# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'McBurney, Roy' 'Slawin, Alexandra' 'Smart, Laura' 'Yu, Yanping' 'Walton, J' _publ_contact_author_name 'Dr J Walton' _publ_contact_author_email JCW@ST-ANDREWS.AC.UK _publ_section_title ; UV Promoted Phenanthridine Syntheses from Oxime Carbonate Derived Iminyl Radicals ; # Attachment '- 1b.cif' data_1b _database_code_depnum_ccdc_archive 'CCDC 824855' #TrackingRef '- 1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration unk _chemical_formula_moiety 'C21 H17 N O4' _chemical_formula_sum 'C21 H17 N O4' _chemical_formula_weight 347.36 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5885(19) _cell_length_b 13.388(3) _cell_length_c 15.162(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1743.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6377 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.851 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11104 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.33 _reflns_number_total 3181 _reflns_number_gt 2846 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0385P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(9) _refine_ls_number_reflns 3181 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 C1 C 0.31086(19) 0.50198(11) 0.37441(11) 0.0247(4) Uani 1 1 d . . . C2 C 0.2931(2) 0.40268(12) 0.34502(11) 0.0251(4) Uani 1 1 d . . . C3 C 0.3260(2) 0.32359(13) 0.40258(11) 0.0314(4) Uani 1 1 d . . . H3A H 0.3120 0.2567 0.3832 0.038 Uiso 1 1 calc R . . C4 C 0.3786(2) 0.34161(13) 0.48723(11) 0.0338(5) Uani 1 1 d . . . H4A H 0.3985 0.2876 0.5262 0.041 Uiso 1 1 calc R . . C5 C 0.4021(2) 0.43916(14) 0.51476(12) 0.0346(5) Uani 1 1 d . . . H5A H 0.4411 0.4519 0.5723 0.042 Uiso 1 1 calc R . . C6 C 0.3693(2) 0.51796(13) 0.45913(12) 0.0298(4) Uani 1 1 d . . . H6A H 0.3868 0.5844 0.4789 0.036 Uiso 1 1 calc R . . C7 C 0.2671(2) 0.58851(11) 0.31800(10) 0.0236(4) Uani 1 1 d . . . C8 C 0.1116(2) 0.59991(12) 0.28991(11) 0.0261(4) Uani 1 1 d . . . H8A H 0.0354 0.5525 0.3076 0.031 Uiso 1 1 calc R . . C9 C 0.0690(2) 0.67932(13) 0.23692(10) 0.0270(4) Uani 1 1 d . . . H9A H -0.0361 0.6863 0.2185 0.032 Uiso 1 1 calc R . . C10 C 0.1793(2) 0.74887(12) 0.21062(11) 0.0273(4) Uani 1 1 d . . . O10 O 0.12432(14) 0.82566(8) 0.15882(8) 0.0342(3) Uani 1 1 d . . . C11 C 0.3333(2) 0.73914(12) 0.23774(11) 0.0280(4) Uani 1 1 d . . . H11A H 0.4092 0.7864 0.2195 0.034 Uiso 1 1 calc R . . C12 C 0.3750(2) 0.65944(12) 0.29189(11) 0.0261(4) Uani 1 1 d . . . H12A H 0.4798 0.6536 0.3113 0.031 Uiso 1 1 calc R . . C13 C 0.24726(19) 0.38275(11) 0.25382(11) 0.0263(4) Uani 1 1 d . . . H13A H 0.2116 0.4359 0.2175 0.032 Uiso 1 1 calc R . . N14 N 0.25485(17) 0.29472(9) 0.22289(8) 0.0262(3) Uani 1 1 d . . . O15 O 0.19839(15) 0.29774(7) 0.13300(7) 0.0283(3) Uani 1 1 d . . . C16 C 0.2067(2) 0.20612(12) 0.09529(11) 0.0250(4) Uani 1 1 d . . . O16 O 0.25677(14) 0.13157(8) 0.12582(7) 0.0296(3) Uani 1 1 d . . . O17 O 0.14388(15) 0.21847(8) 0.01462(7) 0.0318(3) Uani 1 1 d . . . C18 C 0.1497(2) 0.13385(12) -0.04107(11) 0.0277(4) Uani 1 1 d . . . C19 C 0.2805(2) 0.11890(13) -0.09121(11) 0.0326(4) Uani 1 1 d . . . H19A H 0.3677 0.1622 -0.0862 0.039 Uiso 1 1 calc R . . C20 C 0.2825(2) 0.03885(14) -0.14949(12) 0.0377(5) Uani 1 1 d . . . H20A H 0.3721 0.0273 -0.1848 0.045 Uiso 1 1 calc R . . C21 C 0.1563(3) -0.02386(14) -0.15662(13) 0.0392(5) Uani 1 1 d . . . H21A H 0.1588 -0.0785 -0.1965 0.047 Uiso 1 1 calc R . . C22 C 0.0251(3) -0.00680(14) -0.10509(13) 0.0397(5) Uani 1 1 d . . . H22A H -0.0624 -0.0499 -0.1099 0.048 Uiso 1 1 calc R . . C23 C 0.0214(2) 0.07333(13) -0.04645(12) 0.0333(4) Uani 1 1 d . . . H23A H -0.0679 0.0857 -0.0111 0.040 Uiso 1 1 calc R . . C24 C 0.2376(2) 0.88852(13) 0.11733(12) 0.0420(5) Uani 1 1 d . . . H24A H 0.2951 0.9256 0.1625 0.063 Uiso 1 1 calc R . . H24B H 0.1850 0.9356 0.0778 0.063 Uiso 1 1 calc R . . H24C H 0.3102 0.8473 0.0832 0.063 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 C1 0.0227(9) 0.0256(9) 0.0257(9) -0.0048(7) 0.0014(8) -0.0014(8) C2 0.0263(10) 0.0262(8) 0.0227(9) -0.0015(7) 0.0010(8) -0.0025(8) C3 0.0392(11) 0.0263(9) 0.0288(10) 0.0003(8) 0.0013(9) -0.0031(9) C4 0.0405(12) 0.0344(10) 0.0265(10) 0.0046(8) -0.0003(9) -0.0015(9) C5 0.0403(12) 0.0404(10) 0.0231(10) -0.0018(8) -0.0036(9) -0.0016(10) C6 0.0342(11) 0.0292(9) 0.0262(10) -0.0052(8) -0.0036(9) -0.0014(9) C7 0.0280(10) 0.0220(8) 0.0208(9) -0.0046(7) 0.0001(7) 0.0008(8) C8 0.0261(10) 0.0252(9) 0.0269(9) -0.0048(7) 0.0000(8) 0.0005(8) C9 0.0236(9) 0.0297(9) 0.0276(9) -0.0061(8) -0.0003(8) 0.0031(8) C10 0.0359(10) 0.0215(9) 0.0246(9) -0.0041(7) -0.0014(8) 0.0040(9) O10 0.0406(8) 0.0262(6) 0.0358(7) 0.0030(5) -0.0022(6) 0.0050(6) C11 0.0291(10) 0.0231(9) 0.0318(10) -0.0031(7) 0.0014(8) -0.0029(8) C12 0.0246(10) 0.0263(9) 0.0272(9) -0.0045(7) -0.0030(8) 0.0010(8) C13 0.0309(10) 0.0215(8) 0.0265(9) 0.0007(7) 0.0002(8) 0.0001(8) N14 0.0335(9) 0.0258(7) 0.0194(7) -0.0015(6) -0.0050(6) -0.0016(7) O15 0.0413(8) 0.0203(6) 0.0232(6) -0.0025(5) -0.0055(6) 0.0009(5) C16 0.0283(10) 0.0235(8) 0.0231(9) -0.0011(7) -0.0026(8) -0.0010(8) O16 0.0374(8) 0.0225(6) 0.0288(7) -0.0012(5) -0.0079(6) 0.0046(6) O17 0.0474(9) 0.0247(6) 0.0235(7) -0.0038(5) -0.0098(6) 0.0065(6) C18 0.0401(12) 0.0205(9) 0.0225(9) -0.0011(7) -0.0078(9) 0.0051(8) C19 0.0331(11) 0.0340(10) 0.0306(10) 0.0010(8) -0.0015(9) 0.0004(9) C20 0.0393(12) 0.0433(11) 0.0306(10) -0.0038(9) 0.0006(9) 0.0131(10) C21 0.0543(14) 0.0311(10) 