# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_far18 #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# _audit_creation_date 2012-05-11T18:05:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H19 F1 N2 O3' _chemical_formula_sum 'C20 H19 F N2 O3' _chemical_formula_weight 354.37 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _space_group_IT_number 2 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9499(5) _cell_length_b 9.4914(7) _cell_length_c 13.2856(11) _cell_angle_alpha 104.262(7) _cell_angle_beta 91.624(6) _cell_angle_gamma 100.777(6) _cell_volume 831.83(11) _cell_formula_units_Z 2 _cell_measurement_temperature 132(2) _cell_measurement_reflns_used 1537 _cell_measurement_theta_min 3.4889 _cell_measurement_theta_max 29.4218 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_T_max 0.9993 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 132(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10.4685 _diffrn_orient_matrix_ub_11 0.0353822 _diffrn_orient_matrix_ub_12 -0.0256437 _diffrn_orient_matrix_ub_13 0.0414121 _diffrn_orient_matrix_ub_21 0.06381 _diffrn_orient_matrix_ub_22 -0.0359856 _diffrn_orient_matrix_ub_23 -0.0333748 _diffrn_orient_matrix_ub_31 0.0744049 _diffrn_orient_matrix_ub_32 0.0651253 _diffrn_orient_matrix_ub_33 0.0149781 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_unetI/netI 0.0565 _diffrn_reflns_number 6150 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.5 _diffrn_reflns_theta_max 29.49 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.829 _reflns_number_total 3838 _reflns_number_gt 2363 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _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 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0747P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3838 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.132 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.933 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.293 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 O5 O 0.36724(16) 0.61939(12) 0.44994(8) 0.0242(3) Uani 1 1 d . . . N3 N 0.4851(2) 1.04513(16) 0.65971(11) 0.0245(3) Uani 1 1 d . . . F1 F 0.82119(16) 1.55569(11) 0.95839(8) 0.0398(3) Uani 1 1 d . . . O3 O 0.58780(18) 0.79452(13) 0.55328(10) 0.0319(3) Uani 1 1 d . . . N4 N -0.0722(2) 0.21254(15) 0.22290(11) 0.0253(3) Uani 1 1 d . . . C2 C 0.2612(2) 0.84144(18) 0.54289(12) 0.0223(4) Uani 1 1 d . . . O4 O 0.16025(17) 1.05535(13) 0.64199(9) 0.0306(3) Uani 1 1 d . . . C21 C 0.0300(2) 0.63999(18) 0.42622(12) 0.0217(4) Uani 1 1 d . . . C3 C -0.0360(2) 0.35227(18) 0.28683(13) 0.0227(4) Uani 1 1 d . . . C4 C 0.1520(2) 0.41988(18) 0.33763(13) 0.0230(4) Uani 1 1 d . . . H4 H 0.2584 0.3695 0.3257 0.028 Uiso 1 1 calc R . . C5 C 0.0760(2) 0.78111(18) 0.49655(12) 0.0225(4) Uani 1 1 d . . . H5 H -0.0249 0.8364 0.5124 0.027 Uiso 1 1 calc R . . C6 C 0.1794(2) 0.55821(18) 0.40405(12) 0.0210(4) Uani 1 1 d . . . C7 C -0.1570(2) 0.57184(18) 0.37524(13) 0.0244(4) Uani 1 1 d . . . H7 H -0.263 0.6225 0.3887 0.029 Uiso 1 1 calc R . . C8 C 0.4154(3) 0.75641(18) 0.51879(13) 0.0238(4) Uani 1 1 d . . . C9 C 0.2959(2) 0.98993(18) 0.61866(13) 0.0231(4) Uani 1 1 d . . . C10 C 0.7664(3) 1.21261(18) 0.75829(13) 0.0256(4) Uani 1 1 d . . . H10 H 0.8454 1.1481 0.7222 0.031 Uiso 1 1 calc R . . C11 C -0.1893(2) 0.43542(19) 0.30732(13) 0.0253(4) Uani 1 1 d . . . H11 H -0.3162 0.3942 0.2726 0.03 Uiso 1 1 calc R . . C12 C -0.2571(3) 0.15211(19) 0.15789(13) 0.0275(4) Uani 1 1 d . . . H12A H -0.3677 0.1703 0.2014 0.033 Uiso 1 1 calc R . . H12B H -0.2703 0.0434 0.1317 0.033 Uiso 1 1 calc R . . C13 C 0.5617(3) 1.17772(18) 0.73510(13) 0.0238(4) Uani 1 1 d . . . C14 C 0.8536(3) 1.33891(19) 0.83253(13) 0.0274(4) Uani 1 1 d . . . H14 H 0.9919 1.3623 0.8481 0.033 Uiso 1 1 calc R . . C15 C 0.5359(3) 1.4009(2) 0.86229(14) 0.0307(4) Uani 1 1 d . . . H15 H 0.4589 1.4671 0.8983 0.037 Uiso 1 1 calc R . . C16 C 0.7363(3) 1.43079(19) 0.88375(13) 0.0288(4) Uani 1 1 d . . . C17 C 0.4477(3) 1.27413(19) 0.78799(13) 0.0294(4) Uani 1 1 d . . . H17 H 0.3093 1.2525 0.7729 0.035 Uiso 1 1 calc R . . C18 C 0.0769(3) 0.12095(19) 0.20914(14) 0.0292(4) Uani 1 1 d . . . H18A H 0.0102 0.0153 0.1927 0.035 Uiso 1 1 calc R . . H18B H 0.1575 0.1431 0.2759 0.035 Uiso 1 1 calc R . . C19 C -0.2724(3) 0.2188(2) 0.06554(14) 0.0333(4) Uani 1 1 d . . . H19A H -0.2602 0.3264 0.0908 0.05 Uiso 1 1 calc R . . H19B H -0.4 0.1754 0.0261 0.05 Uiso 1 1 calc R . . H19C H -0.1669 0.1975 0.0203 0.05 Uiso 1 1 calc R . . C20 C 0.2123(3) 0.1428(2) 0.12434(16) 0.0388(5) Uani 1 1 d . . . H20A H 0.1343 0.1207 0.0577 0.058 Uiso 1 1 calc R . . H20B H 0.3055 0.076 0.1189 0.058 Uiso 1 1 calc R . . H20C H 0.2845 0.2458 0.1416 0.058 Uiso 1 1 calc R . . H1A H 0.567(3) 0.985(2) 0.6341(16) 0.042(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O5 0.0181(6) 0.0279(6) 0.0277(6) 0.0045(5) 0.0008(5) 0.0106(5) N3 0.0203(8) 0.0257(8) 0.0290(8) 0.0044(7) 0.0028(6) 0.0117(6) F1 0.0381(7) 0.0341(6) 0.0418(6) 0.0000(5) -0.0044(5) 0.0076(5) O3 0.0197(7) 0.0357(7) 0.0391(7) 0.0031(6) -0.0021(6) 0.0123(5) N4 0.0206(7) 0.0275(8) 0.0289(8) 0.0058(7) -0.0011(6) 0.0099(6) C2 0.0210(9) 0.0267(9) 0.0240(9) 0.0106(7) 0.0065(7) 0.0101(7) O4 0.0228(7) 0.0312(7) 0.0387(7) 0.0048(6) 0.0034(6) 0.0132(5) C21 0.0190(9) 0.0274(9) 0.0229(8) 0.0097(7) 0.0044(7) 0.0101(7) C3 0.0220(9) 0.0274(9) 0.0222(8) 0.0096(7) 0.0037(7) 0.0091(7) C4 0.0192(9) 0.0291(9) 0.0250(9) 0.0091(8) 0.0034(7) 0.0120(7) C5 0.0191(8) 0.0269(9) 0.0263(9) 0.0099(8) 0.0058(7) 0.0120(7) C6 0.0159(8) 0.0276(9) 0.0233(8) 0.0115(7) 0.0029(7) 0.0067(7) C7 0.0175(8) 0.0318(9) 0.0277(9) 0.0096(8) 0.0042(7) 0.0113(7) C8 0.0223(9) 0.0271(9) 0.0252(9) 0.0082(8) 0.0043(7) 0.0100(7) C9 0.0220(9) 0.0270(9) 0.0246(9) 0.0110(7) 0.0040(7) 0.0095(7) C10 0.0246(9) 0.0279(9) 0.0294(9) 0.0114(8) 0.0051(8) 0.0117(7) C11 0.0177(8) 0.0327(9) 0.0272(9) 0.0080(8) 0.0016(7) 0.0086(7) C12 0.0207(9) 0.0295(9) 0.0313(10) 0.0053(8) 0.0009(8) 0.0061(7) C13 0.0245(9) 0.0259(9) 0.0234(9) 0.0090(8) 0.0018(7) 0.0076(7) C14 0.0209(9) 0.0325(10) 0.0313(9) 0.0113(8) 0.0016(7) 0.0072(7) C15 0.0300(10) 0.0327(10) 0.0319(10) 0.0053(8) 0.0028(8) 0.0163(8) C16 0.0338(11) 0.0264(9) 0.0268(9) 0.0065(8) 0.0002(8) 0.0084(8) C17 0.0240(9) 0.0344(10) 0.0317(10) 0.0060(8) 0.0039(8) 0.0135(8) C18 0.0253(9) 0.0257(9) 0.0359(10) 0.0025(8) -0.0030(8) 0.0111(7) C19 0.0273(10) 0.0425(11) 0.0317(10) 0.0098(9) 0.0002(8) 0.0108(8) C20 0.0254(10) 0.0446(11) 0.0459(12) 0.0037(9) 0.0040(9) 0.0159(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O5 C8 1.369(2) . ? O5 C6 1.382(2) . ? N3 C9 1.365(2) . ? N3 C13 1.403(2) . ? N3 H1A 0.90(2) . ? F1 C16 1.365(2) . ? O3 C8 1.225(2) . ? N4 C3 1.361(2) . ? N4 C18 1.460(2) . ? N4 C12 1.464(2) . ? C2 C5 1.368(3) . ? C2 C8 1.455(2) . ? C2 C9 1.489(2) . ? O4 C9 1.229(2) . ? C21 C6 1.405(2) . ? C21 C5 1.406(2) . ? C21 C7 1.409(3) . ? C3 C4 1.414(3) . ? C3 C11 1.434(3) . ? C4 C6 1.366(2) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C7 C11 1.358(2) . ? C7 H7 0.95 . ? C10 C14 1.374(3) . ? C10 C13 1.406(3) . ? C10 H10 0.95 . ? C11 H11 0.95 . ? C12 C19 1.522(2) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 C17 1.394(2) . ? C14 C16 1.376(3) . ? C14 H14 0.95 . ? C15 C16 1.375(3) . ? C15 C17 1.380(3) . ? C15 H15 0.95 . ? C17 H17 0.95 . ? C18 C20 1.516(2) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O5 C6 122.99(15) . . ? C9 N3 C13 128.81(17) . . ? C9 N3 H1A 112.7(13) . . ? C13 N3 H1A 118.5(14) . . ? C3 N4 C18 121.76(16) . . ? C3 N4 C12 121.20(16) . . ? C18 N4 C12 116.83(14) . . ? C5 C2 C8 118.85(15) . . ? C5 C2 C9 118.59(17) . . ? C8 C2 C9 122.52(16) . . ? C6 C21 C5 118.61(17) . . ? C6 C21 C7 116.35(15) . . ? C5 C21 C7 125.04(17) . . ? N4 C3 C4 121.58(17) . . ? N4 C3 C11 121.06(17) . . ? C4 C3 C11 117.34(15) . . ? C6 C4 C3 119.46(17) . . ? C6 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C2 C5 C21 122.13(17) . . ? C2 C5 H5 118.9 . . ? C21 C5 H5 118.9 . . ? C4 C6 O5 116.73(17) . . ? C4 C6 C21 123.85(17) . . ? O5 C6 C21 119.42(15) . . ? C11 C7 C21 121.53(18) . . ? C11 C7 H7 119.2 . . ? C21 C7 H7 119.2 . . ? O3 C8 O5 115.15(17) . . ? O3 C8 C2 126.88(16) . . ? O5 C8 C2 117.98(16) . . ? O4 C9 N3 123.51(16) . . ? O4 C9 C2 121.04(17) . . ? N3 C9 C2 115.44(17) . . ? C14 C10 C13 120.82(18) . . ? C14 C10 H10 119.6 . . ? C13 C10 H10 119.6 . . ? C7 C11 C3 121.45(17) . . ? C7 C11 H11 119.3 . . ? C3 C11 H11 119.3 . . ? N4 C12 C19 113.48(14) . . ? N4 C12 H12A 108.9 . . ? C19 C12 H12A 108.9 . . ? N4 C12 H12B 108.9 . . ? C19 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C17 C13 N3 124.12(17) . . ? C17 C13 C10 118.98(17) . . ? N3 C13 C10 116.90(17) . . ? C10 C14 C16 118.58(17) . . ? C10 C14 H14 120.7 . . ? C16 C14 H14 120.7 . . ? C16 C15 C17 119.45(18) . . ? C16 C15 H15 120.3 . . ? C17 C15 H15 120.3 . . ? F1 C16 C15 118.78(17) . . ? F1 C16 C14 119.06(17) . . ? C15 C16 C14 122.16(18) . . ? C15 C17 C13 120.00(17) . . ? C15 C17 H17 120 . . ? C13 C17 H17 120 . . ? N4 C18 C20 114.53(15) . . ? N4 C18 H18A 108.6 . . ? C20 C18 H18A 108.6 . . ? N4 C18 H18B 108.6 . . ? C20 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C12 C19 H19A 109.5 . . ? C12 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C12 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 C18 N4 C3 C4 4.5(2) . . . . ? C12 N4 C3 C4 -170.18(14) . . . . ? C18 N4 C3 C11 -173.94(14) . . . . ? C12 N4 C3 C11 11.4(2) . . . . ? N4 C3 C4 C6 -177.60(14) . . . . ? C11 C3 C4 C6 0.9(2) . . . . ? C8 C2 C5 C21 -0.2(2) . . . . ? C9 C2 C5 C21 -178.37(13) . . . . ? C6 C21 C5 C2 0.7(2) . . . . ? C7 C21 C5 C2 -179.51(15) . . . . ? C3 C4 C6 O5 -178.93(13) . . . . ? C3 C4 C6 C21 0.2(2) . . . . ? C8 O5 C6 C4 -179.35(13) . . . . ? C8 O5 C6 C21 1.5(2) . . . . ? C5 C21 C6 C4 179.61(14) . . . . ? C7 C21 C6 C4 -0.2(2) . . . . ? C5 C21 C6 O5 -1.3(2) . . . . ? C7 C21 C6 O5 178.89(13) . . . . ? C6 C21 C7 C11 -0.9(2) . . . . ? C5 C21 C7 C11 179.30(15) . . . . ? C6 O5 C8 O3 179.47(14) . . . . ? C6 O5 C8 C2 -1.0(2) . . . . ? C5 C2 C8 O3 179.81(16) . . . . ? C9 C2 C8 O3 -2.1(3) . . . . ? C5 C2 C8 O5 0.3(2) . . . . ? C9 C2 C8 O5 178.40(13) . . . . ? C13 N3 C9 O4 2.1(3) . . . . ? C13 N3 C9 C2 -177.26(14) . . . . ? C5 C2 C9 O4 2.4(2) . . . . ? C8 C2 C9 O4 -175.72(14) . . . . ? C5 C2 C9 N3 -178.28(14) . . . . ? C8 C2 C9 N3 3.6(2) . . . . ? C21 C7 C11 C3 2.0(2) . . . . ? N4 C3 C11 C7 176.50(14) . . . . ? C4 C3 C11 C7 -2.0(2) . . . . ? C3 N4 C12 C19 73.02(19) . . . . ? C18 N4 C12 C19 -101.89(17) . . . . ? C9 N3 C13 C17 4.9(3) . . . . ? C9 N3 C13 C10 -175.75(15) . . . . ? C14 C10 C13 C17 0.6(2) . . . . ? C14 C10 C13 N3 -178.78(14) . . . . ? C13 C10 C14 C16 -0.1(2) . . . . ? C17 C15 C16 F1 -179.18(14) . . . . ? C17 C15 C16 C14 0.8(3) . . . . ? C10 C14 C16 F1 179.31(14) . . . . ? C10 C14 C16 C15 -0.6(3) . . . . ? C16 C15 C17 C13 -0.2(3) . . . . ? N3 C13 C17 C15 178.87(15) . . . . ? C10 C13 C17 C15 -0.5(2) . . . . ? C3 N4 C18 C20 -87.4(2) . . . . ? C12 N4 C18 C20 87.49(19) . . . . ? 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 N3 H1A O3 0.90(2) 1.89(2) 2.683(2) 145.9(19) . # END of CIF _database_code_depnum_ccdc_archive 'CCDC 957820' ####################################################################### # # 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_san622 #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2012-06-20 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #------------------ AUTHOR DETAILS -------------------------------------------# #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound X' _chemical_formula_moiety 'C22 H22 N2 O5' _chemical_formula_sum 'C22 H22 N2 O5' _chemical_formula_weight 394.42 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _space_group_IT_number 2 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.44890(40) _cell_length_b 8.95140(40) _cell_length_c 12.90330(70) _cell_angle_alpha 92.3649(30) _cell_angle_beta 104.6020(25) _cell_angle_gamma 92.5782(30) _cell_volume 941.996(80) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 21251 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.325 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.9553 _exptl_absorpt_correction_T_max 1.046 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.608089E-1 _diffrn_orient_matrix_ub_12 -0.464864E-1 _diffrn_orient_matrix_ub_13 0.665095E-1 _diffrn_orient_matrix_ub_21 0.104483 _diffrn_orient_matrix_ub_22 0.154372E-1 _diffrn_orient_matrix_ub_23 -0.221831E-1 _diffrn_orient_matrix_ub_31 0.198563E-1 _diffrn_orient_matrix_ub_32 0.100714 _diffrn_orient_matrix_ub_33 0.389521E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_unetI/netI 0.0394 _diffrn_reflns_number 15696 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.974 _diffrn_measured_fraction_theta_max 0.974 _reflns_number_total 4202 _reflns_number_gt 3185 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0572P)^2^+0.2720P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4202 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.049 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.227 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.038 _iucr_refine_instructions_details ; TITL san622 in P -1 CELL 0.71073 8.4490 8.9510 12.9030 92.365 104.602 92.578 ZERR 2.00 0.0000 0.0000 0.0000 0.000 0.000 0.000 LATT 1 SFAC C H O N UNIT 44 44 10 4 MERG 2 HTAB N1 O1 FMAP 2 PLAN 25 ACTA bond $h CONF LIST 4 L.S. 8 TEMP -100.00 WGHT 0.057200 0.272000 FVAR 2.13322 O1 3 -0.028288 0.125780 0.081760 11.00000 0.03299 0.02937 = 0.04402 -0.00175 0.00303 0.00668 O2 3 -0.717145 -0.493989 -0.324984 11.00000 0.03237 0.03538 = 0.04487 -0.00285 0.00403 0.00188 O3 3 -0.910306 -0.329694 -0.373652 11.00000 0.03264 0.04751 = 0.06723 -0.01079 -0.00668 0.00615 O4 3 -0.472654 0.296059 -0.090684 11.00000 0.03073 0.04030 = 0.05429 -0.00539 -0.00113 0.00986 N1 4 -0.327889 0.085539 -0.065132 11.00000 0.02576 0.03404 = 0.03344 -0.00082 0.00449 0.00430 N2 4 0.285472 0.828343 0.315346 11.00000 0.03147 0.02991 = 0.03773 -0.00290 0.00799 0.00242 O5 3 0.059051 0.351556 0.152078 11.00000 0.02812 0.02769 = 0.03746 -0.00255 0.00337 0.00713 C2 1 -0.061205 0.256594 0.085656 11.00000 0.02841 0.03066 = 0.03099 0.00079 0.00871 0.00398 C3 1 0.170542 0.585047 0.234415 11.00000 0.02737 0.03240 = 0.03195 0.00105 0.00746 0.00702 AFIX 43 H3 2 0.265987 0.537520 0.270014 11.00000 -1.20000 AFIX 0 C4 1 0.041649 0.502574 0.166438 11.00000 0.02961 0.02590 = 0.03116 0.00106 0.01087 0.00702 C5 1 -0.113066 0.720192 0.130772 11.00000 0.03265 0.03292 = 0.03519 0.00420 0.00720 0.01113 AFIX 43 H5 2 -0.210118 0.766307 0.096270 11.00000 -1.20000 AFIX 0 C6 1 -0.227567 0.470663 0.044767 11.00000 0.02685 0.03342 = 0.03158 0.00280 0.00826 0.00762 AFIX 43 H6 2 -0.326880 0.512168 0.008931 11.00000 -1.20000 AFIX 0 C7 1 -0.103417 0.565280 0.112718 11.00000 0.02843 0.03102 = 0.03134 0.00169 0.00887 0.00619 C8 1 -0.210137 0.321756 0.028675 11.00000 0.02638 0.03255 = 0.03003 0.00048 0.00901 0.00392 C9 1 0.159959 0.741038 0.250922 11.00000 0.03081 0.03055 = 0.03073 0.00140 0.01116 0.00376 C10 1 -0.441088 -0.019873 -0.130729 11.00000 0.02546 0.03630 = 0.02870 0.00047 0.00907 0.00269 C11 1 -0.348772 0.233730 -0.047358 11.00000 0.02696 0.03537 = 0.03355 0.00063 0.00929 0.00446 C12 1 -0.654527 -0.244336 -0.256503 11.00000 0.02746 0.03771 = 0.03021 -0.00066 0.00915 0.00232 C13 1 -0.594316 0.015415 -0.193284 11.00000 0.02910 0.03561 = 0.03578 -0.00066 0.00635 0.00724 AFIX 43 H13 2 -0.626574 0.115745 -0.193679 11.00000 -1.20000 AFIX 0 C14 1 0.437090 0.764145 0.371402 11.00000 0.03077 0.03514 = 0.04076 -0.00189 0.00545 0.00166 AFIX 23 H14A 2 0.526535 0.843553 0.386831 11.00000 -1.20000 H14B 2 0.464812 0.686016 0.323375 11.00000 -1.20000 AFIX 0 C15 1 -0.774541 -0.357061 -0.323879 11.00000 0.03009 0.04033 = 0.03580 -0.00071 0.01004 0.00303 C16 1 -0.396407 -0.168219 -0.133558 11.00000 0.02617 0.03914 = 0.03382 0.00051 0.00413 0.00614 AFIX 43 H16 2 -0.291869 -0.193009 -0.092368 11.00000 -1.20000 AFIX 0 C17 1 0.263947 0.985377 0.342978 11.00000 0.03895 0.03075 = 0.04781 -0.00541 0.01000 -0.00006 AFIX 23 H17A 2 0.207895 1.033524 0.277000 11.00000 -1.20000 H17B 2 0.373226 1.037621 0.370756 11.00000 -1.20000 AFIX 0 C18 1 -0.698289 -0.096691 -0.254439 11.00000 0.02621 0.04255 = 0.03469 0.00087 0.00463 0.00693 AFIX 43 H18 2 -0.802552 -0.072185 -0.296225 11.00000 -1.20000 AFIX 0 C19 1 0.012626 0.805967 0.196248 11.00000 0.03794 0.02774 = 0.03623 0.00236 0.01040 0.00822 AFIX 43 H19 2 0.002253 0.910559 0.205743 11.00000 -1.20000 AFIX 0 C20 1 -0.500947 -0.278955 -0.194854 11.00000 0.03006 0.03491 = 0.03592 0.00064 0.00742 0.00624 AFIX 43 H20 2 -0.468550 -0.379201 -0.195230 11.00000 -1.20000 AFIX 0 C21 1 -0.830514 -0.607737 -0.389246 11.00000 0.03541 0.03857 = 0.05368 -0.00707 0.00764 -0.00251 AFIX 137 H21A 2 -0.934823 -0.607017 -0.369083 11.00000 -1.50000 H21B 2 -0.784897 -0.706127 -0.377018 11.00000 -1.50000 H21C 2 -0.848787 -0.587289 -0.465263 11.00000 -1.50000 AFIX 0 C22 1 0.429389 0.695638 0.475619 11.00000 0.05597 0.04426 = 0.04591 0.00470 0.00820 0.00713 AFIX 137 H22A 2 0.409603 0.773564 0.525736 11.00000 -1.50000 H22B 2 0.533469 0.651246 0.507014 11.00000 -1.50000 H22C 2 0.340115 0.617810 0.461494 11.00000 -1.50000 AFIX 0 C23 1 0.165710 1.005310 0.426132 11.00000 0.05095 0.04899 = 0.04907 -0.00967 0.01102 0.01499 AFIX 137 H23A 2 0.061027 0.946650 0.402239 11.00000 -1.50000 H23B 2 0.145187 1.111416 0.434784 11.00000 -1.50000 H23C 2 0.227689 0.970692 0.494891 11.00000 -1.50000 AFIX 0 H1A 2 -0.229160 0.053337 -0.029439 11.00000 0.06160 HKLF 4 REM san622 in P -1 REM R1 = 0.0490 for 3185 Fo > 4sig(Fo) and 0.0702 for all 4202 data REM 269 parameters refined using 0 restraints END WGHT 0.0563 0.2755 REM Highest difference peak 0.227, deepest hole -0.235, 1-sigma level 0.038 Q1 1 -0.7072 -0.3021 -0.2818 11.00000 0.05 0.23 Q2 1 -0.1540 0.2982 0.0433 11.00000 0.05 0.21 Q3 1 -0.0490 0.5421 0.1271 11.00000 0.05 0.20 Q4 1 -0.1596 0.5210 0.0735 11.00000 0.05 0.18 Q5 1 -0.5876 -0.2598 -0.2326 11.00000 0.05 0.18 Q6 1 0.0849 0.5434 0.2259 11.00000 0.05 0.18 Q7 1 -0.1037 0.6367 0.1156 11.00000 0.05 0.18 Q8 1 -0.5223 -0.0119 -0.1412 11.00000 0.05 0.17 Q9 1 -0.2546 0.2831 -0.0113 11.00000 0.05 0.17 Q10 1 0.0884 0.7651 0.2364 11.00000 0.05 0.16 Q11 1 -0.2042 0.3929 0.0247 11.00000 0.05 0.16 Q12 1 0.1264 0.5623 0.1798 11.00000 0.05 0.16 Q13 1 -0.3761 0.0395 -0.0993 11.00000 0.05 0.15 Q14 1 0.2080 0.7628 0.3409 11.00000 0.05 0.15 Q15 1 -0.4315 -0.0914 -0.1205 11.00000 0.05 0.14 Q16 1 -0.4612 -0.2231 -0.1539 11.00000 0.05 0.14 Q17 1 -0.1107 0.0576 0.0571 11.00000 0.05 0.14 Q18 1 -0.0269 0.7575 0.1475 11.00000 0.05 0.14 Q19 1 -0.5756 0.3875 -0.1608 11.00000 0.05 0.13 Q20 1 -0.6878 -0.1869 -0.2464 11.00000 0.05 0.13 Q21 1 -0.9896 -0.3875 -0.3995 11.00000 0.05 0.13 Q22 1 -0.6553 -0.0505 -0.1936 11.00000 0.05 0.13 Q23 1 0.3963 0.9870 0.4564 11.00000 0.05 0.13 Q24 1 -0.9888 -0.5337 -0.4548 11.00000 0.05 0.13 Q25 1 0.1675 0.6543 0.2407 11.00000 0.05 0.12 ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 -0.02829(12) 0.12578(11) 0.08176(9) 0.0366(3) Uani 1 1 d . . . O2 O -0.71715(12) -0.49399(12) -0.32498(9) 0.0387(3) Uani 1 1 d . . . O3 O -0.91031(14) -0.32969(13) -0.37365(11) 0.0529(3) Uani 1 1 d . . . O4 O -0.47265(13) 0.29606(12) -0.09068(9) 0.0439(3) Uani 1 1 d . . . N1 N -0.32789(15) 0.08554(14) -0.06513(10) 0.0316(3) Uani 1 1 d . . . N2 N 0.28547(15) 0.82834(13) 0.31535(10) 0.0333(3) Uani 1 1 d . . . O5 O 0.05905(11) 0.35156(10) 0.15208(8) 0.0319(2) Uani 1 1 d . . . C2 C -0.06121(17) 0.25659(15) 0.08566(11) 0.0298(3) Uani 1 1 d . . . C3 C 0.17054(17) 0.58505(16) 0.23442(11) 0.0304(3) Uani 1 1 d . . . H3 H 0.266 0.5375 0.27 0.037 Uiso 1 1 calc R . . C4 C 0.04165(17) 0.50257(15) 0.16644(11) 0.0282(3) Uani 1 1 d . . . C5 C -0.11307(18) 0.72019(16) 0.13077(12) 0.0335(3) Uani 1 1 d . . . H5 H -0.2101 0.7663 0.0963 0.04 Uiso 1 1 calc R . . C6 C -0.22757(17) 0.47066(16) 0.04477(11) 0.0303(3) Uani 1 1 d . . . H6 H -0.3269 0.5122 0.0089 0.036 Uiso 1 1 calc R . . C7 C -0.10342(17) 0.56528(16) 0.11272(11) 0.0299(3) Uani 1 1 d . . . C8 C -0.21014(16) 0.32176(16) 0.02868(11) 0.0293(3) Uani 1 1 d . . . C9 C 0.15996(17) 0.74104(15) 0.25092(11) 0.0300(3) Uani 1 1 d . . . C10 C -0.44109(16) -0.01987(16) -0.13073(11) 0.0298(3) Uani 1 1 d . . . C11 C -0.34877(17) 0.23373(16) -0.04736(12) 0.0316(3) Uani 1 1 d . . . C12 C -0.65453(17) -0.24434(16) -0.25650(11) 0.0315(3) Uani 1 1 d . . . C13 C -0.59432(17) 0.01542(17) -0.19328(12) 0.0337(3) Uani 1 1 d . . . H13 H -0.6266 0.1157 -0.1937 0.04 Uiso 1 1 calc R . . C14 C 0.43709(18) 0.76415(17) 0.37140(12) 0.0363(3) Uani 1 1 d . . . H14A H 0.5265 0.8436 0.3868 0.044 Uiso 1 1 calc R . . H14B H 0.4648 0.686 0.3234 0.044 Uiso 1 1 calc R . . C15 C -0.77454(18) -0.35706(17) -0.32388(12) 0.0352(3) Uani 1 1 d . . . C16 C -0.39641(17) -0.16822(17) -0.13356(12) 0.0336(3) Uani 1 1 d . . . H16 H -0.2919 -0.193 -0.0924 0.04 Uiso 1 1 calc R . . C17 C 0.2639(2) 0.98538(17) 0.34298(14) 0.0396(4) Uani 1 1 d . . . H17A H 0.2079 1.0335 0.277 0.048 Uiso 1 1 calc R . . H17B H 0.3732 1.0376 0.3708 0.048 Uiso 1 1 calc R . . C18 C -0.69829(17) -0.09669(17) -0.25444(12) 0.0349(3) Uani 1 1 d . . . H18 H -0.8026 -0.0722 -0.2962 0.042 Uiso 1 1 calc R . . C19 C 0.01263(18) 0.80597(16) 0.19625(12) 0.0336(3) Uani 1 1 d . . . H19 H 0.0023 0.9106 0.2057 0.04 Uiso 1 1 calc R . . C20 C -0.50095(17) -0.27895(17) -0.19485(12) 0.0337(3) Uani 1 1 d . . . H20 H -0.4686 -0.3792 -0.1952 0.04 Uiso 1 1 calc R . . C21 C -0.8305(2) -0.60774(18) -0.38925(15) 0.0436(4) Uani 1 1 d . . . H21A H -0.9348 -0.607 -0.3691 0.065 Uiso 1 1 calc R . . H21B H -0.7849 -0.7061 -0.377 0.065 Uiso 1 1 calc R . . H21C H -0.8488 -0.5873 -0.4653 0.065 Uiso 1 1 calc R . . C22 C 0.4294(2) 0.6956(2) 0.47562(14) 0.0494(4) Uani 1 1 d . . . H22A H 0.4096 0.7736 0.5257 0.074 Uiso 1 1 calc R . . H22B H 0.5335 0.6512 0.507 0.074 Uiso 1 1 calc R . . H22C H 0.3401 0.6178 0.4615 0.074 Uiso 1 1 calc R . . C23 C 0.1657(2) 1.0053(2) 0.42613(15) 0.0500(4) Uani 1 1 d . . . H23A H 0.061 0.9466 0.4022 0.075 Uiso 1 1 calc R . . H23B H 0.1452 1.1114 0.4348 0.075 Uiso 1 1 calc R . . H23C H 0.2277 0.9707 0.4949 0.075 Uiso 1 1 calc R . . H1A H -0.229(3) 0.053(2) -0.0294(17) 0.062(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0330(5) 0.0294(5) 0.0440(6) -0.0017(4) 0.0030(4) 0.0067(4) O2 0.0324(5) 0.0354(6) 0.0449(6) -0.0029(5) 0.0040(5) 0.0019(4) O3 0.0326(6) 0.0475(7) 0.0672(8) -0.0108(6) -0.0067(5) 0.0062(5) O4 0.0307(5) 0.0403(6) 0.0543(7) -0.0054(5) -0.0011(5) 0.0099(5) N1 0.0258(6) 0.0340(6) 0.0334(7) -0.0008(5) 0.0045(5) 0.0043(5) N2 0.0315(6) 0.0299(6) 0.0377(7) -0.0029(5) 0.0080(5) 0.0024(5) O5 0.0281(5) 0.0277(5) 0.0375(6) -0.0026(4) 0.0034(4) 0.0071(4) C2 0.0284(7) 0.0307(7) 0.0310(7) 0.0008(6) 0.0087(6) 0.0040(6) C3 0.0274(7) 0.0324(7) 0.0320(7) 0.0010(6) 0.0075(6) 0.0070(6) C4 0.0296(7) 0.0259(7) 0.0312(7) 0.0011(5) 0.0109(6) 0.0070(5) C5 0.0327(7) 0.0329(7) 0.0352(8) 0.0042(6) 0.0072(6) 0.0111(6) C6 0.0269(7) 0.0334(7) 0.0316(7) 0.0028(6) 0.0083(5) 0.0076(6) C7 0.0284(7) 0.0310(7) 0.0313(8) 0.0017(6) 0.0089(6) 0.0062(6) C8 0.0264(7) 0.0326(7) 0.0300(7) 0.0005(6) 0.0090(6) 0.0039(5) C9 0.0308(7) 0.0306(7) 0.0307(7) 0.0014(6) 0.0112(6) 0.0038(6) C10 0.0255(7) 0.0363(7) 0.0287(7) 0.0005(6) 0.0091(5) 0.0027(6) C11 0.0270(7) 0.0354(7) 0.0335(8) 0.0006(6) 0.0093(6) 0.0045(6) C12 0.0275(7) 0.0377(8) 0.0302(7) -0.0007(6) 0.0092(6) 0.0023(6) C13 0.0291(7) 0.0356(8) 0.0358(8) -0.0007(6) 0.0063(6) 0.0072(6) C14 0.0308(7) 0.0351(8) 0.0408(9) -0.0019(6) 0.0054(6) 0.0017(6) C15 0.0301(7) 0.0403(8) 0.0358(8) -0.0007(6) 0.0100(6) 0.0030(6) C16 0.0262(7) 0.0391(8) 0.0338(8) 0.0005(6) 0.0041(6) 0.0061(6) C17 0.0390(8) 0.0308(8) 0.0478(9) -0.0054(6) 0.0100(7) -0.0001(6) C18 0.0262(7) 0.0426(8) 0.0347(8) 0.0009(6) 0.0046(6) 0.0069(6) C19 0.0379(8) 0.0277(7) 0.0362(8) 0.0024(6) 0.0104(6) 0.0082(6) C20 0.0301(7) 0.0349(8) 0.0359(8) 0.0006(6) 0.0074(6) 0.0062(6) C21 0.0354(8) 0.0386(8) 0.0537(10) -0.0071(7) 0.0076(7) -0.0025(7) C22 0.0560(11) 0.0443(9) 0.0459(10) 0.0047(7) 0.0082(8) 0.0071(8) C23 0.0509(10) 0.0490(10) 0.0491(10) -0.0097(8) 0.0110(8) 0.0150(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.2175(17) . ? O2 C15 1.3391(18) . ? O2 C21 1.4435(18) . ? O3 C15 1.2063(18) . ? O4 C11 1.2258(17) . ? N1 C11 1.3637(19) . ? N1 C10 1.4022(18) . ? N1 H1A 0.91(2) . ? N2 C9 1.3615(18) . ? N2 C14 1.4587(18) . ? N2 C17 1.4664(18) . ? O5 C4 1.3763(16) . ? O5 C2 1.3829(16) . ? C2 C8 1.4488(19) . ? C3 C4 1.376(2) . ? C3 C9 1.414(2) . ? C3 H3 0.95 . ? C4 C7 1.4012(19) . ? C5 C19 1.361(2) . ? C5 C7 1.406(2) . ? C5 H5 0.95 . ? C6 C8 1.361(2) . ? C6 C7 1.408(2) . ? C6 H6 0.95 . ? C8 C11 1.493(2) . ? C9 C19 1.429(2) . ? C10 C16 1.398(2) . ? C10 C13 1.3994(19) . ? C12 C18 1.389(2) . ? C12 C20 1.396(2) . ? C12 C15 1.481(2) . ? C13 C18 1.381(2) . ? C13 H13 0.95 . ? C14 C22 1.516(2) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C16 C20 1.376(2) . ? C16 H16 0.95 . ? C17 C23 1.523(2) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? 