# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ponnusamy Shanmugam' _publ_contact_author_email SHANMU196@REDIFFMAIL.COM _publ_section_title ; An efficient regioselective synthesis of 3-spirocyclopentene- and 3-spiropyrazole-2-oxindoles via 1,3-dipolar cycloaddition reaction ; loop_ _publ_author_name 'Ponnusamy Shanmugam' 'Kodirajan Selvakumar' 'Vadivel Vaithiyanathan' # Attachment 'sks01.cif' data_sks01 _database_code_depnum_ccdc_archive 'CCDC 744689' #TrackingRef 'sks01.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 N4 O5' _chemical_formula_weight 446.46 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 P21/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 9.7647(4) _cell_length_b 16.6810(8) _cell_length_c 14.5367(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.224(2) _cell_angle_gamma 90.00 _cell_volume 2322.52(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4909 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 22.57 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9775 _exptl_absorpt_correction_T_max 0.9820 _exptl_absorpt_process_details 'SADABS (Bruker 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'bruker axs kappa apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 20097 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 24.06 _reflns_number_total 3667 _reflns_number_gt 2673 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (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^)+(0.0789P)^2^+0.8113P] 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 0.0029(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3667 _refine_ls_number_parameters 308 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1537 _refine_ls_wR_factor_gt 0.1342 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.039 _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 1.1023(3) -0.05896(15) 0.12991(17) 0.0578(6) Uani 1 1 d . . . H1 H 1.1685 -0.0784 0.0974 0.069 Uiso 1 1 calc R . . C2 C 1.0686(2) 0.01730(15) 0.13354(16) 0.0526(6) Uani 1 1 d . . . C3 C 0.9567(2) 0.02807(13) 0.19131(15) 0.0489(6) Uani 1 1 d . . . C4 C 1.0131(2) 0.08507(14) 0.27454(15) 0.0516(6) Uani 1 1 d . . . C5 C 0.8196(2) 0.14305(14) 0.18741(15) 0.0529(6) Uani 1 1 d . . . C6 C 0.7109(3) 0.19505(17) 0.15898(18) 0.0694(7) Uani 1 1 d . . . H6 H 0.7069 0.2444 0.1882 0.083 Uiso 1 1 calc R . . C7 C 0.6079(3) 0.1714(2) 0.0856(2) 0.0810(9) Uani 1 1 d . . . H7 H 0.5335 0.2058 0.0645 0.097 Uiso 1 1 calc R . . C8 C 0.6120(3) 0.0986(2) 0.0426(2) 0.0777(8) Uani 1 1 d . . . H8 H 0.5400 0.0840 -0.0063 0.093 Uiso 1 1 calc R . . C9 C 0.7228(3) 0.04663(16) 0.07170(16) 0.0615(7) Uani 1 1 d . . . H9 H 0.7264 -0.0028 0.0428 0.074 Uiso 1 1 calc R . . C10 C 0.8267(2) 0.07002(14) 0.14400(15) 0.0498(6) Uani 1 1 d . . . C11 C 0.9555(3) 0.22022(15) 0.32533(16) 0.0613(7) Uani 1 1 d . . . H11A H 1.0239 