# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/166 data_p12499 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H15 N3 O9 .C2 H6 S O' _chemical_formula_sum 'C29 H21 N3 O10 S' _chemical_formula_weight 603.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.8116(2) _cell_length_b 12.1494(2) _cell_length_c 18.2432(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.197(1) _cell_angle_gamma 90.00 _cell_volume 2712.67(7) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 6667 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.35 _exptl_crystal_description octagonal _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.186 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9394 _exptl_absorpt_correction_T_max 0.9853 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'long-fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49620 _diffrn_reflns_av_R_equivalents 0.05 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 26.39 _reflns_number_total 5548 _reflns_number_gt 4026 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 1999)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1999)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0435P)^2^+0.5600P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5548 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0845 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.61637(10) 0.38386(9) 1.03665(7) 0.0369(3) Uani 1 1 d . . . O2 O 0.54582(10) 0.85632(10) 0.93833(8) 0.0494(4) Uani 1 1 d . . . O3 O 0.96379(10) 0.73183(10) 1.19929(7) 0.0423(3) Uani 1 1 d . . . O4 O 0.38722(12) 0.23397(13) 0.65915(8) 0.0636(4) Uani 1 1 d . . . O5 O 0.49847(12) 0.34333(13) 0.62728(8) 0.0600(4) Uani 1 1 d . . . O6 O 0.83642(10) 1.33932(9) 0.97724(8) 0.0441(3) Uani 1 1 d . . . O7 O 0.97371(10) 1.24781(10) 0.96369(8) 0.0451(3) Uani 1 1 d . . . O8 O 1.27459(13) 0.25783(12) 1.29247(8) 0.0625(4) Uani 1 1 d . . . O9 O 1.26549(13) 0.24425(13) 1.17339(9) 0.0658(5) Uani 1 1 d . . . N1 N 0.45899(13) 0.30377(14) 0.67465(9) 0.0446(4) Uani 1 1 d . . . N2 N 0.88126(11) 1.25287(11) 0.96998(8) 0.0327(3) Uani 1 1 d . . . N3 N 1.24038(12) 0.28777(12) 1.22598(9) 0.0392(4) Uani 1 1 d . . . C1 C 0.62632(12) 0.44483(12) 0.98628(10) 0.0278(4) Uani 1 1 d . . . C2 C 0.58008(12) 0.41317(12) 0.90366(9) 0.0284(4) Uani 1 1 d . . . C3 C 0.50680(13) 0.32530(13) 0.88529(10) 0.0321(4) Uani 1 1 d . . . H3 H 0.4846 0.2903 0.9242 0.039 Uiso 1 1 calc R . . C4 C 0.46657(14) 0.28930(14) 0.81037(10) 0.0362(4) Uani 1 1 d . . . H4 H 0.4169 0.2304 0.7977 0.043 Uiso 1 1 calc R . . C5 C 0.50098(13) 0.34186(14) 0.75465(10) 0.0351(4) Uani 1 1 d . . . C6 C 0.57418(14) 0.42840(15) 0.77074(10) 0.0395(4) Uani 1 1 d . . . H6 H 0.5967 0.4624 0.7317 0.047 Uiso 1 1 calc R . . C7 C 0.61339(14) 0.46347(14) 0.84593(10) 0.0358(4) Uani 1 1 d . . . H7 H 0.6633 0.5222 0.8582 0.043 Uiso 1 1 calc R . . C8 C 0.68719(12) 0.55106(12) 1.00739(9) 0.0265(3) Uani 1 1 d . . . C9 C 0.64478(13) 0.64981(12) 0.97350(9) 0.0279(4) Uani 1 1 d . . . H9 H 0.5790 0.6505 0.9333 0.033 Uiso 1 1 calc R . . C10 C 0.69960(12) 0.74848(12) 