# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Simon Pope' _publ_contact_author_email POPESJ@CARDIFF.AC.UK _publ_section_title ; The coordination chemistry of fluorescent pyridyl- and quinolyl-phthalimide ligands with the {AuI-PPh3} cationic unit ; loop_ _publ_author_name 'Simon Pope' 'Michael Coogan' 'Benson M Kariuki' 'Rebecca Laye' 'Lucy A. Mullice' ; F.Thorp-Greenwood ; # Attachment 'Au-L1b.CIF' data_irl42 _database_code_depnum_ccdc_archive 'CCDC 723934' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _publ_section_exptl_refinement ; The structure was solved by direct methods. Data processing was carried out to 0.77 angstroms. The asymmetric unit contains one molecule of [AuL(PPh3)][CF3SO3] and one molecule of chloroform. All non-hydrogen atoms were refined anistropically. Hydrogens were included in calculated positions using the riding model. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H24 Au Cl3 F3 N2 O5 P S' _chemical_formula_weight 951.89 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 17.6586(10) _cell_length_b 11.2141(6) _cell_length_c 17.6983(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.781(3) _cell_angle_gamma 90.00 _cell_volume 3472.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9934 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.821 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 4.634 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3676 _exptl_absorpt_correction_T_max 0.8014 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42366 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 27.59 _reflns_number_total 8025 _reflns_number_gt 6710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Kappa Apex2(v2.1)' _computing_cell_refinement 'Bruker Kappa Apex2(v2.1)' _computing_data_reduction 'Bruker Kappa Apex2(v2.1)' _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^)+(0.0159P)^2^+4.5326P] 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 8025 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_ref 0.0478 _refine_ls_wR_factor_gt 0.0433 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.218217(6) 0.490936(8) 0.339544(6) 0.02219(3) Uani 1 1 d . . . P1 P 0.29742(4) 0.64669(6) 0.36204(4) 0.02023(14) Uani 1 1 d . . . N1 N 0.00703(12) 0.23062(18) 0.16280(12) 0.0214(5) Uani 1 1 d . . . N2 N 0.14240(12) 0.34963(18) 0.32023(12) 0.0230(5) Uani 1 1 d . . . O1 O -0.00419(12) 0.02400(16) 0.16343(12) 0.0318(5) Uani 1 1 d . . . O2 O 0.00545(12) 0.42697(16) 0.11934(11) 0.0307(4) Uani 1 1 d . . . C1 C -0.01587(15) 0.1180(2) 0.13123(15) 0.0238(6) Uani 1 1 d . . . C2 C -0.01069(15) 0.3235(2) 0.10890(15) 0.0242(6) Uani 1 1 d . . . C3 C -0.05682(15) 0.1439(2) 0.05431(15) 0.0259(6) Uani 1 1 d . . . C4 C -0.09540(17) 0.0667(3) 0.00174(17) 0.0347(7) Uani 1 1 d . . . H4A H -0.0965 -0.0167 0.0107 0.042 Uiso 1 1 calc R . . C5 C -0.13257(19) 0.1173(3) -0.06496(18) 0.0429(8) Uani 1 1 d . . . H5A H -0.1602 0.0674 -0.1024 0.051 Uiso 1 1 calc R . . C6 C -0.13003(19) 0.2391(3) -0.07791(18) 0.0437(8) Uani 1 1 d . . . H6A H -0.1561 0.2709 -0.1240 0.052 Uiso 1 1 calc R . . C7 C -0.09019(18) 0.3161(3) -0.02503(17) 0.0371(7) Uani 1 1 d . . . H7A H -0.0879 0.3994 -0.0341 0.045 Uiso 1 1 calc R . . C8 C -0.05422(16) 0.2652(2) 0.04110(16) 0.0272(6) Uani 1 1 d . . . C9 C 0.04698(14) 0.2462(2) 0.23716(15) 0.0207(5) Uani 1 1 d . . . C10 C 0.10411(14) 0.3318(2) 0.25001(15) 0.0222(5) Uani 1 1 d . . . H10A H 0.1164 0.3785 0.2086 0.027 Uiso 1 1 calc R . . C11 C 0.12709(16) 0.2810(2) 0.37839(16) 0.0268(6) Uani 1 1 d . . . H11A H 0.1551 0.2929 0.4275 0.032 Uiso 1 1 calc R . . C12 C 0.07165(16) 0.1937(2) 0.36861(16) 0.0284(6) Uani 1 1 d . . . H12A H 0.0620 0.1457 0.4105 0.034 Uiso 1 1 calc R . . C13 C 0.03028(15) 0.1764(2) 0.29773(16) 0.0250(6) Uani 1 1 d . . . H13A H -0.0089 0.1179 0.2903 0.030 Uiso 1 1 calc R . . C14 C 0.25709(14) 0.7828(2) 0.31832(14) 0.0204(5) Uani 1 1 d . . . C15 C 0.17782(16) 0.7926(3) 0.30304(17) 0.0297(6) Uani 1 1 d . . . H15A H 0.1465 0.7277 0.3139 0.036 Uiso 1 1 calc R . . C16 C 0.14457(16) 0.8968(3) 0.27203(17) 0.0334(7) Uani 1 1 d . . . H16A H 0.0905 0.9033 0.2619 0.040 Uiso 1 1 calc R . . C17 C 0.18983(16) 0.9908(2) 0.25591(16) 0.0283(6) Uani 1 1 d . . . H17A H 0.1669 1.0623 0.2351 0.034 Uiso 1 1 calc R . . C18 C 0.26832(17) 0.9817(2) 0.26988(17) 0.0299(6) Uani 1 1 d . . . H18A H 0.2994 1.0463 0.2578 0.036 Uiso 1 1 calc R . . C19 C 0.30198(16) 0.8780(2) 0.30163(17) 0.0287(6) Uani 1 1 d . . . H19A H 0.3561 0.8724 0.3119 0.034 Uiso 1 1 calc R . . C20 C 0.31992(15) 0.6755(2) 0.46299(15) 0.0222(5) Uani 1 1 d . . . C21 C 0.32260(16) 0.5782(2) 0.51212(16) 0.0274(6) Uani 1 1 d . . . H21A H 0.3111 0.5007 0.4921 0.033 Uiso 1 1 calc R . . C22 C 0.34199(18) 0.5937(3) 0.59019(17) 0.0355(7) Uani 1 1 d . . . H22A H 0.3431 0.5272 0.6236 0.043 Uiso 1 1 calc R . . C23 C 0.35958(19) 0.7060(3) 0.61894(17) 0.0392(8) Uani 1 1 d . . . H23A H 0.3740 0.7166 0.6722 0.047 Uiso 1 1 calc R . . C24 C 0.35639(19) 0.8032(3) 0.57078(18) 0.0398(8) Uani 1 1 d . . . H24A H 0.3682 0.8804 0.5912 0.048 Uiso 1 1 calc R . . C25 C 0.33609(17) 0.7890(2) 0.49287(16) 0.0321(7) Uani 1 1 d . . . H25A H 0.3332 0.8564 0.4600 0.038 Uiso 1 1 calc R . . C26 C 0.38715(15) 0.6236(2) 0.32565(16) 0.0254(6) Uani 1 1 d . . . C27 C 0.38916(18) 0.5455(3) 0.26455(17) 0.0336(7) Uani 1 1 d . . . H27A H 0.3442 0.5039 0.2440 0.040 Uiso 1 1 calc R . . C28 C 0.4563(2) 0.5285(3) 0.2338(2) 0.0481(9) Uani 1 1 d . . . H28A H 0.4575 0.4752 0.1923 0.058 Uiso 1 1 calc R . . C29 C 0.5215(2) 0.5888(4) 0.2636(2) 0.0529(10) Uani 1 1 d . . . H29A H 0.5674 0.5775 0.2420 0.064 Uiso 1 1 calc R . . C30 C 0.52083(18) 0.6654(3) 0.3243(2) 0.0490(9) Uani 1 1 d . . . H30A H 0.5662 0.7064 0.3445 0.059 Uiso 1 1 calc R . . C31 C 0.45368(16) 0.6828(3) 0.35602(19) 0.0356(7) Uani 1 1 d . . . H31A H 0.4533 0.7349 0.3983 0.043 Uiso 1 1 calc R . . C32 C 0.2398(2) 0.3979(3) 0.07622(19) 0.0426(8) Uani 1 1 d . . . O3 O 0.26044(19) 0.2287(2) 0.17178(14) 0.0704(9) Uani 1 1 d . . . O4 O 0.14500(14) 0.2279(2) 0.08337(17) 0.0640(8) Uani 1 1 d . . . O5 O 0.26287(13) 0.18412(18) 0.03785(14) 0.0440(6) Uani 1 1 d . . . S1 S 0.22588(4) 0.24131(6) 0.09524(4) 0.02897(15) Uani 1 1 d . . . F1 F 0.2113(2) 0.4290(2) 0.00756(13) 0.1002(11) Uani 1 1 d . . . F2 F 0.31461(16) 0.4212(2) 0.08367(18) 0.0899(9) Uani 1 1 d . . . F3 