0.2061 0.3808 0.074 Uiso 1 1 calc R . . H11B H 0.8686 0.2326 0.3452 0.074 Uiso 1 1 calc R . . C12 C 1.0050(3) 0.29378(15) 0.28132(16) 0.0577(6) Uani 1 1 d . . . C13 C 1.1117(3) 0.2897(2) 0.2316(2) 0.0763(8) Uani 1 1 d . . . H13 H 1.1515 0.2404 0.2227 0.092 Uiso 1 1 calc R . . C14 C 1.1594(4) 0.3579(3) 0.1953(2) 0.0923(10) Uani 1 1 d . . . H14 H 1.2308 0.3544 0.1615 0.111 Uiso 1 1 calc R . . C15 C 1.1027(4) 0.4310(2) 0.2085(2) 0.0917(10) Uani 1 1 d . . . H15 H 1.1359 0.4772 0.1844 0.110 Uiso 1 1 calc R . . C16 C 0.9966(4) 0.43539(19) 0.2574(2) 0.0856(9) Uani 1 1 d . . . H16 H 0.9576 0.4849 0.2667 0.103 Uiso 1 1 calc R . . C17 C 0.9472(3) 0.36745(16) 0.2929(2) 0.0685(7) Uani 1 1 d . . . H17 H 0.8740 0.3712 0.3251 0.082 Uiso 1 1 calc R . . C18 C 0.9719(3) -0.18039(16) 0.14741(19) 0.0666(7) Uani 1 1 d . . . C19 C 1.0040(5) -0.2920(2) 0.0607(4) 0.1374(17) Uani 1 1 d D . . C21 C 0.9260(3) -0.07510(16) 0.31032(17) 0.0567(6) Uani 1 1 d . . . C22 C 0.8176(4) -0.0319(2) 0.43169(19) 0.0847(9) Uani 1 1 d . . . H22A H 0.9020 -0.0445 0.4767 0.102 Uiso 1 1 calc R . . H22B H 0.7531 -0.0764 0.4295 0.102 Uiso 1 1 calc R . . C23 C 0.7547(4) 0.0414(2) 0.4592(2) 0.1118(13) Uani 1 1 d . . . H23A H 0.8205 0.0846 0.4631 0.168 Uiso 1 1 calc R . . H23B H 0.7294 0.0337 0.5191 0.168 Uiso 1 1 calc R . . H23C H 0.6728 0.0541 0.4133 0.168 Uiso 1 1 calc R . . C24 C 1.1294(3) 0.08174(17) 0.09306(18) 0.0646(7) Uani 1 1 d . . . N1 N 1.0278(2) -0.10634(12) 0.18017(14) 0.0587(5) Uani 1 1 d . . . N2 N 0.9389(2) -0.05523(11) 0.21963(13) 0.0533(5) Uani 1 1 d . . . N3 N 1.1764(3) 0.13425(17) 0.0609(2) 0.0982(9) Uani 1 1 d . . . N4 N 0.9337(2) 0.15181(11) 0.26267(12) 0.0534(5) Uani 1 1 d . . . O1 O 1.11426(18) 0.07197(11) 0.33523(12) 0.0665(5) Uani 1 1 d . . . O2 O 0.8649(2) -0.20610(12) 0.16096(14) 0.0804(6) Uani 1 1 d . . . O3 O 1.0618(2) -0.21597(12) 0.10425(18) 0.0956(7) Uani 1 1 d . A . O4 O 0.9696(2) -0.13486(11) 0.35010(13) 0.0741(5) Uani 1 1 d . . . O5 O 0.84989(19) -0.01858(11) 0.34029(11) 0.0637(5) Uani 1 1 d . . . C20 C 1.1139(5) -0.3237(4) 0.0138(5) 0.153(4) Uani 0.768(12) 1 d PD A 1 H20A H 1.2013 -0.3248 0.0575 0.229 Uiso 0.768(12) 1 calc PR A 1 H20B H 1.1221 -0.2898 -0.0382 0.229 Uiso 0.768(12) 1 calc PR A 1 H20C H 1.0896 -0.3770 -0.0085 0.229 Uiso 0.768(12) 1 calc PR A 1 C20' C 1.0906(16) -0.3519(8) 0.1208(11) 0.196(8) Uiso 0.430(13) 1 d PD A 2 H20D H 1.1043 -0.3978 0.0838 0.295 Uiso 0.430(13) 1 calc PR A 2 H20E H 1.0442 -0.3681 0.1703 0.295 Uiso 0.430(13) 1 calc PR A 2 H20F H 1.1795 -0.3287 0.1474 0.295 Uiso 0.430(13) 1 calc PR A 2 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 0.0591(14) 0.0599(17) 0.0593(14) -0.0036(12) 0.0233(12) -0.0008(12) C2 0.0581(14) 0.0526(15) 0.0498(13) -0.0026(11) 0.0169(11) -0.0026(11) C3 0.0557(13) 0.0469(14) 0.0459(12) -0.0012(10) 0.0141(10) -0.0024(10) C4 0.0565(14) 0.0555(15) 