0.99893(9) 0.0265(3) Uani 1 1 d . . . C11 C 0.79764(12) 0.74676(12) 1.05746(9) 0.0273(3) Uani 1 1 d . . . H11 H 0.8349 0.8130 1.0744 0.033 Uiso 1 1 calc R . . C12 C 0.84156(12) 0.64739(12) 1.09152(9) 0.0263(3) Uani 1 1 d . . . C13 C 0.78547(12) 0.54994(13) 1.06686(9) 0.0276(4) Uani 1 1 d . . . H13 H 0.8137 0.4830 1.0902 0.033 Uiso 1 1 calc R . . C14 C 0.64450(13) 0.85344(13) 0.96651(10) 0.0311(4) Uani 1 1 d . . . C15 C 0.71034(12) 0.95592(12) 0.96910(9) 0.0277(4) Uani 1 1 d . . . C16 C 0.66673(13) 1.05531(13) 0.98424(10) 0.0318(4) Uani 1 1 d . . . H16 H 0.5983 1.0562 0.9934 0.038 Uiso 1 1 calc R . . C17 C 0.72314(13) 1.15245(13) 0.98595(10) 0.0317(4) Uani 1 1 d . . . H17 H 0.6953 1.2193 0.9982 0.038 Uiso 1 1 calc R . . C18 C 0.82164(13) 1.14912(12) 0.96928(9) 0.0272(3) Uani 1 1 d . . . C19 C 0.86640(13) 1.05231(13) 0.95280(9) 0.0300(4) Uani 1 1 d . . . H19 H 0.9332 1.0525 0.9412 0.036 Uiso 1 1 calc R . . C20 C 0.81086(13) 0.95497(13) 0.95372(9) 0.0304(4) Uani 1 1 d . . . H20 H 0.8409 0.8879 0.9440 0.037 Uiso 1 1 calc R . . C21 C 0.94388(13) 0.65150(13) 1.15795(9) 0.0297(4) Uani 1 1 d . . . C22 C 1.01927(12) 0.55416(13) 1.17413(9) 0.0275(4) Uani 1 1 d . . . C23 C 1.07568(13) 0.52976(14) 1.25013(10) 0.0344(4) Uani 1 1 d . . . H23 H 1.0655 0.5736 1.2899 0.041 Uiso 1 1 calc R . . C24 C 1.14663(14) 0.44112(14) 1.26726(10) 0.0359(4) Uani 1 1 d . . . H24 H 1.1826 0.4222 1.3185 0.043 Uiso 1 1 calc R . . C25 C 1.16333(13) 0.38124(13) 1.20759(10) 0.0308(4) Uani 1 1 d . . . C26 C 1.11071(13) 0.40462(14) 1.13158(10) 0.0333(4) Uani 1 1 d . . . H26 H 1.1245 0.3632 1.0920 0.040 Uiso 1 1 calc R . . C27 C 1.03690(13) 0.49100(14) 1.11548(10) 0.0320(4) Uani 1 1 d . . . H27 H 0.9983 0.5071 1.0642 0.038 Uiso 1 1 calc R . . S1 S 0.76220(4) 0.97316(4) 0.18085(3) 0.04290(19) Uani 0.9195(18) 1 d P A 1 S1' S 0.6866(7) 0.9694(8) 0.2156(6) 0.080(3) Uani 0.0805(18) 1 d P A 2 C1S C 0.69131(18) 1.0870(2) 0.20437(15) 0.0695(7) Uani 1 1 d . . . H1SA H 0.6535 1.1266 0.1579 0.104 Uiso 1 1 calc R A 1 H1SB H 0.7430 1.1359 0.2389 0.104 Uiso 1 1 calc R A 1 H1SC H 0.6387 1.0609 0.2292 0.104 Uiso 1 1 calc R A 1 C2S C 0.81998(19) 0.92001(19) 0.27457(12) 0.0603(6) Uani 1 1 d . . . H2SA H 0.8634 0.8554 0.2722 0.090 Uiso 1 1 calc R A 1 H2SB H 0.7620 0.9000 0.2963 0.090 Uiso 1 1 calc R A 1 H2SC H 0.8662 0.9755 0.3065 0.090 Uiso 1 1 calc R A 1 O1S O 0.67591(13) 0.89409(12) 0.13948(9) 0.0633(4) Uani 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 0.0457(7) 0.0309(6) 0.0344(7) 0.0009(5) 0.0122(6) -0.0097(5) O2 0.0276(7) 0.0324(7) 0.0763(10) 0.0043(6) -0.0029(6) 0.0005(5) O3 0.0434(7) 0.0335(7) 0.0407(8) -0.0100(6) -0.0020(6) 0.0015(6) O4 0.0571(9) 0.0785(11) 0.0493(9) -0.0273(8) 0.0067(7) -0.0200(8) O5 0.0657(10) 0.0796(11) 0.0350(8) -0.0079(7) 0.0153(7) -0.0007(8) O6 0.0510(8) 0.0253(6) 0.0578(9) -0.0010(6) 0.0190(7) -0.0019(6) O7 0.0359(7) 0.0445(8) 0.0582(9) 0.0060(6) 0.0188(6) -0.0067(6) O8 0.0712(10) 0.0665(10) 0.0455(9) 0.0137(7) 0.0104(8) 0.0332(8) O9 0.0724(10) 0.0698(10) 0.0499(9) -0.0119(8) 0.0097(8) 0.0351(9) N1 0.0391(9) 0.0527(10) 