# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Peter T. Sunderland' Dhami 'Mary F. Mahon' 'Matthew D. Lloyd' 'Andrew S. Thompson' 'Hashim Jawaid' 'Niall M. B. Martin' 'Michael D. Threadgill' _publ_contact_author_name 'Mary F Mahon' _publ_contact_author_email m.f.mahon@bath.ac.uk data_Compound-26a_k08farm7 _database_code_depnum_ccdc_archive 'CCDC 781105' #TrackingRef 'bigcif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 N2 O3' _chemical_formula_weight 280.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.4710(1) _cell_length_b 8.3050(1) _cell_length_c 21.1940(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1315.02(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 18039 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.908 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23576 _diffrn_reflns_av_R_equivalents 0.0757 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3016 _reflns_number_gt 2288 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack(Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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. The asymmetric unit in this structure contains 1 molecule of compound X, plus 1/2 of a molecule of ethyl acetate. O4 in the latter is located on a crystallographic 2-fold rotation axis, which necessarily means that the carbonyl oxygen (O5) has half-occupancy. The hydrogen attached to C31 were omitted from the refinement due to the symmetry related disorder in the solvent. ; _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^)+(0.0568P)^2^+0.0116P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.021(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.7(12) _refine_ls_number_reflns 3016 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1022 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.22161(19) 0.00894(15) 0.10297(5) 0.0389(3) Uani 1 1 d . . . O2 O 0.08170(19) -0.06175(16) 0.39575(6) 0.0406(4) Uani 1 1 d . . . O3 O 0.2203(2) -0.28674(16) 0.41404(6) 0.0493(4) Uani 1 1 d . . . N1 N 0.3111(2) 0.18029(17) 0.18184(7) 0.0337(4) Uani 1 1 d . . . N2 N 0.1674(2) -0.17974(18) 0.37832(7) 0.0351(4) Uani 1 1 d . . . C1 C 0.3446(2) 0.1991(2) 0.24486(8) 0.0326(4) Uani 1 1 d . . . H1 H 0.3906 0.3004 0.2578 0.039 Uiso 1 1 calc R . . C2 C 0.3184(2) 0.08647(19) 0.29105(7) 0.0283(4) Uani 1 1 d . . . C3 C 0.2482(2) -0.0669(2) 0.27139(8) 0.0281(4) Uani 1 1 d . . . C4 C 0.1990(2) -0.1990(2) 0.31050(8) 0.0298(4) Uani 1 1 d . . . C5 C 0.1590(2) -0.3483(2) 0.28687(9) 0.0347(4) Uani 1 1 d . . . H5 H 0.1339 -0.4344 0.3150 0.042 Uiso 1 1 calc R . . C6 C 0.1548(3) -0.3749(2) 0.22200(9) 0.0369(4) Uani 1 1 d . . . H6 H 0.1331 -0.4797 0.2058 0.044 Uiso 1 1 calc R . . C7 C 0.1823(3) -0.2482(2) 0.18186(9) 0.0344(4) Uani 1 1 d . . . H7 H 0.1701 -0.2635 0.1377 0.041 Uiso 1 1 calc R . . C8 C 0.2286(2) -0.0953(2) 0.20551(8) 0.0301(4) Uani 1 1 d . . . C9 C 0.2571(2) 0.0383(2) 0.16407(8) 0.0303(4) Uani 1 1 d . . . C10 C 0.2624(3) 0.1341(2) 0.05791(9) 0.0441(5) Uani 1 1 d . . . H10A H 0.1847 0.2272 0.0656 0.066 Uiso 1 1 calc R . . H10B H 0.2422 0.0936 0.0151 0.066 Uiso 1 1 calc R . . H10C H 0.3878 0.1665 0.0625 0.066 Uiso 1 1 calc R . . C11 C 0.3796(2) 0.1265(2) 0.35606(8) 0.0296(4) Uani 1 1 d . . . C12 C 0.3384(3) 0.2754(2) 0.38230(9) 0.0354(4) Uani 1 1 d . . . H12 H 0.2623 0.3472 0.3600 0.043 Uiso 1 1 calc R . . C13 C 0.4063(3) 0.3208(2) 0.44041(9) 0.0407(5) Uani 1 1 d . . . H13 H 0.3789 0.4239 0.4572 0.049 Uiso 1 1 calc R . . C14 C 0.5137(3) 0.2162(2) 0.47378(9) 0.0416(5) Uani 1 1 d . . . H14 H 0.5586 0.2459 0.5141 0.050 Uiso 1 1 calc R . . C15 C 0.5558(3) 0.0673(2) 0.44818(9) 0.0385(5) Uani 1 1 d . . . H15 H 0.6298 -0.0050 0.4711 0.046 Uiso 1 1 calc R . . C16 C 0.4914(3) 0.0232(2) 0.38974(9) 0.0325(4) Uani 1 1 d . . . H16 H 0.5235 -0.0781 0.3723 0.039 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0456(8) 0.0442(7) 0.0269(7) 0.0019(6) -0.0027(6) -0.0027(6) O2 0.0390(8) 0.0450(8) 0.0380(7) 0.0019(6) 