0.0442(12) 0.0011(11) 0.0130(11) -0.0020(11) C5 0.0582(14) 0.0538(15) 0.0468(12) -0.0014(11) 0.0102(11) 0.0014(11) C6 0.0758(18) 0.0636(17) 0.0661(16) -0.0053(13) 0.0072(14) 0.0146(14) C7 0.0731(18) 0.085(2) 0.0776(19) 0.0011(17) -0.0024(15) 0.0205(16) C8 0.0679(18) 0.096(2) 0.0612(16) -0.0013(16) -0.0069(13) 0.0005(16) C9 0.0676(16) 0.0659(16) 0.0506(13) -0.0079(12) 0.0103(12) -0.0055(13) C10 0.0554(13) 0.0529(14) 0.0426(11) 0.0002(10) 0.0130(10) -0.0016(11) C11 0.0733(16) 0.0585(16) 0.0515(13) -0.0114(12) 0.0110(12) -0.0003(12) C12 0.0610(15) 0.0579(16) 0.0505(13) -0.0097(11) 0.0014(11) -0.0092(12) C13 0.0717(18) 0.084(2) 0.0744(18) -0.0127(16) 0.0176(15) -0.0093(15) C14 0.080(2) 0.115(3) 0.084(2) -0.007(2) 0.0229(17) -0.032(2) C15 0.096(2) 0.087(3) 0.086(2) 0.0088(19) 0.0021(19) -0.033(2) C16 0.094(2) 0.0614(19) 0.094(2) -0.0016(16) 0.0005(19) -0.0100(16) C17 0.0697(17) 0.0614(17) 0.0728(17) -0.0081(14) 0.0097(13) -0.0059(13) C18 0.0773(18) 0.0515(16) 0.0746(17) -0.0053(13) 0.0236(15) -0.0003(14) C19 0.166(4) 0.069(2) 0.184(5) -0.055(3) 0.052(4) -0.008(3) C21 0.0638(15) 0.0545(15) 0.0537(14) 0.0002(12) 0.0160(11) -0.0068(12) C22 0.105(2) 0.101(2) 0.0563(16) 0.0017(15) 0.0375(16) -0.0078(19) C23 0.138(3) 0.138(3) 0.069(2) -0.012(2) 0.043(2) 0.035(3) C24 0.0764(17) 0.0615(17) 0.0627(15) -0.0041(13) 0.0301(13) -0.0069(14) N1 0.0658(13) 0.0486(12) 0.0666(13) -0.0039(10) 0.0251(10) 0.0011(10) N2 0.0644(12) 0.0467(11) 0.0540(11) -0.0001(9) 0.0239(9) 0.0007(9) N3 0.127(2) 0.0789(19) 0.104(2) 0.0049(15) 0.0607(19) -0.0155(17) N4 0.0600(12) 0.0514(12) 0.0473(10) -0.0068(9) 0.0068(9) 0.0019(9) O1 0.0658(11) 0.0734(12) 0.0552(10) -0.0011(9) -0.0008(9) 0.0057(9) O2 0.0884(14) 0.0691(13) 0.0899(14) -0.0105(10) 0.0327(11) -0.0197(11) O3 0.0990(16) 0.0638(13) 0.1349(19) -0.0345(12) 0.0499(14) -0.0016(11) O4 0.0968(14) 0.0588(12) 0.0681(11) 0.0129(9) 0.0200(10) 0.0039(10) O5 0.0777(11) 0.0660(11) 0.0539(10) 0.0027(8) 0.0291(8) 0.0027(9) C20 0.148(6) 0.135(6) 0.165(7) -0.074(5) 0.006(4) 0.017(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 C1 C2 1.318(3) . ? C1 N1 1.377(3) . ? C1 H1 0.9300 . ? C2 C24 1.411(4) . ? C2 C3 1.512(3) . ? C3 N2 1.469(3) . ? C3 C10 1.495(3) . ? C3 C4 1.553(3) . ? C4 O1 1.209(3) . ? C4 N4 1.349(3) . ? C5 C6 1.371(3) . ? C5 C10 1.380(3) . ? C5 N4 1.409(3) . ? C6 C7 1.373(4) . ? C6 H6 0.9300 . ? C7 C8 1.369(4) . ? C7 H7 0.9300 . ? C8 C9 1.387(4) . ? C8 H8 0.9300 . ? C9 C10 1.367(3) . ? C9 H9 0.9300 . ? C11 N4 1.450(3) . ? C11 C12 1.506(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.376(4) . ? C12 C13 1.380(4) . ? C13 C14 1.373(4) . ? C13 H13 0.9300 . ? C14 C15 1.368(5) . ? C14 H14 0.9300 . ? C15 C16 1.368(5) . ? C15 H15 0.9300 . ? C16 C17 1.371(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 O2 1.181(3) . ? C18 O3 1.315(3) . ? C18 N1 1.396(3) . ? C19 C20 1.4764(10) . ? C19 C20' 1.4787(10) . ? C19 O3 1.480(4) . ? C21 O4 1.189(3) . ? C21 O5 1.325(3) . ? C21 N2 1.389(3) . ? C22 O5 1.441(3) . ? C22 C23 1.459(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 N3 1.131(3) . ? N1 N2 1.415(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C20' H20D 0.9600 . ? C20' H20E 0.9600 . ? C20' H20F 0.9600 . ? 