0.0386(10) -0.0113(8) 0.0063(8) 0.0062(8) N2 0.0347(8) 0.0324(8) 0.0287(8) 0.0023(6) 0.0061(6) -0.0046(6) N3 0.0337(8) 0.0382(9) 0.0417(10) -0.0016(7) 0.0047(7) 0.0060(7) C1 0.0260(8) 0.0240(8) 0.0337(10) -0.0009(7) 0.0093(7) 0.0001(6) C2 0.0260(8) 0.0248(8) 0.0334(10) -0.0027(7) 0.0075(7) -0.0020(7) C3 0.0320(9) 0.0288(9) 0.0353(10) -0.0014(7) 0.0095(7) -0.0041(7) C4 0.0332(9) 0.0318(9) 0.0403(11) -0.0081(8) 0.0058(8) -0.0050(7) C5 0.0317(9) 0.0404(10) 0.0301(10) -0.0079(8) 0.0044(7) 0.0030(8) C6 0.0418(10) 0.0453(11) 0.0329(11) -0.0010(8) 0.0135(8) -0.0057(8) C7 0.0359(9) 0.0352(9) 0.0358(10) -0.0054(8) 0.0096(8) -0.0098(8) C8 0.0272(8) 0.0240(8) 0.0290(9) -0.0026(7) 0.0096(7) -0.0019(6) C9 0.0258(8) 0.0276(8) 0.0292(9) -0.0009(7) 0.0066(7) -0.0003(7) C10 0.0264(8) 0.0239(8) 0.0294(9) 0.0007(7) 0.0087(7) 0.0001(6) C11 0.0296(8) 0.0234(8) 0.0292(9) -0.0026(7) 0.0091(7) -0.0036(7) C12 0.0271(8) 0.0262(8) 0.0255(9) -0.0004(6) 0.0074(7) -0.0007(7) C13 0.0302(8) 0.0244(8) 0.0278(9) 0.0018(7) 0.0080(7) 0.0007(7) C14 0.0300(9) 0.0268(8) 0.0340(10) -0.0003(7) 0.0056(7) 0.0008(7) C15 0.0275(8) 0.0257(8) 0.0268(9) 0.0024(7) 0.0031(7) 0.0015(7) C16 0.0286(9) 0.0287(9) 0.0388(10) 0.0041(7) 0.0111(8) 0.0017(7) C17 0.0350(9) 0.0246(8) 0.0357(10) 0.0018(7) 0.0109(7) 0.0031(7) C18 0.0280(8) 0.0258(8) 0.0246(9) 0.0030(6) 0.0031(7) -0.0028(7) C19 0.0267(8) 0.0326(9) 0.0301(9) 0.0032(7) 0.0074(7) 0.0014(7) C20 0.0313(9) 0.0261(8) 0.0326(10) -0.0010(7) 0.0075(7) 0.0050(7) C21 0.0310(9) 0.0280(8) 0.0296(9) 0.0001(7) 0.0079(7) -0.0030(7) C22 0.0241(8) 0.0273(8) 0.0293(9) -0.0006(7) 0.0050(7) -0.0041(6) C23 0.0339(9) 0.0369(9) 0.0286(9) -0.0070(8) 0.0033(7) 0.0022(8) C24 0.0342(9) 0.0408(10) 0.0272(9) -0.0002(8) 0.0005(7) 0.0037(8) C25 0.0258(8) 0.0287(8) 0.0353(10) 0.0000(7) 0.0050(7) -0.0007(7) C26 0.0334(9) 0.0365(9) 0.0303(10) -0.0031(7) 0.0101(8) 0.0006(7) C27 0.0315(9) 0.0368(9) 0.0262(9) 0.0020(7) 0.0061(7) -0.0003(7) S1 0.0451(3) 0.0465(3) 0.0435(3) -0.0074(2) 0.0229(2) -0.0081(2) S1' 0.070(6) 0.081(6) 0.100(7) -0.005(5) 0.042(5) -0.016(4) C1S 0.0515(13) 0.0655(16) 0.0844(18) -0.0279(13) 0.0092(12) 0.0040(12) C2S 0.0700(15) 0.0580(13) 0.0537(14) -0.0027(11) 0.0195(12) -0.0070(12) O1S 0.0743(10) 0.0627(9) 0.0553(9) -0.0218(8) 0.0227(8) -0.0246(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2161(19) . ? O2 C14 1.2163(19) . ? O3 C21 1.2135(19) . ? O4 N1 1.221(2) . ? O5 N1 1.221(2) . ? O6 N2 1.2229(18) . ? O7 N2 1.2248(18) . ? O8 N3 1.2170(19) . ? O9 N3 1.219(2) . ? N1 C5 1.473(2) . ? N2 C18 1.472(2) . ? N3 C25 1.477(2) . ? C1 C2 1.498(2) . ? C1 C8 1.498(2) . ? C2 C7 1.389(2) . ? C2 C3 1.395(2) . ? C3 C4 1.382(2) . ? C4 C5 1.379(3) . ? C5 C6 1.381(2) . ? C6 C7 1.381(2) . ? C8 C9 1.385(2) . ? C8 C13 1.398(2) . ? C9 C10 1.397(2) . ? C10 C11 1.388(2) . ? C10 C14 1.493(2) . ? C11 C12 1.398(2) . ? C12 C13 1.389(2) . ? C12 C21 1.500(2) . ? C14 C15 1.497(2) . ? C15 C16 1.392(2) . ? C15 C20 1.397(2) . ? C16 C17 1.379(2) . ? C17 C18 1.383(2) . ? C18 C19 1.380(2) . ? C19 C20 1.383(2) . ? C21 C22 1.500(2) . ? C22 C27 1.388(2) . ? C22 C23 1.393(2) . ? C23 C24 1.384(2) . ? C24 C25 1.378(2) . ? C25 C26 1.380(2) . ? C26 C27 1.385(2) . ? S1 O1S 1.4903(15) . ? S1 C2S 1.772(2) . ? S1 C1S 1.776(2) . ? S1' C1S 1.448(9) . ? S1' O1S 1.634(10) . ? S1' C2S 1.830(10) . ? 