# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Lightfoot, Andrew P.' 'Pritchard, Robin G.' 'Wan, Hayley' 'Warren, John E.' 'Andrew Whiting' _publ_contact_author_name 'Dr Andrew Whiting' _publ_contact_author_address ; Chemistry University of Durham Science Labs South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email 'ANDY.WHITING@DURHAM.AC.UK' _publ_requested_journal 'Chemical Communications' _publ_section_title ; A Novel Scandium ortho-Methoxynitrosobenzene-Dimer Complex: Mechanistic Implications for the Nitroso-Diels-Alder Reaction. ; data_b _database_code_CSD 176704 _audit_creation_date 2001-12-21T12:32:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C28 H28 N4 O8' _chemical_formula_sum 'C28 H28 N4 O8' _chemical_formula_weight 548.54 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.9465(3) _cell_length_b 8.98220(10) _cell_length_c 15.6262(2) _cell_angle_alpha 90 _cell_angle_beta 107.2590 _cell_angle_gamma 90 _cell_volume 2673.58(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 32066 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; ? ; _exptl_absorpt_correction_T_min 0.9702 _exptl_absorpt_correction_T_max 0.9874 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(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_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.33934E-1 _diffrn_orient_matrix_ub_12 0.444685E-1 _diffrn_orient_matrix_ub_13 -0.462009E-1 _diffrn_orient_matrix_ub_21 0.442339E-1 _diffrn_orient_matrix_ub_22 -0.434982E-1 _diffrn_orient_matrix_ub_23 -0.218841E-1 _diffrn_orient_matrix_ub_31 -0.371822E-1 _diffrn_orient_matrix_ub_32 -0.923316E-1 _diffrn_orient_matrix_ub_33 -0.119414E-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 0.0955 _diffrn_reflns_av_unetI/netI 0.0488 _diffrn_reflns_number 43598 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.29 _diffrn_reflns_theta_full 27.29 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 5959 _reflns_number_gt 4274 _reflns_threshold_expression >2sigma(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 (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.8594P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5959 _refine_ls_number_parameters 473 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.204 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.052 #----------------------------------------------------------------------------# # 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.36086(7) 0.35280(16) 0.21428(9) 0.0308(3) Uani 1 d . . . N2 N 0.38627(7) 0.48197(16) 0.24875(9) 0.0322(3) Uani 1 d . . . O1 O 0.49678(6) 0.45957(14) 0.18343(8) 0.0385(3) Uani 1 d . . . O2 O 0.24293(6) 0.47622(14) 0.11217(7) 0.0375(3) Uani 1 d . . . O10 O 0.34965(7) 0.25141(15) 0.26405(8) 0.0431(3) Uani 1 d . . . O11 O 0.39843(7) 0.50525(15) 0.33219(7) 0.0419(3) Uani 1 d . . . C2 C 0.34097(9) 0.33302(18) 0.11795(10) 0.0299(4) Uani 1 d . . . C3 C 0.38171(11) 0.2429(2) 0.08138(13) 0.0394(4) Uani 1 d . . . C4 C 0.35933(13) 0.2190(2) -0.01080(15) 0.0508(6) Uani 1 d . . . C5 C 0.29776(13) 0.2819(2) -0.06210(13) 0.0496(5) Uani 1 d . . . C6 C 0.25637(12) 0.3684(2) -0.02520(12) 0.0424(5) Uani 1 d . . . C7 C 0.27783(9) 0.39467(18) 0.06692(10) 0.0316(4) Uani 1 d . . . C8 C 0.18091(12) 0.5528(3) 0.06098(16) 0.0516(5) Uani 1 d . . . C9 C 0.40041(9) 0.59851(19) 0.19205(10) 0.0310(4) Uani 1 d . . . C10 C 0.35824(10) 0.7241(2) 0.17647(12) 0.0370(4) Uani 1 d . . . C11 C 0.37592(10) 0.8428(2) 0.13051(13) 0.0422(4) Uani 1 d . . . C12 C 0.43510(10) 0.8326(2) 0.10219(13) 0.0439(5) Uani 1 d . . . C13 C 0.47707(10) 0.7079(2) 0.11743(12) 0.0381(4) Uani 1 d . . . C14 C 0.45995(9) 0.58762(19) 0.16333(11) 0.0327(4) Uani 1 d . . . C15 C 0.55145(11) 0.4354(3) 0.14230(14) 0.0442(5) Uani 1 d . . . H3 H 0.4258(9) 0.2054(19) 0.1195(11) 0.028(4) Uiso 1 d . . . H4 H 0.3876(12) 0.161(3) -0.0345(16) 0.068(7) Uiso 1 d . . . H5 H 0.2828(11) 0.268(2) -0.1291(16) 0.060(6) Uiso 1 d . . . H6 H 0.2115(13) 0.409(3) -0.0646(16) 0.065(7) Uiso 1 d . . . H8A H 0.1934(12) 0.621(3) 0.0144(17) 0.074(7) Uiso 1 d . . . H8B H 0.1437(14) 0.475(3) 0.0282(17) 0.080(8) Uiso 1 d . . . H8C H 0.1660(13) 0.616(3) 0.1054(17) 0.073(7) Uiso 1 d . . . H10 H 0.3182(11) 0.725(2) 0.1990(13) 0.049(6) Uiso 1 d . . . H11 