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 C2 C1 N1 111.8(2) . . ? C2 C1 H1 124.1 . . ? N1 C1 H1 124.1 . . ? C1 C2 C24 126.1(2) . . ? C1 C2 C3 110.5(2) . . ? C24 C2 C3 123.3(2) . . ? N2 C3 C10 115.79(19) . . ? N2 C3 C2 100.44(18) . . ? C10 C3 C2 116.15(18) . . ? N2 C3 C4 113.84(18) . . ? C10 C3 C4 102.27(18) . . ? C2 C3 C4 108.68(18) . . ? O1 C4 N4 127.6(2) . . ? O1 C4 C3 125.0(2) . . ? N4 C4 C3 107.32(19) . . ? C6 C5 C10 121.7(2) . . ? C6 C5 N4 128.1(2) . . ? C10 C5 N4 110.1(2) . . ? C5 C6 C7 117.3(3) . . ? C5 C6 H6 121.3 . . ? C7 C6 H6 121.3 . . ? C8 C7 C6 121.8(3) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 120.4(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 118.3(3) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? C9 C10 C5 120.5(2) . . ? C9 C10 C3 131.0(2) . . ? C5 C10 C3 108.45(19) . . ? N4 C11 C12 113.23(19) . . ? N4 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? N4 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C17 C12 C13 118.5(3) . . ? C17 C12 C11 120.2(2) . . ? C13 C12 C11 121.3(2) . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.2(3) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C12 120.7(3) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? O2 C18 O3 127.6(3) . . ? O2 C18 N1 124.3(2) . . ? O3 C18 N1 108.0(2) . . ? C20 C19 C20' 69.4(8) . . ? C20 C19 O3 104.7(4) . . ? C20' C19 O3 101.5(8) . . ? O4 C21 O5 127.4(2) . . ? O4 C21 N2 124.9(2) . . ? O5 C21 N2 107.6(2) . . ? O5 C22 C23 107.6(3) . . ? O5 C22 H22A 110.2 . . ? C23 C22 H22A 110.2 . . ? O5 C22 H22B 110.2 . . ? C23 C22 H22B 110.2 . . ? H22A C22 H22B 108.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N3 C24 C2 178.8(3) . . ? C1 N1 C18 122.6(2) . . ? C1 N1 N2 107.38(19) . . ? C18 N1 N2 116.2(2) . . ? C21 N2 N1 114.65(19) . . ? C21 N2 C3 121.96(19) . . ? N1 N2 C3 109.91(16) . . ? C4 N4 C5 111.22(18) . . ? C4 N4 C11 123.97(19) . . ? C5 N4 C11 124.54(19) . . ? C18 O3 C19 110.9(3) . . ? C21 O5 C22 115.5(2) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? C19 C20' H20D 109.5 . . ? C19 C20' H20E 109.5 . . ? H20D C20' H20E 109.5 . . ? C19 C20' H20F 109.5 . . ? H20D C20' H20F 109.5 . . ? H20E C20' H20F 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 N1 C1 C2 C24 177.2(2) . . . . ? N1 C1 C2 C3 -0.7(3) . . . . ? C1 C2 C3 N2 1.2(3) . . . . ? C24 C2 C3 N2 -176.7(2) . . . . ? C1 C2 C3 C10 -124.5(2) . . . . ? C24 C2 C3 C10 57.6(3) . . . . ? C1 C2 C3 C4 121.0(2) . . . . ? C24 C2 C3 C4 -56.9(3) . . . . ? N2 C3 C4 O1 