0.0057(6) -0.0004(7) O3 0.0632(10) 0.0432(7) 0.0415(8) 0.0173(6) -0.0076(7) -0.0030(8) N1 0.0368(9) 0.0356(8) 0.0288(8) 0.0043(6) -0.0001(7) -0.0034(7) N2 0.0353(9) 0.0363(8) 0.0336(8) 0.0062(7) 0.0003(7) -0.0060(8) C1 0.0311(10) 0.0313(9) 0.0354(10) 0.0040(8) -0.0001(8) -0.0031(8) C2 0.0254(9) 0.0300(8) 0.0295(9) 0.0007(7) -0.0008(8) 0.0013(8) C3 0.0217(9) 0.0312(8) 0.0313(9) 0.0033(7) 0.0007(7) 0.0029(7) C4 0.0238(9) 0.0336(9) 0.0320(9) 0.0037(7) -0.0019(7) -0.0004(8) C5 0.0290(10) 0.0316(9) 0.0434(11) 0.0065(8) -0.0033(8) -0.0014(8) C6 0.0319(10) 0.0304(8) 0.0484(11) -0.0017(8) -0.0025(9) -0.0018(8) C7 0.0276(10) 0.0379(10) 0.0377(10) -0.0042(8) -0.0006(8) 0.0010(8) C8 0.0239(9) 0.0335(9) 0.0328(9) 0.0015(8) -0.0002(7) 0.0005(7) C9 0.0263(10) 0.0373(10) 0.0273(9) 0.0020(7) -0.0006(7) 0.0024(8) C10 0.0533(14) 0.0504(11) 0.0286(9) 0.0104(9) 0.0000(9) -0.0012(10) C11 0.0283(10) 0.0311(9) 0.0293(9) 0.0017(7) 0.0031(7) -0.0025(8) C12 0.0362(11) 0.0349(9) 0.0351(10) 0.0016(8) 0.0041(8) 0.0043(8) C13 0.0426(12) 0.0389(10) 0.0405(11) -0.0071(9) 0.0062(9) -0.0033(9) C14 0.0415(12) 0.0512(11) 0.0322(10) -0.0079(9) 0.0010(9) -0.0055(10) C15 0.0384(12) 0.0430(10) 0.0340(10) -0.0002(9) -0.0052(8) 0.0009(9) C16 0.0308(10) 0.0317(9) 0.0350(10) 0.0011(8) 0.0001(8) 0.0004(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 C9 1.344(2) . ? O1 C10 1.444(2) . ? O2 N2 1.2274(19) . ? O3 N2 1.2325(18) . ? N1 C9 1.302(2) . ? N1 C1 1.368(2) . ? N2 C4 1.465(2) . ? C1 C2 1.368(2) . ? C1 H1 0.9500 . ? C2 C3 1.439(2) . ? C2 C11 1.489(2) . ? C3 C4 1.423(2) . ? C3 C8 1.424(2) . ? C4 C5 1.370(2) . ? C5 C6 1.393(3) . ? C5 H5 0.9500 . ? C6 C7 1.369(2) . ? C6 H6 0.9500 . ? C7 C8 1.408(2) . ? C7 H7 0.9500 . ? C8 C9 1.431(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.391(2) . ? C11 C16 1.394(3) . ? C12 C13 1.384(3) . ? C12 H12 0.9500 . ? C13 C14 1.378(3) . ? C13 H13 0.9500 . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C15 C16 1.378(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C10 117.70(13) . . ? C9 N1 C1 116.26(15) . . ? O2 N2 O3 123.91(15) . . ? O2 N2 C4 117.80(14) . . ? O3 N2 C4 118.18(16) . . ? N1 C1 C2 126.50(16) . . ? N1 C1 H1 116.8 . . ? C2 C1 H1 116.8 . . ? C1 C2 C3 116.74(15) . . ? C1 C2 C11 117.76(15) . . ? C3 C2 C11 125.25(15) . . ? C4 C3 C8 114.64(15) . . ? C4 C3 C2 127.43(15) . . ? C8 C3 C2 117.91(15) . . ? C5 C4 C3 122.75(16) . . ? C5 C4 N2 114.95(16) . . ? C3 C4 N2 121.93(16) . . ? C4 C5 C6 120.61(17) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 119.22(17) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C8 120.60(17) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C3 121.58(15) . . ? C7 C8 C9 121.14(16) . . ? C3 C8 C9 117.27(15) . . ? N1 C9 O1 120.28(15) . . ? N1 C9 C8 124.80(16) . . ? O1 C9 C8 114.91(15) . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 118.36(17) . . ? C12 C11 C2 120.03(16) . . ? C16 C11 C2 121.37(16) . . ? C13 C12 C11 121.12(18) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C13 C12 119.89(17) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 119.58(18) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 120.63(18) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 120.39(17) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 C1 C2 -3.5(3) . . . . ? N1 C1 C2 C3 -0.1(3) . . . . ? N1 C1 C2 C11 174.43(17) . . . . ? C1 C2 C3 C4 -175.71(17) . . . . ? C11 C2 C3 C4 10.2(3) . . . . ? C1 C2 C3 C8 6.1(2) . . . . ? C11 C2 C3 C8 -167.99(15) . . . . ? C8 C3 C4 C5 8.4(3) . . . . ? C2 C3 C4 C5 -169.87(17) . . . . ? C8 C3 C4 N2 -164.39(15) . . . . ? C2 C3 C4 N2 17.4(3) . . . . ? O2 N2 C4 C5 -130.60(18) . . . . ? O3 N2 C4 C5 45.8(2) . . . . ? O2 N2 C4 C3 42.7(2) . . . . ? O3 N2 C4 C3 -140.94(18) . . . . ? C3 C4 C5 C6 -3.8(3) . . . . ? N2 C4 C5 C6 169.41(16) . . . . ? C4 C5 C6 C7 -3.2(3) . . . . ? C5 C6 C7 C8 5.1(3) . . . . ? C6 C7 C8 C3 0.0(3) . . . . ? C6 C7 C8 C9 -179.77(17) . . . . ? C4 C3 C8 C7 -6.4(2) . . . . ? C2 