F 0.21050(13) 0.46906(16) 0.12534(12) 0.0544(5) Uani 1 1 d . . . C33 C 0.39564(19) 0.2527(3) 0.4411(2) 0.0414(8) Uani 1 1 d . . . H33 H 0.3609 0.2674 0.4803 0.050 Uiso 1 1 calc R . . Cl1 Cl 0.46345(5) 0.36690(8) 0.44646(6) 0.0511(2) Uani 1 1 d . . . Cl2 Cl 0.44060(6) 0.11265(8) 0.45928(7) 0.0638(3) Uani 1 1 d . . . Cl3 Cl 0.34103(6) 0.25287(9) 0.35058(7) 0.0679(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.02151(5) 0.02074(5) 0.02355(5) -0.00119(4) 0.00025(4) -0.00235(4) P1 0.0198(3) 0.0200(3) 0.0205(3) 0.0010(2) 0.0012(3) -0.0009(3) N1 0.0200(11) 0.0203(10) 0.0231(12) -0.0013(8) 0.0003(9) -0.0001(9) N2 0.0235(12) 0.0200(10) 0.0248(12) -0.0005(9) 0.0009(9) 0.0005(9) O1 0.0353(11) 0.0205(9) 0.0379(12) -0.0002(8) -0.0017(9) -0.0019(8) O2 0.0390(12) 0.0211(9) 0.0308(11) 0.0001(8) 0.0001(9) 0.0017(8) C1 0.0183(13) 0.0257(13) 0.0278(15) -0.0049(11) 0.0042(11) -0.0011(10) C2 0.0229(14) 0.0266(13) 0.0237(14) 0.0009(10) 0.0050(11) 0.0044(11) C3 0.0220(14) 0.0306(14) 0.0255(15) -0.0044(11) 0.0044(11) 0.0000(11) C4 0.0305(16) 0.0402(16) 0.0336(17) -0.0092(13) 0.0045(13) -0.0067(13) C5 0.0372(18) 0.060(2) 0.0307(18) -0.0144(15) 0.0009(14) -0.0073(16) C6 0.0415(19) 0.063(2) 0.0235(16) -0.0008(15) -0.0050(14) 0.0035(17) C7 0.0388(18) 0.0429(17) 0.0286(16) 0.0006(13) 0.0007(14) 0.0048(14) C8 0.0244(14) 0.0328(14) 0.0246(15) -0.0035(11) 0.0035(12) 0.0047(11) C9 0.0192(13) 0.0182(11) 0.0243(14) -0.0018(10) 0.0010(11) 0.0032(10) C10 0.0222(13) 0.0195(12) 0.0249(14) 0.0003(10) 0.0031(11) 0.0024(10) C11 0.0300(15) 0.0274(13) 0.0223(14) 0.0014(11) 0.0004(12) 0.0010(11) C12 0.0328(16) 0.0251(13) 0.0270(15) 0.0055(11) 0.0036(12) -0.0010(12) C13 0.0227(14) 0.0214(12) 0.0313(15) 0.0011(11) 0.0049(12) -0.0021(10) C14 0.0210(13) 0.0227(12) 0.0179(13) 0.0013(10) 0.0035(10) 0.0004(10) C15 0.0221(14) 0.0316(14) 0.0362(17) 0.0103(12) 0.0066(12) -0.0001(11) C16 0.0192(14) 0.0404(16) 0.0414(18) 0.0114(13) 0.0066(13) 0.0061(12) C17 0.0313(15) 0.0259(13) 0.0284(14) 0.0035(11) 0.0062(12) 0.0081(12) C18 0.0303(15) 0.0239(13) 0.0355(16) 0.0045(11) 0.0043(12) -0.0036(11) C19 0.0183(13) 0.0292(14) 0.0376(17) 0.0047(12) 0.0000(12) -0.0023(11) C20 0.0209(13) 0.0238(12) 0.0218(13) 0.0007(10) 0.0027(11) 0.0005(10) C21 0.0284(15) 0.0253(13) 0.0285(15) 0.0018(11) 0.0040(12) -0.0005(11) C22 0.0406(18) 0.0407(16) 0.0246(16) 0.0086(12) 0.0028(13) 0.0024(14) C23 0.051(2) 0.0436(17) 0.0209(15) -0.0026(13) -0.0020(14) 0.0064(15) C24 0.053(2) 0.0300(15) 0.0339(17) -0.0095(13) -0.0050(15) 0.0055(14) C25 0.0417(18) 0.0243(13) 0.0279(15) 0.0009(11) -0.0036(13) 0.0010(12) C26 0.0219(14) 0.0283(13) 0.0261(15) 0.0102(11) 0.0033(11) 0.0036(11) C27 0.0314(16) 0.0434(16) 0.0261(15) 0.0046(12) 0.0040(13) 0.0083(13) C28 0.049(2) 0.064(2) 0.0346(18) 0.0081(16) 0.0156(16) 0.0241(18) C29 0.0328(19) 0.077(3) 0.053(2) 0.022(2) 0.0208(17) 0.0218(19) C30 0.0201(15) 0.061(2) 0.066(3) 0.0189(19) 0.0048(16) 0.0014(15) C31 0.0246(15) 0.0387(16) 0.0433(19) 0.0068(14) 0.0034(14) -0.0002(13) C32 0.070(3) 0.0264(15) 0.0332(18) -0.0007(13) 0.0140(17) 0.0036(15) O3 0.113(2) 0.0543(16) 0.0374(15) 0.0168(12) -0.0142(15) 0.0031(16) O4 0.0379(14) 0.0672(17) 0.092(2) -0.0382(16) 0.0257(14) -0.0180(13) O5 0.0512(14) 0.0275(11) 0.0586(15) -0.0076(10) 0.0269(12) 0.0017(10) S1 0.0346(4) 0.0230(3) 0.0302(4) 0.0011(3) 0.0075(3) -0.0007(3) F1 0.215(4) 0.0434(13) 0.0400(14) 0.0139(10) 0.0072(17) 0.0299(17) F2 0.0862(19) 0.0515(14) 0.146(3) -0.0295(15) 0.0655(19) -0.0366(13) F3 0.0793(15) 0.0304(9) 0.0573(13) -0.0134(9) 0.0230(11) 0.0027(10) C33 0.0361(18) 0.0358(16) 0.054(2) -0.0007(15) 0.0136(16) 0.0065(14) Cl1 0.0451(5) 0.0442(5) 0.0612(6) 0.0012(4) -0.0032(4) -0.0015(4) Cl2 0.0570(6) 0.0418(5) 0.0951(8) 0.0162(5) 0.0192(6) 0.0134(4) Cl3 0.0521(6) 0.0546(5) 0.0881(8) -0.0273(5) -0.0231(5) 0.0186(5) _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 Au1 N2 2.073(2) . ? Au1 P1 2.2394(7) . ? P1 C20 1.806(3) . ? P1 C26 1.808(3) . ? P1 C14 1.813(3) . ? N1 C9 1.417(3) . ? N1 C1 1.418(3) . ? N1 C2 1.418(3) . ? N2 C11 1.342(3) . ? N2 C10 1.347(3) . ? O1 C1 1.203(3) . ? O2 C2 1.203(3) . ? C1 C3 1.481(4) . ? C2 C8 1.486(4) . ? C3 C4 1.381(4) . ? C3 C8 1.383(4) . ? C4 C5 1.391(4) . ? C4 H4A 0.9500 . ? C5 C6 1.388(5) . ? C5 H5A 0.9500 . ? C6 C7 1.392(4) . ? C6 H6A 0.9500 . ? C7 C8 1.377(4) . ? C7 H7A 0.9500 . ? C9 C10 1.389(3) . ? C9 C13 1.391(4) . ? C10 H10A 0.9500 . ? C11 C12 1.379(4) . ? C11 H11A 0.9500 . ? C12 C13 1.377(4) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C19 1.385(4) . ? C14 C15 1.394(4) . ? C15 C16 1.387(4) . ? C15 H15A 0.9500 . ? C16 C17 1.376(4) . ? C16 H16A 0.9500 . ? C17 C18 1.378(4) . ? C17 H17A 0.9500 . ? C18 C19 1.390(4) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 C21 1.392(4) . ? C20 C25 1.393(4) . ? C21 C22 1.389(4) . ? C21 H21A 0.9500 . ? C22 C23 1.379(4) . ? C22 H22A 0.9500 . ? C23 C24 1.380(4) . ? C23 H23A 0.9500 . ? C24 C25 1.386(4) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 C31 1.393(4) . ? C26 C27 1.395(4) . ? C27 C28 1.383(4) . ? C27 H27A 0.9500 . ? C28 C29 1.376(5) . ? C28 H28A 0.9500 . ? C29 C30 1.377(5) . ? C29 H29A 0.9500 . ? C30 C31 1.393(4) . ? C30 H30A 0.9500 . ? C31 H31A 0.9500 . ? C32 F1 1.298(4) . ? C32 F3 1.335(4) . ? C32 F2 1.335(4) . ? C32 S1 1.811(3) . ? O3 S1 1.415(2) . ? O4 S1 1.423(2) . ? O5 S1 1.432(2) . ? C33 Cl1 1.747(3) . ? C33 Cl3 1.754(4) . ? C33 Cl2 1.770(3) . ? C33 H33 1.0000 . ? 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 N2 Au1 P1 178.25(6) . . ? C20 P1 C26 106.98(12) . . ? C20 P1 C14 107.00(12) . . ? C26 P1 C14 106.34(12) . . ? C20 P1 Au1 111.35(9) . . ? C26 P1 Au1 112.40(9) . . ? C14 P1 Au1 112.40(9) . . ? C9 N1 C1 123.7(2) . . ? C9 N1 C2 124.8(2) . . ? C1 N1 C2 111.3(2) . . ? C11 N2 C10 119.6(2) . . ? C11 N2 Au1 120.31(18) . . ? C10 N2 Au1 119.89(17) . . ? O1 C1 N1 124.9(2) . . ? O1 C1 C3 129.7(2) . . ? N1 C1 C3 105.4(2) . . ? O2 C2 N1 125.4(2) . . ? O2 C2 C8 129.3(2) . . ? N1 C2 C8 105.3(2) . . ? C4 C3 C8 121.8(3) . . ? C4 C3 C1 129.2(3) . . ? C8 C3 C1 109.0(2) . . ? C3 C4 C5 116.7(3) . . ? C3 C4 H4A 121.6 . . ? C5 C4 H4A 121.6 . . ? C6 C5 C4 121.3(3) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C5 C6 C7 121.6(3) . . ? C5 C6 H6A 119.2 . . ? C7 C6 H6A 119.2 . . ? C8 C7 C6 116.6(3) . . ? C8 C7 H7A 121.7 . . ? C6 C7 H7A 121.7 . . ? C7 C8 C3 121.9(3) . . ? C7 C8 C2 129.3(3) . . ? C3 C8 C2 108.8(2) . . ? C10 C9 C13 119.2(2) . . ? C10 C9 N1 119.8(2) . . ? C13 C9 N1 121.0(2) . . ? N2 C10 C9 121.1(2) . . ? N2 C10 H10A 119.4 . . ? C9 C10 H10A 119.4 . . ? N2 C11 C12 121.6(2) . . ? N2 C11 H11A 119.2 . . ? C12 C11 H11A 119.2 . . ? C13 C12 C11 119.6(3) . . ? C13 C12 H12A 120.2 . . ? C11 C12 H12A 120.2 . . ? C12 C13 C9 118.8(2) . . ? C12 C13 H13A 120.6 . . ? C9 C13 H13A 120.6 . . ? C19 C14 C15 119.1(2) . . ? C19 C14 P1 122.5(2) . . ? C15 C14 P1 118.36(19) . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C17 C16 C15 120.0(3) . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C16 C17 C18 120.3(2) . . ? C16 C17 H17A 119.8 . . ? C18 C17 H17A 119.8 . . ? C17 C18 C19 119.9(3) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C14 C19 C18 120.3(3) . . ? C14 C19 H19A 119.8 . . ? C18 C19 H19A 119.8 . . ? C21 C20 C25 119.4(2) . . ? C21 C20 P1 117.5(2) . . ? C25 C20 P1 123.1(2) . . ? C22 C21 C20 120.4(3) . . ? C22 C21 H21A 119.8 . . ? C20 C21 H21A 119.8 . . ? C23 C22 C21 119.6(3) . . ? C23 C22 H22A 120.2 . . ? C21 C22 H22A 120.2 . . ? C22 C23 C24 120.4(3) . . ? C22 C23 H23A 119.8 . . ? C24 C23 H23A 119.8 . . ? C23 C24 C25 120.5(3) . . ? C23 C24 H24A 119.8 . . ? C25 C24 H24A 119.8 . . ? C24 C25 C20 119.6(3) . . ? C24 C25 H25A 120.2 . . ? C20 C25 H25A 120.2 . . ? C31 C26 C27 119.3(3) . . ? C31 C26 P1 121.9(2) . . ? C27 C26 P1 118.8(2) . . ? C28 C27 C26 120.3(3) . . ? C28 C27 H27A 119.9 . . ? C26 C27 H27A 119.9 . . ? C29 C28 C27 119.9(3) . . ? C29 C28 H28A 120.0 . . ? C27 C28 H28A 120.0 . . ? C28 C29 C30 120.7(3) . . ? C28 C29 H29A 119.7 . . ? C30 C29 H29A 119.7 . . ? C29 C30 C31 120.0(3) . . ? C29 C30 H30A 120.0 . . ? C31 C30 H30A 120.0 . . ? C26 C31 C30 119.8(3) . . ? C26 C31 H31A 120.1 . . ? C30 C31 H31A 120.1 . . ? F1 C32 F3 108.3(3) . . ? F1 C32 F2 107.0(3) . . ? F3 C32 F2 106.5(3) . . ? F1 C32 S1 112.9(2) . . ? F3 C32 S1 112.6(2) . . ? F2 C32 S1 109.2(2) . . ? O3 S1 O4 115.13(19) . . ? O3 S1 O5 117.08(17) . . ? O4 S1 O5 113.15(15) . . ? O3 S1 C32 102.90(16) . . ? O4 S1 C32 103.53(18) . . ? O5 S1 C32 102.47(14) . . ? Cl1 C33 Cl3 109.70(19) . . ? Cl1 C33 Cl2 110.68(18) . . ? Cl3 C33 Cl2 110.15(18) . . ? Cl1 C33 H33 108.8 . . ? Cl3 C33 H33 108.8 . . ? Cl2 C33 H33 108.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Au1 P1 C20 63(2) . . . . ? N2 Au1 P1 C26 -177(100) . . . . ? N2 Au1 P1 C14 -57(2) . . . . ? P1 Au1 N2 C11 -73(2) . . . . ? P1 Au1 N2 C10 102(2) . . . . ? C9 N1 C1 O1 0.0(4) . . . . ? C2 N1 C1 O1 176.1(3) . . . . ? C9 N1 C1 C3 178.7(2) . . . . ? C2 N1 C1 C3 -5.1(3) . . . . ? C9 N1 C2 O2 -0.4(4) . . . . ? C1 N1 C2 O2 -176.5(3) . . . . ? C9 N1 C2 C8 -178.5(2) . . . . ? C1 N1 C2 C8 5.4(3) . . . . ? O1 C1 C3 C4 3.8(5) . . . . ? N1 C1 C3 C4 -174.9(3) . . . . ? O1 C1 C3 C8 -178.6(3) . . . . ? N1 C1 C3 C8 2.7(3) . . . . ? C8 C3 C4 C5 -0.9(4) . . . . ? C1 C3 C4 C5 176.5(3) . . . . ? C3 C4 C5 C6 0.7(5) . . . . ? C4 C5 C6 C7 0.1(6) . . . . ? C5 C6 C7 C8 -0.7(5) . . . . ? C6 C7 C8 C3 0.5(5) . . . . ? C6 C7 C8 C2 -177.1(3) . . . . ? C4 C3 C8 C7 0.3(5) . . . . ? C1 C3 C8 C7 -177.5(3) . . . . ? C4 C3 C8 C2 178.3(3) . . . . ? C1 C3 C8 C2 0.5(3) . . . . ? O2 C2 C8 C7 -3.7(5) . . . . ? N1 C2 C8 C7 174.3(3) . . . . ? O2 C2 C8 C3 178.5(3) . . . . ? N1 C2 C8 C3 -3.5(3) . . . . ? C1 N1 C9 C10 141.7(3) . . . . ? C2 N1 C9 C10 -33.9(4) . . . . ? C1 N1 C9 C13 -37.8(4) . . . . ? C2 N1 C9 C13 146.5(3) . . . . ? C11 N2 C10 C9 2.3(4) . . . . ? Au1 N2 C10 C9 -172.88(18) . . . . ? C13 C9 C10 N2 -1.3(4) . . . . ? N1 C9 C10 N2 179.2(2) . . . . ? C10 N2 C11 C12 -1.4(4) . . . . ? Au1 N2 C11 C12 173.7(2) . . . . ? N2 C11 C12 C13 -0.5(4) . . . . ? C11 C12 C13 C9 1.5(4) . . . . ? C10 C9 C13 C12 -0.7(4) . . . . ? N1 C9 C13 C12 178.9(2) . . . . ? C20 P1 C14 C19 80.0(3) . . . . ? C26 P1 C14 C19 -34.0(3) . . . . ? Au1 P1 C14 C19 -157.4(2) . . . . ? C20 P1 C14 C15 -98.2(2) . . . . ? C26 P1 C14 C15 147.8(2) . . . . ? Au1 P1 C14 C15 24.4(2) . . . . ? C19 C14 C15 C16 -0.5(4) . . . . ? P1 C14 C15 C16 177.8(2) . . . . ? C14 C15 C16 C17 0.3(5) . . . . ? C15 C16 C17 C18 0.5(5) . . . . ? C16 C17 C18 C19 -1.1(4) . . . . ? C15 C14 C19 C18 -0.2(4) . . . . ? P1 C14 C19 C18 -178.4(2) . . . . ? C17 C18 C19 C14 1.0(4) . . . . ? C26 P1 C20 C21 -91.2(2) . . . . ? C14 P1 C20 C21 155.2(2) . . . . ? Au1 P1 C20 C21 32.0(2) . . . . ? C26 P1 C20 C25 87.3(3) . . . . ? C14 P1 C20 C25 -26.3(3) . . . . ? Au1 P1 C20 C25 -149.5(2) . . . . ? C25 C20 C21 C22 -0.7(4) . . . . ? P1 C20 C21 C22 177.9(2) . . . . ? C20 C21 C22 C23 -0.8(5) . . . . ? C21 C22 C23 C24 1.4(5) . . . . ? C22 C23 C24 C25 -0.5(5) . . . . ? C23 C24 C25 C20 -1.0(5) . . . . ? C21 C20 C25 C24 1.6(4) . . . . ? P1 C20 C25 C24 -177.0(2) . . . . ? C20 P1 C26 C31 -32.8(3) . . . . ? C14 P1 C26 C31 81.3(2) . . . . ? Au1 P1 C26 C31 -155.3(2) . . . . ? C20 P1 C26 C27 148.3(2) . . . . ? C14 P1 C26 C27 -97.6(2) . . . . ? Au1 P1 C26 C27 25.8(2) . . . . ? C31 C26 C27 C28 -0.9(4) . . . . ? P1 C26 C27 C28 178.1(2) . . . . ? C26 C27 C28 C29 -0.1(5) . . . . ? C27 C28 C29 C30 0.7(5) . . . . ? C28 C29 C30 C31 -0.3(5) . . . . ? C27 C26 C31 C30 1.3(4) . . . . ? P1 C26 C31 C30 -177.6(2) . . . . ? C29 C30 C31 C26 -0.7(5) . . . . ? F1 C32 S1 O3 -179.7(3) . . . . ? F3 C32 S1 O3 -56.7(3) . . . . ? F2 C32 S1 O3 61.4(3) . . . . ? F1 C32 S1 O4 -59.5(3) . . . . ? F3 C32 S1 O4 63.5(3) . . . . ? F2 C32 S1 O4 -178.4(2) . . . . ? F1 C32 S1 O5 58.4(3) . . . . ? F3 C32 S1 O5 -178.6(3) . . . . ? F2 C32 S1 O5 -60.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.048 _refine_diff_density_min -0.733 _refine_diff_density_rms 0.082 # Attachment 'Au-L3b.cif' data_sp0804 _database_code_depnum_ccdc_archive 'CCDC 723935' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H25 Au N2 O2 P, C F3 O3 S' _chemical_formula_sum 'C33 H25 Au F3 N2 O5 P S' _chemical_formula_weight 846.