49.9(3) . . . . ? C10 C3 C4 O1 175.6(2) . . . . ? C2 C3 C4 O1 -61.1(3) . . . . ? N2 C3 C4 N4 -133.4(2) . . . . ? C10 C3 C4 N4 -7.7(2) . . . . ? C2 C3 C4 N4 115.6(2) . . . . ? C10 C5 C6 C7 0.5(4) . . . . ? N4 C5 C6 C7 -177.1(2) . . . . ? C5 C6 C7 C8 0.6(4) . . . . ? C6 C7 C8 C9 -1.0(5) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? C8 C9 C10 C5 0.9(4) . . . . ? C8 C9 C10 C3 179.3(2) . . . . ? C6 C5 C10 C9 -1.2(4) . . . . ? N4 C5 C10 C9 176.7(2) . . . . ? C6 C5 C10 C3 -179.9(2) . . . . ? N4 C5 C10 C3 -2.0(3) . . . . ? N2 C3 C10 C9 -48.4(3) . . . . ? C2 C3 C10 C9 69.0(3) . . . . ? C4 C3 C10 C9 -172.8(2) . . . . ? N2 C3 C10 C5 130.1(2) . . . . ? C2 C3 C10 C5 -112.5(2) . . . . ? C4 C3 C10 C5 5.7(2) . . . . ? N4 C11 C12 C17 135.6(2) . . . . ? N4 C11 C12 C13 -46.7(3) . . . . ? C17 C12 C13 C14 0.5(4) . . . . ? C11 C12 C13 C14 -177.3(3) . . . . ? C12 C13 C14 C15 0.5(5) . . . . ? C13 C14 C15 C16 -0.7(5) . . . . ? C14 C15 C16 C17 -0.1(5) . . . . ? C15 C16 C17 C12 1.1(4) . . . . ? C13 C12 C17 C16 -1.3(4) . . . . ? C11 C12 C17 C16 176.5(2) . . . . ? C1 C2 C24 N3 168(16) . . . . ? C3 C2 C24 N3 -15(16) . . . . ? C2 C1 N1 C18 138.3(2) . . . . ? C2 C1 N1 N2 -0.2(3) . . . . ? O2 C18 N1 C1 -145.0(3) . . . . ? O3 C18 N1 C1 38.0(3) . . . . ? O2 C18 N1 N2 -9.8(4) . . . . ? O3 C18 N1 N2 173.2(2) . . . . ? O4 C21 N2 N1 -9.1(4) . . . . ? O5 C21 N2 N1 174.86(18) . . . . ? O4 C21 N2 C3 -145.8(2) . . . . ? O5 C21 N2 C3 38.1(3) . . . . ? C1 N1 N2 C21 -140.7(2) . . . . ? C18 N1 N2 C21 77.8(3) . . . . ? C1 N1 N2 C3 1.1(2) . . . . ? C18 N1 N2 C3 -140.5(2) . . . . ? C10 C3 N2 C21 -96.9(3) . . . . ? C2 C3 N2 C21 137.1(2) . . . . ? C4 C3 N2 C21 21.2(3) . . . . ? C10 C3 N2 N1 124.6(2) . . . . ? C2 C3 N2 N1 -1.4(2) . . . . ? C4 C3 N2 N1 -117.3(2) . . . . ? O1 C4 N4 C5 -176.3(2) . . . . ? C3 C4 N4 C5 7.0(2) . . . . ? O1 C4 N4 C11 -2.1(4) . . . . ? C3 C4 N4 C11 -178.7(2) . . . . ? C6 C5 N4 C4 174.4(2) . . . . ? C10 C5 N4 C4 -3.4(3) . . . . ? C6 C5 N4 C11 0.2(4) . . . . ? C10 C5 N4 C11 -177.6(2) . . . . ? C12 C11 N4 C4 111.7(3) . . . . ? C12 C11 N4 C5 -74.8(3) . . . . ? O2 C18 O3 C19 7.8(5) . . . . ? N1 C18 O3 C19 -175.3(3) . . . . ? C20 C19 O3 C18 178.7(4) . . . . ? C20' C19 O3 C18 -109.7(8) . . . . ? O4 C21 O5 C22 0.2(4) . . . . ? N2 C21 O5 C22 176.1(2) . . . . ? C23 C22 O5 C21 170.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.06 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.380 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.037 # end Validation Reply Form # Attachment 'sks02.cif' data_shelxl02 _database_code_depnum_ccdc_archive 'CCDC 744690' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 N2 O3' _chemical_formula_weight 281.28 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' 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4197(7) _cell_length_b 8.7349(5) _cell_length_c 