0.0321(11) -0.0067(8) -0.0106(10) 0.0099(10) C22 0.0472(13) 0.0331(10) 0.0389(11) -0.0043(9) -0.0100(10) -0.0038(10) C23 0.0322(11) 0.0350(10) 0.0326(10) -0.0005(8) -0.0025(9) 0.0000(9) C24 0.0543(14) 0.0300(10) 0.0418(12) 0.0098(9) -0.0049(11) -0.0027(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.396(2) . ? C1 C2 1.410(2) . ? C1 C7 1.488(2) . ? C2 C3 1.401(2) . ? C2 C13 1.462(2) . ? C3 C4 1.382(2) . ? C3 H3A 0.9500 . ? C4 C5 1.386(2) . ? C4 H4A 0.9500 . ? C5 C6 1.380(2) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C12 1.385(2) . ? C7 C8 1.410(2) . ? C8 C9 1.382(2) . ? C8 H8A 0.9500 . ? C9 C10 1.387(2) . ? C9 H9A 0.9500 . ? C10 O10 1.3773(19) . ? C10 C11 1.391(3) . ? O10 C24 1.432(2) . ? C11 C12 1.393(2) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 N14 1.2700(19) . ? C13 H13A 0.9500 . ? N14 O15 1.4473(17) . ? O15 C16 1.3551(18) . ? C16 O16 1.1814(18) . ? C16 O17 1.3468(19) . ? O17 C18 1.4139(19) . ? C18 C19 1.371(2) . ? C18 C23 1.370(3) . ? C19 C20 1.389(2) . ? C19 H19A 0.9500 . ? C20 C21 1.375(3) . ? C20 H20A 0.9500 . ? C21 C22 1.391(3) . ? C21 H21A 0.9500 . ? C22 C23 1.394(2) . ? C22 H22A 0.9500 . ? C23 H23A 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 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 C6 C1 C2 118.31(15) . . ? C6 C1 C7 120.03(14) . . ? C2 C1 C7 121.66(14) . . ? C3 C2 C1 119.59(15) . . ? C3 C2 C13 120.36(15) . . ? C1 C2 C13 119.99(14) . . ? C4 C3 C2 120.84(16) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C3 C4 C5 119.46(17) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C6 C5 C4 120.44(17) . . ? C6 C5 H5A 119.8 . . ? C4 C5 H5A 119.8 . . ? C5 C6 C1 121.25(16) . . ? C5 C6 H6A 119.4 . . ? C1 C6 H6A 119.4 . . ? C12 C7 C8 118.26(15) . . ? C12 C7 C1 121.91(15) . . ? C8 C7 C1 119.83(15) . . ? C9 C8 C7 120.64(16) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C8 C9 C10 120.19(16) . . ? C8 C9 H9A 119.9 . . ? C10 C9 H9A 119.9 . . ? O10 C10 C9 115.52(15) . . ? O10 C10 C11 124.38(16) . . ? C9 C10 C11 120.09(16) . . ? C10 O10 C24 117.14(14) . . ? C12 C11 C10 119.40(16) . . ? C12 C11 H11A 120.3 . . ? C10 C11 H11A 120.3 . . ? C7 C12 C11 121.40(16) . . ? C7 C12 H12A 119.3 . . ? C11 C12 H12A 119.3 . . ? N14 C13 C2 120.30(15) . . ? N14 C13 H13A 119.8 . . ? C2 C13 H13A 119.8 . . ? C13 N14 O15 107.73(12) . . ? C16 O15 N14 110.76(11) . . ? O16 C16 O17 127.26(15) . . ? O16 C16 O15 128.21(15) . . ? O17 C16 O15 104.53(13) . . ? C16 O17 C18 115.45(13) . . ? C19 C18 C23 122.67(16) . . ? C19 C18 O17 118.49(16) . . ? C23 C18 O17 118.74(17) . . ? C18 C19 C20 118.38(17) . . ? C18 C19 H19A 120.8 . . ? C20 C19 H19A 120.8 . . ? C21 C20 C19 120.75(18) . . ? C21 C20 H20A 119.6 . . ? C19 C20 H20A 119.6 . . ? C20 C21 C22 119.64(17) . . ? C20 C21 H21A 120.2 . . ? C22 C21 H21A 120.2 . . ? C21 C22 C23 120.23(19) . . ? C21 C22 H22A 119.9 . . ? C23 C22 H22A 119.9 . . ? C18 C23 C22 118.34(18) . . ? C18 C23 H23A 120.8 . . ? C22 C23 H23A 120.8 . . ? O10 C24 H24A 109.5 . . ? O10 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O10 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 C6 C1 C2 C3 3.5(2) . . . . ? C7 C1 C2 C3 -175.70(16) . . . . ? C6 C1 C2 C13 -173.87(15) . . . . ? C7 C1 C2 C13 7.0(3) . . . . ? C1 C2 C3 C4 -1.3(3) . . . . ? C13 C2 C3 C4 176.02(18) . . . . ? C2 C3 C4 C5 -1.3(3) . . . . ? C3 C4 C5 C6 1.8(3) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C2 C1 C6 C5 -3.1(3) . . . . ? C7 C1 C6 C5 176.10(17) . . . . ? C6 C1 C7 C12 61.8(2) . . . . ? C2 C1 C7 C12 -119.05(18) . . . . ? C6 C1 C7 C8 -118.04(18) . . . . ? C2 C1 C7 C8 61.1(2) . . . . ? C12 C7 C8 C9 0.7(2) . . . . ? C1 C7 C8 C9 -179.47(14) . . . . ? C7 C8 C9 C10 0.1(2) . . . . ? C8 C9 C10 O10 -179.25(14) . . . . ? C8 C9 C10 C11 -0.2(2) . . . . ? C9 C10 O10 C24 -169.05(14) . . . . ? C11 C10 O10 C24 12.0(2) . . . . ? O10 C10 C11 C12 178.51(14) . . . . ? C9 C10 C11 C12 -0.4(2) . . . . ? C8 C7 C12 C11 -1.4(2) . . . . ? C1 C7 C12 C11 178.80(14) . . . . ? C10 C11 C12 C7 1.2(2) . . . . ? C3 C2 C13 N14 -8.5(3) . . . . ? C1 C2 C13 N14 168.81(16) . . . . ? C2 C13 N14 O15 178.39(14) . . . . ? C13 N14 O15 C16 178.64(15) . . . . ? N14 O15 C16 O16 -2.8(2) . . . . ? N14 O15 C16 O17 176.94(12) . . . . ? O16 C16 O17 C18 -4.9(3) . . . . ? O15 C16 O17 C18 175.40(14) . . . . ? C16 O17 C18 C19 -86.57(19) . . . . ? C16 O17 C18 C23 97.02(19) . . . . ? C23 C18 C19 C20 -0.2(3) . . . . ? O17 C18 C19 C20 -176.47(14) . . . . ? C18 C19 C20 C21 0.0(3) . . . . ? C19 C20 C21 C22 0.2(3) . . . . ? C20 C21 C22 C23 -0.1(3) . . . . ? C19 C18 C23 C22 0.3(3) . . . . ? O17 C18 C23 C22 176.57(15) . . . . ? C21 C22 C23 C18 -0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.147 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.039 # Attachment '- 4f.cif' data_4f _database_code_depnum_ccdc_archive 'CCDC 824856' #TrackingRef '- 4f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration ad _chemical_formula_moiety 'C17 H16 Cl N O3' _chemical_formula_sum 'C17 H16 Cl N O3' _chemical_formula_weight 317.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 24.039(14) _cell_length_b 7.017(5) _cell_length_c 19.280(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.759(14) _cell_angle_gamma 90.00 _cell_volume 3236(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1443 _cell_measurement_theta_min 21.3 _cell_measurement_theta_max 68.6 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 2.