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 8.5090(2) _cell_length_b 21.2850(5) _cell_length_c 18.1110(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.8970(10) _cell_angle_gamma 90.00 _cell_volume 3262.80(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5781 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.52 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.723 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 4.682 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4544 _exptl_absorpt_correction_T_max 0.4544 _exptl_absorpt_process_details Denzo/scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12672 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0654 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.52 _reflns_number_total 7455 _reflns_number_gt 5781 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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. Analysis reveals solvent accessible voids in the structure but they contain no significant electron density. ; _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^)+(0.0102P)^2^+5.3775P] 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 7455 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0746 _refine_ls_wR_factor_gt 0.0680 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.1250(6) 0.8730(2) 0.6888(2) 0.0286(11) Uani 1 1 d . . . C2 C 0.1979(5) 0.8191(2) 0.7327(2) 0.0245(10) Uani 1 1 d . . . C3 C 0.1266(6) 0.7702(2) 0.7682(2) 0.0310(11) Uani 1 1 d . . . H3 H 0.0151 0.7675 0.7678 0.037 Uiso 1 1 calc R . . C4 C 0.2257(7) 0.7260(2) 0.8038(3) 0.0367(13) Uani 1 1 d . . . H4 H 0.1814 0.6924 0.8293 0.044 Uiso 1 1 calc R . . C5 C 0.3882(7) 0.7293(2) 0.8034(3) 0.0374(13) Uani 1 1 d . . . H5 H 0.4525 0.6974 0.8275 0.045 Uiso 1 1 calc R . . C6 C 0.4594(6) 0.7784(2) 0.7685(2) 0.0330(12) Uani 1 1 d . . . H6 H 0.5709 0.7810 0.7687 0.040 Uiso 1 1 calc R . . C7 C 0.3611(5) 0.8228(2) 0.7336(2) 0.0251(10) Uani 1 1 d . . . C8 C 0.3982(6) 0.8804(2) 0.6923(2) 0.0282(11) Uani 1 1 d . . . C9 C 0.2380(6) 0.9656(2) 0.6252(2) 0.0316(12) Uani 1 1 d . . . H9A H 0.3178 0.9955 0.6481 0.038 Uiso 1 1 calc R . . H9B H 0.1323 0.9835 0.6305 0.038 Uiso 1 1 calc R . . C10 C 0.2582(5) 0.9595(2) 0.5432(2) 0.0227(10) Uani 1 1 d . . . C11 C 0.2018(6) 1.0066(2) 0.4952(2) 0.0301(11) Uani 1 1 d . . . H11 H 0.1450 1.0409 0.5131 0.036 Uiso 1 1 calc R . . C12 C 0.2277(6) 1.0039(2) 0.4217(2) 0.0288(11) Uani 1 1 d . . . H12 H 0.1901 1.0373 0.3898 0.035 Uiso 1 1 calc R . . C13 C 0.3571(6) 0.9096(2) 0.4390(2) 0.0305(11) Uani 1 1 d . . . H13 H 0.4118 0.8754 0.4196 0.037 Uiso 1 1 calc R . . C14 C 0.3352(6) 0.9099(2) 0.5136(2) 0.0311(11) Uani 1 1 d . . . H14 H 0.3731 0.8759 0.5445 0.037 Uiso 1 1 calc R . . C15 C 0.6113(5) 0.9799(2) 0.1667(2) 0.0254(10) Uani 1 1 d . . . C16 C 0.7181(6) 0.9373(3) 0.2034(2) 0.0389(13) Uani 1 1 d . . . H16 H 0.6807 0.8989 0.2217 0.047 Uiso 1 1 calc R . . C17 C 0.8777(6) 0.9511(3) 0.2131(3) 0.0504(17) Uani 1 1 d . . . H17 H 0.9507 0.9218 0.2366 0.060 Uiso 1 1 calc R . . C18 C 0.9292(6) 1.0077(3) 0.1885(3) 0.0497(17) Uani 1 1 d . . . H18 H 1.0381 1.0181 0.1972 0.060 Uiso 1 1 calc R . . C19 C 0.8265(7) 1.0497(3) 0.1514(3) 0.0438(15) Uani 1 1 d . . . H19 H 0.8647 1.0882 0.1335 0.053 Uiso 1 1 calc R . . C20 C 0.6655(6) 1.0354(2) 0.1403(2) 0.0330(12) Uani 1 1 d . . . H20 H 0.5938 1.0640 0.1145 0.040 Uiso 1 1 calc R . . C21 C 0.3677(5) 0.8912(2) 0.1104(2) 0.0259(10) Uani 1 1 d . . . C22 C 0.4528(6) 0.8787(3) 0.0501(3) 0.0359(12) Uani 1 1 d . . . H22 H 0.5354 0.9062 0.0393 0.043 Uiso 1 1 calc R . . C23 C 0.4174(7) 0.8265(3) 0.0061(3) 0.0442(14) Uani 1 1 d . . . H23 H 0.4751 0.8184 -0.0351 0.053 Uiso 1 1 calc R . . C24 C 0.2981(7) 0.7863(3) 0.0220(3) 0.0460(14) Uani 1 1 d . . . H24 H 0.2735 0.7506 -0.0085 0.055 Uiso 1 1 calc R . . C25 C 0.2148(6) 0.7977(2) 0.0818(3) 0.0380(13) Uani 1 1 d . . . H25 H 0.1341 0.7694 0.0929 0.046 Uiso 1 1 calc R . . C26 C 0.2483(6) 0.8503(2) 0.1260(2) 0.0319(12) Uani 1 1 d . . . H26 H 0.1896 0.8583 0.1669 0.038 Uiso 1 1 calc R . . C27 C 0.2973(5) 1.0242(2) 0.1125(2) 0.0218(10) Uani 1 1 d . . . C28 C 0.2288(5) 1.0147(2) 0.0399(2) 0.0251(10) Uani 1 1 d . . . H28 H 0.2377 0.9751 0.0165 0.030 Uiso 1 1 calc R . . C29 C 0.1476(6) 1.0636(2) 0.0019(2) 0.0305(11) Uani 1 1 d . . . H29 H 0.1007 1.0572 -0.0474 0.037 Uiso 1 1 calc R . . C30 C 0.1348(6) 1.1210(2) 0.0352(3) 0.0327(11) Uani 1 1 d . . . H30 H 0.0797 1.1542 0.0087 0.039 Uiso 1 1 calc R . . C31 C 0.2019(6) 1.1308(2) 0.1075(3) 0.0339(12) Uani 1 1 d . . . H31 H 0.1932 1.1707 0.1304 0.041 Uiso 1 1 calc R . . C32 C 0.2812(6) 1.0824(2) 0.1460(3) 0.0300(11) Uani 1 1 d . . . H32 H 0.3253 1.0889 0.1958 0.036 Uiso 1 1 calc R . . C33 C 0.8140(10) 0.8071(3) 0.4683(4) 0.069(2) Uani 1 1 d . . . O1 O -0.0112(4) 0.88679(16) 0.67479(17) 0.0368(8) Uani 1 1 d . . . O2 O 0.5262(4) 0.90285(17) 0.68224(17) 0.0357(8) Uani 1 1 d . . . O3 O 0.6744(4) 0.88249(16) 0.37334(17) 0.0361(8) Uani 1 1 d . . . O4 O 0.8128(5) 0.79404(19) 0.3269(2) 0.0544(11) Uani 1 1 d . . . O5 O 0.9591(5) 0.88264(19) 0.3867(2) 0.0612(12) Uani 1 1 d . . . P1 P 0.40190(14) 0.96165(6) 0.16470(6) 0.0219(3) Uani 1 1 d . . . N1 N 0.2539(5) 0.90627(17) 0.66573(18) 0.0245(9) Uani 1 1 d . . . N2 N 0.3038(4) 0.95602(17) 0.39327(18) 0.0201(8) Uani 1 1 d . . . Au1 Au 0.34447(2) 0.956161(8) 0.282405(8) 0.02237(6) Uani 1 1 d . . . S1 S 0.81639(15) 0.84578(6) 0.37827(7) 0.0353(3) Uani 1 1 d . . . F1 F 0.6892(6) 0.77076(19) 0.4693(2) 0.0888(14) Uani 1 1 d . . . F2 F 0.8138(8) 0.84851(19) 0.5222(2) 0.130(2) Uani 1 1 d . . . F3 F 0.9421(7) 0.7712(2) 0.4810(3) 0.140(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(3) 0.030(3) 0.019(2) 0.000(2) 0.0044(19) 0.000(2) C2 0.033(3) 0.026(3) 0.014(2) -0.0002(19) 0.0002(17) -0.001(2) C3 0.033(3) 0.034(3) 0.027(2) 0.001(2) 0.007(2) -0.005(2) C4 0.058(4) 0.026(3) 0.028(3) 0.009(2) 0.010(2) -0.005(3) C5 0.047(3) 0.031(3) 0.033(3) 0.009(2) 0.000(2) 0.004(3) C6 0.035(3) 0.037(3) 0.027(2) 0.003(2) 0.000(2) -0.004(2) C7 0.029(3) 0.027(3) 0.019(2) 0.002(2) 0.0001(18) -0.003(2) C8 0.037(3) 0.031(3) 0.016(2) 0.000(2) 0.0001(19) -0.001(2) C9 0.055(3) 0.021(3) 0.020(2) 0.002(2) 0.010(2) 0.007(2) C10 0.032(3) 0.018(2) 0.017(2) -0.0029(19) 0.0023(18) -0.003(2) C11 0.046(3) 0.020(3) 0.025(2) -0.001(2) 0.008(2) 0.006(2) C12 0.042(3) 0.023(3) 0.022(2) 0.005(2) 0.004(2) 0.012(2) C13 0.040(3) 0.031(3) 0.021(2) -0.001(2) 0.006(2) 0.012(2) C14 0.046(3) 0.025(3) 0.022(2) 0.007(2) 0.003(2) 0.014(2) C15 0.024(2) 0.038(3) 0.014(2) -0.005(2) 0.0054(17) -0.004(2) C16 0.034(3) 0.063(4) 0.022(2) 0.008(3) 0.008(2) 0.008(3) C17 0.031(3) 0.095(5) 0.026(3) 0.003(3) 0.009(2) 0.014(3) C18 0.027(3) 0.089(5) 0.035(3) -0.035(3) 0.012(2) -0.012(3) C19 0.043(3) 0.053(4) 0.039(3) -0.019(3) 0.020(3) -0.022(3) C20 0.032(3) 0.044(3) 0.024(2) -0.013(2) 