 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 C10 C9 C14 116.2(2) . . ? C10 C9 C7 122.9(2) . . ? C14 C9 C7 120.86(18) . . ? C8 N1 C1 111.92(18) . . ? C8 N1 H1 124.0 . . ? C1 N1 H1 124.0 . . ? C6 C7 C9 112.19(16) . . ? C6 C7 C15 115.78(18) . . ? C9 C7 C15 109.80(16) . . ? C6 C7 C8 101.09(17) . . ? C9 C7 C8 107.49(16) . . ? C15 C7 C8 109.88(16) . . ? C5 C6 C1 120.0(2) . . ? C5 C6 C7 131.3(2) . . ? C1 C6 C7 108.68(18) . . ? C22 C17 C18 118.6(2) . . ? C22 C17 C16 122.9(2) . . ? C18 C17 C16 118.5(2) . . ? C12 O1 C23 117.1(2) . . ? C2 C1 C6 122.5(2) . . ? C2 C1 N1 128.0(2) . . ? C6 C1 N1 109.38(19) . . ? O2 C8 N1 126.01(19) . . ? O2 C8 C7 126.14(19) . . ? N1 C8 C7 107.84(18) . . ? C11 C12 O1 124.7(2) . . ? C11 C12 C13 118.7(2) . . ? O1 C12 C13 116.6(2) . . ? C16 C15 C7 114.47(16) . . ? C16 C15 H15A 108.6 . . ? C7 C15 H15A 108.6 . . ? C16 C15 H15B 108.6 . . ? C7 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? O3 C16 C17 120.3(2) . . ? O3 C16 C15 120.92(19) . . ? C17 C16 C15 118.74(18) . . ? C13 C14 C9 122.0(2) . . ? C13 C14 H14 119.0 . . ? C9 C14 H14 119.0 . . ? C6 C5 C4 118.2(2) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C1 C2 C3 117.2(2) . . ? C1 C2 H2 121.4 . . ? C3 C2 H2 121.4 . . ? C9 C10 C11 122.4(2) . . ? C9 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? C17 C18 C19 120.6(2) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C17 C22 C21 120.5(2) . . ? C17 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C20 C21 C22 119.9(2) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C3 C4 C5 120.6(2) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C19 C20 C21 120.9(2) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C20 C19 C18 119.5(3) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C4 C3 C2 121.4(2) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? O1 C23 H23A 109.5 . . ? O1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C10 C9 C7 C6 17.5(3) . . . . ? C14 C9 C7 C6 -164.41(19) . . . . ? C10 C9 C7 C15 -112.7(2) . . . . ? C14 C9 C7 C15 65.3(2) . . . . ? C10 C9 C7 C8 127.8(2) . . . . ? C14 C9 C7 C8 -54.2(2) . . . . ? C9 C7 C6 C5 -73.0(3) . . . . ? C15 C7 C6 C5 54.1(3) . . . . ? C8 C7 C6 C5 172.8(2) . . . . ? C9 C7 C6 C1 104.93(18) . . . . ? C15 C7 C6 C1 -127.97(18) . . . . ? C8 C7 C6 C1 -9.3(2) . . . . ? C5 C6 C1 C2 2.0(3) . . . . ? C7 C6 C1 C2 -176.17(18) . . . . ? C5 C6 C1 N1 -176.37(17) . . . . ? C7 C6 C1 N1 5.5(2) . . . . ? C8 N1 C1 C2 -176.7(2) . . . . ? C8 N1 C1 C6 1.6(2) . . . . ? C1 N1 C8 O2 173.9(2) . . . . ? C1 N1 C8 C7 -7.8(2) . . . . ? C6 C7 C8 O2 -171.5(2) . . . . ? C9 C7 C8 O2 70.8(3) . . . . ? C15 C7 C8 O2 -48.7(3) . . . . ? C6 C7 C8 N1 10.2(2) . . . . ? C9 C7 C8 N1 -107.53(19) . . . . ? C15 C7 C8 N1 133.03(18) . . . . ? C23 O1 C12 C11 11.3(3) . . . . ? C23 O1 C12 C13 -168.4(2) . . . . ? C6 C7 C15 C16 60.6(2) . . . . ? C9 C7 C15 C16 -171.06(17) . . . . ? C8 C7 C15 C16 -53.0(2) . . . . ? C22 C17 C16 O3 172.3(2) . . . . ? C18 C17 C16 O3 -6.7(3) . . . . ? C22 C17 C16 C15 -7.1(3) . . . . ? C18 C17 C16 C15 173.88(19) . . . . ? C7 C15 C16 O3 -6.0(3) . . . . ? C7 C15 C16 C17 173.33(17) . . . . ? C10 C9 C14 C13 0.9(3) . . . . ? C7 C9 C14 C13 -177.3(2) . . . . ? C1 C6 C5 C4 -1.1(3) . . . . ? C7 C6 C5 C4 176.6(2) . . . . ? O1 C12 C11 C10 -178.3(2) . . . . ? C13 C12 C11 C10 1.5(3) . . . . ? C6 C1 C2 C3 -1.1(3) . . . . ? N1 C1 C2 C3 177.0(2) . . . . ? C14 C9 C10 C11 -1.4(3) . . . . ? C7 C9 C10 C11 176.74(19) . . . . ? C12 C11 C10 C9 0.2(3) . . . . ? C22 C17 C18 C19 0.9(3) . . . . ? C16 C17 C18 C19 -180.0(2) . . . . ? C9 C14 C13 C12 0.7(4) . . . . ? C11 C12 C13 C14 -1.9(4) . . . . ? O1 C12 C13 C14 177.9(2) . . . . ? C18 C17 C22 C21 -0.6(3) . . . . ? C16 C17 C22 C21 -179.6(2) . . . . ? C17 C22 C21 C20 -0.3(3) . . . . ? C6 C5 C4 C3 -0.6(3) . . . . ? C22 C21 C20 C19 0.9(4) . . . . ? C21 C20 C19 C18 -0.5(4) . . . . ? C17 C18 C19 C20 -0.4(4) . . . . ? C5 C4 C3 C2 1.6(4) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.171 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 933799' ####################################################################### # # 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_LAX #TrackingRef '9d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H17 N O4' _chemical_formula_weight 371.38 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_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 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 10.8852(16) _cell_length_b 12.4799(18) _cell_length_c 13.7493(18) _cell_angle_alpha 90.00 _cell_angle_beta 103.481(5) _cell_angle_gamma 90.00 _cell_volume 1816.