C3 C8 C7 171.99(16) . . . . ? C4 C3 C8 C9 173.35(15) . . . . ? C2 C3 C8 C9 -8.3(2) . . . . ? C1 N1 C9 O1 -179.79(16) . . . . ? C1 N1 C9 C8 1.0(3) . . . . ? C10 O1 C9 N1 6.0(3) . . . . ? C10 O1 C9 C8 -174.73(15) . . . . ? C7 C8 C9 N1 -175.39(18) . . . . ? C3 C8 C9 N1 4.8(3) . . . . ? C7 C8 C9 O1 5.4(2) . . . . ? C3 C8 C9 O1 -174.38(14) . . . . ? C1 C2 C11 C12 46.9(2) . . . . ? C3 C2 C11 C12 -139.00(18) . . . . ? C1 C2 C11 C16 -127.37(19) . . . . ? C3 C2 C11 C16 46.7(3) . . . . ? C16 C11 C12 C13 0.0(3) . . . . ? C2 C11 C12 C13 -174.47(17) . . . . ? C11 C12 C13 C14 -1.4(3) . . . . ? C12 C13 C14 C15 1.3(3) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C14 C15 C16 C11 -1.4(3) . . . . ? C12 C11 C16 C15 1.4(3) . . . . ? C2 C11 C16 C15 175.78(17) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.468 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.156 #===end data_Compound-33_h09mt1 _database_code_depnum_ccdc_archive 'CCDC 781106' #TrackingRef 'bigcif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H11 Br N2 O3' _chemical_formula_weight 359.18 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6180(4) _cell_length_b 9.9120(4) _cell_length_c 10.2260(5) _cell_angle_alpha 114.347(2) _cell_angle_beta 108.553(2) _cell_angle_gamma 100.738(2) _cell_volume 701.65(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10926 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.700 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 2.944 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.264 _exptl_absorpt_correction_T_max 0.325 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11401 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0410 _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 -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 27.42 _reflns_number_total 3168 _reflns_number_gt 2680 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick 1997)' _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^)+(0.0318P)^2^+0.1879P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3168 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0680 _refine_ls_wR_factor_gt 0.0642 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 Br1 Br -0.51013(3) 0.46375(3) 0.74138(3) 0.03080(10) Uani 1 1 d . . . O1 O -0.1656(2) 0.8535(2) 0.9271(2) 0.0453(4) Uani 1 1 d . . . O2 O -0.2832(2) 0.6782(2) 0.6743(2) 0.0355(4) Uani 1 1 d . . . O3 O 0.01223(18) 0.15154(16) 0.72365(17) 0.0253(3) Uani 1 1 d . . . N1 N -0.1858(2) 0.7289(2) 0.8145(2) 0.0281(4) Uani 1 1 d . . . N2 N -0.2742(2) 0.1357(2) 0.6495(2) 0.0254(4) Uani 1 1 d . . . C1 C -0.1067(3) 0.2214(2) 0.7186(2) 0.0218(4) Uani 1 1 d . . . C2 C -0.0357(3) 0.3915(2) 0.7915(2) 0.0203(4) Uani 1 1 d . . . C3 C 0.1478(3) 0.4756(2) 0.8662(2) 0.0223(4) Uani 1 1 d . . . H3 H 0.2256 0.4194 0.8702 0.027 Uiso 1 1 calc R . . C4 C 0.2143(3) 0.6372(3) 0.9327(3) 0.0264(5) Uani 1 1 d . . . H4 H 0.3380 0.6936 0.9864 0.032 Uiso 1 1 calc R . . C5 C 0.0998(3) 0.7193(3) 0.9215(3) 0.0254(4) Uani 1 1 d . . . H5 H 0.1454 0.8313 0.9656 0.030 Uiso 1 1 calc R . . C6 C -0.0779(3) 0.6378(2) 0.8468(2) 0.0225(4) Uani 1 1 d . . . C7 C -0.1549(3) 0.4717(2) 0.7845(2) 0.0196(4) Uani 1 1 d . . . C8 C -0.3360(3) 0.3761(2) 0.7192(2) 0.0223(4) Uani 1 1 d . . . C9 C -0.3866(3) 0.2157(3) 0.6543(3) 0.0263(5) Uani 1 1 d . . . H9 H -0.5084 0.1555 0.6094 0.032 Uiso 1 1 calc R . . C10 C -0.0555(3) -0.0184(2) 0.6571(3) 0.0301(5) Uani 1 1 d . . . H10A H -0.1392 -0.0713 0.5427 0.036 Uiso 1 1 calc R . . H10B H -0.1191 -0.0448 0.7139 0.036 Uiso 1 1 calc R . . C11 C 0.0941(3) -0.0764(2) 0.6741(3) 0.0256(5) Uani 1 1 d . . . C12 C 0.2683(3) 0.0219(3) 0.7753(3) 0.0419(6) Uani 1 1 d . . . H12 H 0.2982 0.1332 0.8387 0.050 Uiso 1 1 calc R . . C13 C 0.3996(3) -0.0410(3) 0.7850(4) 0.0508(7) Uani 1 1 d . . . H13 H 0.5189 0.0281 0.8545 0.061 Uiso 1 1 calc R . . C14 C 0.3597(3) -0.2019(3) 0.6953(3) 0.0359(6) Uani 1 1 d . . . H14 H 0.4506 -0.2439 0.7025 0.043 Uiso 1 1 calc R . . C15 C 0.1864(3) -0.3015(3) 0.5950(3) 0.0287(5) Uani 1 1 d . . . H15 H 0.1571 -0.4130 0.5332 0.034 Uiso 1 1 calc R . . C16 C 0.0547(3) -0.2388(2) 0.5841(3) 0.0263(5) Uani 1 1 d . . . H16 H -0.0644 -0.3081 0.5140 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02268(13) 0.03052(14) 0.04436(16) 0.01901(11) 0.01764(11) 0.01495(10) O1 0.0466(11) 0.0258(9) 0.0557(11) 0.0117(8) 0.0216(9) 0.0207(8) O2 0.0323(9) 0.0414(10) 0.0425(10) 0.0286(8) 0.0147(8) 0.0188(8) O3 0.0219(8) 0.0180(7) 0.0367(8) 0.0138(6) 0.0122(7) 0.0098(6) N1 0.0274(10) 0.0239(10) 0.0407(11) 0.0192(9) 0.0180(9) 0.0126(8) N2 0.0211(9) 0.0205(9) 0.0310(10) 0.0114(8) 0.0094(8) 0.0082(7) C1 0.0221(10) 0.0215(10) 0.0238(10) 0.0114(9) 0.0111(9) 0.0105(9) C2 0.0208(10) 0.0195(10) 0.0213(10) 0.0107(8) 0.0098(9) 0.0069(8) C3 0.0203(10) 0.0260(11) 0.0246(10) 0.0144(9) 0.0108(9) 0.0110(9) C4 0.0201(10) 0.0248(11) 0.0299(11) 0.0132(9) 0.0091(9) 0.0046(9) C5 0.0259(11) 0.0199(10) 0.0283(11) 0.0119(9) 0.0112(10) 0.0064(9) C6 0.0254(11) 0.0208(10) 0.0240(10) 0.0113(9) 0.0124(9) 0.0115(9) C7 0.0214(10) 0.0190(10) 0.0183(10) 0.0094(8) 0.0085(9) 0.0080(8) C8 0.0186(10) 0.0242(11) 0.0249(10) 0.0119(9) 0.0101(9) 0.0100(9) C9 0.0185(10) 0.0240(11) 0.0319(12) 0.0119(9) 0.0097(9) 0.0070(9) C10 0.0264(12) 0.0187(11) 0.0432(13) 0.0149(10) 0.0135(11) 0.0094(9) C11 0.0268(11) 0.0217(11) 0.0313(11) 0.0145(9) 0.0138(10) 0.0109(9) C12 0.0276(13) 0.0224(12) 0.0592(17) 0.0129(12) 0.0101(12) 0.0105(10) C13 0.0257(13) 0.0311(14) 0.074(2) 0.0189(14) 0.0088(14) 0.0098(11) C14 0.0323(13) 0.0341(13) 0.0546(15) 0.0272(12) 0.0222(12) 0.0220(11) C15 0.0385(13) 0.0244(11) 0.0322(12) 0.0161(10) 0.0201(11) 0.0175(10) C16 0.0284(11) 0.0220(11) 0.0269(11) 0.0117(9) 0.0112(10) 0.0094(9) _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 Br1 C8 1.897(2) . ? O1 N1 1.226(2) . ? O2 N1 1.223(2) . ? O3 C1 1.339(2) . ? O3 C10 1.441(2) . ? N1 C6 1.467(3) . ? N2 C1 1.305(3) . ? N2 C9 1.362(3) . ? C1 C2 1.436(3) . ? C2 C7 1.413(3) . ? C2 C3 1.412(3) . ? C3 C4 1.367(3) . ? C3 H3 0.9500 . ? C4 C5 1.397(3) . ? C4 H4 0.9500 . ? C5 C6 1.366(3) . ? C5 H5 0.9500 . ? C6 C7 1.420(3) . ? C7 C8 1.430(3) . ? C8 C9 1.358(3) . ? C9 H9 0.9500 . ? C10 C11 1.497(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.381(3) . ? C11 C16 1.389(3) . ? C12 C13 1.386(3) . ? C12 H12 0.9500 . ? C13 C14 1.376(3) . ? C13 H13 0.9500 . ? C14 C15 1.377(3) . ? C14 H14 0.9500 . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 O3 C10 116.21(16) . . ? O2 N1 O1 124.67(19) . . ? O2 N1 C6 116.74(17) . . ? O1 N1 C6 118.47(18) . . ? C1 N2 C9 116.86(18) . . ? N2 C1 O3 120.27(18) . . ? N2 C1 C2 124.43(18) . . ? O3 C1 C2 115.29(17) . . ? C7 C2 C3 121.11(18) . . ? C7 C2 C1 118.05(18) . . ? C3 C2 C1 120.84(18) . . ? C4 C3 C2 120.54(19) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 119.79(19) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.77(19) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 123.13(19) . . ? C5 C6 N1 115.16(18) . . ? C7 C6 N1 121.18(18) . . ? C2 C7 C6 115.44(18) . . ? C2 C7 C8 115.97(18) . . ? C6 C7 C8 128.57(18) . . ? C9 C8 C7 120.02(18) . . ? C9 C8 Br1 116.51(15) . . ? C7 C8 Br1 122.99(15) . . ? C8 C9 N2 124.27(19) . . ? C8 C9 H9 117.9 . . ? N2 C9 H9 117.9 . . ? O3 C10 C11 109.23(17) . . ? O3 C10 H10A 109.8 . . ? C11 C10 H10A 109.8 . . ? O3 C10 H10B 109.8 . . ? C11 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? C12 C11 C16 118.3(2) . . ? C12 C11 C10 123.78(19) . . ? C16 C11 C10 117.87(19) . . ? C11 C12 C13 120.4(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 121.0(2) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 119.2(2) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C14 C15 C16 119.9(2) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C11 121.1(2) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N2 C1 O3 177.62(18) . . . . ? C9 N2 C1 C2 -3.1(3) . . . . ? C10 O3 C1 N2 -3.1(3) . . . . ? C10 O3 C1 C2 177.50(17) . . . . ? N2 C1 