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 O4 N1 O5 123.40(17) . . ? O4 N1 C5 118.50(17) . . ? O5 N1 C5 118.10(16) . . ? O6 N2 O7 123.46(14) . . ? O6 N2 C18 118.51(13) . . ? O7 N2 C18 118.03(14) . . ? O8 N3 O9 123.62(16) . . ? O8 N3 C25 118.42(15) . . ? O9 N3 C25 117.96(15) . . ? O1 C1 C2 120.36(14) . . ? O1 C1 C8 119.56(15) . . ? C2 C1 C8 120.06(14) . . ? C7 C2 C3 119.35(15) . . ? C7 C2 C1 122.08(14) . . ? C3 C2 C1 118.42(15) . . ? C4 C3 C2 120.49(16) . . ? C5 C4 C3 118.41(16) . . ? C4 C5 C6 122.73(16) . . ? C4 C5 N1 118.85(16) . . ? C6 C5 N1 118.42(17) . . ? C7 C6 C5 118.07(17) . . ? C6 C7 C2 120.93(16) . . ? C9 C8 C13 119.95(14) . . ? C9 C8 C1 121.72(14) . . ? C13 C8 C1 118.16(14) . . ? C8 C9 C10 120.17(14) . . ? C11 C10 C9 119.63(14) . . ? C11 C10 C14 122.16(14) . . ? C9 C10 C14 117.97(14) . . ? C10 C11 C12 120.59(14) . . ? C13 C12 C11 119.38(14) . . ? C13 C12 C21 122.33(14) . . ? C11 C12 C21 118.11(14) . . ? C12 C13 C8 120.26(14) . . ? O2 C14 C10 120.18(15) . . ? O2 C14 C15 119.68(14) . . ? C10 C14 C15 120.14(13) . . ? C16 C15 C20 119.67(14) . . ? C16 C15 C14 118.18(14) . . ? C20 C15 C14 122.09(14) . . ? C17 C16 C15 120.55(15) . . ? C16 C17 C18 118.42(15) . . ? C19 C18 C17 122.53(15) . . ? C19 C18 N2 118.93(14) . . ? C17 C18 N2 118.54(14) . . ? C18 C19 C20 118.54(15) . . ? C19 C20 C15 120.24(15) . . ? O3 C21 C12 120.11(15) . . ? O3 C21 C22 120.46(14) . . ? C12 C21 C22 119.40(14) . . ? C27 C22 C23 119.66(15) . . ? C27 C22 C21 121.74(15) . . ? C23 C22 C21 118.56(14) . . ? C24 C23 C22 120.20(16) . . ? C25 C24 C23 118.53(16) . . ? C24 C25 C26 122.77(15) . . ? C24 C25 N3 118.43(15) . . ? C26 C25 N3 118.79(15) . . ? C25 C26 C27 117.98(16) . . ? C26 C27 C22 120.78(16) . . ? O1S S1 C2S 106.82(10) . . ? O1S S1 C1S 105.60(10) . . ? C2S S1 C1S 98.53(12) . . ? C1S S1' O1S 115.4(6) . . ? C1S S1' C2S 109.6(5) . . ? O1S S1' C2S 98.4(5) . . ? S1' C1S S1 46.4(3) . . ? S1 C2S S1' 42.4(3) . . ? S1 O1S S1' 49.1(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.186 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.043 data_p11399 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H15 N3 O9 . C H2 Cl2' _chemical_formula_sum 'C28 H17 Cl2 N3 O9' _chemical_formula_weight 610.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7093(1) _cell_length_b 10.3943(2) _cell_length_c 14.4467(2) _cell_angle_alpha 83.177(1) _cell_angle_beta 84.037(1) _cell_angle_gamma 73.265(1) _cell_volume 1382.62(4) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.5 _exptl_crystal_description rectangular _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.295 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9089 _exptl_absorpt_correction_T_max 0.9488 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'long-fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18778 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5130 _reflns_number_gt 3372 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 1999)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1999)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1305P)^2^+1.1455P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5130 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1030 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.2276 _refine_ls_wR_factor_gt 0.1956 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5900(4) 0.2870(4) 0.6612(2) 0.0822(11) Uani 1 1 d . . . O2 O 0.7325(4) 0.3785(4) 0.5735(2) 0.0716(9) Uani 1 1 d . . . O3 O 0.3342(3) 0.1635(3) 0.26299(18) 0.0518(7) Uani 1 1 d . . . O4 O 0.3836(3) 0.4374(3) -0.14983(17) 0.0482(7) Uani 1 1 d . . . O5 O 0.2881(4) -0.1818(3) -0.1972(3) 0.0827(11) Uani 1 1 d . . . O6 O 0.1089(3) -0.1372(3) -0.0966(2) 0.0563(7) Uani 1 1 d . . . O7 O 0.3258(3) 0.8119(3) 0.06147(19) 0.0528(7) Uani 1 1 d . . . O8 O -0.2194(5) 0.9696(4) 0.4390(3) 0.1062(15) Uani 1 1 d . . . O9 O -0.0978(4) 1.1127(4) 0.4341(3) 0.0849(11) Uani 1 1 d . . . N1 N 0.6375(4) 0.3252(4) 0.5844(2) 0.0554(9) Uani 1 1 d . . . N2 N 0.2122(4) -0.1112(3) -0.1403(2) 0.0448(8) Uani 1 1 d . . . N3 N -0.1201(5) 1.0133(4) 0.4083(3) 0.0677(11) Uani 1 1 d . . . C1 C 0.5677(4) 0.3093(4) 0.5019(2) 0.0446(9) Uani 1 1 d . . . C2 C 0.6031(4) 0.3735(4) 0.4171(2) 0.0408(8) Uani 1 1 d . . . H2 H 0.6717 0.4224 0.4120 0.049 Uiso 1 1 calc R . . C3 C 0.5349(4) 0.3635(3) 0.3400(2) 0.0375(8) Uani 1 1 d . . . H3 H 0.5548 0.4085 0.2820 0.045 Uiso 1 1 calc R . . C4 C 0.4371(4) 0.2876(3) 0.3475(2) 0.0357(8) Uani 1 1 d . . . C5 C 0.4072(5) 0.2216(4) 0.4341(3) 0.0515(10) Uani 1 1 d . . . H5 H 0.3428 0.1682 0.4394 0.062 Uiso 1 1 calc R . . C6 C 0.4716(5) 0.2347(4) 0.5115(3) 0.0548(11) Uani 1 1 d . . . H6 H 0.4497 0.1926 0.5702 0.066 Uiso 1 1 calc R . . C7 C 0.3700(4) 0.2662(3) 0.2646(2) 0.0369(8) Uani 1 1 d . . . C8 C 0.3496(4) 0.3694(3) 0.1820(2) 0.0340(7) Uani 1 1 d . . . C9 C 0.3120(4) 0.5070(3) 0.1911(2) 0.0362(8) Uani 1 1 d . . . H9 H 0.3006 0.5383 0.2506 0.043 Uiso 1 1 calc R . . C10 C 0.2911(4) 0.5992(3) 0.1110(2) 0.0383(8) Uani 1 1 d . . . C11 C 0.3072(4) 0.5520(3) 0.0236(2) 0.0395(8) Uani 1 1 d . . . H11 H 0.2969 0.6136 -0.0301 0.047 Uiso 1 1 calc R . . C12 C 0.3385(4) 0.4147(3) 0.0146(2) 0.0372(8) Uani 1 1 d . . . C13 C 0.3608(4) 0.3234(3) 0.0937(2) 0.0361(8) Uani 1 1 d . . . H13 H 0.3835 0.2304 0.0878 0.043 Uiso 1 1 calc R . . C14 C 0.3498(4) 0.3695(4) -0.0818(2) 0.0397(8) Uani 1 1 d . . . C15 C 0.3144(4) 0.2415(3) -0.0930(2) 0.0360(8) Uani 1 1 d . . . C16 C 0.3858(4) 0.1679(4) -0.1665(2) 0.0423(8) Uani 1 1 d . . . H16 H 0.4559 0.1977 -0.2059 0.051 Uiso 1 1 calc R . . C17 C 0.3545(4) 0.0516(4) -0.1819(3) 0.0432(9) Uani 1 1 d . . . H17 H 0.4037 0.0004 -0.2308 0.052 Uiso 1 1 calc R . . C18 C 0.2493(4) 0.0119(3) -0.1240(2) 0.0376(8) Uani 1 1 d . . . C19 C 0.1740(4) 0.0836(4) -0.0512(2) 0.0386(8) Uani 1 1 d . . . H19 H 0.1019 0.0548 -0.0132 0.046 Uiso 1 1 calc R . . C20 C 0.2081(4) 0.1986(4) -0.0365(2) 0.0394(8) Uani 1 1 d . . . H20 H 0.1587 0.2492 