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 30.42 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9907 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16754 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 28.70 _reflns_number_total 4679 _reflns_number_gt 3091 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+0.5534P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4679 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0864 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1388 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instruction_details ; TITL TRY1 in P2(1)/n CELL 0.71073 10.8852 12.4799 13.7493 90.000 103.481 90.000 ZERR 4.00 0.0016 0.0018 0.0018 0.000 0.005 0.000 LATT 1 SYMM -x+1/2, y+1/2, -z+1/2 SFAC C H N O UNIT 92 68 4 16 MERG 2 L.S. 12 ACTA BOND $H CONF HTAB SIZE 0.1 0.1 0.1 TEMP 25 FMAP 2 PLAN 5 WGHT 0.055700 0.553400 FVAR 0.20792 O1 4 0.636400 0.216656 0.892304 11.00000 0.03267 0.12546 = 0.07270 0.02525 0.01603 -0.00360 O2 4 0.706550 0.147203 1.050214 11.00000 0.03628 0.08395 = 0.05673 -0.00640 0.00455 0.00877 O3 4 -0.071022 0.239185 0.825017 11.00000 0.03588 0.04204 = 0.10306 -0.00908 0.01651 -0.00696 O4 4 0.081543 0.131561 1.029050 11.00000 0.05573 0.04568 = 0.05984 -0.00959 0.03197 -0.01620 N1 3 0.063092 0.019609 0.894060 11.00000 0.04060 0.03184 = 0.05578 -0.00115 0.02007 -0.00723 AFIX 43 H10 2 0.027837 -0.033966 0.916029 11.00000 -1.20000 AFIX 0 C1 1 0.743104 0.173727 0.960305 11.00000 0.03568 0.10360 = 0.06659 -0.00126 0.01120 0.00773 AFIX 23 H1 2 0.810969 0.225942 0.973885 11.00000 -1.20000 H3 2 0.772780 0.110230 0.932115 11.00000 -1.20000 AFIX 0 C2 1 0.534600 0.186651 0.930087 11.00000 0.03484 0.05277 = 0.05031 0.00423 0.01506 -0.00117 C3 1 0.409492 0.196070 0.885355 11.00000 0.03487 0.05974 = 0.04906 0.01706 0.01091 -0.00241 AFIX 43 H17 2 0.383116 0.221899 0.820377 11.00000 -1.20000 AFIX 0 C4 1 0.321748 0.165588 0.940389 11.00000 0.03300 0.03035 = 0.04625 -0.00187 0.01272 -0.00225 C5 1 0.179549 0.176987 0.889392 11.00000 0.03042 0.03535 = 0.04833 0.00163 0.01470 -0.00324 C6 1 0.141222 0.295252 0.887586 11.00000 0.03260 0.03372 = 0.05872 0.00035 0.01684 -0.00349 AFIX 23 H8 2 0.167588 0.323994 0.954778 11.00000 -1.20000 H9 2 0.185965 0.334366 0.845543 11.00000 -1.20000 AFIX 0 C7 1 0.000564 0.314318 0.849470 11.00000 0.03389 0.03949 = 0.05583 -0.00168 0.01784 -0.00293 C8 1 -0.048234 0.426028 0.845086 11.00000 0.03511 0.04007 = 0.05091 -0.00031 0.01479 0.00123 C9 1 -0.177510 0.443360 0.814898 11.00000 0.03774 0.04977 = 0.10041 -0.00092 0.00908 -0.00053 AFIX 43 H5 2 -0.231959 0.385461 0.797359 11.00000 -1.20000 AFIX 0 C10 1 -0.225734 0.545931 0.810749 11.00000 0.04359 0.05887 = 0.11898 0.00249 0.00921 0.01329 AFIX 43 H4 2 -0.312582 0.556503 0.791175 11.00000 -1.20000 AFIX 0 C11 1 -0.147248 0.632091 0.835090 11.00000 0.06523 0.04635 = 0.07959 0.00235 0.01543 0.01538 AFIX 43 H2 2 -0.180313 0.701073 0.831573 11.00000 -1.20000 AFIX 0 C12 1 0.576218 0.147256 1.024574 11.00000 0.03581 0.04836 = 0.04675 -0.00894 0.00598 0.00302 C13 1 0.029597 0.513840 0.869416 11.00000 0.03978 0.04478 = 0.08180 -0.00406 0.00947 0.00075 AFIX 43 H7 2 0.116567 0.504168 0.889328 11.00000 -1.20000 AFIX 0 C14 1 -0.020172 0.616246 0.864559 11.00000 0.06189 0.03951 = 0.09155 -0.00366 0.00812 -0.00124 AFIX 43 H6 2 0.033543 0.674699 0.881543 11.00000 -1.20000 AFIX 0 C15 1 0.150049 0.120191 0.789031 11.00000 0.02647 0.03846 = 0.04868 0.00215 0.00971 0.00286 C16 1 0.087243 0.024684 0.798490 11.00000 0.03053 0.03762 = 0.04914 -0.00102 0.01026 0.00412 C17 1 0.101894 0.109013 0.947376 11.00000 0.03341 0.03392 = 0.05435 -0.00102 0.01693 -0.00349 C18 1 0.052593 -0.046863 0.720959 11.00000 0.04061 0.04272 = 0.06108 -0.00773 0.00900 0.00049 AFIX 43 H14 2 0.012294 -0.110854 0.728977 11.00000 -1.20000 AFIX 0 C19 1 0.079841 -0.020265 0.630374 11.00000 0.04910 0.06119 = 0.05111 -0.01135 0.00345 0.00664 AFIX 43 H13 2 0.058628 -0.067616 0.576848 11.00000 -1.20000 AFIX 0 C20 1 0.137829 0.075215 0.618575 11.00000 0.04474 0.07277 = 0.04408 0.00432 0.00670 0.00998 AFIX 43 H12 2 0.153057 0.092430 0.556628 11.00000 -1.20000 AFIX 0 C21 1 0.173965 0.146277 0.697838 11.00000 0.03558 0.05187 = 0.05046 0.00748 0.00963 0.00210 AFIX 43 