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.756 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20550 _diffrn_reflns_av_R_equivalents 0.2075 _diffrn_reflns_av_sigmaI/netI 0.1329 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 68.08 _reflns_number_total 5616 _reflns_number_gt 3630 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0053(8) _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 0.09(5) _refine_ls_number_reflns 5616 _refine_ls_number_parameters 400 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1656 _refine_ls_R_factor_gt 0.1423 _refine_ls_wR_factor_ref 0.3976 _refine_ls_wR_factor_gt 0.3619 _refine_ls_goodness_of_fit_ref 1.203 _refine_ls_restrained_S_all 1.203 _refine_ls_shift/su_max 0.075 _refine_ls_shift/su_mean 0.020 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 C1 C 0.8610(3) 0.9547(13) 0.3978(4) 0.0730(19) Uani 1 1 d . . . C2 C 0.8789(3) 1.0488(14) 0.3405(4) 0.079(2) Uani 1 1 d . . . C3 C 0.9185(3) 1.1961(14) 0.3527(5) 0.085(2) Uani 1 1 d . . . H3A H 0.9316 1.2597 0.3140 0.103 Uiso 1 1 calc R . . C4 C 0.9388(3) 1.2502(16) 0.4186(5) 0.089(3) Uani 1 1 d . . . H4A H 0.9646 1.3527 0.4256 0.107 Uiso 1 1 calc R . . C5 C 0.9212(4) 1.1534(17) 0.4747(5) 0.092(3) Uani 1 1 d . . . H5A H 0.9362 1.1849 0.5207 0.110 Uiso 1 1 calc R . . C6 C 0.8823(3) 1.0130(14) 0.4641(4) 0.078(2) Uani 1 1 d . . . H6A H 0.8693 0.9525 0.5034 0.094 Uiso 1 1 calc R . . C7 C 0.8206(3) 0.7902(14) 0.3907(4) 0.0744(19) Uani 1 1 d . . . C8 C 0.8299(3) 0.6323(15) 0.3498(5) 0.086(2) Uani 1 1 d . . . H8A H 0.8617 0.6302 0.3242 0.103 Uiso 1 1 calc R . . C9 C 0.7943(3) 0.4802(16) 0.3455(5) 0.091(2) Uani 1 1 d . . . H9A H 0.8010 0.3751 0.3165 0.109 Uiso 1 1 calc R . . C10 C 0.7483(3) 0.4792(14) 0.3838(5) 0.084(2) Uani 1 1 d . . . Cl10 Cl 0.70158(9) 0.2903(4) 0.37836(11) 0.0966(8) Uani 1 1 d . . . C11 C 0.7377(3) 0.6433(17) 0.4228(4) 0.088(2) Uani 1 1 d . . . H11A H 0.7048 0.6496 0.4463 0.105 Uiso 1 1 calc R . . C12 C 0.7740(3) 0.7924(16) 0.4271(4) 0.079(2) Uani 1 1 d . . . H12A H 0.7672 0.8991 0.4554 0.095 Uiso 1 1 calc R . . C13 C 0.8571(3) 1.0053(14) 0.2692(5) 0.080(2) Uani 1 1 d . . . N14 N 0.8960(3) 0.9810(14) 0.2262(3) 0.089(2) Uani 1 1 d . . . O15 O 0.8696(2) 0.9536(11) 0.1574(3) 0.0904(17) Uani 1 1 d . . . C16 C 0.9092(4) 0.9266(16) 0.1111(5) 0.093(3) Uani 1 1 d . . . O16 O 0.9594(2) 0.9368(12) 0.1254(3) 0.098(2) Uani 1 1 d . . . O17 O 0.8803(2) 0.8922(13) 0.0508(3) 0.107(2) Uani 1 1 d . . . C18 C 0.9135(5) 0.866(3) -0.0073(6) 0.125(5) Uani 1 1 d . . . H18A H 0.8927 0.7869 -0.0438 0.150 Uiso 1 1 calc R . . H18B H 0.9488 0.7990 0.0087 0.150 Uiso 1 1 calc R . . C19 C 0.9260(6) 1.056(3) -0.0362(6) 0.145(7) Uani 1 1 d . . . H19A H 0.9493 1.0406 -0.0748 0.217 Uiso 1 1 calc R . . H19B H 0.9461 1.1342 0.0004 0.217 Uiso 1 1 calc R . . H19C H 0.8910 1.1197 -0.0533 0.217 Uiso 1 1 calc R . . C20 C 0.7967(3) 0.9977(14) 0.2456(4) 0.082(2) Uani 1 1 d . . . H20A H 0.7867 1.1054 0.2145 0.124 Uiso 1 1 calc R . . H20B H 0.7752 1.0045 0.2861 0.124 Uiso 1 1 calc R . . H20C H 0.7882 0.8780 0.2206 0.124 Uiso 1 1 calc R . . C21 C 1.0646(3) 0.4447(15) 0.3134(5) 0.088(2) Uani 1 1 d . . . C22 C 1.0161(3) 0.5433(14) 0.2843(5) 0.086(2) Uani 1 1 d . . . C23 C 0.9933(4) 0.6913(14) 0.3241(6) 0.099(3) Uani 1 1 d . . . H23A H 0.9623 0.7636 0.3043 0.119 Uiso 1 1 calc R . . C24 C 1.0160(4) 0.7286(14) 0.3900(5) 0.092(3) Uani 1 1 d . . . H24A H 0.9996 0.8251 0.4159 0.110 Uiso 1 1 calc R . . C25 C 1.0619(4) 0.6316(16) 0.4208(5) 0.098(3) Uani 1 1 d . . . H25A H 1.0764 0.6577 0.4675 0.117 Uiso 1 1 calc R . . C26 C 1.0864(4) 0.4945(16) 0.3815(6) 0.098(3) Uani 1 1 d . . . H26A H 1.1191 0.4317 0.4015 0.118 Uiso 1 1 calc R . . C27 C 1.0907(3) 0.2803(17) 0.2789(4) 0.083(2) Uani 1 1 d . . . C28 C 1.0589(3) 0.1277(15) 0.2543(5) 0.089(2) Uani 1 1 d . . . H28A H 1.0198 0.1268 0.2587 0.107 Uiso 1 1 calc R . . C29 C 1.0829(4) -0.0242(16) 0.2234(5) 0.093(3) Uani 1 1 d . . . H29A H 1.0605 -0.1293 0.2069 0.112 Uiso 1 1 calc R . . C30 C 1.1404(3) -0.0250(18) 0.2159(5) 0.092(3) Uani 1 1 d . . . Cl30 Cl 1.17159(9) -0.2100(5) 0.17719(14) 0.1075(9) Uani 1 1 d . . . C31 C 1.1715(3) 0.1398(19) 0.2366(5) 0.101(3) Uani 1 1 d . . . H31A H 1.2099 0.1465 0.2292 0.121 Uiso 1 1 calc R . . C32 C 1.1466(3) 0.2928(18) 0.2677(5) 0.092(2) Uani 1 1 d . . . H32A H 1.1676 0.4039 0.2810 0.111 Uiso 1 1 calc R . . C33 C 0.9914(3) 0.5050(15) 0.2125(5) 0.088(2) Uani 1 1 d . . . N34 N 0.9374(3) 0.4905(14) 0.2087(4) 0.093(2) Uani 1 1 d . . . O35 O 0.9167(2) 0.4619(12) 0.1372(3) 0.0974(19) Uani 1 1 d . . . C36 C 0.8600(4) 0.4412(17) 0.1284(7) 0.103(3) Uani 1 1 d . . . O36 O 0.8297(3) 0.4458(17) 0.1760(4) 0.125(3) Uani 1 1 d . . . O37 O 0.8466(3) 0.4154(12) 0.0621(4) 0.108(2) Uani 1 1 d . . . C38 C 0.7878(4) 0.387(2) 0.0395(7) 0.128(5) Uani 1 1 d . . . H38A H 0.7751 0.2633 0.0571 0.154 Uiso 1 1 calc R . . H38B H 0.7653 0.4895 0.0583 0.154 Uiso 1 1 calc R . . C39 C 0.7803(6) 0.389(3) -0.0360(8) 0.147(6) Uani 1 1 d . . . H39A H 0.7407 0.3713 -0.0520 0.221 Uiso 1 1 calc R . . H39B H 0.8022 0.2860 -0.0541 0.221 Uiso 1 1 calc R . . H39C H 0.7931 0.5118 -0.0530 0.221 Uiso 1 1 calc R . . C40 C 1.0244(4) 0.4860(19) 0.1506(5) 0.098(3) Uani 1 1 d . . . H40A H 1.0144 0.3665 0.1262 0.147 Uiso 1 1 calc R . . H40B H 1.0644 0.4856 0.1665 0.147 Uiso 1 1 calc R . . H40C H 1.0159 0.5936 0.1189 0.147 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 C1 0.048(3) 0.070(5) 0.103(5) 0.003(4) 0.016(3) 0.008(4) C2 0.058(4) 0.094(6) 0.086(5) 0.000(4) 0.015(3) -0.002(4) C3 0.060(4) 0.073(5) 0.127(7) 0.000(5) 0.027(4) -0.002(4) C4 0.059(4) 