H 0.3451(11) 0.937(2) 0.1199(13) 0.049(5) Uiso 1 d . . . H12 H 0.4487(12) 0.919(3) 0.0688(15) 0.067(7) Uiso 1 d . . . H13 H 0.5167(11) 0.704(2) 0.0996(13) 0.047(6) Uiso 1 d . . . H15A H 0.5328(10) 0.452(2) 0.0748(14) 0.048(5) Uiso 1 d . . . H15B H 0.5657(10) 0.327(3) 0.1573(14) 0.050(6) Uiso 1 d . . . H15C H 0.5938(13) 0.506(3) 0.1676(15) 0.066(7) Uiso 1 d . . . N51 N 0.09823(6) -0.12778(14) 0.30148(8) 0.0247(3) Uani 1 d . . . N52 N 0.10841(7) -0.01275(14) 0.25435(8) 0.0251(3) Uani 1 d . . . O51 O 0.01615(6) -0.15749(13) 0.11452(7) 0.0318(3) Uani 1 d . . . O52 O 0.23672(6) -0.18541(12) 0.34413(8) 0.0338(3) Uani 1 d . . . O60 O 0.07551(6) -0.10654(13) 0.36799(7) 0.0338(3) Uani 1 d . . . O61 O 0.09983(6) 0.11781(12) 0.27987(8) 0.0339(3) Uani 1 d . . . C52 C 0.12158(8) -0.27485(16) 0.28466(10) 0.0241(3) Uani 1 d . . . C53 C 0.07253(9) -0.38590(18) 0.25429(11) 0.0287(4) Uani 1 d . . . C54 C 0.09566(9) -0.52898(19) 0.24644(12) 0.0333(4) Uani 1 d . . . C55 C 0.16691(9) -0.55796(19) 0.27010(11) 0.0327(4) Uani 1 d . . . C56 C 0.21605(9) -0.44717(18) 0.30294(11) 0.0286(4) Uani 1 d . . . C57 C 0.19365(8) -0.30292(17) 0.31114(10) 0.0247(3) Uani 1 d . . . C58 C 0.30321(9) -0.2210(3) 0.40573(14) 0.0415(5) Uani 1 d . . . C59 C 0.12396(8) -0.03464(16) 0.17042(10) 0.0260(3) Uani 1 d . . . C60 C 0.18434(9) 0.03054(18) 0.16089(12) 0.0326(4) Uani 1 d . . . C61 C 0.19678(10) 0.0255(2) 0.07838(13) 0.0402(4) Uani 1 d . . . C62 C 0.14900(11) -0.0454(2) 0.00713(13) 0.0411(5) Uani 1 d . . . C63 C 0.08890(10) -0.11091(19) 0.01667(12) 0.0351(4) Uani 1 d . . . C64 C 0.07503(8) -0.10460(17) 0.09850(10) 0.0273(3) Uani 1 d . . . C65 C -0.02719(11) -0.2580(2) 0.04971(14) 0.0424(5) Uani 1 d . . . H53 H 0.0247(10) -0.365(2) 0.2393(12) 0.038(5) Uiso 1 d . . . H54 H 0.0625(10) -0.609(2) 0.2249(12) 0.043(5) Uiso 1 d . . . H55 H 0.1842(10) -0.661(2) 0.2642(12) 0.040(5) Uiso 1 d . . . H56 H 0.2654(10) -0.4696(19) 0.3213(11) 0.031(5) Uiso 1 d . . . H58C H 0.3239(10) -0.124(2) 0.4293(13) 0.045(5) Uiso 1 d . . . H58A H 0.2957(13) -0.283(3) 0.4534(18) 0.081(8) Uiso 1 d . . . H58B H 0.3313(12) -0.274(3) 0.3769(15) 0.058(6) Uiso 1 d . . . H60 H 0.2159(10) 0.080(2) 0.2113(13) 0.042(5) Uiso 1 d . . . H61 H 0.2390(11) 0.073(2) 0.0730(13) 0.052(6) Uiso 1 d . . . H62 H 0.1555(10) -0.044(2) -0.0525(13) 0.046(5) Uiso 1 d . . . H63 H 0.0562(10) -0.161(2) -0.0349(13) 0.043(5) Uiso 1 d . . . H65A H 0.0003(10) -0.341(2) 0.0370(13) 0.043(5) Uiso 1 d . . . H65C H -0.0493(10) -0.205(2) -0.0045(14) 0.048(6) Uiso 1 d . . . H65B H -0.0625(11) -0.296(2) 0.0773(14) 0.056(6) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0350(8) 0.0317(8) 0.0276(7) 0.0069(6) 0.0121(6) 0.0056(6) N2 0.0364(8) 0.0375(8) 0.0231(7) 0.0015(6) 0.0092(6) 0.0077(6) O1 0.0362(7) 0.0416(7) 0.0405(7) 0.0078(6) 0.0155(5) 0.0106(6) O2 0.0387(7) 0.0413(7) 0.0288(6) 0.0028(5) 0.0043(5) 0.0083(6) O10 0.0518(8) 0.0444(8) 0.0355(7) 0.0184(6) 0.0169(6) 0.0031(6) O11 0.0478(7) 0.0567(8) 0.0209(6) -0.0017(5) 0.0096(5) 0.0112(6) C2 0.0414(10) 0.0251(8) 0.0265(8) 0.0000(7) 0.0150(7) -0.0053(7) C3 0.0517(12) 0.0256(9) 0.0494(11) -0.0031(8) 0.0278(9) -0.0052(8) C4 0.0794(16) 0.0337(11) 0.0560(13) -0.0172(10) 0.0458(12) -0.0190(11) C5 0.0802(16) 0.0404(11) 0.0327(10) -0.0084(9) 0.0239(10) -0.0243(11) C6 0.0620(13) 0.0350(10) 0.0272(9) 0.0006(8) 0.0086(9) -0.0174(9) C7 0.0420(10) 0.0261(9) 0.0269(8) 0.0015(7) 0.0105(7) -0.0059(7) C8 0.0432(12) 0.0572(14) 0.0467(12) 0.0103(11) 0.0015(10) 0.0138(11) C9 0.0347(9) 0.0321(9) 0.0239(8) -0.0038(7) 0.0053(7) -0.0004(7) C10 0.0367(10) 0.0314(10) 0.0371(9) -0.0058(8) 0.0018(8) 0.0044(8) C11 0.0406(11) 0.0290(10) 0.0498(11) -0.0017(8) 0.0025(8) 0.0027(8) C12 0.0447(11) 0.0327(10) 0.0480(11) 0.0009(9) 0.0041(9) -0.0051(9) C13 0.0358(10) 0.0364(10) 0.0395(10) -0.0008(8) 0.0072(8) -0.0041(8) C14 0.0338(9) 0.0316(9) 0.0289(8) -0.0019(7) 0.0035(7) 0.0035(7) C15 0.0418(11) 0.0487(13) 0.0460(12) 0.0048(10) 0.0190(9) 0.0112(10) N51 0.0271(7) 0.0227(7) 0.0234(6) 0.0002(5) 0.0063(5) 0.0021(5) N52 0.0284(7) 0.0178(6) 0.0281(7) -0.0018(5) 0.0067(5) 0.0001(5) O51 0.0312(6) 0.0302(6) 0.0309(6) -0.0005(5) 0.0045(5) -0.0052(5) O52 0.0292(6) 0.0248(6) 0.0407(7) -0.0011(5) 0.0003(5) -0.0025(5) O60 0.0425(7) 0.0344(7) 0.0266(6) 