H11 2 0.213683 0.210462 0.689485 11.00000 -1.20000 AFIX 0 C22 1 0.364994 0.127870 1.036259 11.00000 0.04589 0.06524 = 0.04200 -0.00062 0.01649 -0.00631 AFIX 43 H16 2 0.306661 0.109218 1.073156 11.00000 -1.20000 AFIX 0 C23 1 0.494249 0.116621 1.080194 11.00000 0.05143 0.07815 = 0.03880 0.00463 0.00717 0.00054 AFIX 43 H15 2 0.522545 0.089417 1.144500 11.00000 -1.20000 HKLF 4 END ; 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 0.63640(12) 0.21666(15) 0.89230(11) 0.0763(5) Uani 1 1 d . . . O2 O 0.70655(11) 0.14720(12) 1.05021(10) 0.0600(4) Uani 1 1 d . . . O3 O -0.07102(11) 0.23919(10) 0.82502(12) 0.0603(4) Uani 1 1 d . . . O4 O 0.08154(12) 0.13156(10) 1.02905(10) 0.0507(3) Uani 1 1 d . . . N1 N 0.06309(13) 0.01961(11) 0.89406(11) 0.0413(3) Uani 1 1 d . . . H10 H 0.0278 -0.0340 0.9160 0.050 Uiso 1 1 calc R . . C1 C 0.74310(18) 0.1737(2) 0.96031(16) 0.0687(6) Uani 1 1 d . . . H1 H 0.8110 0.2259 0.9739 0.082 Uiso 1 1 calc R . . H3 H 0.7728 0.1102 0.9321 0.082 Uiso 1 1 calc R . . C2 C 0.53460(16) 0.18665(15) 0.93009(14) 0.0451(4) Uani 1 1 d . . . C3 C 0.40949(15) 0.19607(15) 0.88535(14) 0.0477(4) Uani 1 1 d . . . H17 H 0.3831 0.2219 0.8204 0.057 Uiso 1 1 calc R . . C4 C 0.32175(14) 0.16559(12) 0.94039(12) 0.0360(3) Uani 1 1 d . . . C5 C 0.17955(14) 0.17699(12) 0.88939(12) 0.0371(4) Uani 1 1 d . . . C6 C 0.14122(14) 0.29525(12) 0.88759(14) 0.0407(4) Uani 1 1 d . . . H8 H 0.1676 0.3240 0.9548 0.049 Uiso 1 1 calc R . . H9 H 0.1860 0.3344 0.8455 0.049 Uiso 1 1 calc R . . C7 C 0.00056(15) 0.31432(13) 0.84947(13) 0.0419(4) Uani 1 1 d . . . C8 C -0.04823(15) 0.42603(13) 0.84509(13) 0.0412(4) Uani 1 1 d . . . C9 C -0.17751(18) 0.44336(17) 0.81490(18) 0.0638(6) Uani 1 1 d . . . H5 H -0.2320 0.3855 0.7974 0.077 Uiso 1 1 calc R . . C10 C -0.2257(2) 0.54593(18) 0.8107(2) 0.0754(7) Uani 1 1 d . . . H4 H -0.3126 0.5565 0.7912 0.090 Uiso 1 1 calc R . . C11 C -0.1472(2) 0.63209(17) 0.83509(17) 0.0640(6) Uani 1 1 d . . . H2 H -0.1803 0.7011 0.8316 0.077 Uiso 1 1 calc R . . C12 C 0.57622(15) 0.14726(14) 1.02457(13) 0.0442(4) Uani 1 1 d . . . C13 C 0.02960(18) 0.51384(15) 0.86942(16) 0.0562(5) Uani 1 1 d . . . H7 H 0.1166 0.5042 0.8893 0.067 Uiso 1 1 calc R . . C14 C -0.0202(2) 0.61625(16) 0.86456(18) 0.0659(6) Uani 1 1 d . . . H6 H 0.0335 0.6747 0.8815 0.079 Uiso 1 1 calc R . . C15 C 0.15005(14) 0.12019(13) 0.78903(12) 0.0377(4) Uani 1 1 d . . . C16 C 0.08724(14) 0.02468(13) 0.79849(13) 0.0389(4) Uani 1 1 d . . . C17 C 0.10189(15) 0.10901(13) 0.94738(13) 0.0395(4) Uani 1 1 d . . . C18 C 0.05259(16) -0.04686(15) 0.72096(14) 0.0486(4) Uani 1 1 d . . . H14 H 0.0123 -0.1109 0.7290 0.058 Uiso 1 1 calc R . . C19 C 0.07984(18) -0.02026(17) 0.63037(15) 0.0552(5) Uani 1 1 d . . . H13 H 0.0586 -0.0676 0.5768 0.066 Uiso 1 1 calc R . . C20 C 0.13783(17) 0.07521(17) 0.61857(14) 0.0545(5) Uani 1 1 d . . . H12 H 0.1531 0.0924 0.5566 0.065 Uiso 1 1 calc R . . C21 C 0.17397(15) 0.14628(15) 0.69784(13) 0.0460(4) Uani 1 1 d . . . H11 H 0.2137 0.2105 0.6895 0.055 Uiso 1 1 calc R . . C22 C 0.36499(17) 0.12787(16) 1.03626(13) 0.0500(4) Uani 1 1 d . . . H16 H 0.3067 0.1092 1.0732 0.060 Uiso 1 1 calc R . . C23 C 0.49425(18) 0.11662(18) 1.08019(14) 0.0567(5) Uani 1 1 d . . . H15 H 0.5225 0.0894 1.1445 0.068 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 0.0327(7) 0.1255(14) 0.0727(10) 0.0253(9) 0.0160(6) -0.0036(8) O2 0.0363(6) 0.0840(10) 0.0567(8) -0.0064(7) 0.0045(6) 0.0088(6) O3 0.0359(7) 0.0420(7) 0.1031(11) -0.0091(7) 0.0165(7) -0.0070(5) O4 0.0557(7) 0.0457(7) 0.0598(8) -0.0096(6) 0.0320(6) -0.0162(6) N1 0.0406(7) 0.0318(7) 0.0558(9) -0.0011(6) 0.0201(6) -0.0072(6) C1 0.0357(10) 0.1036(18) 0.0666(14) -0.0013(13) 0.0112(9) 0.0077(11) C2 0.0348(8) 0.0528(10) 0.0503(10) 0.0042(8) 0.0151(7) -0.0012(7) C3 0.0349(8) 0.0597(11) 0.0491(10) 0.0171(9) 0.0109(7) -0.0024(8) C4 0.0330(8) 0.0303(7) 0.0462(9) -0.0019(7) 0.0127(6) -0.0023(6) C5 0.0304(7) 0.0353(8) 0.0483(9) 0.0016(7) 0.0147(6) -0.0032(6) C6 0.0326(8) 0.0337(8) 0.0587(11) 0.0003(7) 0.0168(7) -0.0035(6) C7 0.0339(8) 0.0395(9) 0.0558(10) -0.0017(8) 0.0178(7) -0.0029(7) C8 0.0351(8) 0.0401(9) 0.0509(10) -0.0003(8) 0.0148(7) 0.0012(7) C9 0.0377(10) 0.0498(11) 0.1004(17) -0.0009(11) 0.0091(10) -0.0005(8) C10 0.0436(11) 0.0589(13) 0.119(2) 0.0025(13) 0.0092(12) 0.0133(10) C11 0.0652(13) 0.0464(11) 0.0796(15) 0.0023(10) 0.0154(11) 0.0154(10) C12 0.0358(8) 0.0484(10) 0.0468(10) -0.0089(8) 0.0060(7) 