0.096(7) 0.112(6) -0.016(5) 0.009(4) 0.006(4) C5 0.073(5) 0.102(7) 0.102(6) 0.000(5) 0.017(4) 0.006(5) C6 0.058(4) 0.085(6) 0.093(5) -0.014(4) 0.013(3) 0.019(4) C7 0.054(3) 0.080(5) 0.091(4) 0.009(4) 0.015(3) 0.017(4) C8 0.056(4) 0.079(6) 0.126(6) -0.003(5) 0.024(4) -0.003(4) C9 0.059(4) 0.092(7) 0.126(6) -0.003(5) 0.030(4) 0.004(5) C10 0.053(4) 0.074(5) 0.128(6) 0.020(5) 0.024(4) 0.002(4) Cl10 0.0825(13) 0.0937(16) 0.1161(15) -0.0033(13) 0.0220(10) -0.0215(13) C11 0.064(4) 0.103(7) 0.096(5) 0.013(5) 0.010(4) 0.017(5) C12 0.053(3) 0.090(6) 0.095(5) -0.003(5) 0.009(3) -0.004(4) C13 0.044(3) 0.084(6) 0.115(6) 0.019(5) 0.026(3) 0.006(4) N14 0.056(3) 0.119(7) 0.095(4) 0.009(4) 0.015(3) -0.009(4) O15 0.055(3) 0.119(5) 0.100(4) -0.013(4) 0.025(2) 0.005(3) C16 0.075(5) 0.099(7) 0.109(6) 0.000(5) 0.036(5) 0.003(5) O16 0.055(3) 0.131(6) 0.111(4) 0.003(4) 0.014(2) 0.003(4) O17 0.069(3) 0.160(8) 0.095(4) -0.008(4) 0.022(3) -0.005(4) C18 0.095(7) 0.192(15) 0.093(6) -0.014(8) 0.034(5) 0.000(8) C19 0.125(9) 0.216(19) 0.098(7) 0.022(9) 0.032(6) 0.069(11) C20 0.051(3) 0.091(6) 0.107(5) 0.007(5) 0.019(3) 0.011(4) C21 0.065(4) 0.086(6) 0.116(6) 0.017(5) 0.021(4) -0.013(5) C22 0.061(4) 0.089(6) 0.110(6) 0.001(5) 0.021(4) -0.019(4) C23 0.077(5) 0.066(6) 0.159(9) 0.005(5) 0.033(5) -0.003(5) C24 0.093(6) 0.077(6) 0.105(6) -0.011(5) 0.009(5) -0.012(5) C25 0.100(7) 0.084(7) 0.109(6) -0.017(5) 0.010(5) -0.008(6) C26 0.072(5) 0.086(7) 0.138(8) 0.002(6) 0.021(5) -0.024(5) C27 0.055(4) 0.094(6) 0.099(5) 0.010(5) 0.009(3) 0.003(4) C28 0.059(4) 0.087(6) 0.124(7) 0.012(5) 0.024(4) -0.003(4) C29 0.072(5) 0.089(7) 0.120(6) 0.013(5) 0.015(4) 0.008(5) C30 0.058(4) 0.114(8) 0.107(5) 0.007(6) 0.018(4) 0.022(5) Cl30 0.0766(12) 0.115(2) 0.1324(17) -0.0060(17) 0.0192(11) 0.0173(15) C31 0.057(4) 0.114(9) 0.133(7) 0.021(7) 0.015(4) 0.002(5) C32 0.056(4) 0.098(7) 0.122(6) 0.004(6) 0.005(4) -0.004(5) C33 0.061(4) 0.089(6) 0.116(6) 0.016(5) 0.015(4) 0.009(4) N34 0.067(4) 0.115(6) 0.100(5) -0.005(4) 0.019(3) 0.006(4) O35 0.065(3) 0.113(5) 0.115(4) 0.006(4) 0.018(3) -0.005(4) C36 0.060(4) 0.094(7) 0.157(9) -0.004(7) 0.025(5) -0.012(5) O36 0.067(3) 0.167(8) 0.143(5) -0.007(6) 0.023(3) -0.022(5) O37 0.075(4) 0.126(6) 0.121(5) -0.013(4) 0.006(3) -0.015(4) C38 0.064(5) 0.159(13) 0.159(10) 0.017(9) 0.005(6) -0.017(7) C39 0.098(8) 0.183(17) 0.159(11) -0.010(11) 0.006(7) 0.008(9) C40 0.079(5) 0.115(8) 0.101(6) 0.009(6) 0.017(4) -0.005(6) _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 C1 C6 1.390(11) . ? C1 C2 1.392(12) . ? C1 C7 1.505(12) . ? C2 C3 1.410(13) . ? C2 C13 1.454(13) . ? C3 C4 1.368(13) . ? C3 H3A 0.9500 . ? C4 C5 1.380(13) . ? C4 H4A 0.9500 . ? C5 C6 1.359(14) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C12 1.381(9) . ? C7 C8 1.391(13) . ? C8 C9 1.366(14) . ? C8 H8A 0.9500 . ? C9 C10 1.389(11) . ? C9 H9A 0.9500 . ? C10 C11 1.413(15) . ? C10 Cl10 1.733(9) . ? C11 C12 1.360(14) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 N14 1.321(10) . ? C13 C20 1.477(10) . ? N14 O15 1.425(9) . ? O15 C16 1.383(9) . ? C16 O16 1.211(10) . ? C16 O17 1.316(12) . ? O17 C18 1.453(11) . ? C18 C19 1.49(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C26 1.408(14) . ? C21 C22 1.422(13) . ? C21 C27 1.499(15) . ? C22 C23 1.432(14) . ? C22 C33 1.475(13) . ? C23 C24 1.357(15) . ? C23 H23A 0.9500 . ? C24 C25 1.380(14) . ? C24 H24A 0.9500 . ? C25 C26 1.391(15) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C27 C28 1.373(15) . ? C27 C32 1.385(11) . ? C28 C29 1.377(14) . ? C28 H28A 0.9500 . ? C29 C30 1.403(12) . ? C29 H29A 0.9500 . ? C30 C31 1.412(16) . ? C30 Cl30 1.708(11) . ? C31 C32 1.394(16) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? C33 N34 1.295(10) . ? C33 C40 1.503(13) . ? N34 O35 1.431(10) . ? O35 C36 1.363(10) . ? C36 O36 1.227(12) . ? C36 O37 1.300(13) . ? O37 C38 1.451(11) . ? C38 C39 1.449(18) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 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 C6 C1 C2 118.3(8) . . ? C6 C1 C7 119.0(7) . . ? C2 C1 C7 122.6(7) . . ? C1 C2 C3 118.2(8) . . ? C1 C2 C13 122.7(8) . . ? C3 C2 C13 119.0(8) . . ? C4 C3 C2 122.1(9) . . ? C4 C3 H3A 119.0 . . ? C2 C3 H3A 119.0 . . ? C3 C4 C5 118.8(9) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C6 C5 C4 119.9(9) . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? C5 C6 C1 122.5(9) . . ? C5 C6 H6A 118.7 . . ? C1 C6 H6A 118.7 . . ? C12 C7 C8 118.8(9) . . ? C12 C7 C1 119.6(8) . . ? C8 C7 C1 121.6(6) . . ? C9 C8 C7 121.3(7) . . ? C9 C8 H8A 119.3 . . ? C7 C8 H8A 119.3 . . ? C8 C9 C10 120.0(9) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C9 C10 C11 118.3(8) . . ? C9 C10 Cl10 121.2(8) . . ? C11 C10 Cl10 120.3(6) . . ? C12 C11 C10 120.7(7) . . ? C12 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C11 C12 C7 120.6(9) . . ? C11 C12 H12A 119.7 . . ? C7 C12 H12A 119.7 . . ? N14 C13 C2 114.2(7) . . ? N14 C13 C20 122.5(8) . . ? C2 C13 C20 123.2(7) . . ? C13 N14 O15 108.9(6) . . ? C16 O15 N14 110.4(6) . . ? O16 C16 O17 129.6(8) . . ? O16 C16 O15 125.4(9) . . ? O17 C16 O15 104.9(7) . . ? C16 O17 C18 114.9(7) . . ? O17 C18 C19 108.7(12) . . ? O17 C18 H18A 110.0 . . ? C19 C18 H18A 109.9 . . ? O17 C18 H18B 110.0 . . ? C19 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C13 C20 H20A 109.5 . . ? C13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C26 C21 C22 117.4(10) . . ? C26 C21 C27 118.2(9) . . ? C22 C21 C27 124.2(9) . . ? C21 C22 C23 118.9(9) . . ? C21 C22 C33 