C2 C7 -1.8(3) . . . . ? O3 C1 C2 C7 177.54(17) . . . . ? N2 C1 C2 C3 178.98(19) . . . . ? O3 C1 C2 C3 -1.7(3) . . . . ? C7 C2 C3 C4 -0.5(3) . . . . ? C1 C2 C3 C4 178.76(19) . . . . ? C2 C3 C4 C5 -2.5(3) . . . . ? C3 C4 C5 C6 1.3(3) . . . . ? C4 C5 C6 C7 2.9(3) . . . . ? C4 C5 C6 N1 -168.78(18) . . . . ? O2 N1 C6 C5 119.2(2) . . . . ? O1 N1 C6 C5 -56.9(3) . . . . ? O2 N1 C6 C7 -52.7(3) . . . . ? O1 N1 C6 C7 131.2(2) . . . . ? C3 C2 C7 C6 4.2(3) . . . . ? C1 C2 C7 C6 -174.99(17) . . . . ? C3 C2 C7 C8 -174.44(18) . . . . ? C1 C2 C7 C8 6.3(3) . . . . ? C5 C6 C7 C2 -5.5(3) . . . . ? N1 C6 C7 C2 165.67(18) . . . . ? C5 C6 C7 C8 172.9(2) . . . . ? N1 C6 C7 C8 -15.8(3) . . . . ? C2 C7 C8 C9 -6.4(3) . . . . ? C6 C7 C8 C9 175.2(2) . . . . ? C2 C7 C8 Br1 165.49(14) . . . . ? C6 C7 C8 Br1 -13.0(3) . . . . ? C7 C8 C9 N2 1.6(3) . . . . ? Br1 C8 C9 N2 -170.71(17) . . . . ? C1 N2 C9 C8 3.2(3) . . . . ? C1 O3 C10 C11 -179.38(17) . . . . ? O3 C10 C11 C12 16.3(3) . . . . ? O3 C10 C11 C16 -164.63(18) . . . . ? C16 C11 C12 C13 0.6(4) . . . . ? C10 C11 C12 C13 179.7(3) . . . . ? C11 C12 C13 C14 -0.5(5) . . . . ? C12 C13 C14 C15 -0.2(4) . . . . ? C13 C14 C15 C16 0.6(4) . . . . ? C14 C15 C16 C11 -0.5(3) . . . . ? C12 C11 C16 C15 -0.1(3) . . . . ? C10 C11 C16 C15 -179.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.369 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.083 #===end data_Compound-35_k09mt1 _database_code_depnum_ccdc_archive 'CCDC 781107' #TrackingRef 'bigcif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 N2 O4' _chemical_formula_weight 500.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 13.9880(2) _cell_length_b 10.9970(2) _cell_length_c 16.1970(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.645(1) _cell_angle_gamma 90.00 _cell_volume 2479.44(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 28481 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44827 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5661 _reflns_number_gt 4556 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick 1997)' _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^)+(0.0752P)^2^+2.4946P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.018(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5661 _refine_ls_number_parameters 350 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.1860 _refine_ls_wR_factor_gt 0.1729 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.83118(12) -0.06426(16) 0.49971(10) 0.0376(4) Uani 1 1 d . . . O2 O 0.84787(11) 0.11701(15) 0.55239(10) 0.0334(4) Uani 1 1 d . . . O3 O 0.39555(10) 0.24223(15) 0.52309(9) 0.0322(4) Uani 1 1 d . . . O4 O 0.5000 0.5115(5) 0.7500 0.184(4) Uani 1 2 d S . . O5 O 0.5766(6) 0.6703(6) 0.7306(4) 0.115(3) Uani 0.50 1 d P . . N1 N 0.80008(13) 0.03613(17) 0.51625(11) 0.0276(4) Uani 1 1 d . . . N2 N 0.49368(13) 0.19579(18) 0.64126(11) 0.0316(4) Uani 1 1 d . . . C1 C 0.47805(15) 0.19572(19) 0.56073(13) 0.0271(4) Uani 1 1 d . . . C2 C 0.54508(15) 0.14997(19) 0.50631(12) 0.0254(4) Uani 1 1 d . . . C3 C 0.52243(16) 0.1477(2) 0.41938(13) 0.0292(5) Uani 1 1 d . . . H3 H 0.4628 0.1795 0.3957 0.035 Uiso 1 1 calc R . . C4 C 0.58615(17) 0.0998(2) 0.36912(14) 0.0337(5) Uani 1 1 d . . . H4 H 0.5695 0.0951 0.3109 0.040 Uiso 1 1 calc R . . C5 C 0.67603(16) 0.0576(2) 0.40367(13) 0.0301(5) Uani 1 1 d . . . H5 H 0.7202 0.0239 0.3690 0.036 Uiso 1 1 calc R . . C6 C 0.69966(14) 0.06518(19) 0.48770(13) 0.0258(4) Uani 1 1 d . . . C7 C 0.63552(14) 0.10752(18) 0.54387(12) 0.0250(4) Uani 1 1 d . . . C8 C 0.65169(15) 0.1076(2) 0.63270(13) 0.0274(4) Uani 1 1 d . . . C9 C 0.57933(16) 0.1510(2) 0.67512(13) 0.0322(5) Uani 1 1 d . . . H9 H 0.5898 0.1499 0.7340 0.039 Uiso 1 1 calc R . . C10 C 0.32590(16) 0.2875(2) 0.57741(14) 0.0335(5) Uani 1 1 d . . . H10A H 0.3597 0.3184 0.6298 0.040 Uiso 1 1 calc R . . H10B H 0.2824 0.2210 0.5910 0.040 Uiso 1 1 calc R . . C11 C 0.26933(15) 0.3877(2) 0.53336(13) 0.0299(5) Uani 1 1 d . . . C12 C 