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 C15 O2 C21 115.10(12) . . ? C11 N1 C10 127.14(12) . . ? C11 N1 H1A 115.1(13) . . ? C10 N1 H1A 117.8(13) . . ? C9 N2 C14 121.16(12) . . ? C9 N2 C17 120.87(12) . . ? C14 N2 C17 117.39(12) . . ? C4 O5 C2 122.84(10) . . ? O1 C2 O5 115.20(12) . . ? O1 C2 C8 127.27(13) . . ? O5 C2 C8 117.53(12) . . ? C4 C3 C9 119.54(12) . . ? C4 C3 H3 120.2 . . ? C9 C3 H3 120.2 . . ? C3 C4 O5 117.22(12) . . ? C3 C4 C7 123.11(13) . . ? O5 C4 C7 119.67(12) . . ? C19 C5 C7 121.89(13) . . ? C19 C5 H5 119.1 . . ? C7 C5 H5 119.1 . . ? C8 C6 C7 122.22(13) . . ? C8 C6 H6 118.9 . . ? C7 C6 H6 118.9 . . ? C4 C7 C5 116.77(13) . . ? C4 C7 C6 118.45(13) . . ? C5 C7 C6 124.78(13) . . ? C6 C8 C2 119.25(13) . . ? C6 C8 C11 117.27(12) . . ? C2 C8 C11 123.48(12) . . ? N2 C9 C3 121.89(12) . . ? N2 C9 C19 120.39(13) . . ? C3 C9 C19 117.72(13) . . ? C16 C10 C13 118.72(13) . . ? C16 C10 N1 117.51(12) . . ? C13 C10 N1 123.77(13) . . ? O4 C11 N1 123.57(13) . . ? O4 C11 C8 119.73(13) . . ? N1 C11 C8 116.69(12) . . ? C18 C12 C20 118.59(13) . . ? C18 C12 C15 117.94(13) . . ? C20 C12 C15 123.47(13) . . ? C18 C13 C10 119.51(13) . . ? C18 C13 H13 120.2 . . ? C10 C13 H13 120.2 . . ? N2 C14 C22 114.11(13) . . ? N2 C14 H14A 108.7 . . ? C22 C14 H14A 108.7 . . ? N2 C14 H14B 108.7 . . ? C22 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? O3 C15 O2 122.75(14) . . ? O3 C15 C12 124.04(14) . . ? O2 C15 C12 113.21(12) . . ? C20 C16 C10 121.25(13) . . ? C20 C16 H16 119.4 . . ? C10 C16 H16 119.4 . . ? N2 C17 C23 113.69(13) . . ? N2 C17 H17A 108.8 . . ? C23 C17 H17A 108.8 . . ? N2 C17 H17B 108.8 . . ? C23 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C13 C18 C12 121.78(13) . . ? C13 C18 H18 119.1 . . ? C12 C18 H18 119.1 . . ? C5 C19 C9 120.97(13) . . ? C5 C19 H19 119.5 . . ? C9 C19 H19 119.5 . . ? C16 C20 C12 120.14(14) . . ? C16 C20 H20 119.9 . . ? C12 C20 H20 119.9 . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C14 C22 H22A 109.5 . . ? C14 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C14 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17 C23 H23A 109.5 . . ? C17 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C17 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 C4 O5 C2 O1 -179.55(12) . . . . ? C4 O5 C2 C8 0.68(19) . . . . ? C9 C3 C4 O5 179.16(12) . . . . ? C9 C3 C4 C7 -1.0(2) . . . . ? C2 O5 C4 C3 -179.78(12) . . . . ? C2 O5 C4 C7 0.3(2) . . . . ? C3 C4 C7 C5 0.2(2) . . . . ? O5 C4 C7 C5 -179.88(12) . . . . ? C3 C4 C7 C6 179.86(13) . . . . ? O5 C4 C7 C6 -0.3(2) . . . . ? C19 C5 C7 C4 0.7(2) . . . . ? C19 C5 C7 C6 -178.91(14) . . . . ? C8 C6 C7 C4 -0.9(2) . . . . ? C8 C6 C7 C5 178.66(14) . . . . ? C7 C6 C8 C2 2.0(2) . . . . ? C7 C6 C8 C11 -178.51(13) . . . . ? O1 C2 C8 C6 178.46(14) . . . . ? O5 C2 C8 C6 -1.8(2) . . . . ? O1 C2 C8 C11 -1.0(2) . . . . ? O5 C2 C8 C11 178.70(12) . . . . ? C14 N2 C9 C3 -0.6(2) . . . . ? C17 N2 C9 C3 -171.59(13) . . . . ? C14 N2 C9 C19 -179.71(13) . . . . ? C17 N2 C9 C19 9.3(2) . . . . ? C4 C3 C9 N2 -178.43(13) . . . . ? C4 C3 C9 C19 0.8(2) . . . . ? C11 N1 C10 C16 -177.22(13) . . . . ? C11 N1 C10 C13 3.2(2) . . . . ? C10 N1 C11 O4 -2.1(2) . . . . ? C10 N1 C11 C8 178.48(13) . . . . ? C6 C8 C11 O4 -1.3(2) . . . . ? C2 C8 C11 O4 178.25(13) . . . . ? C6 C8 C11 N1 178.18(12) . . . . ? C2 C8 C11 N1 -2.3(2) . . . . ? C16 C10 C13 C18 1.1(2) . . . . ? N1 C10 C13 C18 -179.25(13) . . . . ? C9 N2 C14 C22 -82.76(18) . . . . ? C17 N2 C14 C22 88.58(16) . . . . ? C21 O2 C15 O3 -0.7(2) . . . . ? C21 O2 C15 C12 179.66(13) . . . . ? C18 C12 C15 O3 -3.1(2) . . . . ? C20 C12 C15 O3 176.52(15) . . . . ? C18 C12 C15 O2 176.50(12) . . . . ? C20 C12 C15 O2 -3.9(2) . . . . ? C13 C10 C16 C20 -1.1(2) . . . . ? N1 C10 C16 C20 179.26(13) . . . . ? C9 N2 C17 C23 75.45(18) . . . . ? C14 N2 C17 C23 -95.91(16) . . . . ? C10 C13 C18 C12 -0.6(2) . . . . ? C20 C12 C18 C13 -0.1(2) . . . . ? C15 C12 C18 C13 179.57(14) . . . . ? C7 C5 C19 C9 -0.9(2) . . . . ? N2 C9 C19 C5 179.32(13) . . . . ? C3 C9 C19 C5 0.1(2) . . . . ? C10 C16 C20 C12 0.5(2) . . . . ? C18 C12 C20 C16 0.1(2) . . . . ? C15 C12 C20 C16 -179.50(14) . . . . ? 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 N1 H1A O1 0.91(2) 1.99(2) 2.7518(16) 140.3(18) . # END of CIF _database_code_depnum_ccdc_archive 'CCDC 957821' ####################################################################### # # 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_san625 #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2012-06-19 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #------------------ AUTHOR DETAILS -------------------------------------------# #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound X' _chemical_formula_moiety 'C21 H19 N3 O3' _chemical_formula_sum 'C21 H19 N3 O3' _chemical_formula_weight 361.39 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt P-1 _space_group_name_Hall '-P 1' _space_group_IT_number 2 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.90260(20) _cell_length_b 7.37510(20) _cell_length_c 19.53700(59) _cell_angle_alpha 81.8816(18) _cell_angle_beta 82.0634(18) _cell_angle_gamma 65.3173(18) _cell_volume 891.184(46) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 64648 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.025 _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.8856 _exptl_absorpt_correction_T_max 1.1083 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.879301E-1 _diffrn_orient_matrix_ub_12 -0.103549 _diffrn_orient_matrix_ub_13 0.350321E-1 _diffrn_orient_matrix_ub_21 -0.121498 _diffrn_orient_matrix_ub_22 0.495612E-1 _diffrn_orient_matrix_ub_23 0.365828E-1 _diffrn_orient_matrix_ub_31 -0.559099E-1 _diffrn_orient_matrix_ub_32 -0.963496E-1 _diffrn_orient_matrix_ub_33 -0.113353E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_unetI/netI 0.0387 _diffrn_reflns_number 15502 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _reflns_number_total 4015 _reflns_number_gt 2854 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0677P)^2^+0.3479P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4015 _refine_ls_number_parameters 250 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1789 _refine_ls_wR_factor_gt 0.1597 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.388 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.041 _iucr_refine_instructions_details ; TITL SAN625 IN P -1 CELL 0.71073 6.9030 7.3750 19.5370 81.882 82.063 65.317 ZERR 2.00 0.0000 0.0000 0.0000 0.000 0.000 0.000 LATT 1 SFAC C H O N UNIT 42 38 6 6 MERG 2 OMIT 0 0 1 OMIT 0 0 2 OMIT 0 1 1 OMIT 6 3 2 OMIT 5 5 3 HTAB N2 O2 SIMU .001 N3 C20 DELU .001 N3 C20 FMAP 2 PLAN 25 ACTA HTAB 2.00000 BOND $H CONF LIST 4 L.S. 5 WGHT 0.067700 0.347900 FVAR 3.39345 O1 3 0.250645 0.181458 0.348942 11.00000 0.04739 