0.012(2) -0.011(2) C21 0.029(3) 0.029(3) 0.020(2) 0.002(2) 0.0010(18) 0.005(2) C22 0.040(3) 0.038(3) 0.032(3) -0.003(2) 0.013(2) 0.001(3) C23 0.056(4) 0.041(3) 0.037(3) -0.014(3) 0.013(3) 0.005(3) C24 0.062(4) 0.036(3) 0.039(3) -0.008(3) -0.003(3) 0.002(3) C25 0.045(3) 0.029(3) 0.038(3) 0.002(2) -0.005(2) -0.008(3) C26 0.037(3) 0.034(3) 0.024(2) 0.005(2) 0.000(2) -0.004(2) C27 0.024(2) 0.020(2) 0.022(2) 0.0035(19) 0.0028(18) -0.0035(19) C28 0.029(3) 0.031(3) 0.016(2) -0.001(2) 0.0027(18) -0.006(2) C29 0.033(3) 0.038(3) 0.020(2) 0.001(2) 0.0004(19) -0.004(2) C30 0.033(3) 0.031(3) 0.034(3) 0.009(2) 0.000(2) 0.000(2) C31 0.042(3) 0.025(3) 0.035(3) -0.001(2) 0.002(2) 0.000(2) C32 0.034(3) 0.029(3) 0.027(2) -0.003(2) 0.000(2) -0.005(2) C33 0.112(6) 0.031(4) 0.053(4) -0.002(3) -0.034(4) -0.005(4) O1 0.036(2) 0.037(2) 0.0365(19) 0.0031(16) -0.0002(15) 0.0044(17) O2 0.037(2) 0.042(2) 0.0268(17) 0.0027(16) -0.0010(14) -0.0106(17) O3 0.035(2) 0.035(2) 0.0383(19) 0.0015(16) 0.0033(15) 0.0070(17) O4 0.050(3) 0.047(3) 0.068(3) -0.029(2) 0.012(2) 0.001(2) O5 0.036(2) 0.049(3) 0.098(3) -0.012(2) 0.006(2) -0.007(2) P1 0.0231(6) 0.0268(7) 0.0161(5) 0.0009(5) 0.0038(4) -0.0018(5) N1 0.036(2) 0.020(2) 0.0174(18) 0.0013(16) 0.0023(16) -0.0010(18) N2 0.0221(19) 0.024(2) 0.0144(17) 0.0013(16) 0.0038(14) -0.0022(17) Au1 0.02431(10) 0.02797(11) 0.01521(9) 0.00154(8) 0.00380(6) -0.00138(8) S1 0.0327(7) 0.0298(7) 0.0429(7) -0.0061(6) 0.0010(6) 0.0022(6) F1 0.146(4) 0.051(2) 0.072(3) 0.012(2) 0.021(3) -0.033(3) F2 0.296(7) 0.046(3) 0.038(2) 0.009(2) -0.028(3) -0.033(4) F3 0.149(5) 0.059(3) 0.187(5) 0.041(3) -0.110(4) 0.005(3) _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 O1 1.198(5) . ? C1 N1 1.405(6) . ? C1 C2 1.493(7) . ? C2 C7 1.390(6) . ? C2 C3 1.394(6) . ? C3 C4 1.379(7) . ? C3 H3 0.9500 . ? C4 C5 1.385(7) . ? C4 H4 0.9500 . ? C5 C6 1.392(7) . ? C5 H5 0.9500 . ? C6 C7 1.373(6) . ? C6 H6 0.9500 . ? C7 C8 1.487(6) . ? C8 O2 1.220(5) . ? C8 N1 1.386(6) . ? C9 N1 1.460(5) . ? C9 C10 1.519(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.379(6) . ? C10 C14 1.380(6) . ? C11 C12 1.374(6) . ? C11 H11 0.9500 . ? C12 N2 1.338(5) . ? C12 H12 0.9500 . ? C13 N2 1.338(6) . ? C13 C14 1.383(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.373(7) . ? C15 C16 1.401(7) . ? C15 P1 1.820(5) . ? C16 C17 1.383(7) . ? C16 H16 0.9500 . ? C17 C18 1.373(8) . ? C17 H17 0.9500 . ? C18 C19 1.377(8) . ? C18 H18 0.9500 . ? C19 C20 1.398(7) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C26 1.389(6) . ? C21 C22 1.397(6) . ? C21 P1 1.801(5) . ? C22 C23 1.381(7) . ? C22 H22 0.9500 . ? C23 C24 1.381(8) . ? C23 H23 0.9500 . ? C24 C25 1.375(7) . ? C24 H24 0.9500 . ? C25 C26 1.389(7) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.393(6) . ? C27 C28 1.397(6) . ? C27 P1 1.812(4) . ? C28 C29 1.392(7) . ? C28 H28 0.9500 . ? C29 C30 1.372(7) . ? C29 H29 0.9500 . ? C30 C31 1.390(6) . ? C30 H30 0.9500 . ? C31 C32 1.382(7) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 F2 1.315(7) . ? C33 F1 1.316(8) . ? C33 F3 1.332(8) . ? C33 S1 1.829(7) . ? O3 S1 1.434(3) . ? O4 S1 1.440(4) . ? O5 S1 1.440(4) . ? P1 Au1 2.2384(10) . ? N2 Au1 2.072(3) . ? 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 O1 C1 N1 125.5(5) . . ? O1 C1 C2 129.9(5) . . ? N1 C1 C2 104.6(4) . . ? C7 C2 C3 121.3(4) . . ? C7 C2 C1 108.8(4) . . ? C3 C2 C1 130.0(4) . . ? C4 C3 C2 116.8(5) . . ? C4 C3 H3 121.6 . . ? C2 C3 H3 121.6 . . ? C3 C4 C5 121.7(5) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C4 C5 C6 121.5(5) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C7 C6 C5 117.0(5) . . ? C7 C6 H6 121.5 . . ? C5 C6 H6 121.5 . . ? C6 C7 C2 121.8(4) . . ? C6 C7 C8 130.5(4) . . ? C2 C7 C8 107.7(4) . . ? O2 C8 N1 124.4(4) . . ? O2 C8 C7 129.5(4) . . ? N1 C8 C7 106.0(4) . . ? N1 C9 C10 113.8(4) . . ? N1 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? N1 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C14 117.4(4) . . ? C11 C10 C9 119.1(4) . . ? C14 C10 C9 123.4(4) . . ? C12 C11 C10 120.0(4) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? N2 C12 C11 122.5(4) . . ? N2 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? N2 C13 C14 122.0(4) . . ? N2 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C10 C14 C13 119.9(4) . . ? C10 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C20 C15 C16 119.8(5) . . ? C20 C15 P1 122.6(4) . . ? C16 C15 P1 117.2(4) . . ? C17 C16 C15 120.2(5) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 119.2(6) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 121.4(5) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C20 119.5(5) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C15 C20 C19 119.8(5) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C26 C21 C22 119.3(4) . . ? C26 C21 P1 119.4(3) . . ? C22 C21 P1 121.2(4) . . ? C23 C22 C21 120.3(5) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C24 C23 C22 120.0(5) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C25 C24 C23 120.3(5) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 120.3(5) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C21 119.9(5) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? C32 C27 C28 119.2(4) . . ? C32 C27 P1 119.4(3) . . ? C28 C27 P1 121.3(3) . . ? C29 C28 C27 119.7(4) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C30 C29 C28 120.5(4) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 120.3(4) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C32 C31 C30 119.7(5) . . ? C32 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C31 C32 C27 120.6(4) . . ? C31 C32 H32 119.7 . . ? C27 C32 H32 119.7 . . ? F2 C33 F1 108.8(7) . . ? F2 C33 F3 108.6(6) . . ? F1 C33 F3 107.9(6) . . ? F2 C33 S1 111.2(4) . . ? F1 C33 S1 111.0(4) . . ? F3 C33 S1 109.2(6) . . ? C21 P1 C27 106.5(2) . . ? C21 P1 C15 106.9(2) . . ? C27 P1 C15 106.3(2) . . ? C21 P1 Au1 115.96(15) . . ? C27 P1 Au1 113.04(14) . . ? C15 P1 Au1 107.54(14) . . ? C8 N1 C1 112.8(4) . . ? C8 N1 C9 123.4(4) . . ? C1 N1 C9 123.5(4) . . ? C12 N2 C13 118.1(4) . . ? C12 N2 Au1 120.5(3) . . ? C13 N2 Au1 121.4(3) . . ? N2 Au1 P1 175.83(10) . . ? O3 S1 O4 114.5(2) . . ? O3 S1 O5 113.9(2) . . ? O4 S1 O5 116.6(2) . . ? O3 S1 C33 102.4(3) . . ? O4 S1 C33 103.3(3) . . ? O5 S1 C33 103.7(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.052 _refine_diff_density_min -0.955 _refine_diff_density_rms 0.145 # Attachment 'Au-L6b.cif' data_sp0801 _database_code_depnum_ccdc_archive 'CCDC 723936' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H25 Au N2 O2 P, C F3 O3 S1, C H1 Cl3' _chemical_formula_sum 'C37 H26 Au Cl3 F3 N2 O5 P S' _chemical_formula_weight 1001.