14.6663(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.935(2) _cell_angle_gamma 90.00 _cell_volume 1448.95(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3509 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 24.99 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8921 _exptl_absorpt_correction_T_max 0.9821 _exptl_absorpt_process_details 'SADABS (Bruker 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker axs kappa apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17470 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 29.35 _reflns_number_total 3976 _reflns_number_gt 2686 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (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^)+(0.0925P)^2^+0.2901P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3976 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1792 _refine_ls_wR_factor_gt 0.1577 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.81316(15) 0.3301(2) 0.78085(12) 0.0405(4) Uani 1 1 d . . . C2 C 0.93971(17) 0.2791(2) 0.81564(14) 0.0555(5) Uani 1 1 d . . . H2 H 0.9995 0.2533 0.7813 0.067 Uiso 1 1 calc R . . C3 C 0.94419(17) 0.2809(2) 0.91698(14) 0.0531(5) Uani 1 1 d . . . H3 H 1.0045 0.2365 0.9575 0.064 Uiso 1 1 calc R . . C4 C 0.85215(15) 0.3532(2) 0.94332(12) 0.0418(4) Uani 1 1 d . . . C5 C 0.76786(13) 0.41581(18) 0.86284(11) 0.0353(3) Uani 1 1 d . . . C7 C 0.63751(14) 0.3781(2) 0.86865(12) 0.0420(4) Uani 1 1 d . . . N1 N 0.57701(12) 0.51221(18) 0.86759(11) 0.0442(4) Uani 1 1 d . . . C9 C 0.65158(15) 0.63806(19) 0.86202(11) 0.0400(4) Uani 1 1 d . . . C10 C 0.6230(2) 0.7921(2) 0.85917(14) 0.0559(5) Uani 1 1 d . . . H10 H 0.5456 0.8249 0.8595 0.067 Uiso 1 1 calc R . . C11 C 0.7143(2) 0.8956(2) 0.85576(15) 0.0634(6) Uani 1 1 d . . . H11 H 0.6977 0.9999 0.8546 0.076 Uiso 1 1 calc R . . C12 C 0.8289(2) 0.8481(2) 0.85398(15) 0.0590(5) Uani 1 1 d . . . H12 H 0.8886 0.9200 0.8518 0.071 Uiso 1 1 calc R . . C13 C 0.85565(17) 0.6923(2) 0.85551(12) 0.0459(4) Uani 1 1 d . . . H13 H 0.9328 0.6592 0.8540 0.055 Uiso 1 1 calc R . . C14 C 0.76624(14) 0.58850(18) 0.85933(10) 0.0356(3) Uani 1 1 d . . . C15 C 0.80046(15) 0.4246(2) 0.69429(12) 0.0428(4) Uani 1 1 d . . . C16 C 0.6619(3) 0.5482(4) 0.58526(19) 0.0954(10) Uani 1 1 d . . . H16A H 0.7142 0.6348 0.5913 0.143 Uiso 1 1 calc R . . H16B H 0.5815 0.5832 0.5795 0.143 Uiso 1 1 calc R . . H16C H 0.6735 0.4907 0.5315 0.143 Uiso 1 1 calc R . . C17 C 0.83496(16) 0.3869(2) 1.03580(13) 0.0485(4) Uani 1 1 d . . . C18 C 0.45083(17) 0.5229(3) 0.87038(18) 0.0677(6) Uani 1 1 d . . . H18A H 0.4181 0.4218 0.8717 0.102 Uiso 1 1 calc R . . H18B H 0.4139 0.5760 0.8167 0.102 Uiso 1 1 calc R . . H18C H 0.4370 0.5778 0.9246 0.102 Uiso 1 1 calc R . . N2 N 0.82009(17) 0.4176(3) 1.10881(13) 0.0708(6) Uani 1 1 d . . . O1 O 0.59682(13) 0.25087(16) 0.87354(13) 0.0676(4) Uani 1 1 d . . . O2 