121.3(9) . . ? C23 C22 C33 119.7(9) . . ? C24 C23 C22 120.1(10) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C23 C24 C25 122.5(10) . . ? C23 C24 H24A 118.7 . . ? C25 C24 H24A 118.8 . . ? C24 C25 C26 118.0(9) . . ? C24 C25 H25A 121.0 . . ? C26 C25 H25A 121.0 . . ? C25 C26 C21 122.8(10) . . ? C25 C26 H26A 118.6 . . ? C21 C26 H26A 118.6 . . ? C28 C27 C32 120.8(10) . . ? C28 C27 C21 120.7(7) . . ? C32 C27 C21 118.4(9) . . ? C27 C28 C29 120.6(8) . . ? C27 C28 H28A 119.7 . . ? C29 C28 H28A 119.7 . . ? C28 C29 C30 120.6(10) . . ? C28 C29 H29A 119.7 . . ? C30 C29 H29A 119.7 . . ? C29 C30 C31 117.8(10) . . ? C29 C30 Cl30 121.8(9) . . ? C31 C30 Cl30 120.2(6) . . ? C32 C31 C30 121.0(8) . . ? C32 C31 H31A 119.5 . . ? C30 C31 H31A 119.5 . . ? C27 C32 C31 118.9(10) . . ? C27 C32 H32A 120.5 . . ? C31 C32 H32A 120.6 . . ? N34 C33 C22 112.0(8) . . ? N34 C33 C40 123.6(9) . . ? C22 C33 C40 124.4(7) . . ? C33 N34 O35 108.5(7) . . ? C36 O35 N34 112.5(7) . . ? O36 C36 O37 129.2(9) . . ? O36 C36 O35 124.4(11) . . ? O37 C36 O35 106.4(8) . . ? C36 O37 C38 116.8(8) . . ? C39 C38 O37 108.5(10) . . ? C39 C38 H38A 110.0 . . ? O37 C38 H38A 110.0 . . ? C39 C38 H38B 110.0 . . ? O37 C38 H38B 110.0 . . ? H38A C38 H38B 108.4 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.4 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C33 C40 H40A 109.5 . . ? C33 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C33 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 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 C6 C1 C2 C3 1.2(12) . . . . ? C7 C1 C2 C3 -177.4(7) . . . . ? C6 C1 C2 C13 -176.9(8) . . . . ? C7 C1 C2 C13 4.5(12) . . . . ? C1 C2 C3 C4 -1.2(13) . . . . ? C13 C2 C3 C4 177.0(8) . . . . ? C2 C3 C4 C5 2.1(13) . . . . ? C3 C4 C5 C6 -3.1(13) . . . . ? C4 C5 C6 C1 3.3(13) . . . . ? C2 C1 C6 C5 -2.3(12) . . . . ? C7 C1 C6 C5 176.4(8) . . . . ? C6 C1 C7 C12 52.2(10) . . . . ? C2 C1 C7 C12 -129.2(8) . . . . ? C6 C1 C7 C8 -125.9(8) . . . . ? C2 C1 C7 C8 52.7(11) . . . . ? C12 C7 C8 C9 -0.6(13) . . . . ? C1 C7 C8 C9 177.5(8) . . . . ? C7 C8 C9 C10 -1.4(15) . . . . ? C8 C9 C10 C11 4.1(14) . . . . ? C8 C9 C10 Cl10 178.8(7) . . . . ? C9 C10 C11 C12 -5.0(13) . . . . ? Cl10 C10 C11 C12 -179.8(6) . . . . ? C10 C11 C12 C7 3.1(13) . . . . ? C8 C7 C12 C11 -0.3(12) . . . . ? C1 C7 C12 C11 -178.4(7) . . . . ? C1 C2 C13 N14 -131.6(10) . . . . ? C3 C2 C13 N14 50.3(13) . . . . ? C1 C2 C13 C20 51.2(13) . . . . ? C3 C2 C13 C20 -126.9(9) . . . . ? C2 C13 N14 O15 -175.7(8) . . . . ? C20 C13 N14 O15 1.6(13) . . . . ? C13 N14 O15 C16 -179.7(9) . . . . ? N14 O15 C16 O16 -4.5(15) . . . . ? N14 O15 C16 O17 176.5(8) . . . . ? O16 C16 O17 C18 -1.1(18) . . . . ? O15 C16 O17 C18 177.9(10) . . . . ? C16 O17 C18 C19 -84.8(13) . . . . ? C26 C21 C22 C23 2.3(12) . . . . ? C27 C21 C22 C23 176.5(8) . . . . ? C26 C21 C22 C33 178.1(8) . . . . ? C27 C21 C22 C33 -7.7(13) . . . . ? C21 C22 C23 C24 -3.7(13) . . . . ? C33 C22 C23 C24 -179.6(9) . . . . ? C22 C23 C24 C25 1.7(14) . . . . ? C23 C24 C25 C26 1.8(15) . . . . ? C24 C25 C26 C21 -3.2(15) . . . . ? C22 C21 C26 C25 1.1(14) . . . . ? C27 C21 C26 C25 -173.4(9) . . . . ? C26 C21 C27 C28 123.4(9) . . . . ? C22 C21 C27 C28 -50.8(13) . . . . ? C26 C21 C27 C32 -61.5(11) . . . . ? C22 C21 C27 C32 124.4(9) . . . . ? C32 C27 C28 C29 5.7(14) . . . . ? C21 C27 C28 C29 -179.2(8) . . . . ? C27 C28 C29 C30 -0.5(14) . . . . ? C28 C29 C30 C31 -4.3(14) . . . . ? C28 C29 C30 Cl30 -179.5(8) . . . . ? C29 C30 C31 C32 4.2(14) . . . . ? Cl30 C30 C31 C32 179.5(7) . . . . ? C28 C27 C32 C31 -5.8(13) . . . . ? C21 C27 C32 C31 179.1(8) . . . . ? C30 C31 C32 C27 0.7(14) . . . . ? C21 C22 C33 N34 135.6(10) . . . . ? C23 C22 C33 N34 -48.7(12) . . . . ? C21 C22 C33 C40 -44.8(15) . . . . ? C23 C22 C33 C40 131.0(11) . . . . ? C22 C33 N34 O35 177.5(8) . . . . ? C40 C33 N34 O35 -2.2(16) . . . . ? C33 N34 O35 C36 178.7(9) . . . . ? N34 O35 C36 O36 -0.1(17) . . . . ? N34 O35 C36 O37 -179.7(9) . . . . ? O36 C36 O37 C38 0(2) . . . . ? O35 C36 O37 C38 179.2(11) . . . . ? C36 O37 C38 C39 171.7(12) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.723 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.105 # Attachment '- 5d.cif' data_5d _database_code_depnum_ccdc_archive 'CCDC 824857' #TrackingRef '- 5d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 N2 O2' _chemical_formula_sum 'C14 H10 N2 O2' _chemical_formula_weight 238.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 4.469(3) _cell_length_b 13.268(10) _cell_length_c 18.459(16) _cell_angle_alpha 90.00 _cell_angle_beta 96.36(2) _cell_angle_gamma 90.00 _cell_volume 1087.8(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1066 _cell_measurement_theta_min 21.6 _cell_measurement_theta_max 68.5 _exptl_crystal_description Prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method ? _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.816 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.516 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13762 _diffrn_reflns_av_R_equivalents 0.1630 _diffrn_reflns_av_sigmaI/netI 0.0708 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _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 4.11 _diffrn_reflns_theta_max 68.25 _reflns_number_total 1978 _reflns_number_gt 1317 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1978 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1570 _refine_ls_R_factor_gt 0.1223 _refine_ls_wR_factor_ref 0.3712 _refine_ls_wR_factor_gt 0.3345 _refine_ls_goodness_of_fit_ref 1.244 _refine_ls_restrained_S_all 1.244 _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 N1 N 0.0596(8) 0.6289(3) 0.1786(2) 0.0666(12) Uani 1 1 d . . . C1A C -0.0102(10) 0.7068(3) 0.2229(2) 0.0653(13) Uani 1 1 d . . . C2 C -0.1904(10) 0.6829(3) 0.2779(2) 0.0670(13) Uani 1 1 d . . . H2A H -0.2560 0.6155 0.2835 0.080 Uiso 1 1 calc R . . C3 C -0.2721(11) 0.7567(3) 0.3239(2) 0.0676(13) Uani 1 1 d . . . N3 N -0.4641(9) 0.7314(3) 0.3797(2) 0.0713(12) Uani 1 1 d . . . O1 O -0.5468(8) 0.6439(3) 0.38422(18) 0.0871(12) Uani 1 1 d . . . O2 O -0.5311(8) 0.7989(2) 0.42105(18) 0.0828(12) Uani 1 1 d . . . C4 C -0.1772(11) 0.8561(3) 0.3177(3) 0.0730(14) Uani 1 1 d . . . H4A H -0.2336 0.9063 0.3503 0.088 Uiso 1 1 calc R . . C5 C -0.0031(11) 0.8804(3) 0.2645(2) 0.0693(13) Uani 1 1 d . . . H5A H 0.0599 0.9482 0.2598 0.083 Uiso 1 1 calc R . . C5A C 0.0861(10) 0.8072(3) 0.2160(2) 0.0640(13) Uani 1 1 d . . . C5B C 0.2703(10) 0.8291(3) 0.1584(2) 0.0656(13) Uani 1 1 d . . . C6 C 0.3794(10) 0.9258(3) 0.1447(3) 0.0686(13) Uani 1 1 d . . . H6A H 0.3324 0.9807 0.1745 0.082 Uiso 1 1 calc R . . C7 C 0.5507(11) 0.9419(3) 0.0896(2) 0.0741(14) Uani 1 1 d . . . H7A H 0.6219 1.0079 0.0812 0.089 Uiso 1 1 calc R . . C8 C 0.6237(11) 0.8625(4) 0.0449(3) 0.0741(14) Uani 1 1 d . . . H8A H 0.7477 0.8744 0.0072 0.089 Uiso 1 1 calc R . . C9 C 0.5166(11) 0.7680(3) 0.0556(3) 0.0720(14) Uani 1 1 d . . . H9A H 0.5627 0.7147 0.0243 0.086 Uiso 1 1 calc R . . C9A C 0.3382(10) 0.7484(3) 0.1125(2) 0.0639(13) Uani 1 1 d . . . C10 C 0.2223(10) 0.6492(3) 0.1256(3) 0.0674(13) Uani 1 1 d . . . C11 C 0.2928(11) 0.5632(3) 0.0773(3) 0.0780(14) Uani 1 1 d . . . H11A H 0.2010 0.5013 0.0935 0.094 Uiso 1 1 calc R . . H11B H 0.5115 0.5544 0.0801 0.094 Uiso 1 1 calc R . . H11C H 0.2120 0.5779 0.0269 0.094 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 N1 0.074(2) 0.054(2) 0.071(2) 0.0014(16) 0.0102(19) 0.0001(17) C1A 0.070(3) 0.054(3) 0.072(3) 0.001(2) 0.009(2) 0.006(2) C2 0.073(3) 0.052(3) 0.076(3) 0.003(2) 0.009(2) 0.001(2) C3 0.071(3) 0.056(3) 0.076(3) 0.000(2) 0.010(2) 0.000(2) N3 0.077(3) 0.063(2) 0.075(2) 0.005(2) 0.012(2) 0.000(2) O1 0.103(3) 0.068(2) 0.095(3) 0.0057(17) 0.028(2) -0.0093(18) O2 0.097(3) 0.071(2) 0.082(2) -0.0045(16) 0.0209(19) 0.0060(17) C4 0.084(3) 0.055(3) 0.081(3) -0.005(2) 0.013(3) 0.000(2) C5 0.082(3) 0.046(2) 0.081(3) -0.004(2) 0.013(3) 0.002(2) C5A 0.070(3) 0.049(2) 0.072(3) 0.001(2) 0.005(2) -0.003(2) C5B 0.068(3) 0.058(3) 0.071(3) 0.005(2) 0.009(2) 0.003(2) C6 0.076(3) 0.054(3) 0.076(3) 0.008(2) 0.010(2) 0.001(2) C7 0.084(3) 0.055(3) 0.084(3) 0.007(2) 0.010(3) -0.008(2) C8 0.076(3) 0.073(3) 0.073(3) 0.015(2) 0.010(2) 0.000(2) C9 0.082(3) 0.062(3) 0.072(3) 0.003(2) 0.008(2) 0.001(2) C9A 0.067(3) 0.054(3) 0.070(3) -0.002(2) 0.006(2) 0.002(2) C10 0.071(3) 0.058(3) 0.072(3) -0.003(2) 0.003(2) 0.003(2) C11 0.093(4) 0.059(3) 0.083(3) -0.001(2) 0.015(3) 0.003(2) _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 C10 1.310(6) . ? N1 C1A 1.376(5) . ? C1A C2 1.401(6) . ? C1A C5A 1.410(6) . ? C2 C3 1.371(6) . ? C2 H2A 0.9500 . ? C3 C4 1.394(6) . ? C3 N3 1.451(6) . ? N3 O1 1.224(4) . ? N3 O2 1.236(5) . ? C4 C5 1.358(6) . ? C4 H4A 0.9500 . ? C5 C5A 1.408(6) . ? C5 H5A 0.9500 . ? C5A C5B 1.443(6) . ? C5B C6 1.406(6) . ? C5B C9A 1.418(6) . ? C6 C7 1.356(6) . ? C6 H6A 0.9500 . ? C7 C8 1.399(6) . ? C7 H7A 0.9500 . ? C8 C9 1.364(6) . ? C8 H8A 0.9500 . ? C9 C9A 1.412(7) . ? C9 H9A 0.9500 . ? C9A C10 1.445(6) . ? C10 C11 1.502(6) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 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 C10 N1 C1A 118.1(4) . . ? N1 C1A C2 116.6(4) . . ? N1 C1A C5A 124.4(4) . . ? C2 C1A C5A 119.1(4) . . ? C3 C2 C1A 120.0(4) . . ? C3 C2 H2A 120.0 . . ? C1A C2 H2A 120.0 . . ? C2 C3 C4 121.4(5) . . ? C2 C3 N3 119.5(4) . . ? C4 C3 N3 119.1(4) . . ? O1 N3 O2 123.3(4) . . ? O1 N3 C3 118.4(4) . . ? O2 N3 C3 118.3(4) . . ? C5 C4 C3 119.2(4) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? C4 C5 C5A 121.5(4) . . ? C4 C5 H5A 119.3 . . ? C5A C5 H5A 119.3 . . ? C5 C5A C1A 118.9(4) . . ? C5 C5A C5B 123.7(4) . . ? C1A C5A C5B 117.5(4) . . ? C6 C5B C9A 118.7(4) . . ? C6 C5B C5A 123.6(4) . . ? C9A C5B C5A 117.7(4) . . ? C7 C6 C5B 121.0(4) . . ? C7 C6 H6A 119.5 . . ? C5B C6 H6A 119.5 . . ? C6 C7 C8 120.8(4) . . ? C6 C7 H7A 119.6 . . ? C8 C7 H7A 119.6 . . ? C9 C8 C7 119.9(5) . . ? C9 C8 H8A 120.0 . . ? C7 C8 H8A 120.0 . . ? C8 C9 C9A 120.9(4) . . ? C8 C9 H9A 119.6 . . ? C9A C9 H9A 119.6 . . ? C9 C9A C5B 118.8(4) . . ? C9 C9A C10 122.3(4) . . ? C5B C9A C10 118.9(4) . . ? N1 C10 C9A 123.4(4) . . ? N1 C10 C11 117.2(4) . . ? C9A C10 C11 119.4(4) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 C1A C2 178.5(4) . . . . ? C10 N1 C1A C5A -1.2(7) . . . . ? N1 C1A C2 C3 -179.4(4) . . . . ? C5A C1A C2 C3 0.4(7) . . . . ? C1A C2 C3 C4 -0.6(7) . . . . ? C1A C2 C3 N3 178.7(4) . . . . ? C2 C3 N3 O1 0.3(7) . . . . ? C4 C3 N3 O1 179.7(4) . . . . ? C2 C3 N3 O2 179.0(4) . . . . ? C4 C3 N3 O2 -1.7(7) . . . . ? C2 C3 C4 C5 0.8(8) . . . . ? N3 C3 C4 C5 -178.5(4) . . . . ? C3 C4 C5 C5A -0.7(7) . . . . ? C4 C5 C5A C1A 0.5(7) . . . . ? C4 C5 C5A C5B 179.9(4) . . . . ? N1 C1A C5A C5 179.4(4) . . . . ? C2 C1A C5A C5 -0.3(7) . . . . ? N1 C1A C5A C5B 0.0(7) . . . . ? C2 C1A C5A C5B -179.7(4) . . . . ? C5 C5A C5B C6 -0.1(8) . . . . ? C1A C5A C5B C6 179.3(4) . . . . ? C5 C5A C5B C9A -178.7(4) . . . . ? C1A C5A C5B C9A 0.7(7) . . . . ? C9A C5B C6 C7 -1.1(7) . . . . ? C5A C5B C6 C7 -179.7(4) . . . . ? C5B C6 C7 C8 -0.1(7) . . . . ? C6 C7 C8 C9 1.5(7) . . . . ? C7 C8 C9 C9A -1.6(7) . . . . ? C8 C9 C9A C5B 0.4(7) . . . . ? C8 C9 C9A C10 -179.7(4) . . . . ? C6 C5B C9A C9 1.0(7) . . . . ? C5A C5B C9A C9 179.7(4) . . . . ? C6 C5B C9A C10 -178.9(4) . . . . ? C5A C5B C9A C10 -0.3(6) . . . . ? C1A N1 C10 C9A 1.7(7) . . . . ? C1A N1 C10 C11 -179.3(4) . . . . ? C9 C9A C10 N1 179.1(4) . . . . ? C5B C9A C10 N1 -1.0(7) . . . . ? C9 C9A C10 C11 0.1(7) . . . . ? C5B C9A C10 C11 180.