0.0127 0.047 Uiso 1 1 calc R . . C21 C 0.2649(4) 0.7478(3) 0.1178(3) 0.0400(8) Uani 1 1 d . . . C22 C 0.1632(4) 0.8139(3) 0.1948(3) 0.0402(8) Uani 1 1 d . . . C23 C 0.0533(4) 0.7630(4) 0.2371(3) 0.0474(9) Uani 1 1 d . . . H23 H 0.0419 0.6836 0.2179 0.057 Uiso 1 1 calc R . . C24 C -0.0403(4) 0.8267(4) 0.3071(3) 0.0519(10) Uani 1 1 d . . . H24 H -0.1155 0.7923 0.3356 0.062 Uiso 1 1 calc R . . C25 C -0.0194(4) 0.9429(4) 0.3340(3) 0.0503(10) Uani 1 1 d . . . C26 C 0.0900(5) 0.9953(4) 0.2945(3) 0.0519(10) Uani 1 1 d . . . H26 H 0.1030 1.0729 0.3156 0.062 Uiso 1 1 calc R . . C27 C 0.1802(4) 0.9319(4) 0.2235(3) 0.0473(9) Uani 1 1 d . . . H27 H 0.2536 0.9682 0.1942 0.057 Uiso 1 1 calc R . . C1S C 0.9289(9) 0.3799(7) 0.2345(5) 0.120(3) Uani 1 1 d . . . H1SA H 0.8235 0.4002 0.2396 0.144 Uiso 1 1 calc R . . H1SB H 0.9683 0.2819 0.2341 0.144 Uiso 1 1 calc R . . Cl1 Cl 0.98210(13) 0.45597(14) 0.12909(10) 0.0781(4) Uani 1 1 d . . . Cl2 Cl 0.9811(2) 0.4280(2) 0.33180(13) 0.1213(7) Uani 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 0.110(3) 0.108(3) 0.0309(17) 0.0052(17) -0.0175(17) -0.033(2) O2 0.066(2) 0.101(3) 0.0512(18) -0.0155(17) -0.0181(15) -0.0201(19) O3 0.0746(19) 0.0412(15) 0.0492(16) -0.0001(12) -0.0083(13) -0.0314(14) O4 0.0659(17) 0.0477(15) 0.0371(14) 0.0019(12) -0.0005(12) -0.0289(13) O5 0.092(2) 0.063(2) 0.104(3) -0.053(2) 0.042(2) -0.0389(18) O6 0.0568(17) 0.0557(17) 0.0673(19) -0.0215(14) 0.0060(14) -0.0300(14) O7 0.079(2) 0.0371(14) 0.0468(15) 0.0002(12) -0.0039(14) -0.0252(14) O8 0.100(3) 0.088(3) 0.127(4) -0.028(3) 0.054(3) -0.037(2) O9 0.089(3) 0.067(2) 0.094(3) -0.036(2) 0.012(2) -0.0088(19) N1 0.058(2) 0.062(2) 0.040(2) -0.0056(16) -0.0137(16) -0.0035(18) N2 0.0535(19) 0.0374(17) 0.0484(18) -0.0129(14) -0.0021(15) -0.0173(15) N3 0.069(3) 0.051(2) 0.074(3) -0.006(2) 0.009(2) -0.0065(19) C1 0.052(2) 0.047(2) 0.0282(18) -0.0045(15) -0.0082(15) -0.0017(18) C2 0.0418(19) 0.044(2) 0.0362(19) -0.0074(15) -0.0046(15) -0.0100(16) C3 0.0440(19) 0.0387(19) 0.0290(17) -0.0013(14) 0.0004(14) -0.0122(15) C4 0.0444(19) 0.0308(17) 0.0299(17) -0.0004(13) -0.0006(14) -0.0090(15) C5 0.064(3) 0.056(2) 0.039(2) 0.0061(18) -0.0026(18) -0.029(2) C6 0.071(3) 0.061(3) 0.031(2) 0.0082(18) -0.0019(18) -0.021(2) C7 0.0425(19) 0.0357(18) 0.0351(18) -0.0019(14) -0.0022(14) -0.0157(15) C8 0.0379(18) 0.0342(18) 0.0345(18) -0.0032(14) -0.0065(14) -0.0161(14) C9 0.0393(18) 0.0382(19) 0.0363(18) -0.0044(14) -0.0077(14) -0.0168(15) C10 0.0443(19) 0.0334(18) 0.042(2) -0.0014(15) -0.0105(15) -0.0172(15) C11 0.050(2) 0.0375(19) 0.0365(19) 0.0012(15) -0.0090(15) -0.0214(16) C12 0.0442(19) 0.0402(19) 0.0328(18) -0.0018(15) -0.0047(15) -0.0207(16) C13 0.0389(18) 0.0340(18) 0.0388(19) -0.0036(14) -0.0038(14) -0.0151(14) C14 0.047(2) 0.0398(19) 0.0358(19) -0.0018(16) -0.0049(15) -0.0175(16) C15 0.0460(19) 0.0377(19) 0.0282(17) -0.0034(14) -0.0035(14) -0.0174(15) C16 0.046(2) 0.046(2) 0.0370(19) -0.0041(16) 0.0036(16) -0.0186(17) C17 0.050(2) 0.043(2) 0.0384(19) -0.0137(16) 0.0055(16) -0.0146(17) C18 0.0425(19) 0.0334(18) 