0.0030(7) C13 0.0398(9) 0.0448(10) 0.0818(14) -0.0041(10) 0.0095(9) 0.0008(8) C14 0.0619(13) 0.0395(10) 0.0915(17) -0.0037(10) 0.0081(11) -0.0012(9) C15 0.0265(7) 0.0385(8) 0.0487(9) 0.0022(7) 0.0097(6) 0.0029(6) C16 0.0305(7) 0.0376(8) 0.0491(10) -0.0010(7) 0.0103(7) 0.0041(6) C17 0.0334(8) 0.0339(8) 0.0543(10) -0.0010(7) 0.0169(7) -0.0035(6) C18 0.0406(9) 0.0427(9) 0.0611(12) -0.0077(8) 0.0090(8) 0.0005(7) C19 0.0491(11) 0.0612(12) 0.0511(11) -0.0113(10) 0.0035(8) 0.0066(9) C20 0.0447(10) 0.0728(13) 0.0441(10) 0.0043(10) 0.0067(8) 0.0100(9) C21 0.0356(8) 0.0519(10) 0.0505(10) 0.0075(8) 0.0096(7) 0.0021(7) C22 0.0459(10) 0.0652(12) 0.0420(10) -0.0006(9) 0.0165(8) -0.0063(9) C23 0.0514(11) 0.0782(14) 0.0388(10) 0.0046(9) 0.0072(8) 0.0005(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.381(2) . ? O1 C1 1.416(2) . ? O2 C12 1.380(2) . ? O2 C1 1.423(3) . ? O3 C7 1.215(2) . ? O4 C17 1.227(2) . ? N1 C17 1.348(2) . ? N1 C16 1.400(2) . ? N1 H10 0.8600 . ? C1 H1 0.9700 . ? C1 H3 0.9700 . ? C2 C3 1.362(2) . ? C2 C12 1.364(2) . ? C3 C4 1.402(2) . ? C3 H17 0.9300 . ? C4 C22 1.375(2) . ? C4 C5 1.550(2) . ? C5 C15 1.518(2) . ? C5 C6 1.532(2) . ? C5 C17 1.544(2) . ? C6 C7 1.517(2) . ? C6 H8 0.9700 . ? C6 H9 0.9700 . ? C7 C8 1.488(2) . ? C8 C13 1.378(2) . ? C8 C9 1.388(2) . ? C9 C10 1.380(3) . ? C9 H5 0.9300 . ? C10 C11 1.366(3) . ? C10 H4 0.9300 . ? C11 C14 1.362(3) . ? C11 H2 0.9300 . ? C12 C23 1.358(3) . ? C13 C14 1.384(3) . ? C13 H7 0.9300 . ? C14 H6 0.9300 . ? C15 C21 1.378(2) . ? C15 C16 1.395(2) . ? C16 C18 1.374(2) . ? C18 C19 1.386(3) . ? C18 H14 0.9300 . ? C19 C20 1.376(3) . ? C19 H13 0.9300 . ? C20 C21 1.389(3) . ? C20 H12 0.9300 . ? C21 H11 0.9300 . ? C22 C23 1.403(3) . ? C22 H16 0.9300 . ? C23 H15 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C1 104.82(15) . . ? C12 O2 C1 104.89(13) . . ? C17 N1 C16 111.68(13) . . ? C17 N1 H10 124.2 . . ? C16 N1 H10 124.2 . . ? O1 C1 O2 108.01(15) . . ? O1 C1 H1 110.1 . . ? O2 C1 H1 110.1 . . ? O1 C1 H3 110.1 . . ? O2 C1 H3 110.1 . . ? H1 C1 H3 108.4 . . ? C3 C2 C12 122.42(16) . . ? C3 C2 O1 127.75(17) . . ? C12 C2 O1 109.79(15) . . ? C2 C3 C4 117.90(16) . . ? C2 C3 H17 121.1 . . ? C4 C3 H17 121.1 . . ? C22 C4 C3 119.08(15) . . ? C22 C4 C5 123.21(14) . . ? C3 C4 C5 117.71(14) . . ? C15 C5 C6 115.85(14) . . ? C15 C5 C17 100.81(12) . . ? C6 C5 C17 110.96(13) . . ? C15 C5 C4 110.23(12) . . ? C6 C5 C4 109.58(12) . . ? C17 C5 C4 108.98(13) . . ? C7 C6 C5 113.93(13) . . ? C7 C6 H8 108.8 . . ? C5 C6 H8 108.8 . . ? C7 C6 H9 108.8 . . ? C5 C6 H9 108.8 . . ? H8 C6 H9 107.7 . . ? O3 C7 C8 120.78(15) . . ? O3 C7 C6 120.33(15) . . ? C8 C7 C6 118.88(14) . . ? C13 C8 C9 118.15(17) . . ? C13 C8 C7 122.81(15) . . ? C9 C8 C7 119.04(16) . . ? C10 C9 C8 120.42(19) . . ? C10 C9 H5 119.8 . . ? C8 C9 H5 119.8 . . ? C11 C10 C9 120.68(19) . . ? C11 C10 H4 119.7 . . ? C9 C10 H4 119.7 . . ? C14 C11 C10 119.51(19) . . ? C14 C11 H2 120.2 . . ? C10 C11 H2 120.2 . . ? C23 C12 C2 121.45(16) . . ? C23 C12 O2 128.84(17) . . ? C2 C12 O2 109.69(15) . . ? C8 C13 C14 120.75(18) . . ? C8 C13 H7 119.6 . . ? C14 C13 H7 119.6 . . ? C11 C14 C13 120.50(19) . . ? C11 C14 H6 119.8 . . ? C13 C14 H6 119.8 . . ? C21 C15 C16 119.17(16) . . ? C21 C15 C5 132.25(15) . . ? C16 C15 C5 108.58(14) . . ? C18 C16 C15 122.32(16) . . ? C18 C16 N1 128.38(16) . . ? C15 C16 N1 109.23(14) . . ? O4 C17 N1 125.96(15) . . ? O4 C17 C5 125.73(14) . . ? N1 C17 C5 108.29(14) . . ? C16 C18 C19 117.64(17) . . ? C16 C18 H14 121.2 . . ? C19 C18 H14 121.2 . . ? C20 C19 C18 120.90(18) . . ? C20 C19 H13 119.5 . . ? C18 C19 H13 119.5 . . ? C19 C20 C21 120.95(18) . . ? C19 C20 H12 119.5 . . ? C21 C20 H12 119.5 . . ? C15 C21 C20 118.96(18) . . ? C15 C21 H11 120.5 . . ? C20 C21 H11 120.5 . . ? C4 C22 C23 122.13(16) . . ? C4 C22 H16 118.9 . . ? C23 C22 H16 118.9 . . ? C12 C23 C22 116.99(17) . . ? C12 C23 H15 121.5 . . ? C22 C23 H15 121.5 . . ? 