0.20103(17) 0.3642(2) 0.46732(16) 0.0371(5) Uani 1 1 d . . . H12 H 0.1899 0.2829 0.4489 0.045 Uiso 1 1 calc R . . C13 C 0.14879(19) 0.4586(2) 0.42790(18) 0.0436(6) Uani 1 1 d . . . H13 H 0.1028 0.4415 0.3822 0.052 Uiso 1 1 calc R . . C14 C 0.16293(19) 0.5768(2) 0.45439(17) 0.0417(6) Uani 1 1 d . . . H14 H 0.1267 0.6410 0.4274 0.050 Uiso 1 1 calc R . . C15 C 0.2303(2) 0.6013(2) 0.52057(18) 0.0456(6) Uani 1 1 d . . . H15 H 0.2404 0.6825 0.5393 0.055 Uiso 1 1 calc R . . C16 C 0.2833(2) 0.5071(2) 0.55966(17) 0.0422(6) Uani 1 1 d . . . H16 H 0.3296 0.5246 0.6050 0.051 Uiso 1 1 calc R . . C17 C 0.73814(15) 0.0592(2) 0.68405(12) 0.0272(4) Uani 1 1 d . . . C18 C 0.80023(15) 0.1429(2) 0.73358(13) 0.0277(4) Uani 1 1 d . . . C19 C 0.78804(17) 0.2699(2) 0.72503(14) 0.0341(5) Uani 1 1 d . . . H19 H 0.7397 0.3009 0.6852 0.041 Uiso 1 1 calc R . . C20 C 0.84492(18) 0.3495(2) 0.77328(16) 0.0390(6) Uani 1 1 d . . . H20 H 0.8360 0.4347 0.7667 0.047 Uiso 1 1 calc R . . C21 C 0.91636(17) 0.3045(2) 0.83245(15) 0.0387(6) Uani 1 1 d . . . H21 H 0.9547 0.3593 0.8669 0.046 Uiso 1 1 calc R . . C22 C 0.93087(16) 0.1819(2) 0.84063(14) 0.0344(5) Uani 1 1 d . . . H22 H 0.9804 0.1529 0.8801 0.041 Uiso 1 1 calc R . . C23 C 0.87398(14) 0.0973(2) 0.79181(13) 0.0286(5) Uani 1 1 d . . . C24 C 0.88706(15) -0.0333(2) 0.80062(13) 0.0292(5) Uani 1 1 d . . . C25 C 0.95489(16) -0.0853(2) 0.86080(14) 0.0352(5) Uani 1 1 d . . . H25 H 0.9963 -0.0337 0.8951 0.042 Uiso 1 1 calc R . . C26 C 0.96203(18) -0.2086(3) 0.87059(16) 0.0423(6) Uani 1 1 d . . . H26 H 1.0074 -0.2416 0.9122 0.051 Uiso 1 1 calc R . . C27 C 0.9031(2) -0.2867(3) 0.81988(18) 0.0455(6) Uani 1 1 d . . . H27 H 0.9088 -0.3723 0.8267 0.055 Uiso 1 1 calc R . . C28 C 0.83679(18) -0.2392(2) 0.76004(15) 0.0378(5) Uani 1 1 d . . . H28 H 0.7970 -0.2924 0.7255 0.045 Uiso 1 1 calc R . . C29 C 0.82732(15) -0.1125(2) 0.74946(13) 0.0295(5) Uani 1 1 d . . . C30 C 0.75325(15) -0.0626(2) 0.69157(13) 0.0294(5) Uani 1 1 d . . . H30 H 0.7136 -0.1164 0.6575 0.035 Uiso 1 1 calc R . . C31 C 0.5540(6) 0.5739(6) 0.7021(3) 0.127(2) Uani 1 1 d . . . C32 C 0.5817(5) 0.5146(5) 0.6345(5) 0.137(3) Uani 1 1 d . . . H32A H 0.5521 0.5535 0.5839 0.206 Uiso 1 1 calc R . . H32B H 0.5611 0.4295 0.6358 0.206 Uiso 1 1 calc R . . H32C H 0.6518 0.5182 0.6353 0.206 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0367(9) 0.0355(9) 0.0400(9) -0.0036(7) 0.0006(7) 0.0107(7) O2 0.0282(8) 0.0368(9) 0.0344(8) -0.0020(7) -0.0011(6) -0.0031(7) O3 0.0268(8) 0.0425(9) 0.0270(7) 0.0010(6) 0.0010(6) 0.0094(7) O4 0.259(8) 0.089(4) 0.238(8) 0.000 0.202(7) 0.000 O5 0.166(6) 0.060(3) 0.104(5) 0.001(3) -0.061(5) -0.033(4) N1 0.0257(9) 0.0326(10) 0.0243(8) 0.0015(7) 0.0023(7) 0.0017(7) N2 0.0271(9) 0.0400(11) 0.0274(9) -0.0008(8) 0.0019(7) 0.0036(8) C1 0.0239(10) 0.0280(10) 0.0288(10) 0.0001(8) -0.0010(8) 0.0023(8) C2 0.0262(10) 0.0259(10) 0.0238(10) -0.0001(8) 0.0004(8) -0.0007(8) C3 0.0279(10) 0.0338(11) 0.0247(10) 0.0007(8) -0.0031(8) 0.0028(9) C4 0.0348(12) 0.0421(13) 0.0231(10) -0.0006(9) -0.0020(9) 0.0038(10) C5 0.0293(11) 0.0362(12) 0.0251(10) -0.0011(9) 0.0037(8) 0.0027(9) C6 0.0240(10) 0.0267(10) 0.0264(10) 0.0011(8) 0.0003(8) 0.0000(8) C7 0.0256(10) 0.0241(10) 0.0249(10) -0.0002(8) 0.0010(8) -0.0018(8) C8 0.0246(10) 0.0325(11) 0.0244(10) 0.0004(8) -0.0006(8) -0.0008(8) C9 0.0301(11) 0.0438(13) 0.0222(10) -0.0009(9) -0.0003(8) 0.0025(9) C10 0.0290(11) 0.0404(13) 0.0314(11) 0.0025(9) 0.0053(9) 0.0093(9) C11 0.0263(10) 0.0341(11) 0.0302(11) 0.0021(9) 0.0074(8) 0.0033(9) C12 0.0355(12) 0.0314(12) 0.0428(13) 0.0012(10) -0.0039(10) 0.0013(9) C13 0.0381(13) 0.0398(14) 0.0501(15) 0.0082(11) -0.0096(11) 0.0002(11) C14 0.0396(13) 0.0351(13) 0.0503(15) 0.0106(11) 0.0041(11) 0.0083(10) C15 0.0554(16) 0.0299(12) 0.0511(15) -0.0009(11) 0.0043(12) 0.0018(11) C16 0.0449(14) 0.0392(13) 0.0409(13) -0.0042(11) -0.0033(11) -0.0012(11) C17 0.0240(10) 0.0367(11) 0.0209(9) -0.0003(8) 0.0025(8) -0.0003(8) C18 0.0239(10) 