0.0397(19) -0.0054(15) -0.0073(15) -0.0126(15) C19 0.046(2) 0.0399(19) 0.0345(18) -0.0077(15) 0.0011(15) -0.0192(16) C20 0.048(2) 0.042(2) 0.0316(18) -0.0089(15) 0.0001(15) -0.0171(16) C21 0.051(2) 0.0323(18) 0.041(2) -0.0007(15) -0.0171(16) -0.0150(16) C22 0.045(2) 0.0302(17) 0.049(2) 0.0006(15) -0.0162(16) -0.0127(15) C23 0.049(2) 0.0347(19) 0.063(3) -0.0017(17) -0.0176(19) -0.0153(16) C24 0.043(2) 0.043(2) 0.070(3) -0.002(2) -0.0032(19) -0.0139(17) C25 0.052(2) 0.042(2) 0.054(2) -0.0037(18) -0.0056(19) -0.0078(18) C26 0.059(2) 0.036(2) 0.064(3) -0.0102(18) -0.008(2) -0.0149(18) C27 0.054(2) 0.0338(19) 0.058(2) -0.0064(17) -0.0091(19) -0.0153(17) C1S 0.155(7) 0.111(5) 0.125(6) 0.031(4) -0.052(5) -0.088(5) Cl1 0.0613(7) 0.0836(9) 0.0944(10) -0.0229(7) -0.0055(6) -0.0225(6) Cl2 0.1434(17) 0.1526(17) 0.0933(12) -0.0065(11) -0.0001(11) -0.0865(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.222(5) . ? O2 N1 1.194(5) . ? O3 C7 1.217(4) . ? O4 C14 1.214(4) . ? O5 N2 1.210(4) . ? O6 N2 1.209(4) . ? O7 C21 1.206(4) . ? O8 N3 1.204(5) . ? O9 N3 1.220(5) . ? N1 C1 1.479(5) . ? N2 C18 1.476(5) . ? N3 C25 1.483(6) . ? C1 C6 1.362(6) . ? C1 C2 1.384(5) . ? C2 C3 1.382(5) . ? C3 C4 1.388(5) . ? C4 C5 1.398(5) . ? C4 C7 1.490(5) . ? C5 C6 1.375(6) . ? C7 C8 1.495(5) . ? C8 C9 1.389(5) . ? C8 C13 1.398(5) . ? C9 C10 1.403(5) . ? C10 C11 1.386(5) . ? C10 C21 1.506(5) . ? C11 C12 1.390(5) . ? C12 C13 1.389(5) . ? C12 C14 1.505(5) . ? C14 C15 1.497(5) . ? C15 C16 1.388(5) . ? C15 C20 1.391(5) . ? C16 C17 1.376(5) . ? C17 C18 1.377(5) . ? C18 C19 1.381(5) . ? C19 C20 1.374(5) . ? C21 C22 1.499(5) . ? C22 C23 1.379(5) . ? C22 C27 1.399(5) . ? C23 C24 1.382(6) . ? C24 C25 1.385(6) . ? C25 C26 1.373(6) . ? C26 C27 1.377(6) . ? C1S Cl2 1.716(7) . ? C1S Cl1 1.732(7) . ? 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 O2 N1 O1 123.5(4) . . ? O2 N1 C1 119.1(4) . . ? O1 N1 C1 117.4(4) . . ? O6 N2 O5 123.1(3) . . ? O6 N2 C18 119.2(3) . . ? O5 N2 C18 117.7(3) . . ? O8 N3 O9 124.0(4) . . ? O8 N3 C25 118.0(4) . . ? O9 N3 C25 118.0(4) . . ? C6 C1 C2 122.6(3) . . ? C6 C1 N1 119.9(3) . . ? C2 C1 N1 117.5(4) . . ? C3 C2 C1 118.1(4) . . ? C2 C3 C4 120.5(3) . . ? C3 C4 C5 119.5(3) . . ? C3 C4 C7 121.9(3) . . ? C5 C4 C7 118.5(3) . . ? C6 C5 C4 120.1(4) . . ? C1 C6 C5 119.1(4) . . ? O3 C7 C4 120.1(3) . . ? O3 C7 C8 119.8(3) . . ? C4 C7 C8 120.1(3) . . ? C9 C8 C13 119.9(3) . . ? C9 C8 C7 122.4(3) . . ? C13 C8 C7 117.5(3) . . ? C8 C9 C10 119.8(3) . . ? C11 C10 C9 119.7(3) . . ? C11 C10 C21 119.2(3) . . ? C9 C10 C21 120.9(3) . . ? C10 C11 C12 120.7(3) . . ? C13 C12 C11 119.6(3) . . ? C13 C12 C14 121.9(3) . . ? C11 C12 C14 118.5(3) . . ? C12 C13 C8 120.2(3) . . ? O4 C14 C15 120.3(3) . . ? O4 C14 C12 120.6(3) . . ? C15 C14 C12 119.1(3) . . ? C16 C15 C20 119.4(3) . . ? C16 C15 C14 117.9(3) . . ? C20 C15 C14 122.6(3) . . ? C17 C16 C15 120.4(3) . . ? C16 C17 C18 118.4(3) . . ? C17 C18 C19 122.9(3) . . ? C17 C18 N2 119.3(3) . . ? C19 C18 N2 117.7(3) . . ? C20 C19 C18 117.7(3) . . ? C19 C20 C15 121.1(3) . . ? O7 C21 C22 121.0(3) . . ? O7 C21 C10 119.7(3) . . ? C22 C21 C10 119.3(3) . . ? C23 C22 C27 119.4(4) . . ? C23 C22 C21 122.3(3) . . ? C27 C22 C21 118.4(3) . . ? C22 C23 C24 121.2(4) . . ? C23 C24 C25 117.8(4) . . ? C26 C25 C24 122.7(4) . . ? C26 C25 N3 118.9(4) . . ? C24 C25 N3 118.4(4) . . ? C25 C26 C27 118.7(4) . . ? C26 C27 C22 120.3(4) . . ? Cl2 C1S Cl1 115.0(3) . . ? 