O 0.87978(13) 0.46984(19) 0.65651(11) 0.0642(4) Uani 1 1 d . . . O3 O 0.68660(12) 0.45182(19) 0.66597(9) 0.0582(4) Uani 1 1 d . . . H1 H 0.7576(18) 0.239(2) 0.7685(14) 0.050(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0389(8) 0.0372(8) 0.0467(9) -0.0026(7) 0.0104(7) 0.0043(7) C2 0.0454(10) 0.0650(13) 0.0579(11) -0.0007(9) 0.0136(8) 0.0257(9) C3 0.0440(10) 0.0588(12) 0.0566(11) 0.0114(9) 0.0071(8) 0.0194(8) C4 0.0359(8) 0.0444(9) 0.0457(9) 0.0095(7) 0.0078(6) 0.0071(7) C5 0.0302(7) 0.0342(8) 0.0424(8) 0.0038(6) 0.0086(6) 0.0037(6) C7 0.0333(8) 0.0435(9) 0.0502(9) 0.0013(7) 0.0087(6) 0.0010(7) N1 0.0289(7) 0.0513(9) 0.0529(8) -0.0003(7) 0.0070(6) 0.0081(6) C9 0.0414(9) 0.0408(9) 0.0381(8) 0.0007(6) 0.0062(6) 0.0100(7) C10 0.0622(12) 0.0496(11) 0.0567(11) 0.0010(9) 0.0104(9) 0.0240(9) C11 0.0973(18) 0.0353(10) 0.0595(12) 0.0022(9) 0.0170(11) 0.0084(10) C12 0.0795(15) 0.0388(10) 0.0610(12) 0.0010(8) 0.0178(10) -0.0095(9) C13 0.0476(10) 0.0449(9) 0.0470(9) 0.0017(7) 0.0123(7) -0.0043(7) C14 0.0383(8) 0.0348(8) 0.0342(7) 0.0016(6) 0.0065(6) 0.0043(6) C15 0.0406(9) 0.0441(9) 0.0446(9) -0.0049(7) 0.0093(7) -0.0004(7) C16 0.0769(17) 0.134(3) 0.0727(16) 0.0430(17) 0.0023(13) 0.0254(17) C17 0.0389(9) 0.0604(12) 0.0469(10) 0.0152(8) 0.0087(7) 0.0105(8) C18 0.0313(9) 0.0891(17) 0.0832(15) -0.0059(13) 0.0100(9) 0.0115(9) N2 0.0588(11) 0.1054(16) 0.0506(10) 0.0124(10) 0.0155(8) 0.0168(11) O1 0.0471(8) 0.0493(9) 0.1096(13) 0.0037(8) 0.0223(8) -0.0081(6) O2 0.0513(8) 0.0753(10) 0.0687(9) 0.0137(8) 0.0178(7) -0.0043(7) O3 0.0445(7) 0.0807(10) 0.0486(7) 0.0116(7) 0.0036(5) 0.0077(7) _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 C15 1.504(2) . ? C1 C2 1.531(2) . ? C1 C5 1.564(2) . ? C1 H1 1.02(2) . ? C2 C3 1.480(3) . ? C2 H2 0.9300 . ? C3 C4 1.329(2) . ? C3 H3 0.9300 . ? C4 C17 1.428(3) . ? C4 C5 1.518(2) . ? C5 C14 1.509(2) . ? C5 C7 1.538(2) . ? C7 O1 1.211(2) . ? C7 N1 1.359(2) . ? N1 C9 1.400(2) . ? N1 C18 1.450(2) . ? C9 C10 1.384(3) . ? C9 C14 1.385(2) . ? C10 C11 1.386(3) . ? C10 H10 0.9300 . ? C11 C12 1.377(3) . ? C11 H11 0.9300 . ? C12 C13 1.395(3) . ? C12 H12 0.9300 . ? C13 C14 1.372(2) . ? C13 H13 0.9300 . ? C15 O2 1.193(2) . ? C15 O3 1.331(2) . ? C16 O3 1.448(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 N2 1.139(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 C1 C2 114.68(15) . . ? C15 C1 C5 112.50(13) . . ? C2 C1 C5 106.27(14) . . ? C15 C1 H1 107.0(11) . . ? C2 C1 H1 111.8(11) . . ? C5 C1 H1 104.2(12) . . ? C3 C2 C1 103.41(15) . . ? C3 C2 H2 128.3 . . ? C1 C2 H2 128.3 . . ? C4 C3 C2 112.20(16) . . ? C4 C3 H3 123.9 . . ? C2 C3 H3 123.9 . . ? C3 C4 C17 126.32(16) . . ? C3 C4 C5 112.78(15) . . ? C17 C4 C5 120.59(15) . . ? C14 C5 C4 112.95(13) . . ? C14 C5 C7 102.03(12) . . ? C4 C5 C7 113.22(13) . . ? C14 C5 C1 117.13(13) . . ? C4 C5 C1 100.60(12) . . ? C7 C5 C1 