0.0012(5) 0.0136(5) 0.0067(5) O61 0.0406(7) 0.0175(6) 0.0446(7) -0.0065(5) 0.0145(5) 0.0008(5) C52 0.0295(8) 0.0179(7) 0.0251(7) 0.0022(6) 0.0083(6) 0.0023(6) C53 0.0271(9) 0.0246(8) 0.0330(9) 0.0039(7) 0.0071(7) -0.0008(7) C54 0.0355(10) 0.0208(8) 0.0417(9) 0.0015(7) 0.0087(7) -0.0054(7) C55 0.0400(10) 0.0199(8) 0.0393(9) 0.0003(7) 0.0133(8) 0.0023(7) C56 0.0276(9) 0.0274(9) 0.0320(8) 0.0035(7) 0.0109(7) 0.0039(7) C57 0.0292(8) 0.0223(8) 0.0224(7) 0.0025(6) 0.0071(6) -0.0032(6) C58 0.0247(9) 0.0450(12) 0.0492(11) -0.0141(10) 0.0026(8) 0.0020(8) C59 0.0316(8) 0.0174(7) 0.0298(8) 0.0030(6) 0.0107(7) 0.0037(6) C60 0.0329(9) 0.0224(8) 0.0426(10) 0.0029(7) 0.0112(8) -0.0006(7) C61 0.0427(11) 0.0310(10) 0.0556(12) 0.0079(8) 0.0282(9) 0.0047(8) C62 0.0588(12) 0.0351(10) 0.0373(10) 0.0041(8) 0.0266(9) 0.0102(9) C63 0.0472(11) 0.0268(9) 0.0306(9) -0.0003(7) 0.0105(8) 0.0061(8) C64 0.0334(9) 0.0182(8) 0.0301(8) 0.0018(6) 0.0091(7) 0.0032(7) C65 0.0445(11) 0.0324(10) 0.0407(11) -0.0032(9) -0.0022(9) -0.0094(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 O10 1.2599(17) . ? N1 N2 1.316(2) . ? N1 C2 1.449(2) . ? N2 O11 1.2708(17) . ? N2 C9 1.452(2) . ? O1 C14 1.351(2) . ? O1 C15 1.437(2) . ? O2 C7 1.347(2) . ? O2 C8 1.434(2) . ? C2 C3 1.385(2) . ? C2 C7 1.390(2) . ? C3 C4 1.392(3) . ? C4 C5 1.373(3) . ? C5 C6 1.379(3) . ? C6 C7 1.395(2) . ? C9 C10 1.385(2) . ? C9 C14 1.392(2) . ? C10 C11 1.388(3) . ? C11 C12 1.381(3) . ? C12 C13 1.376(3) . ? C13 C14 1.394(3) . ? N51 O60 1.2654(16) . ? N51 N52 1.3190(18) . ? N51 C52 1.4506(19) . ? N52 O61 1.2665(16) . ? N52 C59 1.448(2) . ? O51 C64 1.3573(19) . ? O51 C65 1.438(2) . ? O52 C57 1.3619(18) . ? O52 C58 1.425(2) . ? C52 C53 1.379(2) . ? C52 C57 1.396(2) . ? C53 C54 1.383(2) . ? C54 C55 1.383(2) . ? C55 C56 1.384(2) . ? C56 C57 1.389(2) . ? C59 C60 1.386(2) . ? C59 C64 1.400(2) . ? C60 C61 1.384(3) . ? C61 C62 1.387(3) . ? C62 C63 1.383(3) . ? C63 C64 1.387(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O10 N1 N2 120.14(13) . . ? O10 N1 C2 120.56(14) . . ? N2 N1 C2 119.13(13) . . ? O11 N2 N1 119.88(14) . . ? O11 N2 C9 119.66(14) . . ? N1 N2 C9 120.46(13) . . ? C14 O1 C15 117.21(14) . . ? C7 O2 C8 117.57(15) . . ? C3 C2 C7 122.59(16) . . ? C3 C2 N1 119.14(16) . . ? C7 C2 N1 117.99(14) . . ? C2 C3 C4 118.0(2) . . ? C5 C4 C3 119.8(2) . . ? C4 C5 C6 122.05(18) . . ? C5 C6 C7 119.2(2) . . ? O2 C7 C2 115.90(14) . . ? O2 C7 C6 125.85(17) . . ? C2 C7 C6 118.25(17) . . ? C10 C9 C14 122.16(17) . . ? C10 C9 N2 118.47(15) . . ? C14 C9 N2 119.00(15) . . ? C9 C10 C11 118.83(18) . . ? C12 C11 C10 119.16(18) . . ? C13 C12 C11 122.17(19) . . ? C12 C13 C14 119.37(18) . . ? O1 C14 C9 116.23(15) . . ? O1 C14 C13 125.47(16) . . ? C9 C14 C13 118.30(16) . . ? O60 N51 N52 119.50(12) . . ? O60 N51 C52 119.91(12) . . ? N52 N51 C52 120.08(12) . . ? O61 N52 N51 119.47(12) . . ? O61 N52 C59 119.75(12) . . ? N51 N52 C59 120.61(12) . . ? C64 O51 C65 117.52(14) . . ? C57 O52 C58 115.97(14) . . ? C53 C52 C57 122.31(14) . . ? C53 C52 N51 119.20(13) . . ? C57 C52 N51 117.95(13) . . ? C52 C53 C54 118.77(15) . . ? C55 C54 C53 119.64(16) . . ? C54 C55 C56 121.48(16) . . ? C55 C56 C57 119.56(15) . . ? O52 C57 C56 125.03(14) . . ? O52 C57 C52 116.79(13) . . ? C56 C57 C52 118.18(14) . . ? C60 C59 C64 121.63(15) . . ? C60 C59 N52 117.80(14) . . ? C64 C59 N52 120.16(14) . . ? C61 C60 C59 119.20(17) . . ? C60 C61 C62 119.49(17) . . ? C63 C62 C61 121.34(17) . . ? C62 C63 C64 119.89(17) . . ? O51 C64 C63 125.15(15) . . ? O51 C64 C59 116.39(14) . . ? C63 C64 C59 118.43(15) . . ? 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 O10 N1 N2 O11 -1.2(2) . . . . ? C2 N1 N2 O11 174.11(14) . . . . ? O10 N1 N2 C9 178.98(14) . . . . ? C2 N1 N2 C9 -5.8(2) . . . . ? O10 N1 C2 C3 -76.0(2) . . . . ? N2 N1 C2 C3 108.76(18) . . . . ? O10 N1 C2 C7 98.09(18) . . . . ? N2 N1 C2 C7 -77.16(19) . . . . ? C7 C2 C3 C4 2.7(3) . . . . ? N1 C2 C3 C4 176.45(15) . . . . ? C2 C3 C4 C5 -1.2(3) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C4 C5 C6 C7 0.7(3) . . . . ? C8 O2 C7 C2 174.44(17) . . . . ? C8 O2 C7 C6 -5.1(3) . . . . ? C3 C2 C7 O2 178.04(15) . . . . ? N1 C2 C7 O2 4.2(2) . . . . ? C3 C2 C7 C6 -2.3(2) . . . . ? N1 C2 C7 C6 -176.21(15) . . . . ? C5 C6 C7 O2 -179.82(16) . . . . ? C5 C6 C7 C2 0.6(2) . . . . ? O11 N2 C9 C10 -69.4(2) . . . . ? N1 N2 C9 C10 110.44(17) . . . . ? O11 N2 C9 C14 103.78(18) . . . . ? N1 N2 C9 C14 -76.36(19) . . . . ? C14 C9 C10 C11 0.1(3) . . . . ? N2 C9 C10 C11 173.13(15) . . . . ? C9 C10 C11 C12 -0.4(3) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? C11 C12 C13 C14 -0.4(3) . . . . ? C15 O1 C14 C9 170.10(16) . . . . ? C15 O1 C14 C13 -10.4(3) . . . . ? C10 C9 C14 O1 179.51(15) . . . . ? N2 C9 C14 O1 6.6(2) . . . . ? C10 C9 C14 C13 0.0(2) . . . . ? N2 C9 C14 C13 -172.97(15) . . . . ? C12 C13 C14 O1 -179.37(16) . . . . ? C12 C13 C14 C9 0.1(3) . . . . ? O60 N51 N52 O61 4.7(2) . . . . ? C52 N51 N52 O61 -167.14(13) . . . . ? O60 N51 N52 C59 -170.52(13) . . . . ? C52 N51 N52 C59 17.63(19) . . . . ? O60 N51 C52 C53 71.35(18) . . . . ? N52 N51 C52 C53 -116.83(16) . . . . ? O60 N51 C52 C57 -100.40(16) . . . . ? N52 N51 C52 C57 71.42(18) . . . . ? C57 C52 C53 C54 -2.6(2) . . . . ? N51 C52 C53 C54 -174.02(14) . . . . ? C52 C53 C54 C55 0.8(2) . . . . ? C53 C54 C55 C56 1.0(3) . . . . ? C54 C55 C56 C57 -1.0(3) . . . . ? C58 O52 C57 C56 -26.5(2) . . . . ? C58 O52 C57 C52 152.80(15) . . . . ? C55 C56 C57 O52 178.61(14) . . . . ? C55 C56 C57 C52 -0.7(2) . . . . ? C53 C52 C57 O52 -176.78(14) . . . . ? N51 C52 C57 O52 -5.31(19) . . . . ? C53 C52 C57 C56 2.6(2) . . . . ? N51 C52 C57 C56 174.06(13) . . . . ? O61 N52 C59 C60 59.85(19) . . . . ? N51 N52 C59 C60 -124.93(15) . . . . ? O61 N52 C59 C64 -112.89(16) . . . . ? N51 N52 C59 C64 62.34(19) . . . . ? C64 C59 C60 C61 -0.4(2) . . . . ? N52 C59 C60 C61 -173.05(14) . . . . ? C59 C60 C61 C62 -0.4(3) . . . . ? C60 C61 C62 C63 0.2(3) . . . . ? C61 C62 C63 C64 0.9(3) . . . . ? C65 O51 C64 C63 15.7(2) . . . . ? C65 O51 C64 C59 -166.34(15) . . . . ? C62 C63 C64 O51 176.23(15) . . . . ? C62 C63 C64 C59 -1.7(2) . . . . ? C60 C59 C64 O51 -176.62(14) . . . . ? N52 C59 C64 O51 -4.2(2) . . . . ? C60 C59 C64 C63 1.5(2) . . . . ? N52 C59 C64 C63 173.96(14) . . . . ? data_2 _database_code_CSD 177523 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H28 F9 N2 O16 S3 Sc1' _chemical_formula_sum 'C21 H28 F9 N2 O16 S3 Sc' _chemical_formula_weight 876.59 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.04780 _cell_length_b 11.35400 _cell_length_c 14.70440 _cell_angle_alpha 89.3120(10) _cell_angle_beta 80.7060(10) _cell_angle_gamma 83.18 _cell_volume 1807.35(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 23643 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 892 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.22 0 -1 0 0.26 0 0 1 0.28 0 0 -1 0.27 0 1 6 0.3 0 -1 -6 0.24 19 -6 1 0.24 -19 6 -1 0.3 13 10 1 0.22 -13 -10 -1 0.24 -4 1 -6 0.3 4 -1 6 0.3 -3 -2 5 0.28 3 2 -5 0.26 -7 3 8 0.23 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.491 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; ? ; _exptl_absorpt_correction_T_min 0.8667 _exptl_absorpt_correction_T_max 0.9082 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(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_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.773886E-1 _diffrn_orient_matrix_ub_12 -0.176726E-1 _diffrn_orient_matrix_ub_13 0.272625E-1 _diffrn_orient_matrix_ub_21 0.49249E-1 _diffrn_orient_matrix_ub_22 -0.108951E-1 _diffrn_orient_matrix_ub_23 -0.632633E-1 _diffrn_orient_matrix_ub_31 0.108402E-1 _diffrn_orient_matrix_ub_32 0.862402E-1 _diffrn_orient_matrix_ub_33 -0.18877E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_unetI/netI 0.0248 _diffrn_reflns_number 30643 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.6 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.908 _diffrn_measured_fraction_theta_max 0.908 _reflns_number_total 7524 _reflns_number_gt 7324 _reflns_threshold_expression >2sigma(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 (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0265P)^2^+0.7760P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 7524 _refine_ls_number_parameters 581 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.4 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # 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' S S 0.1246 0.1234 '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' Sc Sc 