0.0363(12) 0.0229(10) 0.0007(8) 0.0023(8) -0.0016(8) C19 0.0324(11) 0.0370(12) 0.0321(11) 0.0020(9) -0.0011(9) -0.0013(9) C20 0.0383(13) 0.0352(13) 0.0428(13) 0.0008(10) 0.0000(10) -0.0034(10) C21 0.0326(12) 0.0448(14) 0.0377(13) -0.0034(10) -0.0022(10) -0.0111(10) C22 0.0262(10) 0.0442(13) 0.0320(11) 0.0005(10) -0.0012(9) -0.0035(9) C23 0.0220(10) 0.0412(12) 0.0230(10) 0.0011(8) 0.0038(8) -0.0001(9) C24 0.0221(9) 0.0417(13) 0.0240(10) 0.0012(9) 0.0039(8) 0.0017(9) C25 0.0267(11) 0.0460(14) 0.0319(11) 0.0021(10) -0.0014(9) 0.0036(10) C26 0.0357(12) 0.0479(15) 0.0416(13) 0.0063(11) -0.0050(10) 0.0113(11) C27 0.0478(15) 0.0383(14) 0.0493(15) 0.0028(11) -0.0005(12) 0.0100(12) C28 0.0391(13) 0.0371(13) 0.0365(12) -0.0019(10) -0.0007(10) 0.0036(10) C29 0.0274(10) 0.0367(12) 0.0245(10) 0.0006(9) 0.0032(8) 0.0033(9) C30 0.0264(10) 0.0378(12) 0.0234(10) -0.0031(9) 0.0000(8) -0.0003(9) C31 0.222(8) 0.088(4) 0.073(3) 0.017(3) 0.017(4) 0.004(4) C32 0.153(5) 0.085(4) 0.191(7) 0.026(4) 0.100(5) 0.008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.226(2) . ? O2 N1 1.226(2) . ? O3 C1 1.352(2) . ? O3 C10 1.463(3) . ? O4 C31 1.326(7) . ? O4 C31 1.326(7) 2_656 ? O5 C31 1.187(8) . ? N1 C6 1.470(3) . ? N2 C1 1.301(3) . ? N2 C9 1.360(3) . ? C1 C2 1.439(3) . ? C2 C3 1.413(3) . ? C2 C7 1.427(3) . ? C3 C4 1.370(3) . ? C3 H3 0.9500 . ? C4 C5 1.404(3) . ? C4 H4 0.9500 . ? C5 C6 1.371(3) . ? C5 H5 0.9500 . ? C6 C7 1.418(3) . ? C7 C8 1.434(3) . ? C8 C9 1.364(3) . ? C8 C17 1.497(3) . ? C9 H9 0.9500 . ? C10 C11 1.496(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.387(3) . ? C11 C16 1.388(3) . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 C14 1.377(4) . ? C13 H13 0.9500 . ? C14 C15 1.382(4) . ? C14 H14 0.9500 . ? C15 C16 1.389(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C30 1.359(3) . ? C17 C18 1.452(3) . ? C18 C19 1.413(3) . ? C18 C23 1.419(3) . ? C19 C20 1.374(3) . ? C19 H19 0.9500 . ? C20 C21 1.405(3) . ? C20 H20 0.9500 . ? C21 C22 1.367(4) . ? C21 H21 0.9500 . ? C22 C23 1.414(3) . ? C22 H22 0.9500 . ? C23 C24 1.454(3) . ? C24 C25 1.412(3) . ? C24 C29 1.417(3) . ? C25 C26 1.368(4) . ? C25 H25 0.9500 . ? C26 C27 1.400(4) . ? C26 H26 0.9500 . ? C27 C28 1.377(3) . ? C27 H27 0.9500 . ? C28 C29 1.409(3) . ? C28 H28 0.9500 . ? C29 C30 1.436(3) . ? C30 H30 0.9500 . ? C31 C32 1.362(8) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? 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 O3 C10 116.56(16) . . ? C31 O4 C31 117.7(7) . 2_656 ? O1 N1 O2 124.69(18) . . ? O1 N1 C6 118.40(18) . . ? O2 N1 C6 116.85(17) . . ? C1 N2 C9 117.29(19) . . ? N2 C1 O3 120.26(19) . . ? N2 C1 C2 123.97(19) . . ? O3 C1 C2 115.77(18) . . ? C3 C2 C7 121.43(19) . . ? C3 C2 C1 121.39(19) . . ? C7 C2 C1 117.18(18) . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.0(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 119.6(2) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 123.44(19) . . ? C5 C6 N1 115.37(18) . . ? C7 C6 N1 120.99(17) . . ? C6 C7 C2 115.10(18) . . ? C6 C7 C8 126.63(19) . . ? C2 C7 C8 118.23(18) . . ? C9 C8 C7 116.99(19) . . ? C9 C8 C17 116.34(18) . . ? C7 C8 C17 126.60(19) . . ? N2 C9 C8 126.3(2) . . ? N2 C9 H9 116.9 . . ? C8 C9 H9 116.9 . . ? O3 C10 C11 108.43(17) . . ? O3 C10 H10A 110.0 . . ? C11 C10 H10A 110.0 . . ? O3 C10 H10B 110.0 . . ? C11 C10 H10B 110.0 . . ? H10A C10 H10B 108.4 . . ? C12 C11 C16 118.6(2) . . ? C12 C11 C10 121.5(2) . . ? C16 C11 C10 119.9(2) . . ? C11 C12 C13 120.4(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 120.6(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.4(2) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 120.0(2) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C11 C16 C15 120.9(2) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C30 C17 C18 119.72(19) . . ? C30 C17 C8 120.70(19) . . ? C18 C17 C8 119.21(19) . . ? C19 C18 C23 119.1(2) . . ? C19 C18 C17 120.86(19) . . ? C23 C18 C17 120.0(2) . . ? C20 C19 C18 