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.382 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.085 # Attachment '- 10.cif' data_10 _database_code_depnum_ccdc_archive 'CCDC 824858' #TrackingRef '- 10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H15 N O5' _chemical_formula_sum 'C21 H15 N O5' _chemical_formula_weight 361.34 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.119(8) _cell_length_b 9.581(7) _cell_length_c 10.232(8) _cell_angle_alpha 97.856(18) _cell_angle_beta 96.761(13) _cell_angle_gamma 104.70(2) _cell_volume 845.7(12) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2987 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.4 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8540 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5292 _diffrn_reflns_av_R_equivalents 0.0681 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.32 _reflns_number_total 2969 _reflns_number_gt 2529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1425P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2969 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0858 _refine_ls_R_factor_gt 0.0783 _refine_ls_wR_factor_ref 0.2115 _refine_ls_wR_factor_gt 0.1996 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 C1 C 0.3206(2) 0.0413(2) 0.3664(2) 0.0241(5) Uani 1 1 d . . . C2 C 0.4686(2) 0.1418(2) 0.4078(2) 0.0241(5) Uani 1 1 d . . . C3 C 0.4886(3) 0.2711(2) 0.5017(2) 0.0268(5) Uani 1 1 d . . . H3A H 0.5872 0.3383 0.5309 0.032 Uiso 1 1 calc R . . C4 C 0.3622(3) 0.2962(2) 0.5489(2) 0.0263(5) Uani 1 1 d . . . O4 O 0.34997(18) 0.41301(16) 0.63811(16) 0.0334(5) Uani 1 1 d . . . C5 C 0.2174(2) 0.1953(2) 0.5108(2) 0.0250(5) Uani 1 1 d . . . O5 O 0.11154(17) 0.24665(15) 0.57478(15) 0.0316(5) Uani 1 1 d . . . C6 C 0.1942(2) 0.0673(2) 0.4229(2) 0.0249(5) Uani 1 1 d . . . H6A H 0.0959 -0.0017 0.4006 0.030 Uiso 1 1 calc R . . C7 C 0.2920(2) -0.0864(2) 0.2563(2) 0.0244(5) Uani 1 1 d . . . C8 C 0.3366(2) -0.0679(2) 0.1321(2) 0.0258(5) Uani 1 1 d . . . H8A H 0.3893 0.0270 0.1188 0.031 Uiso 1 1 calc R . . C9 C 0.3050(3) -0.1861(2) 0.0276(2) 0.0304(5) Uani 1 1 d . . . H9A H 0.3373 -0.1720 -0.0557 0.036 Uiso 1 1 calc R . . C10 C 0.2258(3) -0.3249(2) 0.0459(2) 0.0316(6) Uani 1 1 d . . . H10A H 0.2041 -0.4061 -0.0248 0.038 Uiso 1 1 calc R . . C11 C 0.1787(3) -0.3441(2) 0.1681(2) 0.0325(6) Uani 1 1 d . . . H11A H 0.1238 -0.4387 0.1804 0.039 Uiso 1 1 calc R . . C12 C 0.2109(2) -0.2268(2) 0.2716(2) 0.0272(5) Uani 1 1 d . . . H12A H 0.1777 -0.2416 0.3545 0.033 Uiso 1 1 calc R . . C13 C 0.5999(2) 0.1089(2) 0.3539(2) 0.0250(5) Uani 1 1 d . . . H13A H 0.5932 0.0109 0.3156 0.030 Uiso 1 1 calc R . . N14 N 0.7241(2) 0.20981(18) 0.35735(18) 0.0276(5) Uani 1 1 d . . . O15 O 0.82894(16) 0.13897(15) 0.29719(15) 0.0276(4) Uani 1 1 d . . . C16 C 0.9446(2) 0.2361(2) 0.2589(2) 0.0249(5) Uani 1 1 d . . . O16 O 0.97745(19) 0.36635(15) 0.28398(18) 0.0387(5) Uani 1 1 d . . . O17 O 1.01293(17) 0.15219(14) 0.18584(15) 0.0284(4) Uani 1 1 d . . . C18 C 1.1316(2) 0.2180(2) 0.1170(2) 0.0252(5) Uani 1 1 d . . . C19 C 1.1028(3) 0.1775(2) -0.0200(2) 0.0284(5) Uani 1 1 d . . . H19A H 1.0041 0.1200 -0.0640 0.034 Uiso 1 1 calc R . . C20 C 1.2203(3) 0.2220(2) -0.0929(2) 0.0314(6) Uani 1 1 d . . . H20A H 1.2030 0.1926 -0.1872 0.038 Uiso 1 1 calc R . . C21 C 1.3626(3) 0.3090(2) -0.0283(2) 0.0328(6) Uani 1 1 d . . . H21A H 1.4428 0.3402 -0.0781 0.039 Uiso 1 1 calc R . . C22 C 1.3880(3) 0.3508(2) 0.1104(2) 0.0313(6) Uani 1 1 d . . . H22A H 1.4855 0.4110 0.1546 0.038 Uiso 1 1 calc R . . C23 C 1.2719(3) 0.3053(2) 0.1844(2) 0.0283(5) Uani 1 1 d . . . H23A H 1.2886 0.3335 0.2789 0.034 Uiso 1 1 calc R . . C24 C 0.1878(3) 0.3979(2) 0.6279(2) 0.0336(6) Uani 1 1 d . . . H24A H 0.1610 0.4258 0.7170 0.040 Uiso 1 1 calc R . . H24B H 0.1569 0.4617 0.5678 0.040 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 C1 0.0279(12) 0.0267(11) 0.0217(11) 0.0123(9) 0.0045(9) 0.0104(9) C2 0.0266(12) 0.0266(11) 0.0217(11) 0.0114(9) 0.0047(9) 0.0075(9) C3 0.0280(12) 0.0281(11) 0.0242(11) 0.0096(10) 0.0012(9) 0.0060(9) C4 0.0332(12) 0.0282(11) 0.0195(11) 0.0074(9) 0.0056(9) 0.0096(9) O4 0.0346(10) 0.0331(9) 0.0309(9) -0.0002(7) 0.0050(7) 0.0095(7) C5 0.0281(12) 0.0315(11) 0.0199(10) 0.0124(9) 0.0063(9) 0.0110(9) O5 0.0315(9) 0.0338(9) 0.0317(9) 0.0053(7) 0.0095(7) 0.0114(7) C6 0.0258(12) 0.0271(11) 0.0246(11) 0.0120(9) 0.0056(9) 0.0076(9) C7 0.0213(11) 0.0280(11) 0.0259(12) 0.0095(9) 0.0009(9) 0.0089(9) C8 0.0238(11) 0.0282(11) 0.0259(11) 0.0080(9) 0.0039(9) 0.0062(9) C9 0.0292(12) 0.0396(13) 0.0257(12) 0.0082(10) 0.0043(9) 0.0142(10) C10 0.0314(13) 0.0311(12) 0.0312(13) -0.0003(10) -0.0008(10) 0.0122(10) C11 0.0283(12) 0.0257(11) 0.0431(15) 0.0085(11) 0.0019(10) 0.0073(9) C12 0.0251(11) 0.0301(12) 0.0281(12) 0.0111(10) 0.0038(9) 0.0078(9) C13 0.0280(12) 0.0277(11) 0.0207(11) 0.0083(9) 0.0025(9) 0.0085(9) N14 0.0270(10) 0.0314(10) 0.0284(11) 0.0093(8) 0.0090(8) 0.0108(8) O15 0.0261(9) 0.0299(8) 0.0296(9) 