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2880(2) _cell_length_b 11.5000(2) _cell_length_c 15.6380(4) _cell_angle_alpha 74.7300(10) _cell_angle_beta 72.1950(10) _cell_angle_gamma 81.1030(10) _cell_volume 1858.45(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7060 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 27.2 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 4.334 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5625 _exptl_absorpt_correction_T_max 0.8124 _exptl_absorpt_process_details Denzo/scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12868 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0769 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 27.42 _reflns_number_total 8401 _reflns_number_gt 7060 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The solvent site is disordered over two positions. Initial refinement of the occupancy gave a value of 0.501(1) which was subsequently fixed at 0.5. ; _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^)+(0.0200P)^2^+6.1217P] 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 8401 _refine_ls_number_parameters 514 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0865 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.035 _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 0.6847(5) 0.1090(5) 0.0966(4) 0.0288(13) Uani 1 1 d . . . H1 H 0.7364 0.0985 0.1365 0.035 Uiso 1 1 calc R . . C2 C 0.7391(5) 0.0891(6) 0.0078(4) 0.0358(15) Uani 1 1 d . . . H2 H 0.8242 0.0598 -0.0104 0.043 Uiso 1 1 calc R . . C3 C 0.6676(5) 0.1126(5) -0.0525(4) 0.0311(13) Uani 1 1 d . . . H3 H 0.7042 0.1054 -0.1144 0.037 Uiso 1 1 calc R . . C4 C 0.5398(5) 0.1474(5) -0.0219(4) 0.0262(12) Uani 1 1 d . . . C5 C 0.4617(5) 0.1738(5) -0.0811(4) 0.0306(13) Uani 1 1 d . . . H5 H 0.4972 0.1722 -0.1443 0.037 Uiso 1 1 calc R . . C6 C 0.3379(6) 0.2010(6) -0.0499(4) 0.0384(15) Uani 1 1 d . . . H6 H 0.2878 0.2232 -0.0916 0.046 Uiso 1 1 calc R . . C7 C 0.2827(5) 0.1966(6) 0.0452(4) 0.0374(15) Uani 1 1 d . . . H7 H 0.1947 0.2092 0.0681 0.045 Uiso 1 1 calc R . . C8 C 0.3561(5) 0.1740(5) 0.1047(4) 0.0232(11) Uani 1 1 d . . . C9 C 0.4873(5) 0.1549(5) 0.0717(4) 0.0197(11) Uani 1 1 d . . . C10 C 0.2953(5) 0.0488(6) 0.2653(4) 0.0288(13) Uani 1 1 d . . . C11 C 0.2209(5) 0.0726(6) 0.3567(4) 0.0322(14) Uani 1 1 d . . . C12 C 0.1936(6) -0.0049(8) 0.4422(4) 0.0447(18) Uani 1 1 d . . . H12 H 0.2221 -0.0882 0.4510 0.054 Uiso 1 1 calc R . . C13 C 0.1214(6) 0.0456(10) 0.5156(5) 0.060(2) Uani 1 1 d . . . H13 H 0.1002 -0.0045 0.5761 0.072 Uiso 1 1 calc R . . C14 C 0.0803(6) 0.1664(10) 0.5023(5) 0.065(3) Uani 1 1 d . . . H14 H 0.0314 0.1976 0.5539 0.078 Uiso 1 1 calc R . . C15 C 0.1083(6) 0.2436(8) 0.4156(5) 0.055(2) Uani 1 1 d . . . H15 H 0.0798 0.3269 0.4068 0.067 Uiso 1 1 calc R . . C16 C 0.1796(5) 0.1944(7) 0.3422(4) 0.0369(16) Uani 1 1 d . . . C17 C 0.2235(5) 0.2535(7) 0.2419(5) 0.0341(15) Uani 1 1 d . . . C18 C 0.6536(5) 0.3991(5) 0.3202(4) 0.0267(12) Uani 1 1 d . . . C19 C 0.7666(5) 0.3318(6) 0.2958(4) 0.0346(14) Uani 1 1 d . . . H19 H 0.7674 0.2508 0.2915 0.042 Uiso 1 1 calc R . . C20 C 0.8779(6) 0.3814(7) 0.2776(5) 0.0483(18) Uani 1 1 d . . . H20 H 0.9551 0.3348 0.2614 0.058 Uiso 1 1 calc R . . C21 C 0.8758(6) 0.4996(7) 0.2831(5) 0.052(2) Uani 1 1 d . . . H21 H 0.9524 0.5341 0.2703 0.063 Uiso 1 1 calc R . . C22 C 0.7651(6) 0.5681(6) 0.3068(5) 0.0458(17) Uani 1 1 d . . . H22 H 0.7650 0.6491 0.3108 0.055 Uiso 1 1 calc R . . C23 C 0.6532(6) 0.5174(5) 0.3251(4) 0.0326(14) Uani 1 1 d . . . H23 H 0.5762 0.5644 0.3409 0.039 Uiso 1 1 calc R . . C24 C 0.4866(5) 0.2396(5) 0.4638(4) 0.0237(12) Uani 1 1 d . . . C25 C 0.5394(6) 0.2690(6) 0.5234(4) 0.0339(14) Uani 1 1 d . . . H25 H 0.5927 0.3332 0.5019 0.041 Uiso 1 1 calc R . . C26 C 0.5146(6) 0.2050(6) 0.6143(4) 0.0389(15) Uani 1 1 d . . . H26 H 0.5531 0.2234 0.6548 0.047 Uiso 1 1 calc R . . C27 C 0.4349(5) 0.1153(6) 0.6461(4) 0.0352(14) Uani 1 1 d . . . H27 H 0.4167 0.0730 0.7090 0.042 Uiso 1 1 calc R . . C28 C 0.3809(5) 0.0858(6) 0.5881(4) 0.0347(14) Uani 1 1 d . . . H28 H 0.3259 0.0230 0.6106 0.042 Uiso 1 1 calc R . . C29 C 0.4068(5) 0.1479(6) 0.4967(4) 0.0323(14) Uani 1 1 d . . . H29 H 0.3696 0.1274 0.4563 0.039 Uiso 1 1 calc R . . C30 C 0.3865(5) 0.4486(5) 0.3485(4) 0.0255(12) Uani 1 1 d . . . C31 C 0.3694(6) 0.5166(6) 0.2649(4) 0.0374(15) Uani 1 1 d . . . H31 H 0.4180 0.4958 0.2088 0.045 Uiso 1 1 calc R . . C32 C 0.2813(6) 0.6147(7) 0.2636(5) 0.0492(18) Uani 1 1 d . . . H32 H 0.2704 0.6619 0.2064 0.059 Uiso 1 1 calc R . . C33 C 0.2100(7) 0.6440(7) 0.3439(6) 0.053(2) Uani 1 1 d . . . H33 H 0.1507 0.7122 0.3421 0.064 Uiso 1 1 calc R . . C34 C 0.2234(6) 0.5753(7) 0.4281(5) 0.0482(18) Uani 1 1 d . . . H34 H 0.1725 0.5951 0.4840 0.058 Uiso 1 1 calc R . . C35 C 0.3123(5) 0.4771(6) 0.4300(4) 0.0356(14) Uani 1 1 d . . . H35 H 0.3221 0.4293 0.4875 0.043 Uiso 1 1 calc R . . C36 C 0.9465(5) 0.8635(6) 0.2118(4) 0.0328(14) Uani 1 1 d . . . O1 O 0.3461(4) -0.0441(4) 0.2457(3) 0.0326(9) Uani 1 1 d . . . O2 O 0.2030(4) 0.3553(4) 0.2016(3) 0.0425(11) Uani 1 1 d . . . O3 O 0.8450(4) 1.0637(4) 0.2497(3) 0.0378(10) Uani 1 1 d . . . O4 O 1.0621(4) 1.0112(5) 0.2474(4) 0.0607(15) Uani 1 1 d . . . O5 O 1.0027(4) 1.0688(4) 0.1044(3) 0.0440(11) Uani 1 1 d . . . P1 P 0.51068(12) 0.32689(13) 0.34601(9) 0.0200(3) Uani 1 1 d . . . N1 N 0.5634(4) 0.1420(4) 0.1278(3) 0.0197(9) Uani 1 1 d . . . N2 N 0.2981(4) 0.1618(4) 0.2009(3) 0.0253(10) Uani 1 1 d . . . Au1 Au 0.525226(18) 0.223119(19) 0.240082(14) 0.02091(7) Uani 1 1 d . . . S1 S 0.96717(12) 1.02020(14) 0.20172(10) 0.0295(3) Uani 1 1 d . . . F1 F 0.9095(4) 0.8030(3) 0.3001(3) 0.0462(9) Uani 1 1 d . . . F2 F 1.0516(4) 0.8034(4) 0.1728(3) 0.0660(13) Uani 1 1 d . . . F3 F 0.8594(4) 0.8530(3) 0.1734(3) 0.0534(11) Uani 1 1 d . . . C37 C 0.2921(10) 0.4979(11) 0.0168(7) 0.087(7) Uani 0.50 1 d PDU a 1 H37 H 0.2540 0.4233 0.0592 0.105 Uiso 0.50 1 calc PR a 1 Cl1 Cl 0.2886(5) 0.5136(7) -0.0968(4) 0.0850(19) Uani 0.50 1 d PDU a 1 Cl2 Cl 0.2140(7) 