0.06842 = 0.04717 -0.00816 -0.00779 -0.03164 N2 4 0.121351 0.251613 0.564538 11.00000 0.04832 0.05837 = 0.04634 -0.00806 -0.00889 -0.02347 C8 1 0.344193 0.238475 0.456491 11.00000 0.04478 0.04539 = 0.04560 -0.00275 -0.01230 -0.01867 C1 1 0.428730 0.200652 0.313731 11.00000 0.04129 0.03950 = 0.04922 -0.00308 -0.00908 -0.01709 O2 3 0.036942 0.179902 0.442549 11.00000 0.05829 0.12258 = 0.05372 -0.01327 -0.00400 -0.05517 C6 1 0.568527 0.237390 0.349552 11.00000 0.04371 0.04333 = 0.04722 -0.00057 -0.01168 -0.02014 C3 1 0.636597 0.202468 0.204604 11.00000 0.05372 0.04477 = 0.04840 -0.00624 -0.00556 -0.02088 C5 1 0.747083 0.254379 0.310274 11.00000 0.04973 0.06079 = 0.05336 -0.00183 -0.01250 -0.02968 AFIX 43 H89 2 0.845039 0.276862 0.332339 11.00000 -1.20000 AFIX 0 C2 1 0.458717 0.182901 0.243681 11.00000 0.05071 0.04891 = 0.04965 -0.00732 -0.01075 -0.02435 AFIX 43 H6 2 0.361412 0.157966 0.222154 11.00000 -1.20000 AFIX 0 O3 3 0.436353 0.283954 0.562548 11.00000 0.06989 0.10989 = 0.05289 -0.01458 -0.00900 -0.05553 C7 1 0.520645 0.255563 0.421406 11.00000 0.04788 0.04742 = 0.05076 -0.00155 -0.01570 -0.02325 AFIX 43 H90 2 0.612944 0.280063 0.445576 11.00000 -1.20000 AFIX 0 C9 1 0.200322 0.198565 0.419140 11.00000 0.04595 0.05963 = 0.04475 -0.00447 -0.00791 -0.02526 C10 1 0.305340 0.260408 0.532376 11.00000 0.04802 0.05013 = 0.04927 -0.00501 -0.01091 -0.02175 N3 4 0.673081 0.186834 0.134956 11.00000 0.08054 0.08212 = 0.05159 -0.01488 -0.00014 -0.04709 C4 1 0.780668 0.238799 0.240680 11.00000 0.05166 0.06101 = 0.05316 -0.00313 -0.00339 -0.02980 AFIX 43 H10 2 0.900165 0.252151 0.216168 11.00000 -1.20000 AFIX 0 C11 1 0.044905 0.269946 0.634380 11.00000 0.04887 0.03950 = 0.04602 -0.00388 -0.00885 -0.01509 C16 1 0.154168 0.301591 0.683384 11.00000 0.05613 0.06066 = 0.05329 -0.00908 -0.00827 -0.02771 AFIX 43 H12 2 0.284138 0.311897 0.670151 11.00000 -1.20000 AFIX 0 C12 1 -0.150200 0.256105 0.655388 11.00000 0.05265 0.05581 = 0.05488 -0.00787 -0.01077 -0.02264 AFIX 43 H13 2 -0.224666 0.235893 0.623086 11.00000 -1.20000 AFIX 0 C14 1 -0.123921 0.302491 0.772223 11.00000 0.06396 0.03931 = 0.04970 -0.00748 -0.00337 -0.01373 C17 1 -0.204592 0.318073 0.844010 11.00000 0.07065 0.05336 = 0.05974 -0.01027 -0.00079 -0.02146 C13 1 -0.233338 0.272073 0.723397 11.00000 0.05287 0.05724 = 0.05904 -0.00613 -0.00276 -0.02298 AFIX 43 H16 2 -0.363568 0.262480 0.736856 11.00000 -1.20000 AFIX 0 C18 1 0.519811 0.166544 0.094933 11.00000 0.09468 0.07892 = 0.04758 -0.00785 -0.00819 -0.04756 AFIX 23 H17A 2 0.530995 0.226027 0.047800 11.00000 -1.20000 H17B 2 0.375610 0.238483 0.115381 11.00000 -1.20000 AFIX 0 C20 1 0.870180 0.189914 0.095253 11.00000 0.08397 0.08557 = 0.05566 -0.01363 0.00391 -0.04261 AFIX 23 H18A 2 0.900978 0.117425 0.054578 11.00000 -1.20000 H18B 2 0.989417 0.122774 0.123749 11.00000 -1.20000 AFIX 0 C15 1 0.069179 0.317405 0.751043 11.00000 0.06664 0.06164 = 0.05218 -0.01193 -0.00959 -0.02808 AFIX 43 H20 2 0.142712 0.338595 0.783415 11.00000 -1.20000 AFIX 0 C21 1 0.847654 0.397560 0.073357 11.00000 0.12088 0.10207 = 0.08395 0.01282 -0.01464 -0.06032 AFIX 137 H21A 2 0.735013 0.461722 0.042978 11.00000 -1.50000 H21B 2 0.979645 0.395334 0.049385 11.00000 -1.50000 H21C 2 0.813681 0.470425 0.113492 11.00000 -1.50000 AFIX 0 C19 1 0.560116 -0.048333 0.093561 11.00000 0.14582 0.08694 = 0.07843 -0.01131 -0.01298 -0.06776 AFIX 137 H22A 2 0.701285 -0.118913 0.072095 11.00000 -1.50000 H22B 2 0.456468 -0.056905 0.067542 11.00000 -1.50000 H22C 2 0.548498 -0.107283 0.140165 11.00000 -1.50000 AFIX 0 N1 4 -0.261015 0.328409 0.901724 11.00000 0.10434 0.09031 = 0.05982 -0.01907 0.01077 -0.03994 H1A 2 0.039730 0.223205 0.535808 11.00000 0.07925 HKLF 4 REM SAN625 IN P -1 REM R1 = 0.0685 for 2854 Fo > 4sig(Fo) and 0.0975 for all 4015 data REM 250 parameters refined using 7 restraints END WGHT 0.0715 0.3654 REM Highest difference peak 0.388, deepest hole -0.304, 1-sigma level 0.041 Q1 1 0.7440 0.3428 0.0913 11.00000 0.05 0.39 Q2 1 1.0048 0.2017 0.0673 11.00000 0.05 0.37 Q3 1 0.2828 0.2233 0.4412 11.00000 0.05 0.18 Q4 1 -0.0574 0.3011 0.7678 11.00000 0.05 0.16 Q5 1 0.4896 0.2379 0.3312 11.00000 0.05 0.16 Q6 1 0.5207 0.2807 0.3814 11.00000 0.05 0.15 Q7 1 -0.1368 0.2315 0.7572 11.00000 0.05 0.14 Q8 1 0.0904 0.2957 0.6561 11.00000 0.05 0.14 Q9 1 0.3136 0.2571 0.4888 11.00000 0.05 0.14 Q10 1 0.6273 0.0186 0.1178 11.00000 0.05 0.14 Q11 1 0.0659 0.2552 0.5470 11.00000 0.05 0.13 Q12 1 0.9628 0.3453 -0.0142 11.00000 0.05 0.13 Q13 1 1.0475 0.3054 0.0319 11.00000 0.05 0.13 Q14 1 0.8308 0.4421 0.0024 11.00000 0.05 0.13 Q15 1 -0.1124 0.3094 0.8727 11.00000 0.05 0.12 Q16 1 -0.1676 0.2931 0.8054 11.00000 0.05 0.12 Q17 1 -0.2501 0.3138 0.6088 11.00000 0.05 0.12 Q18 1 0.4215 0.2663 0.6107 11.00000 0.05 0.12 Q19 1 -0.3373 0.3264 0.8707 11.00000 0.05 0.12 Q20 1 0.7189 0.1828 0.2241 11.00000 0.05 0.12 Q21 1 -0.2878 0.2843 0.8592 11.00000 0.05 0.11 Q22 1 0.3245 0.3773 0.5503 11.00000 0.05 0.11 Q23 1 0.2824 0.2095 0.2276 11.00000 0.05 0.11 Q24 1 1.0126 0.4257 0.1072 11.00000 0.05 0.11 Q25 1 0.3673 0.1778 0.0773 11.00000 0.05 0.11 ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 0.2506(2) 0.1815(2) 0.34894(7) 0.0509(4) Uani 1 1 d . . . N2 N 0.1214(3) 0.2516(3) 0.56454(9) 0.0496(4) Uani 1 1 d . . . C8 C 0.3442(3) 0.2385(3) 0.45649(10) 0.0444(4) Uani 1 1 d . . . C1 C 0.4287(3) 0.2007(3) 0.31373(10) 0.0427(4) Uani 1 1 d . . . O2 O 0.0369(3) 0.1799(3) 0.44255(8) 0.0715(5) Uani 1 1 d . . . C6 C 0.5685(3) 0.2374(3) 0.34955(10) 0.0435(4) Uani 1 1 d . . . C3 C 0.6366(3) 0.2025(3) 0.20460(10) 0.0484(5) Uani 1 1 d . . . C5 C 0.7471(3) 0.2544(3) 0.31027(11) 0.0517(5) Uani 1 1 d . . . H89 H 0.845 0.2769 0.3323 0.062 Uiso 1 1 calc R . . C2 C 0.4587(3) 0.1829(3) 0.24368(10) 0.0474(5) Uani 1 1 d . . . H6 H 0.3614 0.158 0.2222 0.057 Uiso 1 1 calc R . . O3 O 0.4364(3) 0.2840(3) 0.56255(8) 0.0700(5) Uani 1 1 d . . . C7 C 0.5206(3) 0.2556(3) 0.42141(10) 0.0465(5) Uani 1 1 d . . . H90 H 0.6129 0.2801 0.4456 0.056 Uiso 1 1 calc R . . C9 C 0.2003(3) 0.1986(3) 0.41914(10) 0.0484(5) Uani 1 1 d . . . C10 C 0.3053(3) 0.2604(3) 0.53238(10) 0.0478(5) Uani 1 1 d . . . N3 N 0.6731(3) 0.1868(3) 0.13496(10) 0.0663(5) Uani 1 1 d U . . C4 C 0.7807(3) 0.2388(3) 0.24068(11) 0.0533(5) Uani 1 1 d . . . H10 H 0.9002 0.2522 0.2162 0.064 Uiso 1 1 calc R . . C11 C 0.0449(3) 0.2699(3) 0.63438(10) 0.0453(5) Uani 1 1 d . . . C16 C 0.1542(4) 0.3016(3) 0.68338(11) 0.0546(5) Uani 1 1 d . . . H12 H 0.2841 0.3119 0.6702 0.065 Uiso 1 1 calc R . . C12 C -0.1502(3) 0.2561(3) 0.65539(11) 0.0533(5) Uani 1 1 d . . . H13 H -0.2247 0.2359 0.6231 0.064 Uiso 1 1 calc R . . C14 C -0.1239(4) 0.3025(3) 0.77222(11) 0.0533(5) Uani 1 1 d . . . C17 C -0.2046(4) 0.3181(3) 0.84401(13) 0.0625(6) Uani 1 1 d . . . C13 C -0.2333(4) 0.2721(3) 0.72340(11) 0.0563(5) Uani 1 1 d . . . H16 H -0.3636 0.2625 0.7369 0.068 Uiso 1 1 calc R . . C18 C 0.5198(5) 0.1665(4) 0.09493(12) 0.0691(7) Uani 1 1 d . . . H17A H 0.531 0.226 0.0478 0.083 Uiso 1 1 calc R . . H17B H 0.3756 0.2385 0.1154 0.083 Uiso 1 1 calc R . . C20 C 0.8702(5) 0.1899(4) 0.09525(13) 0.0726(5) Uani 1 1 d U . . H18A H 0.901 0.1174 0.0546 0.087 Uiso 1 1 calc R . . H18B H 0.9894 0.1228 0.1237 0.087 Uiso 1 1 calc R . . C15 C 0.0692(4) 0.3174(3) 0.75104(11) 0.0583(6) Uani 1 1 d . . . H20 H 0.1427 0.3386 0.7834 0.07 Uiso 1 1 calc R . . C21 C 0.8477(6) 0.3976(5) 0.07336(17) 0.0989(10) Uani 1 1 d . . . H21A H 0.735 0.4617 0.043 0.148 Uiso 1 1 calc R . . H21B H 0.9796 0.3953 0.0494 0.148 Uiso 1 1 calc R . . H21C H 0.8137 0.4704 0.1135 0.148 Uiso 1 1 calc R . . C19 C 0.5601(6) -0.0483(5) 0.09356(15) 0.0961(10) Uani 1 1 d . . . H22A H 0.7013 -0.1189 0.0721 0.144 Uiso 1 1 calc R . . H22B H 0.4565 -0.0569 0.0675 0.144 Uiso 1 1 calc R . . H22C H 0.5485 -0.1073 0.1402 0.144 Uiso 1 1 calc R . . N1 N -0.2610(4) 0.3284(4) 0.90172(12) 0.0853(7) Uani 1 1 d . . . H1A H 0.040(4) 0.223(4) 0.5358(13) 0.079(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0474(8) 