0.0092(7) 0.0088(7) 0.0086(6) C16 0.0261(11) 0.0282(12) 0.0214(11) 0.0080(9) 0.0024(9) 0.0078(9) O16 0.0416(10) 0.0269(9) 0.0516(11) 0.0093(8) 0.0216(9) 0.0087(7) O17 0.0310(9) 0.0265(8) 0.0314(9) 0.0100(7) 0.0111(7) 0.0087(7) C18 0.0263(11) 0.0258(11) 0.0283(11) 0.0120(9) 0.0088(9) 0.0101(9) C19 0.0306(12) 0.0287(11) 0.0276(12) 0.0085(10) 0.0031(10) 0.0099(9) C20 0.0394(14) 0.0317(12) 0.0242(12) 0.0077(10) 0.0064(10) 0.0097(10) C21 0.0351(13) 0.0329(12) 0.0373(13) 0.0170(10) 0.0147(10) 0.0117(10) C22 0.0267(12) 0.0295(12) 0.0370(13) 0.0108(10) 0.0018(10) 0.0054(9) C23 0.0316(12) 0.0278(11) 0.0268(12) 0.0085(9) 0.0033(9) 0.0089(9) C24 0.0339(13) 0.0335(12) 0.0342(13) 0.0022(10) 0.0085(10) 0.0112(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.410(3) . ? C1 C2 1.422(3) . ? C1 C7 1.492(3) . ? C2 C3 1.417(3) . ? C2 C13 1.463(3) . ? C3 C4 1.365(3) . ? C3 H3A 0.9500 . ? C4 O4 1.380(3) . ? C4 C5 1.399(3) . ? O4 C24 1.439(3) . ? C5 C6 1.371(3) . ? C5 O5 1.379(3) . ? O5 C24 1.437(3) . ? C6 H6A 0.9500 . ? C7 C8 1.400(3) . ? C7 C12 1.401(3) . ? C8 C9 1.392(3) . ? C8 H8A 0.9500 . ? C9 C10 1.392(3) . ? C9 H9A 0.9500 . ? C10 C11 1.389(4) . ? C10 H10A 0.9500 . ? C11 C12 1.381(3) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 N14 1.282(3) . ? C13 H13A 0.9500 . ? N14 O15 1.451(2) . ? O15 C16 1.353(3) . ? C16 O16 1.191(3) . ? C16 O17 1.339(3) . ? O17 C18 1.421(3) . ? C18 C19 1.378(3) . ? C18 C23 1.380(3) . ? C19 C20 1.389(3) . ? C19 H19A 0.9500 . ? C20 C21 1.384(3) . ? C20 H20A 0.9500 . ? C21 C22 1.396(3) . ? C21 H21A 0.9500 . ? C22 C23 1.389(3) . ? C22 H22A 0.9500 . ? C23 H23A 0.9500 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? 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 C6 C1 C2 119.88(19) . . ? C6 C1 C7 118.26(18) . . ? C2 C1 C7 121.69(19) . . ? C3 C2 C1 120.3(2) . . ? C3 C2 C13 120.50(18) . . ? C1 C2 C13 119.15(19) . . ? C4 C3 C2 118.04(19) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C3 C4 O4 129.5(2) . . ? C3 C4 C5 121.5(2) . . ? O4 C4 C5 108.92(19) . . ? C4 O4 C24 105.03(16) . . ? C6 C5 O5 128.53(19) . . ? C6 C5 C4 122.1(2) . . ? O5 C5 C4 109.41(19) . . ? C5 O5 C24 104.86(17) . . ? C5 C6 C1 118.01(19) . . ? C5 C6 H6A 121.0 . . ? C1 C6 H6A 121.0 . . ? C8 C7 C12 118.05(19) . . ? C8 C7 C1 121.00(18) . . ? C12 C7 C1 120.8(2) . . ? C9 C8 C7 121.12(19) . . ? C9 C8 H8A 119.4 . . ? C7 C8 H8A 119.4 . . ? C8 C9 C10 119.7(2) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? C11 C10 C9 119.7(2) . . ? C11 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? C12 C11 C10 120.5(2) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? C11 C12 C7 121.0(2) . . ? C11 C12 H12A 119.5 . . ? C7 C12 H12A 119.5 . . ? N14 C13 C2 121.21(19) . . ? N14 C13 H13A 119.4 . . ? C2 C13 H13A 119.4 . . ? C13 N14 O15 106.46(17) . . ? C16 O15 N14 112.02(16) . . ? O16 C16 O17 128.0(2) . . ? O16 C16 O15 127.8(2) . . ? O17 C16 O15 104.19(17) . . ? C16 O17 C18 119.93(16) . . ? C19 C18 C23 122.3(2) . . ? C19 C18 O17 115.66(19) . . ? C23 C18 O17 121.7(2) . . ? C18 C19 C20 119.0(2) . . ? C18 C19 H19A 120.5 . . ? C20 C19 H19A 120.5 . . ? C21 C20 C19 120.0(2) . . ? C21 C20 H20A 120.0 . . ? C19 C20 H20A 120.0 . . ? C20 C21 C22 119.8(2) . . ? C20 C21 H21A 120.1 . . ? C22 C21 H21A 120.1 . . ? C23 C22 C21 120.7(2) . . ? C23 C22 H22A 119.7 . . ? C21 C22 H22A 119.7 . . ? C18 C23 C22 118.1(2) . . ? C18 C23 H23A 120.9 . . ? C22 C23 H23A 120.9 . . ? O5 C24 O4 106.60(17) . . ? O5 C24 H24A 110.4 . . ? O4 C24 H24A 110.4 . . ? O5 C24 H24B 110.4 . . ? O4 C24 H24B 110.4 . . ? H24A C24 H24B 108.6 . . ? 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 C6 C1 C2 C3 -2.5(3) . . . . ? C7 C1 C2 C3 172.70(18) . . . . ? C6 C1 C2 C13 176.51(18) . . . . ? C7 C1 C2 C13 -8.3(3) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C13 C2 C3 C4 -179.84(19) . . . . ? C2 C3 C4 O4 -178.90(19) . . . . ? C2 C3 C4 C5 2.6(3) . . . . ? C3 C4 O4 C24 167.5(2) . . . . ? C5 C4 O4 C24 -13.9(2) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? O4 C4 C5 C6 -179.78(19) . . . . ? C3 C4 C5 O5 178.96(19) . . . . ? O4 C4 C5 O5 0.2(2) . . . . ? C6 C5 O5 C24 -166.4(2) . . . . ? C4 C5 O5 C24 13.6(2) . . . . ? O5 C5 C6 C1 177.67(19) . . . . ? C4 C5 C6 C1 -2.4(3) . . . . ? C2 C1 C6 C5 4.0(3) . . . . ? C7 C1 C6 C5 -171.31(18) . . . . ? C6 C1 C7 C8 123.5(2) . . . . ? C2 C1 C7 C8 -51.8(3) . . . . ? C6 C1 C7 C12 -52.4(3) . . . . ? C2 C1 C7 C12 132.4(2) . . . . ? C12 C7 C8 C9 -1.7(3) . . . . ? C1 C7 C8 C9 -177.64(19) . . . . ? C7 C8 C9 C10 0.9(3) . . . . ? C8 C9 C10 C11 0.2(3) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? C10 C11 C12 C7 -0.2(3) . . . . ? C8 C7 C12 C11 1.3(3) . . . . ? C1 C7 C12 C11 177.28(19) . . . . ? C3 C2 C13 N14 -20.5(3) . . . . ? C1 C2 C13 N14 160.5(2) . . . . ? C2 C13 N14 O15 179.55(17) . . . . ? C13 N14 O15 C16 161.75(18) . . . . ? N14 O15 C16 O16 10.2(3) . . . . ? N14 O15 C16 O17 -169.47(14) . . . . ? O16 C16 O17 C18 -6.1(3) . . . . ? O15 C16 O17 C18 173.59(17) . . . . ? C16 O17 C18 C19 -118.7(2) . . . . ? C16 O17 C18 C23 67.4(3) . . . . ? C23 C18 C19 C20 2.1(3) . . . . ? O17 C18 C19 C20 -171.75(18) . . . . ? C18 C19 C20 C21 -1.7(3) . . . . ? C19 C20 C21 C22 0.5(3) . . . . ? C20 C21 C22 C23 0.4(3) . . . . ? C19 C18 C23 C22 -1.2(3) . . . . ? O17 C18 C23 C22 172.26(18) . . . . ? C21 C22 C23 C18 0.0(3) . . . . ? C5 O5 C24 O4 -22.0(2) . . . . ? C4 O4 C24 O5 22.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.633 _refine_diff_density_min -0.543 _refine_diff_density_rms 0.136