0.2519 0.3716 '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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F31 F -0.02570(6) 0.67536(7) 0.29338(7) 0.0512(2) Uani 1 d . . . F32 F 0.07129(6) 0.50099(6) 0.26260(6) 0.04194(17) Uani 1 d . . . F33 F 0.06165(7) 0.57884(8) 0.39659(6) 0.0501(2) Uani 1 d . . . F41 F 0.74462(7) 0.69378(7) 0.19118(6) 0.04551(18) Uani 1 d . . . F42 F 0.86052(8) 0.62085(11) 0.06916(7) 0.0715(3) Uani 1 d . . . F43 F 0.83866(7) 0.51781(8) 0.19270(7) 0.0553(2) Uani 1 d . . . F51 F 0.16250(8) 0.27052(8) 0.48977(5) 0.0494(2) Uani 1 d . . . F52 F 0.04665(6) 0.27364(8) 0.38462(6) 0.0483(2) Uani 1 d . . . F53 F 0.10230(8) 0.11000(7) 0.44852(6) 0.0515(2) Uani 1 d . . . Sc1 Sc 0.430737(14) 0.417759(13) 0.251143(10) 0.01342(3) Uani 1 d . . . O1 O 0.85954(7) 0.23675(7) 0.16045(6) 0.03548(19) Uani 1 d . . . O2 O 0.51359(7) -0.00805(6) 0.18638(5) 0.02629(15) Uani 1 d . . . O10 O 0.49992(6) 0.28059(5) 0.14395(4) 0.01780(13) Uani 1 d . . . O11 O 0.57825(6) 0.28800(6) 0.29044(4) 0.01862(13) Uani 1 d . . . O20 O 0.46522(6) 0.46154(6) 0.38509(4) 0.02031(13) Uani 1 d . . . O21 O 0.34706(7) 0.45652(6) 0.13066(5) 0.02409(15) Uani 1 d . . . O31 O 0.30771(6) 0.57596(6) 0.29355(4) 0.01997(13) Uani 1 d . . . O32 O 0.20196(7) 0.77527(6) 0.31774(6) 0.02960(17) Uani 1 d . . . O33 O 0.22032(8) 0.67604(7) 0.16833(5) 0.03362(18) Uani 1 d . . . O41 O 0.57356(6) 0.51884(6) 0.19340(5) 0.02295(14) Uani 1 d . . . O42 O 0.59847(8) 0.62590(6) 0.04978(5) 0.02806(16) Uani 1 d . . . O43 O 0.70438(7) 0.42636(6) 0.05749(5) 0.02794(16) Uani 1 d . . . O51 O 0.29921(6) 0.30994(6) 0.30796(5) 0.02574(15) Uani 1 d . . . O52 O 0.36825(8) 0.12295(7) 0.37464(6) 0.03698(19) Uani 1 d . . . O53 O 0.23474(8) 0.12873(8) 0.25696(6) 0.03729(19) Uani 1 d . . . S30 S 0.21409(2) 0.667379(19) 0.266484(15) 0.01950(5) Uani 1 d . . . S40 S 0.65211(2) 0.534265(18) 0.104533(14) 0.01690(4) Uani 1 d . . . S50 S 0.27560(2) 0.18657(2) 0.329856(16) 0.02080(5) Uani 1 d . . . N1 N 0.58833(7) 0.20180(6) 0.15620(5) 0.01524(14) Uani 1 d . . . N2 N 0.62989(7) 0.20581(6) 0.23315(5) 0.01579(14) Uani 1 d . . . C2 C 0.63507(8) 0.10897(8) 0.08868(6) 0.01842(17) Uani 1 d . . . C3 C 0.71168(10) 0.13504(9) 0.00879(7) 0.0261(2) Uani 1 d . . . C4 C 0.74865(12) 0.04463(10) -0.05647(7) 0.0338(3) Uani 1 d . . . C5 C 0.70747(11) -0.06526(10) -0.04018(7) 0.0331(2) Uani 1 d . . . C6 C 0.62925(10) -0.08944(9) 0.03998(7) 0.0274(2) Uani 1 d . . . C7 C 0.59090(9) -0.00059(8) 0.10632(6) 0.02036(18) Uani 1 d . . . C8 C 0.46278(11) -0.11740(10) 0.20758(9) 0.0338(2) Uani 1 d . . . C9 C 0.73081(8) 0.12239(8) 0.25461(6) 0.01848(17) Uani 1 d . . . C10 C 0.70430(10) 0.03283(9) 0.31633(7) 0.0272(2) Uani 1 d . . . C11 C 0.80298(12) -0.04166(10) 0.34076(9) 0.0390(3) Uani 1 d . . . C12 C 0.92264(11) -0.02300(10) 0.30472(10) 0.0389(3) Uani 1 d . . . C13 C 0.94788(10) 0.06830(10) 0.24390(9) 0.0325(2) Uani 1 d . . . C14 C 0.85059(9) 0.14364(9) 0.21765(7) 0.0245(2) Uani 1 d . . . C15 C 0.98027(13) 0.25649(15) 0.11509(13) 0.0567(4) Uani 1 d . . . C30 C 0.07187(9) 0.60179(10) 0.30693(8) 0.0307(2) Uani 1 d . . . C40 C 0.78154(10) 0.59562(11) 0.14208(8) 0.0316(2) Uani 1 d . . . C50 C 0.13868(10) 0.21261(10) 0.41836(7) 0.0305(2) Uani 1 d . . . H3 H 0.7394(14) 0.2100(13) 0.0011(10) 0.034(3) Uiso 1 d . . . H4 H 0.7969(14) 0.0603(13) -0.1124(11) 0.040(4) Uiso 1 d . . . H5 H 0.7297(16) -0.1260(15) -0.0849(12) 0.050(4) Uiso 1 d . . . H6 H 0.6009(14) -0.1630(14) 0.0506(10) 0.037(4) Uiso 1 d . . . H8B H 0.4203(16) -0.1389(15) 0.1603(12) 0.047(4) Uiso 1 d . . . H8A H 0.4030(16) -0.0973(15) 0.2621(12) 0.047(4) Uiso 1 d . . . H8C H 0.5252(13) -0.1769(13) 0.2174(10) 0.033(3) Uiso 1 d . . . H10 H 0.6164(14) 0.0257(13) 0.3396(10) 0.037(4) Uiso 1 d . . . H11 H 0.7928(16) -0.1072(16) 0.3805(12) 0.051(4) Uiso 1 d . . . H12 H 0.9894(15) -0.0756(14) 0.3240(11) 0.043(4) Uiso 1 d . . . H13 H 1.0318(15) 0.0816(14) 0.2219(11) 0.041(4) Uiso 1 d . . . H15A H 1.0151(18) 0.1841(17) 0.0824(13) 0.059(5) Uiso 1 d . . . H15B H 0.962(2) 0.3152(19) 0.0728(15) 0.073(6) Uiso 1 d . . . H15C H 1.032(2) 0.2741(18) 0.1615(14) 0.069(6) Uiso 1 d . . . H20A H 0.4335(14) 0.5198(14) 0.4170(11) 0.039(4) Uiso 1 d . . . H20B H 0.5145(14) 0.4195(13) 0.4152(10) 0.034(3) Uiso 1 d . . . H21B H 0.3728(15) 0.4211(14) 0.0806(11) 0.041(4) Uiso 1 d . . . H21A H 0.3091(15) 0.5232(15) 0.1237(11) 0.045(4) Uiso 1 d . . . O62 O 0.38265(6) 0.65294(6) 0.50226(4) 0.02035(13) Uani 1 d . . . C60 C 0.55247(12) 0.74556(13) 0.42215(10) 0.0435(3) Uani 1 d . . . C61 C 0.42080(11) 0.76539(9) 0.46958(8) 0.0307(2) Uani 1 d . . . C63 C 0.25340(9) 0.66510(10) 0.54321(7) 0.0271(2) Uani 1 d . . . C64 C 0.22086(12) 0.54623(14) 0.57635(12) 0.0488(4) Uani 1 d . . . H60A H 0.6065(17) 0.7085(15) 0.4607(12) 0.052(5) Uiso 1 d . . . H60B H 0.5801(19) 0.8185(19) 0.3971(14) 0.068(6) Uiso 1 d . . . H60C H 0.564(2) 0.6921(19) 0.3709(15) 0.073(6) Uiso 1 d . . . H61A H 0.3688(14) 0.7996(13) 0.4288(10) 0.037(4) Uiso 1 d . . . H61B H 0.4077(16) 0.8214(16) 0.5186(12) 0.051(4) Uiso 1 d . . . H63A H 0.2057(13) 0.6970(13) 0.5001(10) 0.033(3) Uiso 1 d . . . H63B H 0.2400(13) 0.7239(13) 0.5904(10) 0.033(3) Uiso 1 d . . . H64A H 0.2661(19) 0.5129(18) 0.6174(14) 0.064(5) Uiso 1 d . . . H64B H 0.237(2) 0.490(2) 0.5298(16) 0.077(6) Uiso 1 d . . . H64C H 0.1382(19) 0.5521(17) 0.6009(13) 0.064(5) Uiso 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 F31 0.0208(3) 0.0445(4) 0.0892(6) -0.0147(4) -0.0199(3) 0.0092(3) F32 0.0321(3) 0.0297(3) 0.0677(5) -0.0104(3) -0.0167(3) -0.0060(3) F33 0.0369(4) 0.0724(5) 0.0405(4) 0.0025(4) 0.0052(3) -0.0204(4) F41 0.0462(4) 0.0396(4) 0.0561(4) -0.0150(3) -0.0161(3) -0.0148(3) F42 0.0507(4) 0.1098(7) 0.0563(5) -0.0078(5) 0.0167(4) -0.0522(5) F43 0.0410(4) 0.0591(5) 0.0733(5) -0.0043(4) -0.0370(4) 0.0025(4) F51 0.0521(4) 0.0657(5) 0.0283(3) -0.0157(3) 0.0071(3) -0.0153(4) F52 0.0217(3) 0.0627(5) 0.0549(4) 0.0056(4) 0.0040(3) 0.0032(3) F53 0.0528(4) 0.0543(4) 0.0470(4) 0.0142(3) 0.0078(3) -0.0279(4) Sc1 0.01308(7) 0.01466(7) 0.01213(7) -0.00053(5) -0.00243(5) 0.00060(5) O1 0.0208(3) 0.0342(4) 0.0480(5) 0.0117(3) 0.0020(3) -0.0004(3) O2 0.0291(3) 0.0223(3) 0.0271(3) -0.0017(3) 0.0004(3) -0.0083(3) O10 0.0181(3) 0.0167(3) 0.0182(3) -0.0019(2) -0.0058(2) 0.0037(2) O11 0.0198(3) 0.0185(3) 0.0165(3) -0.0052(2) -0.0046(2) 0.0048(2) O20 0.0229(3) 0.0222(3) 0.0149(3) -0.0046(2) -0.0069(2) 0.0064(2) O21 0.0303(3) 0.0245(3) 0.0165(3) -0.0030(2) -0.0095(3) 0.0092(3) O31 0.0177(3) 0.0209(3) 0.0203(3) -0.0021(2) -0.0048(2) 0.0048(2) O32 0.0290(3) 0.0192(3) 0.0403(4) -0.0071(3) -0.0083(3) 0.0030(3) O33 0.0440(4) 0.0296(4) 0.0244(3) 0.0039(3) -0.0084(3) 0.0112(3) O41 0.0239(3) 0.0270(3) 0.0181(3) -0.0001(2) 0.0004(2) -0.0086(3) O42 0.0455(4) 0.0192(3) 0.0200(3) 0.0016(2) -0.0105(3) 0.0008(3) O43 0.0343(4) 0.0204(3) 0.0266(3) -0.0033(3) -0.0008(3) 0.0020(3) O51 0.0194(3) 0.0258(3) 0.0311(4) 0.0041(3) 0.0004(3) -0.0056(3) O52 0.0308(4) 0.0340(4) 0.0468(5) 0.0073(3) -0.0119(3) 0.0006(3) O53 0.0325(4) 0.0486(5) 0.0320(4) -0.0153(3) -0.0022(3) -0.0125(3) S30 0.01858(9) 0.01667(9) 0.02259(10) -0.00115(8) -0.00517(8) 0.00323(8) S40 0.02021(9) 0.01586(9) 0.01460(9) 0.00078(7) -0.00225(7) -0.00276(7) S50 0.01791(9) 0.02340(10) 0.02122(10) -0.00116(8) -0.00190(8) -0.00456(8) N1 0.0157(3) 0.0139(3) 0.0156(3) -0.0007(2) -0.0027(3) 0.0002(3) N2 0.0161(3) 0.0147(3) 0.0163(3) -0.0019(3) -0.0035(3) 0.0010(3) C2 0.0203(4) 0.0167(4) 0.0174(4) -0.0046(3) -0.0042(3) 0.0035(3) C3 0.0305(5) 0.0237(4) 0.0214(4) -0.0007(4) 0.0003(4) 0.0018(4) C4 0.0418(6) 0.0333(5) 0.0205(5) -0.0038(4) 0.0041(4) 0.0079(5) C5 0.0451(6) 0.0266(5) 0.0242(5) -0.0109(4) -0.0073(4) 0.0128(4) C6 0.0379(5) 0.0167(4) 0.0289(5) -0.0044(4) -0.0127(4) 0.0025(4) C7 0.0229(4) 0.0181(4) 0.0207(4) -0.0017(3) -0.0075(3) 0.0008(3) C8 0.0394(6) 0.0244(5) 0.0400(6) 0.0063(4) -0.0079(5) -0.0117(4) C9 0.0184(4) 0.0159(4) 0.0217(4) -0.0029(3) -0.0085(3) 0.0033(3) C10 0.0285(5) 0.0223(4) 0.0330(5) 0.0052(4) -0.0124(4) -0.0028(4) C11 0.0427(6) 0.0255(5) 0.0535(7) 0.0136(5) -0.0243(5) -0.0018(4) C12 0.0346(5) 0.0269(5) 0.0589(7) -0.0003(5) -0.0273(5) 0.0083(4) C13 0.0203(4) 0.0289(5) 0.0486(6) -0.0067(4) -0.0119(4) 0.0047(4) C14 0.0198(4) 0.0216(4) 0.0313(5) -0.0032(4) -0.0050(4) 0.0019(3) C15 0.0279(6) 0.0562(8) 0.0774(10) 0.0171(8) 0.0145(7) -0.0032(6) C30 0.0187(4) 0.0305(5) 0.0434(6) -0.0065(4) -0.0085(4) 0.0005(4) C40 0.0237(4) 0.0402(6) 0.0319(5) -0.0025(4) -0.0026(4) -0.0106(4) C50 0.0274(5) 0.0376(5) 0.0258(5) 0.0009(4) 