121.1(2) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C21 119.8(2) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 120.2(2) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 121.6(2) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? C22 C23 C18 118.2(2) . . ? C22 C23 C24 122.5(2) . . ? C18 C23 C24 119.35(19) . . ? C25 C24 C29 118.2(2) . . ? C25 C24 C23 122.5(2) . . ? C29 C24 C23 119.26(19) . . ? C26 C25 C24 121.2(2) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C27 120.5(2) . . ? C25 C26 H26 119.7 . . ? C27 C26 H26 119.7 . . ? C28 C27 C26 119.8(2) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C27 C28 C29 120.6(2) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.7 . . ? C28 C29 C24 119.6(2) . . ? C28 C29 C30 120.7(2) . . ? C24 C29 C30 119.6(2) . . ? C17 C30 C29 122.0(2) . . ? C17 C30 H30 119.0 . . ? C29 C30 H30 119.0 . . ? O5 C31 O4 112.3(7) . . ? O5 C31 C32 130.8(8) . . ? O4 C31 C32 116.5(6) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 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 N2 C1 O3 -178.0(2) . . . . ? C9 N2 C1 C2 0.9(3) . . . . ? C10 O3 C1 N2 -1.9(3) . . . . ? C10 O3 C1 C2 179.11(19) . . . . ? N2 C1 C2 C3 177.3(2) . . . . ? O3 C1 C2 C3 -3.7(3) . . . . ? N2 C1 C2 C7 -2.9(3) . . . . ? O3 C1 C2 C7 176.01(18) . . . . ? C7 C2 C3 C4 2.5(3) . . . . ? C1 C2 C3 C4 -177.7(2) . . . . ? C2 C3 C4 C5 -2.8(4) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C4 C5 C6 C7 3.8(3) . . . . ? C4 C5 C6 N1 -171.1(2) . . . . ? O1 N1 C6 C5 -58.1(3) . . . . ? O2 N1 C6 C5 119.1(2) . . . . ? O1 N1 C6 C7 126.8(2) . . . . ? O2 N1 C6 C7 -56.0(3) . . . . ? C5 C6 C7 C2 -3.9(3) . . . . ? N1 C6 C7 C2 170.73(18) . . . . ? C5 C6 C7 C8 173.8(2) . . . . ? N1 C6 C7 C8 -11.5(3) . . . . ? C3 C2 C7 C6 0.7(3) . . . . ? C1 C2 C7 C6 -179.03(19) . . . . ? C3 C2 C7 C8 -177.3(2) . . . . ? C1 C2 C7 C8 3.0(3) . . . . ? C6 C7 C8 C9 -179.0(2) . . . . ? C2 C7 C8 C9 -1.3(3) . . . . ? C6 C7 C8 C17 -2.2(4) . . . . ? C2 C7 C8 C17 175.4(2) . . . . ? C1 N2 C9 C8 1.2(4) . . . . ? C7 C8 C9 N2 -0.9(4) . . . . ? C17 C8 C9 N2 -178.0(2) . . . . ? C1 O3 C10 C11 150.78(19) . . . . ? O3 C10 C11 C12 72.5(3) . . . . ? O3 C10 C11 C16 -109.0(2) . . . . ? C16 C11 C12 C13 0.8(4) . . . . ? C10 C11 C12 C13 179.4(2) . . . . ? C11 C12 C13 C14 -0.9(4) . . . . ? C12 C13 C14 C15 0.4(4) . . . . ? C13 C14 C15 C16 0.2(4) . . . . ? C12 C11 C16 C15 -0.3(4) . . . . ? C10 C11 C16 C15 -178.9(2) . . . . ? C14 C15 C16 C11 -0.2(4) . . . . ? C9 C8 C17 C30 104.3(3) . . . . ? C7 C8 C17 C30 -72.5(3) . . . . ? C9 C8 C17 C18 -68.7(3) . . . . ? C7 C8 C17 C18 114.5(2) . . . . ? C30 C17 C18 C19 177.9(2) . . . . ? C8 C17 C18 C19 -9.0(3) . . . . ? C30 C17 C18 C23 -2.4(3) . . . . ? C8 C17 C18 C23 170.68(19) . . . . ? C23 C18 C19 C20 -1.4(3) . . . . ? C17 C18 C19 C20 178.3(2) . . . . ? C18 C19 C20 C21 -0.2(4) . . . . ? C19 C20 C21 C22 1.6(4) . . . . ? C20 C21 C22 C23 -1.4(4) . . . . ? C21 C22 C23 C18 -0.3(3) . . . . ? C21 C22 C23 C24 -178.8(2) . . . . ? C19 C18 C23 C22 1.6(3) . . . . ? C17 C18 C23 C22 -178.04(19) . . . . ? C19 C18 C23 C24 -179.8(2) . . . . ? C17 C18 C23 C24 0.6(3) . . . . ? C22 C23 C24 C25 2.6(3) . . . . ? C18 C23 C24 C25 -175.9(2) . . . . ? C22 C23 C24 C29 -180.0(2) . . . . ? C18 C23 C24 C29 1.5(3) . . . . ? C29 C24 C25 C26 -1.0(3) . . . . ? C23 C24 C25 C26 176.5(2) . . . . ? C24 C25 C26 C27 1.2(4) . . . . ? C25 C26 C27 C28 -0.5(4) . . . . ? C26 C27 C28 C29 -0.3(4) . . . . ? C27 C28 C29 C24 0.4(4) . . . . ? C27 C28 C29 C30 -175.1(2) . . . . ? C25 C24 C29 C28 0.2(3) . . . . ? C23 C24 C29 C28 -177.3(2) . . . . ? C25 C24 C29 C30 175.8(2) . . . . ? C23 C24 C29 C30 -1.8(3) . . . . ? C18 C17 C30 C29 2.2(3) . . . . ? C8 C17 C30 C29 -170.81(19) . . . . ? C28 C29 C30 C17 175.4(2) . . . . ? C24 C29 C30 C17 -0.1(3) . . . . ? C31 O4 C31 O5 28.4(5) 2_656 . . . ? C31 O4 C31 C32 -157.8(8) 2_656 . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.442 _refine_diff_density_min -1.102 _refine_diff_density_rms 0.108