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 O2 N1 C1 C6 172.1(4) . . . . ? O1 N1 C1 C6 -10.7(6) . . . . ? O2 N1 C1 C2 -8.5(5) . . . . ? O1 N1 C1 C2 168.8(4) . . . . ? C6 C1 C2 C3 1.7(6) . . . . ? N1 C1 C2 C3 -177.7(3) . . . . ? C1 C2 C3 C4 -2.0(5) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? C2 C3 C4 C7 -175.3(3) . . . . ? C3 C4 C5 C6 1.6(6) . . . . ? C7 C4 C5 C6 177.4(4) . . . . ? C2 C1 C6 C5 0.2(6) . . . . ? N1 C1 C6 C5 179.6(4) . . . . ? C4 C5 C6 C1 -1.9(6) . . . . ? C3 C4 C7 O3 150.5(3) . . . . ? C5 C4 C7 O3 -25.3(5) . . . . ? C3 C4 C7 C8 -28.1(5) . . . . ? C5 C4 C7 C8 156.1(3) . . . . ? O3 C7 C8 C9 144.4(4) . . . . ? C4 C7 C8 C9 -37.0(5) . . . . ? O3 C7 C8 C13 -31.6(5) . . . . ? C4 C7 C8 C13 147.0(3) . . . . ? C13 C8 C9 C10 -2.6(5) . . . . ? C7 C8 C9 C10 -178.5(3) . . . . ? C8 C9 C10 C11 0.4(5) . . . . ? C8 C9 C10 C21 -173.8(3) . . . . ? C9 C10 C11 C12 2.5(5) . . . . ? C21 C10 C11 C12 176.8(3) . . . . ? C10 C11 C12 C13 -3.2(5) . . . . ? C10 C11 C12 C14 177.9(3) . . . . ? C11 C12 C13 C8 1.0(5) . . . . ? C14 C12 C13 C8 179.9(3) . . . . ? C9 C8 C13 C12 1.8(5) . . . . ? C7 C8 C13 C12 178.0(3) . . . . ? C13 C12 C14 O4 -152.3(4) . . . . ? C11 C12 C14 O4 26.6(5) . . . . ? C13 C12 C14 C15 29.6(5) . . . . ? C11 C12 C14 C15 -151.6(3) . . . . ? O4 C14 C15 C16 32.1(5) . . . . ? C12 C14 C15 C16 -149.8(3) . . . . ? O4 C14 C15 C20 -144.2(4) . . . . ? C12 C14 C15 C20 34.0(5) . . . . ? C20 C15 C16 C17 -1.7(5) . . . . ? C14 C15 C16 C17 -178.0(3) . . . . ? C15 C16 C17 C18 1.2(6) . . . . ? C16 C17 C18 C19 0.0(6) . . . . ? C16 C17 C18 N2 178.9(3) . . . . ? O6 N2 C18 C17 -171.4(3) . . . . ? O5 N2 C18 C17 8.9(5) . . . . ? O6 N2 C18 C19 7.5(5) . . . . ? O5 N2 C18 C19 -172.2(4) . . . . ? C17 C18 C19 C20 -0.7(5) . . . . ? N2 C18 C19 C20 -179.6(3) . . . . ? C18 C19 C20 C15 0.2(5) . . . . ? C16 C15 C20 C19 1.0(5) . . . . ? C14 C15 C20 C19 177.1(3) . . . . ? C11 C10 C21 O7 -37.8(5) . . . . ? C9 C10 C21 O7 136.5(4) . . . . ? C11 C10 C21 C22 142.2(3) . . . . ? C9 C10 C21 C22 -43.5(5) . . . . ? O7 C21 C22 C23 154.7(4) . . . . ? C10 C21 C22 C23 -25.2(5) . . . . ? O7 C21 C22 C27 -24.6(5) . . . . ? C10 C21 C22 C27 155.5(3) . . . . ? C27 C22 C23 C24 0.1(6) . . . . ? C21 C22 C23 C24 -179.2(3) . . . . ? C22 C23 C24 C25 -0.5(6) . . . . ? C23 C24 C25 C26 -0.5(6) . . . . ? C23 C24 C25 N3 179.2(4) . . . . ? O8 N3 C25 C26 176.5(4) . . . . ? O9 N3 C25 C26 -3.0(6) . . . . ? O8 N3 C25 C24 -3.3(7) . . . . ? O9 N3 C25 C24 177.3(4) . . . . ? C24 C25 C26 C27 1.9(6) . . . . ? N3 C25 C26 C27 -177.9(4) . . . . ? C25 C26 C27 C22 -2.2(6) . . . . ? C23 C22 C27 C26 1.3(6) . . . . ? C21 C22 C27 C26 -179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.559 _refine_diff_density_min -0.806 _refine_diff_density_rms 0.073