0.6291(5) 0.0493(4) 0.116(2) Uani 0.50 1 d PDU a 1 Cl3 Cl 0.4505(5) 0.4964(7) 0.0096(4) 0.122(3) Uani 0.50 1 d PDU a 1 C38 C 0.8719(9) 0.4682(9) -0.0177(10) 0.092(7) Uani 0.50 1 d PDU b 2 H38 H 0.8722 0.4966 -0.0839 0.110 Uiso 0.50 1 calc PR b 2 Cl4 Cl 0.9476(6) 0.5666(5) 0.0127(6) 0.119(2) Uani 0.50 1 d PDU b 2 Cl5 Cl 0.9463(6) 0.3241(5) 0.0022(6) 0.134(3) Uani 0.50 1 d PDU b 2 Cl6 Cl 0.7214(7) 0.4611(10) 0.0527(9) 0.269(10) Uani 0.50 1 d PDU b 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 0.026(3) 0.036(3) 0.023(3) -0.008(3) -0.004(2) -0.004(2) C2 0.028(3) 0.050(4) 0.030(3) -0.019(3) -0.001(3) -0.002(3) C3 0.036(3) 0.038(4) 0.019(3) -0.009(3) 0.000(2) -0.013(3) C4 0.031(3) 0.027(3) 0.024(3) -0.007(2) -0.008(2) -0.008(2) C5 0.042(3) 0.038(4) 0.015(3) -0.012(3) -0.007(2) -0.006(3) C6 0.048(4) 0.052(4) 0.027(3) -0.013(3) -0.025(3) 0.000(3) C7 0.028(3) 0.056(4) 0.041(4) -0.023(3) -0.019(3) 0.002(3) C8 0.025(3) 0.026(3) 0.019(3) -0.011(2) -0.003(2) -0.001(2) C9 0.026(3) 0.017(3) 0.019(3) -0.006(2) -0.009(2) -0.001(2) C10 0.020(3) 0.051(4) 0.022(3) -0.016(3) -0.007(2) -0.010(3) C11 0.020(3) 0.061(4) 0.023(3) -0.022(3) -0.002(2) -0.010(3) C12 0.036(3) 0.085(5) 0.019(3) -0.016(3) -0.002(3) -0.026(3) C13 0.025(3) 0.134(8) 0.025(4) -0.026(5) 0.005(3) -0.030(4) C14 0.028(3) 0.142(9) 0.039(5) -0.054(5) -0.003(3) 0.000(4) C15 0.028(3) 0.106(7) 0.049(5) -0.055(5) -0.011(3) 0.010(4) C16 0.016(3) 0.068(5) 0.033(4) -0.024(3) -0.003(2) -0.008(3) C17 0.018(3) 0.055(4) 0.039(4) -0.029(3) -0.011(3) 0.003(3) C18 0.023(3) 0.034(3) 0.024(3) -0.012(3) -0.004(2) -0.001(2) C19 0.025(3) 0.037(4) 0.045(4) -0.016(3) -0.011(3) 0.002(3) C20 0.023(3) 0.065(5) 0.063(5) -0.025(4) -0.012(3) -0.003(3) C21 0.036(4) 0.070(5) 0.053(5) -0.010(4) -0.009(3) -0.026(4) C22 0.050(4) 0.039(4) 0.051(4) -0.009(3) -0.011(3) -0.020(3) C23 0.037(3) 0.030(3) 0.034(3) -0.013(3) -0.008(3) -0.008(3) C24 0.021(2) 0.024(3) 0.025(3) -0.012(2) -0.002(2) 0.003(2) C25 0.046(3) 0.030(3) 0.031(3) -0.009(3) -0.015(3) -0.006(3) C26 0.064(4) 0.035(4) 0.024(3) -0.008(3) -0.025(3) 0.005(3) C27 0.040(3) 0.039(4) 0.018(3) -0.001(3) -0.005(3) 0.007(3) C28 0.024(3) 0.042(4) 0.028(3) 0.006(3) -0.003(2) -0.006(3) C29 0.027(3) 0.047(4) 0.028(3) -0.012(3) -0.008(2) -0.009(3) C30 0.026(3) 0.025(3) 0.026(3) -0.005(2) -0.009(2) -0.003(2) C31 0.042(3) 0.040(4) 0.026(3) -0.010(3) -0.007(3) 0.007(3) C32 0.054(4) 0.047(4) 0.046(4) -0.008(4) -0.024(3) 0.015(3) C33 0.049(4) 0.047(4) 0.068(5) -0.022(4) -0.027(4) 0.025(3) C34 0.041(4) 0.060(5) 0.051(5) -0.033(4) -0.017(3) 0.017(3) C35 0.033(3) 0.048(4) 0.030(3) -0.019(3) -0.010(3) 0.006(3) C36 0.029(3) 0.034(4) 0.034(4) -0.007(3) -0.010(3) 0.001(3) O1 0.033(2) 0.044(3) 0.023(2) -0.014(2) -0.0069(17) -0.0010(19) O2 0.038(2) 0.049(3) 0.048(3) -0.025(3) -0.017(2) 0.009(2) O3 0.037(2) 0.037(3) 0.033(2) -0.016(2) 0.0064(19) -0.0051(19) O4 0.043(3) 0.082(4) 0.073(4) -0.013(3) -0.031(3) -0.029(3) O5 0.046(3) 0.046(3) 0.031(3) -0.004(2) 0.002(2) -0.011(2) P1 0.0215(6) 0.0236(8) 0.0173(7) -0.0079(6) -0.0060(5) -0.0022(5) N1 0.025(2) 0.023(2) 0.012(2) -0.0051(18) -0.0059(17) 0.0001(18) N2 0.017(2) 0.041(3) 0.023(3) -0.018(2) -0.0040(18) -0.0032(19) Au1 0.02201(10) 0.02538(12) 0.01811(11) -0.00898(8) -0.00588(7) -0.00248(8) S1 0.0251(7) 0.0377(9) 0.0273(8) -0.0088(7) -0.0041(6) -0.0115(6) F1 0.057(2) 0.042(2) 0.036(2) 0.0033(18) -0.0142(18) -0.0118(18) F2 0.057(3) 0.049(3) 0.073(3) -0.018(2) 0.002(2) 0.019(2) F3 0.071(3) 0.045(2) 0.064(3) -0.015(2) -0.039(2) -0.014(2) C37 0.146(19) 0.078(14) 0.033(10) -0.012(10) -0.004(11) -0.038(13) Cl1 0.068(3) 0.111(5) 0.049(3) 0.024(3) -0.008(3) -0.018(3) Cl2 0.205(7) 0.052(3) 0.102(5) -0.030(3) -0.054(5) 0.003(4) Cl3 0.155(8) 0.146(6) 0.064(4) -0.013(4) -0.011(5) -0.068(6) C38 0.059(11) 0.098(16) 0.105(17) 0.003(13) -0.017(11) -0.020(11) Cl4 0.106(4) 0.081(4) 0.187(7) -0.042(4) -0.067(5) 0.010(3) Cl5 0.122(5) 0.088(4) 0.208(8) -0.077(5) -0.042(5) 0.008(4) Cl6 0.241(12) 0.156(10) 0.189(13) 0.056(10) 0.138(10) 0.058(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.337(7) . ? C1 C2 1.401(8) . ? C1 H1 0.9500 . ? C2 C3 1.369(8) . ? C2 H2 0.9500 . ? C3 C4 1.404(8) . ? C3 H3 0.9500 . ? C4 C5 1.413(8) . ? C4 C9 1.421(7) . ? C5 C6 1.348(8) . ? C5 H5 0.9500 . ? C6 C7 1.416(8) . ? C6 H6 0.9500 . ? C7 C8 1.377(7) . ? C7 H7 0.9500 . ? C8 C9 1.415(7) . ? C8 N2 1.424(7) . ? C9 N1 1.372(6) . ? C10 O1 1.199(7) . ? C10 N2 1.417(8) . ? C10 C11 1.492(7) . ? C11 C12 1.372(9) . ? C11 C16 1.387(9) . ? C12 C13 1.397(10) . ? C12 H12 0.9500 . ? C13 C14 1.377(12) . ? C13 H13 0.9500 . ? C14 C15 1.384(12) . ? C14 H14 0.9500 . ? C15 C16 1.386(8) . ? C15 H15 0.9500 . ? C16 C17 1.495(9) . ? C17 O2 1.200(8) . ? C17 N2 1.407(7) . ? C18 C23 1.382(8) . ? C18 C19 1.387(8) . ? C18 P1 1.815(5) . ? C19 C20 1.379(8) . ? C19 H19 0.9500 . ? C20 C21 1.380(10) . ? C20 H20 0.9500 . ? C21 C22 1.373(10) . ? C21 H21 0.9500 . ? C22 C23 1.391(8) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.380(8) . ? C24 C29 1.384(8) . ? C24 P1 1.811(6) . ? C25 C26 1.382(9) . ? C25 H25 0.9500 . ? C26 C27 1.365(9) . ? C26 H26 0.9500 . ? C27 C28 1.368(8) . ? C27 H27 0.9500 . ? C28 C29 1.382(8) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C35 1.385(8) . ? C30 C31 1.387(8) . ? C30 P1 1.820(6) . ? C31 C32 1.384(9) . ? C31 H31 0.9500 . ? C32 C33 1.364(10) . ? C32 H32 0.9500 . ? C33 C34 1.385(10) . ? C33 H33 0.9500 . ? C34 C35 1.390(9) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 F3 1.332(7) . ? C36 F2 1.336(7) . ? C36 F1 1.341(7) . ? C36 S1 1.812(6) . ? O3 S1 1.437(4) . ? O4 S1 1.437(4) . ? O5 S1 1.428(5) . ? P1 Au1 2.2382(13) . ? N1 Au1 2.101(4) . ? C37 Cl2 1.741(9) . ? C37 Cl1 1.750(9) . ? C37 Cl3 1.755(9) . ? C37 H37 1.0000 . ? C38 Cl6 1.720(9) . ? C38 Cl5 1.733(9) . ? C38 Cl4 1.752(9) . ? C38 H38 1.0000 . ? 