0.0025(4) -0.0105(4) O62 0.0201(3) 0.0222(3) 0.0186(3) -0.0013(2) -0.0037(2) -0.0009(2) C60 0.0369(6) 0.0460(6) 0.0513(7) 0.0186(6) -0.0096(5) -0.0181(5) C61 0.0395(5) 0.0227(4) 0.0318(5) 0.0033(4) -0.0099(4) -0.0065(4) C63 0.0189(4) 0.0360(5) 0.0247(4) -0.0050(4) -0.0038(4) 0.0042(4) C64 0.0229(5) 0.0534(8) 0.0660(9) 0.0189(7) 0.0039(6) -0.0039(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F31 C30 1.3233(13) . ? F32 C30 1.3251(13) . ? F33 C30 1.3302(15) . ? F41 C40 1.3214(14) . ? F42 C40 1.3202(14) . ? F43 C40 1.3177(15) . ? F51 C50 1.3234(14) . ? F52 C50 1.3219(14) . ? F53 C50 1.3254(14) . ? Sc1 O51 2.0769(7) . ? Sc1 O41 2.1217(7) . ? Sc1 O20 2.1407(7) . ? Sc1 O21 2.1449(7) . ? Sc1 O31 2.1532(6) . ? Sc1 O11 2.2078(6) . ? Sc1 O10 2.2093(6) . ? O1 C14 1.3459(13) . ? O1 C15 1.4333(15) . ? O2 C7 1.3464(11) . ? O2 C8 1.4330(13) . ? O10 N1 1.2777(9) . ? O11 N2 1.2819(9) . ? O31 S30 1.4744(6) . ? O32 S30 1.4273(7) . ? O33 S30 1.4365(8) . ? O41 S40 1.4682(7) . ? O42 S40 1.4386(7) . ? O43 S40 1.4271(7) . ? O51 S50 1.4774(7) . ? O52 S50 1.4262(9) . ? O53 S50 1.4239(8) . ? S30 C30 1.8282(11) . ? S40 C40 1.8263(11) . ? S50 C50 1.8265(11) . ? N1 N2 1.2912(10) . ? N1 C2 1.4469(11) . ? N2 C9 1.4476(11) . ? C2 C3 1.3835(13) . ? C2 C7 1.3957(13) . ? C3 C4 1.3925(14) . ? C4 C5 1.3833(17) . ? C5 C6 1.3895(16) . ? C6 C7 1.3919(13) . ? C9 C10 1.3806(14) . ? C9 C14 1.3947(13) . ? C10 C11 1.3904(15) . ? C11 C12 1.3823(18) . ? C12 C13 1.3849(18) . ? C13 C14 1.3942(14) . ? O62 C61 1.4443(12) . ? O62 C63 1.4485(12) . ? C60 C61 1.5004(17) . ? C63 C64 1.4937(18) . ? 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 O51 Sc1 O41 176.46(3) . . ? O51 Sc1 O20 91.19(3) . . ? O41 Sc1 O20 88.54(3) . . ? O51 Sc1 O21 93.81(3) . . ? O41 Sc1 O21 88.07(3) . . ? O20 Sc1 O21 152.18(3) . . ? O51 Sc1 O31 91.74(3) . . ? O41 Sc1 O31 91.58(3) . . ? O20 Sc1 O31 74.18(3) . . ? O21 Sc1 O31 78.32(3) . . ? O51 Sc1 O11 90.04(3) . . ? O41 Sc1 O11 86.54(3) . . ? O20 Sc1 O11 70.49(2) . . ? O21 Sc1 O11 136.77(3) . . ? O31 Sc1 O11 144.65(2) . . ? O51 Sc1 O10 88.54(3) . . ? O41 Sc1 O10 89.30(3) . . ? O20 Sc1 O10 137.97(2) . . ? O21 Sc1 O10 69.59(2) . . ? O31 Sc1 O10 147.85(2) . . ? O11 Sc1 O10 67.48(2) . . ? C14 O1 C15 117.72(10) . . ? C7 O2 C8 118.32(8) . . ? N1 O10 Sc1 119.30(5) . . ? N2 O11 Sc1 119.13(5) . . ? S30 O31 Sc1 145.51(4) . . ? S40 O41 Sc1 139.22(4) . . ? S50 O51 Sc1 144.98(4) . . ? O32 S30 O33 117.57(5) . . ? O32 S30 O31 113.21(4) . . ? O33 S30 O31 112.77(4) . . ? O32 S30 C30 104.93(5) . . ? O33 S30 C30 104.96(5) . . ? O31 S30 C30 101.25(5) . . ? O43 S40 O42 116.26(4) . . ? O43 S40 O41 114.70(4) . . ? O42 S40 O41 112.52(4) . . ? O43 S40 C40 105.40(5) . . ? O42 S40 C40 104.96(5) . . ? O41 S40 C40 100.94(5) . . ? O53 S50 O52 118.07(5) . . ? O53 S50 O51 113.09(5) . . ? O52 S50 O51 112.92(5) . . ? O53 S50 C50 104.50(5) . . ? O52 S50 C50 105.45(5) . . ? O51 S50 C50 100.41(5) . . ? O10 N1 N2 116.95(7) . . ? O10 N1 C2 121.23(7) . . ? N2 N1 C2 121.75(7) . . ? O11 N2 N1 117.06(7) . . ? O11 N2 C9 120.79(7) . . ? N1 N2 C9 122.16(7) . . ? C3 C2 C7 124.06(8) . . ? C3 C2 N1 119.35(8) . . ? C7 C2 N1 116.40(8) . . ? C2 C3 C4 117.27(10) . . ? C5 C4 C3 119.81(10) . . ? C4 C5 C6 122.14(9) . . ? C5 C6 C7 119.20(9) . . ? O2 C7 C6 126.89(9) . . ? O2 C7 C2 115.60(8) . . ? C6 C7 C2 117.50(9) . . ? C10 C9 C14 123.60(9) . . ? C10 C9 N2 118.57(8) . . ? C14 C9 N2 117.59(8) . . ? C9 C10 C11 117.74(10) . . ? C12 C11 C10 119.84(11) . . ? C11 C12 C13 121.77(10) . . ? C12 C13 C14 119.55(10) . . ? O1 C14 C13 126.81(9) . . ? O1 C14 C9 115.71(8) . . ? C13 C14 C9 117.48(9) . . ? F31 C30 F32 108.75(9) . . ? F31 C30 F33 108.16(9) . . ? F32 C30 F33 108.20(10) . . ? F31 C30 S30 110.50(8) . . ? F32 C30 S30 110.57(7) . . ? F33 C30 S30 110.58(8) . . ? F43 C40 F42 108.82(10) . . ? F43 C40 F41 108.46(10) . . ? F42 C40 F41 108.34(10) . . ? F43 C40 S40 110.14(8) . . ? F42 C40 S40 109.35(8) . . ? F41 C40 S40 111.67(8) . . ? F52 C50 F51 109.33(10) . . ? F52 C50 F53 107.99(9) . . ? F51 C50 F53 107.74(9) . . ? F52 C50 S50 110.71(7) . . ? F51 C50 S50 111.01(8) . . ? F53 C50 S50 109.96(8) . . ? C61 O62 C63 111.43(8) . . ? O62 C61 C60 108.85(9) . . ? O62 C63 C64 108.51(9) . . ? 