111.44(13) . . ? O1 C7 N1 126.40(16) . . ? O1 C7 C5 125.59(16) . . ? N1 C7 C5 108.01(14) . . ? C7 N1 C9 111.41(14) . . ? C7 N1 C18 124.10(17) . . ? C9 N1 C18 124.48(16) . . ? C10 C9 C14 121.52(17) . . ? C10 C9 N1 128.51(17) . . ? C14 C9 N1 109.97(14) . . ? C9 C10 C11 117.40(19) . . ? C9 C10 H10 121.3 . . ? C11 C10 H10 121.3 . . ? C12 C11 C10 121.73(19) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 120.0(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 118.89(18) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C9 120.44(16) . . ? C13 C14 C5 130.98(15) . . ? C9 C14 C5 108.58(14) . . ? O2 C15 O3 124.59(18) . . ? O2 C15 C1 125.66(17) . . ? O3 C15 C1 109.74(15) . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 C4 178.1(2) . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 O3 C16 115.54(17) . . ? 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 C15 C1 C2 C3 145.77(17) . . . . ? C5 C1 C2 C3 20.8(2) . . . . ? C1 C2 C3 C4 -13.1(2) . . . . ? C2 C3 C4 C17 -174.12(19) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C3 C4 C5 C14 -112.19(18) . . . . ? C17 C4 C5 C14 61.8(2) . . . . ? C3 C4 C5 C7 132.48(18) . . . . ? C17 C4 C5 C7 -53.5(2) . . . . ? C3 C4 C5 C1 13.5(2) . . . . ? C17 C4 C5 C1 -172.54(16) . . . . ? C15 C1 C5 C14 -24.1(2) . . . . ? C2 C1 C5 C14 102.22(16) . . . . ? C15 C1 C5 C4 -146.85(14) . . . . ? C2 C1 C5 C4 -20.57(18) . . . . ? C15 C1 C5 C7 92.87(16) . . . . ? C2 C1 C5 C7 -140.86(15) . . . . ? C14 C5 C7 O1 -179.42(19) . . . . ? C4 C5 C7 O1 -57.7(2) . . . . ? C1 C5 C7 O1 54.8(2) . . . . ? C14 C5 C7 N1 0.41(17) . . . . ? C4 C5 C7 N1 122.08(16) . . . . ? C1 C5 C7 N1 -125.37(15) . . . . ? O1 C7 N1 C9 179.61(19) . . . . ? C5 C7 N1 C9 -0.22(19) . . . . ? O1 C7 N1 C18 -1.3(3) . . . . ? C5 C7 N1 C18 178.85(17) . . . . ? C7 N1 C9 C10 179.85(18) . . . . ? C18 N1 C9 C10 0.8(3) . . . . ? C7 N1 C9 C14 -0.1(2) . . . . ? C18 N1 C9 C14 -179.16(17) . . . . ? C14 C9 C10 C11 -1.5(3) . . . . ? N1 C9 C10 C11 178.55(17) . . . . ? C9 C10 C11 C12 0.9(3) . . . . ? C10 C11 C12 C13 0.1(3) . . . . ? C11 C12 C13 C14 -0.4(3) . . . . ? C12 C13 C14 C9 -0.3(3) . . . . ? C12 C13 C14 C5 -179.22(17) . . . . ? C10 C9 C14 C13 1.2(3) . . . . ? N1 C9 C14 C13 -178.81(14) . . . . ? C10 C9 C14 C5 -179.59(16) . . . . ? N1 C9 C14 C5 0.36(18) . . . . ? C4 C5 C14 C13 56.7(2) . . . . ? C7 C5 C14 C13 178.59(17) . . . . ? C1 C5 C14 C13 -59.5(2) . . . . ? C4 C5 C14 C9 -122.32(15) . . . . ? C7 C5 C14 C9 -0.46(16) . . . . ? C1 C5 C14 C9 121.49(15) . . . . ? C2 C1 C15 O2 -5.7(3) . . . . ? C5 C1 C15 O2 115.9(2) . . . . ? C2 C1 C15 O3 174.87(15) . . . . ? C5 C1 C15 O3 -63.52(19) . . . . ? C3 C4 C17 N2 139(7) . . . . ? C5 C4 C17 N2 -34(7) . . . . ? O2 C15 O3 C16 -2.3(3) . . . . ? C1 C15 O3 C16 177.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.605 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.065