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 C2 O1 C1 O2 -16.7(2) . . . . ? C12 O2 C1 O1 15.7(2) . . . . ? C1 O1 C2 C3 -170.6(2) . . . . ? C1 O1 C2 C12 11.5(2) . . . . ? C12 C2 C3 C4 1.2(3) . . . . ? O1 C2 C3 C4 -176.44(18) . . . . ? C2 C3 C4 C22 0.0(3) . . . . ? C2 C3 C4 C5 179.70(16) . . . . ? C22 C4 C5 C15 -127.22(17) . . . . ? C3 C4 C5 C15 53.13(19) . . . . ? C22 C4 C5 C6 104.15(18) . . . . ? C3 C4 C5 C6 -75.50(19) . . . . ? C22 C4 C5 C17 -17.4(2) . . . . ? C3 C4 C5 C17 162.90(15) . . . . ? C15 C5 C6 C7 60.88(18) . . . . ? C17 C5 C6 C7 -53.3(2) . . . . ? C4 C5 C6 C7 -173.66(13) . . . . ? C5 C6 C7 O3 1.0(2) . . . . ? C5 C6 C7 C8 179.48(15) . . . . ? O3 C7 C8 C13 -178.17(19) . . . . ? C6 C7 C8 C13 3.4(3) . . . . ? O3 C7 C8 C9 1.6(3) . . . . ? C6 C7 C8 C9 -176.88(17) . . . . ? C13 C8 C9 C10 -0.7(3) . . . . ? C7 C8 C9 C10 179.5(2) . . . . ? C8 C9 C10 C11 0.8(4) . . . . ? C9 C10 C11 C14 -0.6(4) . . . . ? C3 C2 C12 C23 -1.1(3) . . . . ? O1 C2 C12 C23 176.95(18) . . . . ? C3 C2 C12 O2 -179.89(17) . . . . ? O1 C2 C12 O2 -1.9(2) . . . . ? C1 O2 C12 C23 172.7(2) . . . . ? C1 O2 C12 C2 -8.6(2) . . . . ? C9 C8 C13 C14 0.5(3) . . . . ? C7 C8 C13 C14 -179.8(2) . . . . ? C10 C11 C14 C13 0.3(4) . . . . ? C8 C13 C14 C11 -0.3(4) . . . . ? C6 C5 C15 C21 50.1(2) . . . . ? C17 C5 C15 C21 169.96(16) . . . . ? C4 C5 C15 C21 -75.0(2) . . . . ? C6 C5 C15 C16 -129.97(14) . . . . ? C17 C5 C15 C16 -10.15(16) . . . . ? C4 C5 C15 C16 104.90(14) . . . . ? C21 C15 C16 C18 2.7(2) . . . . ? C5 C15 C16 C18 -177.23(15) . . . . ? C21 C15 C16 N1 -174.61(14) . . . . ? C5 C15 C16 N1 5.48(17) . . . . ? C17 N1 C16 C18 -174.48(16) . . . . ? C17 N1 C16 C15 2.61(18) . . . . ? C16 N1 C17 O4 172.10(16) . . . . ? C16 N1 C17 C5 -9.40(18) . . . . ? C15 C5 C17 O4 -169.79(16) . . . . ? C6 C5 C17 O4 -46.5(2) . . . . ? C4 C5 C17 O4 74.2(2) . . . . ? C15 C5 C17 N1 11.71(16) . . . . ? C6 C5 C17 N1 134.97(14) . . . . ? C4 C5 C17 N1 -104.27(15) . . . . ? C15 C16 C18 C19 -1.3(2) . . . . ? N1 C16 C18 C19 175.42(16) . . . . ? C16 C18 C19 C20 -0.9(3) . . . . ? C18 C19 C20 C21 1.9(3) . . . . ? C16 C15 C21 C20 -1.7(2) . . . . ? C5 C15 C21 C20 178.16(16) . . . . ? C19 C20 C21 C15 -0.5(3) . . . . ? C3 C4 C22 C23 -1.4(3) . . . . ? C5 C4 C22 C23 178.92(17) . . . . ? C2 C12 C23 C22 -0.3(3) . . . . ? O2 C12 C23 C22 178.25(18) . . . . ? C4 C22 C23 C12 1.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.70 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.290 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 933800' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H21 N3' _chemical_formula_weight 351.44 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.7467(4) _cell_length_b 12.8110(7) _cell_length_c 21.6174(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1868.43(19) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 22.85 _exptl_crystal_description ? _exptl_crystal_colour ? _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 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9926 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19529 _diffrn_reflns_av_R_equivalents 0.0766 _diffrn_reflns_av_sigmaI/netI 0.0751 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 29.13 _reflns_number_total 5021 _reflns_number_gt 2663 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.3418P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5021 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1550 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.1849 _refine_ls_wR_factor_gt 0.1540 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instruction_details ; TITL TRY1 in P2(1)2(1)2(1) CELL 0.71073 6.7467 12.8110 21.6174 90.000 90.000 90.000 ZERR 4.00 0.0004 0.0007 0.0013 0.000 0.000 0.000 LATT -1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N UNIT 96 84 12 MERG 2 L.S. 12 ACTA BOND $H CONF HTAB SIZE 0.05 0.05 0.1 TEMP 25 FMAP 2 PLAN 10 WGHT 0.080500 0.341800 FVAR 0.25191 C18 1 0.268637 0.828582 0.249205 11.00000 0.05098 0.07063 = 0.04965 0.00398 -0.01114 -0.00363 AFIX 23 H18A 2 0.327235 0.760787 0.241155 11.00000 -1.20000 H18B 2 0.357235 0.866132 0.276658 11.00000 -1.20000 AFIX 0 N3 3 -0.006668 0.651541 0.232465 11.00000 0.10632 0.06318 = 0.10687 0.00229 -0.01865 -0.00657 AFIX 93 H3A 2 0.106576 0.651579 0.214201 11.00000 -1.20000 H3B 2 -0.088559 0.601160 0.226298 11.00000 -1.20000 AFIX 0 C16 1 0.600754 0.966754 0.208616 11.00000 0.05455 0.05040 = 0.06615 0.00605 -0.01356 -0.01033 AFIX 43 H16 2 0.620827 0.935455 0.246923 11.00000 -1.20000 AFIX 0 N2 3 0.730245 1.033991 0.181132 11.00000 0.05045 0.06400 = 0.08440 -0.00471 -0.01572 -0.00949 AFIX 43 H2 2 0.842823 1.053118 0.195955 11.00000 -1.20000 AFIX 0 C10 1 0.720848 1.137462 0.081842 11.00000 0.07287 0.04869 = 0.08214 -0.00993 0.02248 -0.01493 AFIX 43 H10 2 0.841197 1.171568 0.087451 11.00000 -1.20000 AFIX 0 C11 1 0.607259 1.155389 0.030634 11.00000 0.10007 0.05116 = 0.06856 -0.00067 0.01930 -0.00713 AFIX 43 H11 2 0.652480 1.201223 0.000405 11.00000 -1.20000 AFIX 0 C12 1 0.423253 1.105753 0.022859 11.00000 0.09154 0.05846 = 0.05622 0.00226 0.00057 -0.00166 AFIX 43 H12 2 0.347075 1.120542 -0.011908 11.00000 -1.20000 AFIX 0 C8 1 0.018255 0.817674 0.104811 11.00000 0.04714 0.06124 = 0.06132 0.00726 -0.00856 -0.00507 AFIX 43 H8 2 -0.085052 0.864257 0.111823 11.00000 -1.20000 AFIX 0 N1 3 0.014283 0.738750 0.062373 11.00000 0.06024 0.06912 = 0.06666 0.00178 -0.02262 -0.02046 AFIX 43 H1 2 -0.084140 0.724549 0.038534 11.00000 -1.20000 AFIX 0 C24 1 -0.056022 0.730788 0.270920 11.00000 0.07022 0.04925 = 0.06677 0.01878 -0.01825 0.00409 C19 1 0.073709 0.812912 0.281578 11.00000 0.05941 0.05173 = 0.04293 0.00935 -0.00635 -0.00526 C17 1 0.253299 0.889598 0.186882 11.00000 0.04105 0.05278 = 0.04859 0.00073 -0.00571 0.00101 AFIX 13 H17 2 0.145672 0.940284 0.191840 11.00000 -1.20000 AFIX 0 C7 1 0.193979 0.818626 0.135313 11.00000 0.03896 0.05329 = 0.04532 0.00934 -0.00273 -0.00680 C6 1 0.309140 0.733789 0.109047 11.00000 0.04258 0.05622 = 0.04710 0.00814 0.00018 -0.00995 C15 1 0.438598 0.951630 0.172559 11.00000 0.04823 0.04424 = 0.05000 -0.00573 -0.00471 -0.00274 C9 1 0.650347 1.066277 0.125465 11.00000 0.05303 0.04277 = 0.06461 -0.01217 0.00550 -0.00008 C14 1 0.468803 1.014738 0.118232 11.00000 0.04483 0.04090 = 0.05297 -0.00450 0.00422 0.00029 C1 1 0.189101 0.685948 0.063412 11.00000 0.06138 0.05372 = 0.04774 0.00606 -0.00146 -0.01771 C22 1 -0.280218 0.793519 0.346666 11.00000 0.09321 0.15405 = 0.08282 0.05354 0.01489 0.02167 AFIX 43 H22 2 -0.398962 0.786811 0.368151 11.00000 -1.20000 AFIX 0 C23 1 -0.231880 0.720439 0.304487 11.00000 0.05835 0.09423 = 0.09931 0.05723 -0.01376 -0.01663 AFIX 43 H23 2 -0.314848 0.663588 0.297767 11.00000 -1.20000 AFIX 0 C5 1 0.497184 0.693476 0.119987 11.00000 0.04923 0.06956 = 0.07337 -0.00059 0.00054 -0.00746 AFIX 43 H5 2 0.580365 0.723800 0.149209 11.00000 -1.20000 AFIX 0 C4 1 0.557944 0.607102 0.086385 11.00000 0.06426 0.07512 = 0.09942 0.00106 0.02221 0.00231 AFIX 43 H4 2 0.682884 0.578902 0.093527 11.00000 -1.20000 AFIX 0 C3 1 0.436238 0.562186 0.042490 11.00000 0.10089 0.06329 = 0.07911 -0.00878 0.03217 -0.01444 AFIX 43 H3 2 0.481462 0.504322 0.020680 11.00000 -1.20000 AFIX 0 C13 1 0.354158 1.035608 0.065922 11.00000 0.06627 0.05218 = 0.05047 -0.00082 0.00407 -0.00143 AFIX 43 H13 2 0.232779 1.002549 0.060271 11.00000 -1.20000 AFIX 0 C2 1 0.251615 0.600213 0.030187 11.00000 0.08213 0.06407 = 0.05841 -0.00436 0.00741 -0.02775 AFIX 43 H2A 2 0.170854 0.569437 0.000475 11.00000 -1.20000 AFIX 0 C20 1 0.016100 0.886119 0.326381 11.00000 0.10054 0.09563 = 0.04809 0.01362 0.00808 0.01456 AFIX 43 H20 2 0.098251 0.942669 0.334768 11.00000 -1.20000 AFIX 0 C21 1 -0.163032 0.875686 0.358782 11.00000 0.12133 0.13064 = 0.05541 0.01100 0.02158 0.04253 AFIX 43 H21 2 -0.199995 0.924947 0.388201 11.00000 -1.20000 HKLF 4 END ; 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 C18 C 0.2686(5) 0.8286(3) 0.24921(12) 0.0571(8) Uani 1 1 d . . . H18A H 0.3272 0.7608 0.2412 0.069 Uiso 1 1 calc R . . H18B H 0.3572 0.8661 0.2767 0.069 Uiso 1 1 calc R . . N3 N -0.0067(6) 0.6515(2) 0.23246(15) 0.0921(10) Uani 1 1 d . . . H3A H 0.1066 0.6516 0.2142 0.111 Uiso 1 1 calc R . . H3B H -0.0886 0.6012 0.2263 0.111 Uiso 1 1 calc R . . C16 C 0.6008(5) 0.9668(2) 0.20862(15) 0.0570(8) Uani 1 1 d . . . H16 H 0.6208 0.9355 0.2469 0.068 Uiso 1 1 calc R . . N2 N 0.7302(4) 1.0340(2) 0.18113(13) 0.0663(7) Uani 1 1 d . . . H2 H 0.8428 1.0531 0.1960 0.080 Uiso 1 1 calc R . . C10 C 0.7208(6) 1.1375(2) 0.08184(16) 0.0679(10) Uani 1 1 d . . . H10 H 0.8412 1.1716 0.0875 0.081 Uiso 1 1 calc R . . C11 C 0.6073(6) 1.1554(3) 0.03063(17) 0.0733(10) Uani 1 1 d . . . H11 H 0.6525 1.2012 0.0004 0.088 Uiso 1 1 calc R . . C12 C 0.4233(6) 1.1058(3) 0.02286(15) 0.0687(9) Uani 1 1 d . . . H12 H 0.3471 1.1205 -0.0119 0.082 Uiso 1 1 calc R . . C8 C 0.0183(5) 0.8177(2) 0.10481(13) 0.0566(7) Uani 1 1 d . . . H8 H -0.0851 0.8643 0.1118 0.068 Uiso 1 1 calc R . . N1 N 0.0143(4) 0.7387(2) 0.06237(12) 0.0653(8) Uani 1 1 d . . . H1 H -0.0841 0.7245 0.0385 0.078 Uiso 1 1 calc R . . C24 C -0.0560(5) 0.7308(3) 0.27092(15) 0.0621(9) Uani 1 1 d . . . C19 C 0.0737(5) 0.8129(2) 0.28158(12) 0.0514(7) Uani 1 1 d . . . C17 C 0.2533(4) 0.8896(2) 0.18688(12) 0.0475(7) Uani 1 1 d . . . H17 H 0.1457 0.9403 0.1918 0.057 Uiso 1 1 calc R . . C7 C 0.1940(4) 0.8186(2) 