0.0684(9) 0.0472(8) -0.0082(6) -0.0078(6) -0.0316(7) N2 0.0483(10) 0.0584(10) 0.0463(9) -0.0081(7) -0.0089(8) -0.0235(8) C8 0.0448(10) 0.0454(10) 0.0456(10) -0.0027(8) -0.0123(8) -0.0187(8) C1 0.0413(10) 0.0395(9) 0.0492(11) -0.0031(8) -0.0091(8) -0.0171(8) O2 0.0583(10) 0.1226(15) 0.0537(9) -0.0133(9) -0.0040(7) -0.0552(10) C6 0.0437(10) 0.0433(10) 0.0472(11) -0.0006(8) -0.0117(8) -0.0201(8) C3 0.0537(12) 0.0448(10) 0.0484(11) -0.0062(8) -0.0056(9) -0.0209(9) C5 0.0497(11) 0.0608(12) 0.0534(12) -0.0018(9) -0.0125(9) -0.0297(10) C2 0.0507(11) 0.0489(11) 0.0496(11) -0.0073(8) -0.0108(9) -0.0244(9) O3 0.0699(11) 0.1099(13) 0.0529(9) -0.0146(8) -0.0090(8) -0.0555(10) C7 0.0479(11) 0.0474(10) 0.0508(11) -0.0015(8) -0.0157(9) -0.0233(9) C9 0.0459(11) 0.0596(12) 0.0447(11) -0.0045(9) -0.0079(8) -0.0253(9) C10 0.0480(11) 0.0501(11) 0.0493(11) -0.0050(8) -0.0109(9) -0.0218(9) N3 0.0805(12) 0.0821(12) 0.0516(9) -0.0149(8) -0.0001(8) -0.0471(10) C4 0.0517(12) 0.0610(13) 0.0532(12) -0.0031(9) -0.0034(9) -0.0298(10) C11 0.0489(11) 0.0395(10) 0.0460(11) -0.0039(8) -0.0088(9) -0.0151(8) C16 0.0561(12) 0.0607(13) 0.0533(12) -0.0091(10) -0.0083(10) -0.0277(10) C12 0.0527(12) 0.0558(12) 0.0549(12) -0.0079(9) -0.0108(10) -0.0226(10) C14 0.0640(13) 0.0393(10) 0.0497(12) -0.0075(8) -0.0034(10) -0.0137(9) C17 0.0707(15) 0.0534(13) 0.0597(15) -0.0103(10) -0.0008(12) -0.0215(11) C13 0.0529(12) 0.0572(12) 0.0590(13) -0.0061(10) -0.0028(10) -0.0230(10) C18 0.0947(19) 0.0789(16) 0.0476(12) -0.0078(11) -0.0082(12) -0.0476(15) C20 0.0840(13) 0.0856(13) 0.0557(10) -0.0136(9) 0.0039(9) -0.0426(11) C15 0.0666(14) 0.0616(13) 0.0522(12) -0.0119(10) -0.0096(10) -0.0281(11) C21 0.121(3) 0.102(2) 0.084(2) 0.0128(17) -0.0146(18) -0.060(2) C19 0.146(3) 0.087(2) 0.0784(19) -0.0113(15) -0.0130(19) -0.068(2) N1 0.1043(19) 0.0903(17) 0.0598(14) -0.0191(11) 0.0108(12) -0.0399(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.374(2) . ? O1 C9 1.378(2) . ? N2 C10 1.360(3) . ? N2 C11 1.397(3) . ? N2 H1A 0.95(3) . ? C8 C7 1.357(3) . ? C8 C9 1.453(3) . ? C8 C10 1.489(3) . ? C1 C2 1.372(3) . ? C1 C6 1.397(2) . ? O2 C9 1.212(2) . ? C6 C5 1.402(3) . ? C6 C7 1.409(3) . ? C3 N3 1.361(3) . ? C3 C2 1.403(3) . ? C3 C4 1.424(3) . ? C5 C4 1.360(3) . ? C5 H89 0.93 . ? C2 H6 0.93 . ? O3 C10 1.226(2) . ? C7 H90 0.93 . ? N3 C18 1.465(3) . ? N3 C20 1.477(3) . ? C4 H10 0.93 . ? C11 C12 1.394(3) . ? C11 C16 1.396(3) . ? C16 C15 1.370(3) . ? C16 H12 0.93 . ? C12 C13 1.373(3) . ? C12 H13 0.93 . ? C14 C15 1.385(3) . ? C14 C13 1.390(3) . ? C14 C17 1.438(3) . ? C17 N1 1.143(3) . ? C13 H16 0.93 . ? C18 C19 1.494(4) . ? C18 H17A 0.97 . ? C18 H17B 0.97 . ? C20 C21 1.479(4) . ? C20 H18A 0.97 . ? C20 H18B 0.97 . ? C15 H20 0.93 . ? C21 H21A 0.96 . ? C21 H21B 0.96 . ? C21 H21C 0.96 . ? C19 H22A 0.96 . ? C19 H22B 0.96 . ? C19 H22C 0.96 . ? 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 O1 C9 122.86(14) . . ? C10 N2 C11 128.23(17) . . ? C10 N2 H1A 114.8(16) . . ? C11 N2 H1A 116.9(16) . . ? C7 C8 C9 119.19(18) . . ? C7 C8 C10 118.64(16) . . ? C9 C8 C10 122.17(17) . . ? C2 C1 O1 116.99(16) . . ? C2 C1 C6 123.22(18) . . ? O1 C1 C6 119.79(17) . . ? C1 C6 C5 116.57(18) . . ? C1 C6 C7 118.46(18) . . ? C5 C6 C7 124.97(17) . . ? N3 C3 C2 122.09(18) . . ? N3 C3 C4 120.52(19) . . ? C2 C3 C4 117.39(18) . . ? C4 C5 C6 121.64(18) . . ? C4 C5 H89 119.2 . . ? C6 C5 H89 119.2 . . ? C1 C2 C3 119.83(17) . . ? C1 C2 H6 120.1 . . ? C3 C2 H6 120.1 . . ? C8 C7 C6 122.14(17) . . ? C8 C7 H90 118.9 . . ? C6 C7 H90 118.9 . . ? O2 C9 O1 115.09(17) . . ? O2 C9 C8 127.36(19) . . ? O1 C9 C8 117.55(17) . . ? O3 C10 N2 123.54(19) . . ? O3 C10 C8 120.05(18) . . ? N2 C10 C8 116.41(16) . . ? C3 N3 C18 122.20(19) . . ? C3 N3 C20 121.74(19) . . ? C18 N3 C20 116.06(19) . . ? C5 C4 C3 121.34(19) . . ? C5 C4 H10 119.3 . . ? C3 C4 H10 119.3 . . ? C12 C11 C16 119.07(19) . . ? C12 C11 N2 117.78(17) . . ? C16 C11 N2 123.14(19) . . ? C15 C16 C11 119.7(2) . . ? C15 C16 H12 120.1 . . ? C11 C16 H12 120.1 . . ? C13 C12 C11 120.53(19) . . ? C13 C12 H13 119.7 . . ? C11 C12 H13 119.7 . . ? C15 C14 C13 118.9(2) . . ? C15 C14 C17 119.0(2) . . ? C13 C14 C17 122.0(2) . . ? N1 C17 C14 177.4(3) . . ? C12 C13 C14 120.4(2) . . ? C12 C13 H16 119.8 . . ? C14 C13 H16 119.8 . . ? N3 C18 C19 111.3(2) . . ? N3 C18 H17A 109.4 . . ? C19 C18 H17A 109.4 . . ? N3 C18 H17B 109.4 . . ? C19 C18 H17B 109.4 . . ? H17A C18 H17B 108 . . ? N3 C20 C21 111.2(2) . . ? N3 C20 H18A 109.4 . . ? C21 C20 H18A 109.4 . . ? N3 C20 H18B 109.4 . . ? C21 C20 H18B 109.4 . . ? H18A C20 H18B 108 . . ? C16 C15 C14 121.4(2) . . ? C16 C15 H20 119.3 . . ? C14 C15 H20 119.3 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C19 H22A 109.5 . . ? C18 C19 H22B 109.5 . . ? H22A C19 H22B 109.5 . . ? C18 C19 H22C 109.5 . . ? H22A C19 H22C 109.5 . . ? H22B C19 H22C 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 C9 O1 C1 C2 -179.16(17) . . . . ? C9 O1 C1 C6 0.6(3) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? O1 C1 C6 C5 179.75(16) . . . . ? C2 C1 C6 C7 179.16(17) . . . . ? O1 C1 C6 C7 -0.6(3) . . . . ? C1 C6 C5 C4 0.9(3) . . . . ? C7 C6 C5 C4 -178.72(19) . . . . ? O1 C1 C2 C3 179.52(16) . . . . ? C6 C1 C2 C3 -0.2(3) . . . . ? N3 C3 C2 C1 -179.76(18) . . . . ? C4 C3 C2 C1 0.5(3) . . . . ? C9 C8 C7 C6 0.5(3) . . . . ? C10 C8 C7 C6 -179.80(17) . . . . ? C1 C6 C7 C8 0.0(3) . . . . ? C5 C6 C7 C8 179.67(19) . . . . ? C1 O1 C9 O2 179.29(18) . . . . ? C1 O1 C9 C8 -0.1(3) . . . . ? C7 C8 C9 O2 -179.7(2) . . . . ? C10 C8 C9 O2 0.6(3) . . . . ? C7 C8 C9 O1 -0.5(3) . . . . ? C10 C8 C9 O1 179.83(17) . . . . ? C11 N2 C10 O3 1.2(3) . . . . ? C11 N2 C10 C8 -179.17(17) . . . . ? C7 C8 C10 O3 -3.4(3) . . . . ? C9 C8 C10 O3 176.31(19) . . . . ? C7 C8 C10 N2 176.96(17) . . . . ? C9 C8 C10 N2 -3.4(3) . . . . ? C2 C3 N3 C18 5.6(3) . . . . ? C4 C3 N3 C18 -174.7(2) . . . . ? C2 C3 N3 C20 -174.6(2) . . . . ? C4 C3 N3 C20 5.1(3) . . . . ? C6 C5 C4 C3 -0.6(3) . . . . ? N3 C3 C4 C5 -179.8(2) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C10 N2 C11 C12 179.83(19) . . . . ? C10 N2 C11 C16 0.0(3) . . . . ? C12 C11 C16 C15 0.3(3) . . . . ? N2 C11 C16 C15 -179.79(19) . . . . ? C16 C11 C12 C13 -0.4(3) . . . . ? N2 C11 C12 C13 179.73(18) . . . . ? C11 C12 C13 C14 0.1(3) . . . . ? C15 C14 C13 C12 0.3(3) . . . . ? C17 C14 C13 C12 -179.4(2) . . . . ? C3 N3 C18 C19 -88.8(3) . . . . ? C20 N3 C18 C19 91.3(3) . . . . ? C3 N3 C20 C21 -85.6(3) . . . . ? C18 N3 C20 C21 94.2(3) . . . . ? C11 C16 C15 C14 0.1(3) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C17 C14 C15 C16 179.3(2) . . . . ? 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 N2 H1A O2 0.95(3) 1.90(3) 2.701(2) 141(2) . # END of CIF _database_code_depnum_ccdc_archive 'CCDC 957822' ####################################################################### # # 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_san623 #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# _audit_creation_date 2012-06-07T18:26:19-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound X' _chemical_formula_moiety 'C20 H19 N3 O5' _chemical_formula_sum 'C20 H19 N3 O5' _chemical_formula_weight 381.38 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt P-1 _space_group_name_Hall '-P 1' _space_group_IT_number 2 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.94270(20) _cell_length_b 12.55740(40) _cell_length_c 14.66120(50) _cell_angle_alpha 98.1690(21) _cell_angle_beta 99.3016(19) _cell_angle_gamma 92.6732(19) _cell_volume 886.647(55) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 20580 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.325 _exptl_crystal_size_mid 0.175 _exptl_crystal_size_min 0.075 _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.9557 _exptl_absorpt_correction_T_max 1.0103 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.502386E-1 _diffrn_orient_matrix_ub_12 -0.264198E-1 _diffrn_orient_matrix_ub_13 0.566929E-1 _diffrn_orient_matrix_ub_21 -0.146605 _diffrn_orient_matrix_ub_22 -0.510823E-1 _diffrn_orient_matrix_ub_23 -0.406378E-1 _diffrn_orient_matrix_ub_31 0.135012 _diffrn_orient_matrix_ub_32 -0.565502E-1 _diffrn_orient_matrix_ub_33 -0.49167E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_unetI/netI 0.0282 _diffrn_reflns_number 20268 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.01 _diffrn_reflns_theta_max 26.64 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.948 _reflns_number_total 3543 _reflns_number_gt 2737 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0693P)^2^+0.1585P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3543 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1323 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.205 _refine_diff_density_min -0.19 _refine_diff_density_rms 0.034 _iucr_refine_instructions_details ; TITL san623 in P -1 CELL 0.71073 4.9430 12.5570 14.6610 98.169 99.302 92.673 ZERR 2.00 0.0000 0.0000 0.0000 0.000 0.000 0.000 LATT 1 SFAC C H O N UNIT 40 38 10 6 MERG 2 HTAB N1 O2 FMAP 2 PLAN 25 ACTA 50.00 BOND $H CONF LIST 4 L.S. 4 WGHT 0.069300 0.158500 FVAR 2.10214 O1 3 0.046998 0.149623 0.852536 11.00000 0.04367 0.03665 = 0.04446 0.00284 -0.00529 0.00035 N1 4 0.747219 0.209195 1.069601 11.00000 0.04323 0.03971 = 0.04250 0.00447 -0.00440 -0.00372 O2 3 0.391148 0.080166 0.932905 11.00000 0.05665 0.03941 = 0.05882 0.00504 -0.01123 0.00375 O3 3 0.668451 0.387404 1.084864 11.00000 0.05996 0.04192 = 0.06047 -0.00050 -0.01608 -0.00083 N2 4 -0.717805 0.274058 0.664514 11.00000 0.03714 0.05405 = 0.04475 0.00567 -0.00050 0.00225 N3 4 1.657398 0.190320 1.349648 11.00000 0.05016 0.07413 = 0.04801 0.01475 -0.00280 0.00129 O4 3 1.741913 0.271181 1.406115 11.00000 0.06916 0.09332 = 0.05775 -0.00258 -0.01928 -0.00213 O5 3 1.760128 0.104452 1.352048 11.00000 0.08625 0.08858 = 0.08897 0.01697 -0.02608 0.02690 C2 1 0.362171 0.270510 0.969844 11.00000 0.03784 0.03921 = 0.03473 0.00551 0.00482 -0.00209 C4 1 -0.019773 0.339069 0.875141 11.00000 0.03758 0.03937 = 0.03435 0.00412 0.00630 -0.00105 C3 1 0.216930 0.354142 0.944798 11.00000 0.03955 0.03761 = 0.03632 0.00107 0.00630 -0.00305 AFIX 43 H3 2 0.275773 0.423669 0.974647 11.00000 -1.20000 AFIX 0 C7 1 -0.490464 0.293992 0.732690 11.00000 0.03323 0.04835 = 0.03587 0.00565 0.00658 0.00026 C8 1 -0.330031 0.210544 0.760104 11.00000 0.03890 0.04042 = 0.03807 0.00260 0.00363 -0.00397 AFIX 43 H8 2 -0.377253 0.139655 0.731594 11.00000 -1.20000 AFIX 0 C5 1 -0.182800 0.421489 0.847710 11.00000 0.04417 0.03791 = 0.04024 0.00115 0.00614 0.00233 AFIX 43 H5 2 -0.134624 0.492095 0.876830 11.00000 -1.20000 AFIX 0 C9 1 -0.103038 0.234476 0.829302 11.00000 0.03734 0.03722 = 0.03654 0.00493 0.00616 0.00157 C10 1 0.604686 0.294749 1.046292 11.00000 0.04060 0.04077 = 0.03793 0.00585 0.00254 -0.00296 C1 1 0.279230 0.162489 0.920753 11.00000 0.03899 0.04002 = 0.03762 0.00612 0.00087 -0.00138 C11 1 0.973933 0.209799 1.140513 11.00000 0.03876 0.04121 = 0.03728 0.00859 0.00299 -0.00547 C6 1 -0.409230 0.400932 0.779731 11.00000 0.04180 0.04586 = 0.04324 0.00732 0.00713 0.00729 AFIX 43 H6 2 -0.512780 0.457517 0.763656 11.00000 -1.20000 AFIX 0 C16 1 1.113360 0.116286 1.141070 11.00000 0.05287 0.03847 = 0.04806 0.00418 -0.00300 -0.00328 AFIX 43 H16 2 1.054605 0.057365 1.094844 11.00000 -1.20000 AFIX 0 C13 1 1.288626 0.291020 1.277760 11.00000 0.05967 0.04897 = 0.04199 0.00004 -0.00416 -0.00253 AFIX 43 H13 2 1.350085 0.349692 1.323976 11.00000 -1.20000 AFIX 0 C15 1 1.337381 0.109293 1.208972 11.00000 0.05219 0.04500 = 0.05384 0.00920 0.00027 0.00545 AFIX 43 H15 2 1.429738 0.046434 1.208832 11.00000 -1.20000 AFIX 0 C14 1 1.421483 0.197090 1.276878 11.00000 0.04061 0.05667 = 0.03921 0.01232 0.00009 -0.00190 C12 1 1.064004 0.298080 1.209971 11.00000 0.05612 0.04453 = 0.04268 0.00203 -0.00435 0.00600 AFIX 43 H12 2 0.973109 0.361309 1.210553 11.00000 -1.20000 AFIX 0 C19 1 -0.859037 0.362761 0.627565 11.00000 0.04200 0.06936 = 0.05503 0.00758 -0.00488 0.01185 AFIX 23 H19A 2 -0.892167 0.414690 0.679498 11.00000 -1.20000 H19B 2 -1.036168 0.334605 0.591361 11.00000 -1.20000 AFIX 0 C17 1 -0.812719 0.164888 0.618715 11.00000 0.03552 0.06102 = 0.05562 -0.00041 -0.00283 -0.00255 AFIX 23 H17A 2 -1.010091 0.162050 0.598578 11.00000 -1.20000 H17B 2 -0.776799 0.115865 0.664066 11.00000 -1.20000 AFIX 0 C18 1 -0.681179 0.126057 0.535698 11.00000 0.05515 0.07991 = 0.06707 -0.01298 0.00404 0.00489 AFIX 137 H18A 2 -0.726793 0.170796 0.488292 11.00000 -1.50000 H18B 2 -0.747434 0.052819 0.511283 11.00000 -1.50000 H18C 2 -0.485285 0.129753 0.554490 11.00000 -1.50000 AFIX 0 C20 1 -0.700024 0.420026 0.566517 11.00000 0.08276 0.07722 = 0.06263 0.02417 0.00083 0.01219 AFIX 137 H20A 2 -0.518662 0.442966 0.600058 11.00000 -1.50000 H20B 2 -0.793256 0.481757 0.550106 11.00000 -1.50000 H20C 2 -0.687358 0.371656 0.510689 11.00000 -1.50000 AFIX 0 H1 2 0.684821 0.147800 1.037632 11.00000 0.06091 HKLF 4 REM san623 in P -1 REM R1 = 0.0482 for 2737 Fo > 4sig(Fo) and 0.0658 for all 3543 data REM 259 parameters refined using 0 restraints END WGHT 0.0692 0.1583 REM Highest difference peak 0.205, deepest hole -0.190, 1-sigma level 0.034 Q1 1 1.0478 0.2598 1.1613 11.00000 0.05 0.15 Q2 1 1.4295 0.2406 1.2627 11.00000 0.05 0.14 Q3 1 1.4170 0.1747 1.2425 11.00000 0.05 0.14 Q4 1 0.9770 0.2397 1.1872 11.00000 0.05 0.13 Q5 1 -0.1814 0.2307 0.7691 11.00000 0.05 0.12 Q6 1 0.9666 0.1618 1.1603 11.00000 0.05 0.12 Q7 1 -0.2610 0.2190 0.8161 11.00000 0.05 0.12 Q8 1 -0.5529 0.4910 0.7614 11.00000 0.05 0.12 Q9 1 1.3628 0.2181 1.2931 11.00000 0.05 0.11 Q10 1 1.2812 0.1382 1.2597 11.00000 0.05 0.11 Q11 1 -0.4040 0.3527 0.7385 11.00000 0.05 0.11 Q12 1 1.6009 0.0604 1.3422 11.00000 0.05 0.10 Q13 1 0.1360 0.2502 0.8968 11.00000 0.05 0.10 Q14 1 -0.9736 0.2678 0.5918 11.00000 0.05 0.10 Q15 1 -0.5354 0.0764 0.5746 11.00000 0.05 0.10 Q16 1 -0.3575 0.2557 0.7195 11.00000 0.05 0.10 Q17 1 -0.5856 0.2828 0.6591 11.00000 0.05 0.10 Q18 1 0.6409 0.0937 1.0015 11.00000 0.05 0.10 Q19 1 1.8180 0.2420 1.4926 11.00000 0.05 0.10 Q20 1 -0.4883 0.1842 0.5149 11.00000 0.05 0.09 Q21 1 -0.0531 0.5251 0.8732 11.00000 0.05 0.09 Q22 1 0.8745 0.0406 1.1053 11.00000 0.05 0.09 Q23 1 1.9003 0.1782 1.4218 11.00000 0.05 0.09 Q24 1 1.7341 0.1578 1.4642 11.00000 0.05 0.09 Q25 1 0.1765 0.0568 0.8729 11.00000 0.05 0.09 ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 0.0470(2) 0.14962(8) 0.85254(7) 0.0434(3) Uani 1 1 d . . . N1 N 0.7472(3) 0.20920(11) 1.06960(9) 0.0435(3) Uani 1 1 d . . . O2 O 0.3911(2) 0.08017(9) 0.93291(8) 0.0542(3) Uani 1 1 d . . . O3 O 0.6685(2) 0.38740(9) 1.08486(8) 0.0580(3) Uani 1 1 d . . . N2 N -0.7178(3) 0.27406(11) 0.66451(9) 0.0464(3) Uani 1 1 d . . . N3 N 1.6574(3) 0.19032(14) 1.34965(10) 0.0582(4) Uani 1 1 d . . . O4 O 1.7419(3) 0.27118(13) 1.40612(10) 0.0784(4) Uani 1 1 d . . . O5 O 1.7601(3) 0.10445(14) 1.35205(11) 0.0915(5) Uani 1 1 d . . . C2 C 0.3622(3) 0.27051(11) 0.96984(10) 0.0376(3) Uani 1 1 d . . . C4 C -0.0198(3) 0.33907(11) 0.87514(9) 0.0373(3) Uani 1 1 d . . . C3 C 0.2169(3) 0.35414(12) 0.94480(10) 0.0385(3) Uani 1 1 d . . . H3 H 0.2758 0.4237 0.9746 0.046 Uiso 1 1 calc R . . C7 C -0.4905(3) 0.29399(12) 0.73269(10) 0.0392(3) Uani 1 1 d . . . C8 C -0.3300(3) 0.21054(12) 0.76010(10) 0.0400(3) Uani 1 1 d . . . H8 H -0.3773 0.1397 0.7316 0.048 Uiso 1 1 calc R . . C5 C -0.1828(3) 0.42149(12) 0.84771(10) 0.0414(3) Uani 1 1 d . . . H5 H -0.1346 0.4921 0.8768 0.05 Uiso 1 1 calc R . . C9 C -0.1030(3) 0.23448(11) 0.82930(10) 0.0371(3) Uani 1 1 d . . . C10 C 0.6047(3) 0.29475(12) 1.04629(10) 0.0404(3) Uani 1 1 d . . . C1 C 0.2792(3) 0.16249(12) 0.92075(10) 0.0396(3) Uani 1 1 d . . . C11 C 0.9739(3) 0.20980(12) 1.14051(10) 0.0395(3) Uani 1 1 d . . . C6 C -0.4092(3) 0.40093(13) 0.77973(10) 0.0435(4) Uani 1 1 d . . . H6 H -0.5128 0.4575 0.7637 0.052 Uiso 1 1 calc R . . C16 C 1.1134(3) 0.11629(12) 1.14107(11) 0.0482(4) Uani 1 1 d . . . H16 H 1.0546 0.0574 1.0948 0.058 Uiso 1 1 calc R . . C13 C 1.2886(4) 0.29102(14) 