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 O51 Sc1 O10 N1 -92.89(6) . . . . ? O41 Sc1 O10 N1 84.30(6) . . . . ? O20 Sc1 O10 N1 -2.74(8) . . . . ? O21 Sc1 O10 N1 172.50(6) . . . . ? O31 Sc1 O10 N1 176.16(5) . . . . ? O11 Sc1 O10 N1 -2.24(5) . . . . ? O51 Sc1 O11 N2 90.83(6) . . . . ? O41 Sc1 O11 N2 -88.25(6) . . . . ? O20 Sc1 O11 N2 -177.92(7) . . . . ? O21 Sc1 O11 N2 -4.78(8) . . . . ? O31 Sc1 O11 N2 -176.10(5) . . . . ? O10 Sc1 O11 N2 2.43(6) . . . . ? O51 Sc1 O31 S30 -92.71(8) . . . . ? O41 Sc1 O31 S30 88.51(8) . . . . ? O20 Sc1 O31 S30 176.54(8) . . . . ? O21 Sc1 O31 S30 0.81(7) . . . . ? O11 Sc1 O31 S30 174.75(6) . . . . ? O10 Sc1 O31 S30 -2.69(11) . . . . ? O51 Sc1 O41 S40 77.7(5) . . . . ? O20 Sc1 O41 S40 163.34(7) . . . . ? O21 Sc1 O41 S40 -44.28(7) . . . . ? O31 Sc1 O41 S40 -122.53(7) . . . . ? O11 Sc1 O41 S40 92.81(7) . . . . ? O10 Sc1 O41 S40 25.33(7) . . . . ? O41 Sc1 O51 S50 -13.4(5) . . . . ? O20 Sc1 O51 S50 -98.90(9) . . . . ? O21 Sc1 O51 S50 108.49(9) . . . . ? O31 Sc1 O51 S50 -173.11(8) . . . . ? O11 Sc1 O51 S50 -28.42(9) . . . . ? O10 Sc1 O51 S50 39.06(8) . . . . ? Sc1 O31 S30 O32 -157.18(7) . . . . ? Sc1 O31 S30 O33 -20.61(9) . . . . ? Sc1 O31 S30 C30 91.04(8) . . . . ? Sc1 O41 S40 O43 -45.07(8) . . . . ? Sc1 O41 S40 O42 90.80(7) . . . . ? Sc1 O41 S40 C40 -157.81(7) . . . . ? Sc1 O51 S50 O53 -89.75(9) . . . . ? Sc1 O51 S50 O52 47.62(10) . . . . ? Sc1 O51 S50 C50 159.45(8) . . . . ? Sc1 O10 N1 N2 1.88(9) . . . . ? Sc1 O10 N1 C2 178.83(6) . . . . ? Sc1 O11 N2 N1 -2.47(10) . . . . ? Sc1 O11 N2 C9 177.12(6) . . . . ? O10 N1 N2 O11 0.38(11) . . . . ? C2 N1 N2 O11 -176.55(7) . . . . ? O10 N1 N2 C9 -179.21(7) . . . . ? C2 N1 N2 C9 3.86(12) . . . . ? O10 N1 C2 C3 76.76(11) . . . . ? N2 N1 C2 C3 -106.44(10) . . . . ? O10 N1 C2 C7 -98.45(10) . . . . ? N2 N1 C2 C7 78.35(11) . . . . ? C7 C2 C3 C4 -1.62(16) . . . . ? N1 C2 C3 C4 -176.44(9) . . . . ? C2 C3 C4 C5 0.72(17) . . . . ? C3 C4 C5 C6 0.08(18) . . . . ? C4 C5 C6 C7 -0.07(17) . . . . ? C8 O2 C7 C6 -0.54(15) . . . . ? C8 O2 C7 C2 178.60(9) . . . . ? C5 C6 C7 O2 178.39(10) . . . . ? C5 C6 C7 C2 -0.73(15) . . . . ? C3 C2 C7 O2 -177.59(9) . . . . ? N1 C2 C7 O2 -2.64(12) . . . . ? C3 C2 C7 C6 1.63(14) . . . . ? N1 C2 C7 C6 176.59(8) . . . . ? O11 N2 C9 C10 75.75(11) . . . . ? N1 N2 C9 C10 -104.68(10) . . . . ? O11 N2 C9 C14 -98.76(10) . . . . ? N1 N2 C9 C14 80.82(11) . . . . ? C14 C9 C10 C11 -1.69(16) . . . . ? N2 C9 C10 C11 -175.84(10) . . . . ? C9 C10 C11 C12 1.24(18) . . . . ? C10 C11 C12 C13 -0.3(2) . . . . ? C11 C12 C13 C14 -0.22(19) . . . . ? C15 O1 C14 C13 5.54(18) . . . . ? C15 O1 C14 C9 -175.18(12) . . . . ? C12 C13 C14 O1 179.12(11) . . . . ? C12 C13 C14 C9 -0.15(16) . . . . ? C10 C9 C14 O1 -178.21(9) . . . . ? N2 C9 C14 O1 -4.01(13) . . . . ? C10 C9 C14 C13 1.14(15) . . . . ? N2 C9 C14 C13 175.34(9) . . . . ? O32 S30 C30 F31 58.40(9) . . . . ? O33 S30 C30 F31 -66.14(9) . . . . ? O31 S30 C30 F31 176.37(8) . . . . ? O32 S30 C30 F32 178.86(8) . . . . ? O33 S30 C30 F32 54.32(9) . . . . ? O31 S30 C30 F32 -63.18(9) . . . . ? O32 S30 C30 F33 -61.32(9) . . . . ? O33 S30 C30 F33 174.14(7) . . . . ? O31 S30 C30 F33 56.64(8) . . . . ? O43 S40 C40 F43 -56.20(9) . . . . ? O42 S40 C40 F43 -179.47(8) . . . . ? O41 S40 C40 F43 63.44(8) . . . . ? O43 S40 C40 F42 63.33(10) . . . . ? O42 S40 C40 F42 -59.93(10) . . . . ? O41 S40 C40 F42 -177.03(9) . . . . ? O43 S40 C40 F41 -176.78(8) . . . . ? O42 S40 C40 F41 59.96(9) . . . . ? O41 S40 C40 F41 -57.14(9) . . . . ? O53 S50 C50 F52 -56.07(9) . . . . ? O52 S50 C50 F52 178.77(8) . . . . ? O51 S50 C50 F52 61.28(9) . . . . ? O53 S50 C50 F51 -177.69(8) . . . . ? O52 S50 C50 F51 57.15(9) . . . . ? O51 S50 C50 F51 -60.34(9) . . . . ? O53 S50 C50 F53 63.18(9) . . . . ? O52 S50 C50 F53 -61.98(9) . . . . ? O51 S50 C50 F53 -179.47(8) . . . . ? C63 O62 C61 C60 -176.05(9) . . . . ? C61 O62 C63 C64 -179.33(10) . . . . ? 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 O20 H20A O62 0.825(16) 1.947(16) 2.7632(9) 170.5(16) . O20 H20B O62 0.855(15) 1.908(16) 2.7544(9) 170.1(14) 2_666 O21 H21B O42 0.835(16) 1.961(17) 2.7727(10) 163.6(15) 2_665 O21 H21B S40 0.835(16) 2.813(16) 3.4572(7) 135.3(13) 2_665 O21 H21A O33 0.835(17) 1.954(17) 2.7265(10) 153.5(16) . O21 H21A S30 0.835(17) 2.674(16) 3.1954(7) 122.0(13) .