0.13531(12) 0.0459(7) Uani 1 1 d . . . C6 C 0.3091(4) 0.7338(2) 0.10905(12) 0.0486(7) Uani 1 1 d . . . C15 C 0.4386(4) 0.9516(2) 0.17256(13) 0.0475(7) Uani 1 1 d . . . C9 C 0.6503(5) 1.0663(2) 0.12546(14) 0.0535(8) Uani 1 1 d . . . C14 C 0.4688(4) 1.0147(2) 0.11823(13) 0.0462(7) Uani 1 1 d . . . C1 C 0.1891(5) 0.6859(2) 0.06341(13) 0.0543(8) Uani 1 1 d . . . C22 C -0.2802(8) 0.7935(6) 0.3467(2) 0.1100(17) Uani 1 1 d . . . H22 H -0.3990 0.7868 0.3682 0.132 Uiso 1 1 calc R . . C23 C -0.2319(6) 0.7204(4) 0.3045(2) 0.0840(12) Uani 1 1 d . . . H23 H -0.3148 0.6636 0.2978 0.101 Uiso 1 1 calc R . . C5 C 0.4972(5) 0.6935(3) 0.11999(15) 0.0641(8) Uani 1 1 d . . . H5 H 0.5804 0.7238 0.1492 0.077 Uiso 1 1 calc R . . C4 C 0.5579(6) 0.6071(3) 0.08638(18) 0.0796(11) Uani 1 1 d . . . H4 H 0.6829 0.5789 0.0935 0.096 Uiso 1 1 calc R . . C3 C 0.4362(7) 0.5622(3) 0.04249(18) 0.0811(12) Uani 1 1 d . . . H3 H 0.4815 0.5043 0.0207 0.097 Uiso 1 1 calc R . . C13 C 0.3542(5) 1.0356(2) 0.06592(13) 0.0563(8) Uani 1 1 d . . . H13 H 0.2328 1.0025 0.0603 0.068 Uiso 1 1 calc R . . C2 C 0.2516(6) 0.6002(3) 0.03019(14) 0.0682(10) Uani 1 1 d . . . H2A H 0.1709 0.5694 0.0005 0.082 Uiso 1 1 calc R . . C20 C 0.0161(6) 0.8861(3) 0.32638(14) 0.0814(11) Uani 1 1 d . . . H20 H 0.0983 0.9427 0.3348 0.098 Uiso 1 1 calc R . . C21 C -0.1630(9) 0.8757(5) 0.35878(18) 0.1025(16) Uani 1 1 d . . . H21 H -0.2000 0.9249 0.3882 0.123 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 C18 0.0510(18) 0.0706(19) 0.0496(15) 0.0040(14) -0.0111(14) -0.0036(17) N3 0.106(3) 0.0632(18) 0.107(2) 0.0023(18) -0.019(2) -0.007(2) C16 0.0546(18) 0.0504(17) 0.0662(19) 0.0060(15) -0.0136(15) -0.0103(16) N2 0.0504(15) 0.0640(16) 0.0844(19) -0.0047(15) -0.0157(15) -0.0095(15) C10 0.073(2) 0.0487(17) 0.082(2) -0.0099(17) 0.022(2) -0.0149(17) C11 0.100(3) 0.0512(19) 0.069(2) -0.0007(17) 0.019(2) -0.007(2) C12 0.092(3) 0.0585(19) 0.0562(19) 0.0023(16) 0.0006(18) -0.002(2) C8 0.0471(17) 0.0612(17) 0.0613(17) 0.0073(16) -0.0086(14) -0.0051(15) N1 0.0602(17) 0.0691(17) 0.0667(16) 0.0018(14) -0.0226(13) -0.0205(16) C24 0.070(2) 0.0493(17) 0.0668(19) 0.0188(16) -0.0182(17) 0.0041(18) C19 0.0594(18) 0.0517(16) 0.0429(14) 0.0093(13) -0.0063(14) -0.0053(16) C17 0.0411(15) 0.0528(15) 0.0486(15) 0.0007(12) -0.0057(13) 0.0010(14) C7 0.0390(15) 0.0533(16) 0.0453(14) 0.0093(12) -0.0027(12) -0.0068(14) C6 0.0426(16) 0.0562(16) 0.0471(15) 0.0081(14) 0.0002(13) -0.0100(14) C15 0.0482(17) 0.0442(14) 0.0500(15) -0.0057(13) -0.0047(13) -0.0027(13) C9 0.0530(18) 0.0428(16) 0.0646(18) -0.0122(14) 0.0055(15) -0.0001(14) C14 0.0448(16) 0.0409(14) 0.0530(16) -0.0045(12) 0.0042(13) 0.0003(13) C1 0.061(2) 0.0537(17) 0.0477(15) 0.0061(14) -0.0015(15) -0.0177(17) C22 0.093(4) 0.154(5) 0.083(3) 0.054(3) 0.015(3) 0.022(4) C23 0.058(2) 0.094(3) 0.099(3) 0.057(3) -0.014(2) -0.017(2) C5 0.0492(18) 0.070(2) 0.073(2) -0.0006(18) 0.0005(16) -0.0075(17) C4 0.064(2) 0.075(2) 0.099(3) 0.001(2) 0.022(2) 0.002(2) C3 0.101(3) 0.063(2) 0.079(2) -0.0088(19) 0.032(2) -0.014(2) C13 0.066(2) 0.0522(17) 0.0505(17) -0.0008(14) 0.0041(15) -0.0014(16) C2 0.082(3) 0.064(2) 0.0584(19) -0.0044(16) 0.0074(18) -0.028(2) C20 0.101(3) 0.096(3) 0.0481(17) 0.0136(19) 0.008(2) 0.015(3) C21 0.121(4) 0.131(4) 0.055(2) 0.011(3) 0.022(3) 0.043(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C18 C19 1.503(4) . ? C18 C17 1.561(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? N3 C24 1.354(4) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? C16 C15 1.357(4) . ? C16 N2 1.363(4) . ? C16 H16 0.9300 . ? N2 C9 1.382(4) . ? N2 H2 0.8600 . ? C10 C11 1.366(5) . ? C10 C9 1.395(4) . ? C10 H10 0.9300 . ? C11 C12 1.405(5) . ? C11 H11 0.9300 . ? C12 C13 1.375(4) . ? C12 H12 0.9300 . ? C8 C7 1.357(4) . ? C8 N1 1.366(4) . ? C8 H8 0.9300 . ? N1 C1 1.360(4) . ? N1 H1 0.8600 . ? C24 C19 1.388(4) . ? C24 C23 1.397(5) . ? C19 C20 1.403(5) . ? C17 C7 1.493(4) . ? C17 C15 1.513(4) . ? C17 H17 0.9800 . ? C7 C6 1.452(4) . ? C6 C5 1.390(4) . ? C6 C1 1.416(4) . ? C15 C14 1.440(4) . ? C9 C14 1.400(4) . ? C14 C13 1.396(4) . ? C1 C2 1.378(5) . ? C22 C21 1.342(7) . ? C22 C23 1.347(7) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C5 C4 1.386(5) . ? C5 H5 0.9300 . ? C4 C3 1.380(5) . ? C4 H4 0.9300 . ? C3 C2 1.364(5) . ? C3 H3 0.9300 . ? C13 H13 0.9300 . ? C2 H2A 0.9300 . ? C20 C21 1.403(6) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? 