1.27776(11) 0.0525(4) Uani 1 1 d . . . H13 H 1.3501 0.3497 1.324 0.063 Uiso 1 1 calc R . . C15 C 1.3374(3) 0.10929(13) 1.20897(12) 0.0511(4) Uani 1 1 d . . . H15 H 1.4297 0.0464 1.2088 0.061 Uiso 1 1 calc R . . C14 C 1.4215(3) 0.19709(13) 1.27688(11) 0.0459(4) Uani 1 1 d . . . C12 C 1.0640(3) 0.29808(13) 1.20997(11) 0.0496(4) Uani 1 1 d . . . H12 H 0.9731 0.3613 1.2106 0.06 Uiso 1 1 calc R . . C19 C -0.8590(3) 0.36276(15) 0.62756(12) 0.0569(4) Uani 1 1 d . . . H19A H -0.8922 0.4147 0.6795 0.068 Uiso 1 1 calc R . . H19B H -1.0362 0.3346 0.5914 0.068 Uiso 1 1 calc R . . C17 C -0.8127(3) 0.16489(14) 0.61871(12) 0.0530(4) Uani 1 1 d . . . H17A H -1.0101 0.162 0.5986 0.064 Uiso 1 1 calc R . . H17B H -0.7768 0.1159 0.6641 0.064 Uiso 1 1 calc R . . C18 C -0.6812(4) 0.12606(18) 0.53570(14) 0.0705(6) Uani 1 1 d . . . H18A H -0.7268 0.1708 0.4883 0.106 Uiso 1 1 calc R . . H18B H -0.7474 0.0528 0.5113 0.106 Uiso 1 1 calc R . . H18C H -0.4853 0.1298 0.5545 0.106 Uiso 1 1 calc R . . C20 C -0.7000(5) 0.42003(18) 0.56652(14) 0.0740(6) Uani 1 1 d . . . H20A H -0.5187 0.443 0.6001 0.111 Uiso 1 1 calc R . . H20B H -0.7933 0.4818 0.5501 0.111 Uiso 1 1 calc R . . H20C H -0.6874 0.3717 0.5107 0.111 Uiso 1 1 calc R . . H1 H 0.685(4) 0.1478(16) 1.0376(14) 0.061(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0437(6) 0.0367(5) 0.0445(6) 0.0028(4) -0.0053(5) 0.0004(4) N1 0.0432(7) 0.0397(7) 0.0425(7) 0.0045(6) -0.0044(5) -0.0037(6) O2 0.0567(7) 0.0394(6) 0.0588(7) 0.0050(5) -0.0112(5) 0.0037(5) O3 0.0600(7) 0.0419(6) 0.0605(7) -0.0005(5) -0.0161(6) -0.0008(5) N2 0.0371(7) 0.0541(8) 0.0447(7) 0.0057(6) -0.0005(5) 0.0022(6) N3 0.0502(8) 0.0741(10) 0.0480(8) 0.0147(7) -0.0028(7) 0.0013(8) O4 0.0692(9) 0.0933(11) 0.0577(8) -0.0026(7) -0.0193(7) -0.0021(8) O5 0.0863(11) 0.0886(11) 0.0890(11) 0.0170(9) -0.0261(9) 0.0269(9) C2 0.0378(7) 0.0392(8) 0.0347(7) 0.0055(6) 0.0048(6) -0.0021(6) C4 0.0376(7) 0.0394(7) 0.0343(7) 0.0041(6) 0.0063(6) -0.0010(6) C3 0.0395(8) 0.0376(7) 0.0363(7) 0.0011(6) 0.0063(6) -0.0031(6) C7 0.0332(7) 0.0483(8) 0.0359(7) 0.0056(6) 0.0066(6) 0.0003(6) C8 0.0389(8) 0.0404(8) 0.0381(7) 0.0026(6) 0.0036(6) -0.0040(6) C5 0.0442(8) 0.0379(7) 0.0402(8) 0.0012(6) 0.0061(6) 0.0023(6) C9 0.0373(7) 0.0372(7) 0.0365(7) 0.0049(6) 0.0062(6) 0.0016(6) C10 0.0406(8) 0.0408(8) 0.0379(7) 0.0059(6) 0.0025(6) -0.0030(6) C1 0.0390(8) 0.0400(8) 0.0376(7) 0.0061(6) 0.0009(6) -0.0014(6) C11 0.0388(8) 0.0412(8) 0.0373(7) 0.0086(6) 0.0030(6) -0.0055(6) C6 0.0418(8) 0.0459(8) 0.0432(8) 0.0073(6) 0.0071(6) 0.0073(6) C16 0.0529(9) 0.0385(8) 0.0481(9) 0.0042(7) -0.0030(7) -0.0033(7) C13 0.0597(10) 0.0490(9) 0.0420(8) 0.0000(7) -0.0042(7) -0.0025(8) C15 0.0522(9) 0.0450(9) 0.0538(9) 0.0092(7) 0.0003(7) 0.0054(7) C14 0.0406(8) 0.0567(9) 0.0392(8) 0.0123(7) 0.0001(6) -0.0019(7) C12 0.0561(9) 0.0445(9) 0.0427(8) 0.0020(7) -0.0043(7) 0.0060(7) C19 0.0420(9) 0.0694(11) 0.0550(10) 0.0076(8) -0.0049(7) 0.0119(8) C17 0.0355(8) 0.0610(10) 0.0556(10) -0.0004(8) -0.0028(7) -0.0025(7) C18 0.0551(11) 0.0799(13) 0.0671(12) -0.0130(10) 0.0040(9) 0.0049(10) C20 0.0828(14) 0.0772(13) 0.0626(12) 0.0242(10) 0.0008(10) 0.0122(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.3771(17) . ? O1 C1 1.3819(17) . ? N1 C10 1.365(2) . ? N1 C11 1.3990(19) . ? N1 H1 0.86(2) . ? O2 C1 1.2166(18) . ? O3 C10 1.2223(17) . ? N2 C7 1.3653(18) . ? N2 C17 1.458(2) . ? N2 C19 1.464(2) . ? N3 O5 1.216(2) . ? N3 O4 1.225(2) . ? N3 C14 1.462(2) . ? C2 C3 1.359(2) . ? C2 C1 1.450(2) . ? C2 C10 1.490(2) . ? C4 C9 1.3983(19) . ? C4 C5 1.405(2) . ? C4 C3 1.409(2) . ? C3 H3 0.93 . ? C7 C8 1.408(2) . ? C7 C6 1.427(2) . ? C8 C9 1.376(2) . ? C8 H8 0.93 . ? C5 C6 1.361(2) . ? C5 H5 0.93 . ? C11 C16 1.389(2) . ? C11 C12 1.397(2) . ? C6 H6 0.93 . ? C16 C15 1.379(2) . ? C16 H16 0.93 . ? C13 C14 1.376(2) . ? C13 C12 1.381(2) . ? C13 H13 0.93 . ? C15 C14 1.375(2) . ? C15 H15 0.93 . ? C12 H12 0.93 . ? C19 C20 1.514(3) . ? C19 H19A 0.97 . ? C19 H19B 0.97 . ? C17 C18 1.503(3) . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? C20 H20A 0.96 . ? C20 H20B 0.96 . ? C20 H20C 0.96 . ? 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 C9 O1 C1 122.83(11) . . ? C10 N1 C11 127.79(13) . . ? C10 N1 H1 115.1(13) . . ? C11 N1 H1 117.1(13) . . ? C7 N2 C17 121.75(13) . . ? C7 N2 C19 120.86(13) . . ? C17 N2 C19 117.08(13) . . ? O5 N3 O4 122.73(15) . . ? O5 N3 C14 118.63(16) . . ? O4 N3 C14 118.64(16) . . ? C3 C2 C1 119.24(13) . . ? C3 C2 C10 118.01(13) . . ? C1 C2 C10 122.75(13) . . ? C9 C4 C5 116.53(13) . . ? C9 C4 C3 118.41(13) . . ? C5 C4 C3 125.06(13) . . ? C2 C3 C4 122.23(13) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? N2 C7 C8 121.68(13) . . ? N2 C7 C6 120.75(14) . . ? C8 C7 C6 117.57(13) . . ? C9 C8 C7 119.62(13) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C6 C5 C4 121.86(14) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C8 C9 O1 116.95(12) . . ? C8 C9 C4 123.31(14) . . ? O1 C9 C4 119.74(12) . . ? O3 C10 N1 123.00(14) . . ? O3 C10 C2 120.33(14) . . ? N1 C10 C2 116.66(12) . . ? O2 C1 O1 115.27(12) . . ? O2 C1 C2 127.24(13) . . ? O1 C1 C2 117.49(13) . . ? C16 C11 C12 119.08(14) . . ? C16 C11 N1 117.23(13) . . ? C12 C11 N1 123.69(14) . . ? C5 C6 C7 121.11(14) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C15 C16 C11 121.17(14) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? C14 C13 C12 119.93(15) . . ? C14 C13 H13 120 . . ? C12 C13 H13 120 . . ? C14 C15 C16 118.70(15) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C15 C14 C13 121.44(14) . . ? C15 C14 N3 119.18(15) . . ? C13 C14 N3 119.37(15) . . ? C13 C12 C11 119.67(15) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? N2 C19 C20 113.51(15) . . ? N2 C19 H19A 108.9 . . ? C20 C19 H19A 108.9 . . ? N2 C19 H19B 108.9 . . ? C20 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? N2 C17 C18 114.42(15) . . ? N2 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? N2 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C1 C2 C3 C4 2.8(2) . . . . ? C10 C2 C3 C4 -178.22(12) . . . . ? C9 C4 C3 C2 -1.4(2) . . . . ? C5 C4 C3 C2 178.28(14) . . . . ? C17 N2 C7 C8 2.3(2) . . . . ? C19 N2 C7 C8 -171.17(14) . . . . ? C17 N2 C7 C6 -176.90(14) . . . . ? C19 N2 C7 C6 9.7(2) . . . . ? N2 C7 C8 C9 -179.84(13) . . . . ? C6 C7 C8 C9 -0.7(2) . . . . ? C9 C4 C5 C6 -0.3(2) . . . . ? C3 C4 C5 C6 -179.99(13) . . . . ? C7 C8 C9 O1 -179.47(12) . . . . ? C7 C8 C9 C4 0.0(2) . . . . ? C1 O1 C9 C8 -179.99(12) . . . . ? C1 O1 C9 C4 0.6(2) . . . . ? C5 C4 C9 C8 0.5(2) . . . . ? C3 C4 C9 C8 -179.78(13) . . . . ? C5 C4 C9 O1 179.97(12) . . . . ? C3 C4 C9 O1 -0.4(2) . . . . ? C11 N1 C10 O3 2.7(3) . . . . ? C11 N1 C10 C2 -177.42(13) . . . . ? C3 C2 C10 O3 0.2(2) . . . . ? C1 C2 C10 O3 179.12(14) . . . . ? C3 C2 C10 N1 -179.70(13) . . . . ? C1 C2 C10 N1 -0.7(2) . . . . ? C9 O1 C1 O2 -179.42(13) . . . . ? C9 O1 C1 C2 0.9(2) . . . . ? C3 C2 C1 O2 177.82(15) . . . . ? C10 C2 C1 O2 -1.1(2) . . . . ? C3 C2 C1 O1 -2.5(2) . . . . ? C10 C2 C1 O1 178.56(12) . . . . ? C10 N1 C11 C16 -169.42(15) . . . . ? C10 N1 C11 C12 11.1(2) . . . . ? C4 C5 C6 C7 -0.3(2) . . . . ? N2 C7 C6 C5 -179.95(13) . . . . ? C8 C7 C6 C5 0.9(2) . . . . ? C12 C11 C16 C15 0.2(2) . . . . ? N1 C11 C16 C15 -179.30(14) . . . . ? C11 C16 C15 C14 0.1(2) . . . . ? C16 C15 C14 C13 -0.5(3) . . . . ? C16 C15 C14 N3 179.52(14) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? C12 C13 C14 N3 -179.38(15) . . . . ? O5 N3 C14 C15 -5.4(2) . . . . ? O4 N3 C14 C15 175.21(16) . . . . ? O5 N3 C14 C13 174.66(17) . . . . ? O4 N3 C14 C13 -4.8(2) . . . . ? C14 C13 C12 C11 -0.3(3) . . . . ? C16 C11 C12 C13 -0.1(2) . . . . ? N1 C11 C12 C13 179.42(15) . . . . ? C7 N2 C19 C20 71.7(2) . . . . ? C17 N2 C19 C20 -101.99(18) . . . . ? C7 N2 C17 C18 -86.93(19) . . . . ? C19 N2 C17 C18 86.74(18) . . . . ? 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 N1 H1 O2 0.86(2) 1.99(2) 2.7222(17) 141.8(18) . # END of CIF _database_code_depnum_ccdc_archive 'CCDC 957823'