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 C19 C18 C17 114.2(2) . . ? C19 C18 H18A 108.7 . . ? C17 C18 H18A 108.7 . . ? C19 C18 H18B 108.7 . . ? C17 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C24 N3 H3A 120.0 . . ? C24 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C15 C16 N2 110.9(3) . . ? C15 C16 H16 124.6 . . ? N2 C16 H16 124.6 . . ? C16 N2 C9 108.6(3) . . ? C16 N2 H2 125.7 . . ? C9 N2 H2 125.7 . . ? C11 C10 C9 117.8(3) . . ? C11 C10 H10 121.1 . . ? C9 C10 H10 121.1 . . ? C10 C11 C12 121.1(3) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C13 C12 C11 120.9(3) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C7 C8 N1 110.5(3) . . ? C7 C8 H8 124.7 . . ? N1 C8 H8 124.7 . . ? C1 N1 C8 109.9(2) . . ? C1 N1 H1 125.1 . . ? C8 N1 H1 125.1 . . ? N3 C24 C19 121.0(3) . . ? N3 C24 C23 117.2(4) . . ? C19 C24 C23 121.4(4) . . ? C24 C19 C20 116.5(3) . . ? C24 C19 C18 125.1(3) . . ? C20 C19 C18 118.3(3) . . ? C7 C17 C15 112.9(2) . . ? C7 C17 C18 110.9(2) . . ? C15 C17 C18 112.6(2) . . ? C7 C17 H17 106.6 . . ? C15 C17 H17 106.6 . . ? C18 C17 H17 106.6 . . ? C8 C7 C6 105.7(3) . . ? C8 C7 C17 127.1(3) . . ? C6 C7 C17 127.2(2) . . ? C5 C6 C1 118.7(3) . . ? C5 C6 C7 134.4(3) . . ? C1 C6 C7 106.9(3) . . ? C16 C15 C14 105.9(3) . . ? C16 C15 C17 128.6(3) . . ? C14 C15 C17 125.3(2) . . ? N2 C9 C10 130.6(3) . . ? N2 C9 C14 107.3(3) . . ? C10 C9 C14 122.1(3) . . ? C13 C14 C9 119.0(3) . . ? C13 C14 C15 133.6(3) . . ? C9 C14 C15 107.3(2) . . ? N1 C1 C2 130.8(3) . . ? N1 C1 C6 107.0(3) . . ? C2 C1 C6 122.2(3) . . ? C21 C22 C23 122.3(5) . . ? C21 C22 H22 118.8 . . ? C23 C22 H22 118.8 . . ? C22 C23 C24 119.4(4) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C4 C5 C6 118.5(3) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C3 C4 C5 121.1(4) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C2 C3 C4 121.9(4) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C12 C13 C14 119.1(3) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C3 C2 C1 117.5(3) . . ? C3 C2 H2A 121.2 . . ? C1 C2 H2A 121.2 . . ? C19 C20 C21 121.3(4) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C22 C21 C20 119.0(5) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? 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 C15 C16 N2 C9 1.1(3) . . . . ? C9 C10 C11 C12 1.5(5) . . . . ? C10 C11 C12 C13 -1.6(5) . . . . ? C7 C8 N1 C1 -0.6(3) . . . . ? N3 C24 C19 C20 -174.4(3) . . . . ? C23 C24 C19 C20 -1.8(4) . . . . ? N3 C24 C19 C18 5.4(4) . . . . ? C23 C24 C19 C18 178.0(3) . . . . ? C17 C18 C19 C24 86.8(4) . . . . ? C17 C18 C19 C20 -93.4(3) . . . . ? C19 C18 C17 C7 -82.2(3) . . . . ? C19 C18 C17 C15 150.2(3) . . . . ? N1 C8 C7 C6 0.6(3) . . . . ? N1 C8 C7 C17 -177.2(2) . . . . ? C15 C17 C7 C8 -122.3(3) . . . . ? C18 C17 C7 C8 110.2(3) . . . . ? C15 C17 C7 C6 60.3(3) . . . . ? C18 C17 C7 C6 -67.2(3) . . . . ? C8 C7 C6 C5 -179.4(3) . . . . ? C17 C7 C6 C5 -1.6(5) . . . . ? C8 C7 C6 C1 -0.5(3) . . . . ? C17 C7 C6 C1 177.4(2) . . . . ? N2 C16 C15 C14 -0.2(3) . . . . ? N2 C16 C15 C17 -175.4(3) . . . . ? C7 C17 C15 C16 -132.8(3) . . . . ? C18 C17 C15 C16 -6.2(4) . . . . ? C7 C17 C15 C14 52.9(4) . . . . ? C18 C17 C15 C14 179.4(3) . . . . ? C16 N2 C9 C10 177.1(3) . . . . ? C16 N2 C9 C14 -1.6(3) . . . . ? C11 C10 C9 N2 -179.1(3) . . . . ? C11 C10 C9 C14 -0.6(4) . . . . ? N2 C9 C14 C13 178.5(3) . . . . ? C10 C9 C14 C13 -0.4(4) . . . . ? N2 C9 C14 C15 1.5(3) . . . . ? C10 C9 C14 C15 -177.4(3) . . . . ? C16 C15 C14 C13 -177.2(3) . . . . ? C17 C15 C14 C13 -1.8(5) . . . . ? C16 C15 C14 C9 -0.8(3) . . . . ? C17 C15 C14 C9 174.6(2) . . . . ? C8 N1 C1 C2 178.5(3) . . . . ? C8 N1 C1 C6 0.3(3) . . . . ? C5 C6 C1 N1 179.3(3) . . . . ? C7 C6 C1 N1 0.1(3) . . . . ? C5 C6 C1 C2 0.8(4) . . . . ? C7 C6 C1 C2 -178.3(3) . . . . ? C21 C22 C23 C24 -1.4(6) . . . . ? N3 C24 C23 C22 175.2(3) . . . . ? C19 C24 C23 C22 2.3(5) . . . . ? C1 C6 C5 C4 -1.0(4) . . . . ? C7 C6 C5 C4 177.9(3) . . . . ? C6 C5 C4 C3 0.6(5) . . . . ? C5 C4 C3 C2 -0.1(5) . . . . ? C11 C12 C13 C14 0.6(5) . . . . ? C9 C14 C13 C12 0.3(4) . . . . ? C15 C14 C13 C12 176.4(3) . . . . ? C4 C3 C2 C1 -0.1(5) . . . . ? N1 C1 C2 C3 -178.3(3) . . . . ? C6 C1 C2 C3 -0.3(4) . . . . ? C24 C19 C20 C21 0.4(4) . . . . ? C18 C19 C20 C21 -179.4(3) . . . . ? C23 C22 C21 C20 0.1(7) . . . . ? C19 C20 C21 C22 0.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.422 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 950651'