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 N1 C1 C2 122.8(5) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 119.1(5) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 119.3(5) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 121.9(5) . . ? C3 C4 C9 119.0(5) . . ? C5 C4 C9 119.1(5) . . ? C6 C5 C4 121.4(5) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 119.8(5) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 120.4(5) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 120.5(5) . . ? C7 C8 N2 119.3(5) . . ? C9 C8 N2 120.0(5) . . ? N1 C9 C8 121.7(5) . . ? N1 C9 C4 120.0(4) . . ? C8 C9 C4 118.3(4) . . ? O1 C10 N2 124.1(5) . . ? O1 C10 C11 129.8(6) . . ? N2 C10 C11 106.1(5) . . ? C12 C11 C16 122.8(6) . . ? C12 C11 C10 129.9(6) . . ? C16 C11 C10 107.3(6) . . ? C11 C12 C13 116.2(8) . . ? C11 C12 H12 121.9 . . ? C13 C12 H12 121.9 . . ? C14 C13 C12 121.5(8) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 121.7(7) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C14 C15 C16 117.3(8) . . ? C14 C15 H15 121.4 . . ? C16 C15 H15 121.4 . . ? C15 C16 C11 120.4(7) . . ? C15 C16 C17 129.7(7) . . ? C11 C16 C17 109.8(5) . . ? O2 C17 N2 125.3(6) . . ? O2 C17 C16 130.1(6) . . ? N2 C17 C16 104.7(6) . . ? C23 C18 C19 119.4(5) . . ? C23 C18 P1 122.3(4) . . ? C19 C18 P1 118.3(4) . . ? C20 C19 C18 120.6(6) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 119.2(6) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C22 C21 C20 121.2(6) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 119.3(6) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? C18 C23 C22 120.3(6) . . ? C18 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C29 119.3(5) . . ? C25 C24 P1 120.9(4) . . ? C29 C24 P1 119.6(4) . . ? C24 C25 C26 119.9(6) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C27 C26 C25 120.2(6) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C28 120.6(6) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C29 119.7(6) . . ? C27 C28 H28 120.2 . . ? C29 C28 H28 120.2 . . ? C28 C29 C24 120.3(5) . . ? C28 C29 H29 119.9 . . ? C24 C29 H29 119.9 . . ? C35 C30 C31 119.7(6) . . ? C35 C30 P1 122.3(5) . . ? C31 C30 P1 118.0(4) . . ? C32 C31 C30 119.7(6) . . ? C32 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C33 C32 C31 120.5(7) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C32 C33 C34 120.6(6) . . ? C32 C33 H33 119.7 . . ? C34 C33 H33 119.7 . . ? C33 C34 C35 119.3(6) . . ? C33 C34 H34 120.3 . . ? C35 C34 H34 120.3 . . ? C30 C35 C34 120.2(6) . . ? C30 C35 H35 119.9 . . ? C34 C35 H35 119.9 . . ? F3 C36 F2 107.7(5) . . ? F3 C36 F1 106.0(5) . . ? F2 C36 F1 106.2(5) . . ? F3 C36 S1 112.0(4) . . ? F2 C36 S1 112.5(4) . . ? F1 C36 S1 111.9(4) . . ? C24 P1 C18 104.9(2) . . ? C24 P1 C30 106.2(3) . . ? C18 P1 C30 105.7(3) . . ? C24 P1 Au1 116.14(18) . . ? C18 P1 Au1 110.26(18) . . ? C30 P1 Au1 112.82(18) . . ? C1 N1 C9 119.2(4) . . ? C1 N1 Au1 112.5(3) . . ? C9 N1 Au1 125.1(3) . . ? C17 N2 C10 111.8(5) . . ? C17 N2 C8 125.3(5) . . ? C10 N2 C8 122.4(5) . . ? N1 Au1 P1 170.77(12) . . ? O5 S1 O4 115.8(3) . . ? O5 S1 O3 114.8(3) . . ? O4 S1 O3 114.9(3) . . ? O5 S1 C36 103.4(3) . . ? O4 S1 C36 103.1(3) . . ? O3 S1 C36 102.2(3) . . ? Cl2 C37 Cl1 106.0(6) . . ? Cl2 C37 Cl3 108.6(7) . . ? Cl1 C37 Cl3 104.9(6) . . ? Cl2 C37 H37 112.3 . . ? Cl1 C37 H37 112.3 . . ? Cl3 C37 H37 112.3 . . ? Cl6 C38 Cl5 107.4(7) . . ? Cl6 C38 Cl4 108.7(7) . . ? Cl5 C38 Cl4 109.1(6) . . ? Cl6 C38 H38 110.5 . . ? Cl5 C38 H38 110.5 . . ? Cl4 C38 H38 110.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.470 _refine_diff_density_min -1.286 _refine_diff_density_rms 0.169 # Attachment 'L3.cif' data_irl12mono _database_code_depnum_ccdc_archive 'CCDC 723937' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.6402(6) _cell_length_b 5.3085(4) _cell_length_c 24.4905(16) _cell_angle_alpha 90.00 _cell_angle_beta 97.660(5) _cell_angle_gamma 90.00 _cell_volume 1113.27(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3016 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 28.02 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9602 _exptl_absorpt_correction_T_max 0.9961 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14941 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 29.17 _reflns_number_total 2972 _reflns_number_gt 2292 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2 (v2.1)' _computing_cell_refinement 'Bruker Apex2 (v2.1)' _computing_data_reduction 'Bruker Apex2 (v2.1)' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0453P)^2^+0.2804P] 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 2972 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0955 _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 N1 N 0.32232(14) -0.1210(2) 0.22057(5) 0.0271(3) Uani 1 1 d . . . N2 N 0.14553(13) 0.0973(2) 0.40642(4) 0.0191(2) Uani 1 1 d . . . O1 O 0.31906(11) 0.42791(18) 0.42348(4) 0.0234(2) Uani 1 1 d . . . O2 O 0.00156(11) -0.26401(18) 0.41484(4) 0.0228(2) Uani 1 1 d . . . C1 C 0.23369(17) 0.0870(3) 0.21473(6) 0.0263(3) Uani 1 1 d . . . C2 C 0.15731(16) 0.1870(3) 0.25595(5) 0.0225(3) Uani 1 1 d . . . H2A H 0.0964 0.3361 0.2502 0.028(4) Uiso 1 1 d R . . H2B H 0.2240 0.1687 0.1779 0.030(4) Uiso 1 1 d R . . C3 C 0.17036(15) 0.0669(2) 0.30682(5) 0.0186(3) Uani 1 1 d . . . C4 C 0.26153(16) -0.1488(3) 0.31364(5) 0.0212(3) Uani 1 1 d . . . H4 H 0.2760 -0.2454 0.3475 0.025(4) Uiso 1 1 d R . . C5 C 0.33464(16) -0.2333(3) 0.27003(6) 0.0241(3) Uani 1 1 d . . . H5 H 0.3997 -0.3836 0.2744 0.030(4) Uiso 1 1 d R . . C6 C 0.08030(15) 0.1682(3) 0.35091(5) 0.0207(3) Uani 1 1 d . . . H6 H 0.0736 0.3550 0.3496 0.024(4) Uiso 1 1 d R . . C7 C 0.25872(15) 0.2403(3) 0.43888(5) 0.0184(3) Uani 1 1 d . . . C8 C 0.28343(15) 0.1122(2) 0.49346(5) 0.0185(3) Uani 1 1 d . . . C9 C 0.38207(16) 0.1733(3) 0.54075(5) 0.0216(3) Uani 1 1 d . . . H9 H 0.4481 0.3187 0.5419 0.024(4) Uiso 1 1 d R . . C10 C 0.38039(16) 0.0143(3) 0.58591(6) 0.0247(3) Uani 1 1 d . . . H10 H 0.4477 0.0466 0.6198 0.024(4) Uiso 1 1 d R . . C11 C 0.28509(17) -0.1976(3) 0.58324(6) 0.0246(3) Uani 1 1 d . . . H11 H 0.2903 -0.3030 0.6147 0.029(4) Uiso 1 1 d R . . C12 C 0.18599(16) -0.2581(3) 0.53523(6) 0.0218(3) Uani 1 1 d . . . H12 H 0.1206 -0.4018 0.5332 0.028(4) Uiso 1 1 d R . . C13 C 0.18747(15) -0.0991(2) 0.49076(5) 0.0181(3) Uani 1 1 d . . . C14 C 0.09742(15) -0.1113(2) 0.43455(5) 0.0184(3) Uani 1 1 d . . . H14 H -0.0275 0.1026 0.3452 0.027(4) Uiso 1 1 d 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 0.0264(6) 0.0313(7) 0.0240(6) -0.0036(5) 0.0042(5) -0.0024(5) N2 0.0204(6) 0.0195(5) 0.0169(5) 0.0001(4) 0.0009(4) -0.0009(5) O1 0.0228(5) 0.0202(5) 0.0271(5) 0.0022(4) 0.0031(4) -0.0023(4) O2 0.0217(5) 0.0213(5) 0.0251(5) -0.0029(4) 0.0014(4) -0.0029(4) C1 0.0291(8) 0.0308(8) 0.0185(6) 0.0021(6) 0.0014(5) -0.0029(6) C2 0.0226(7) 0.0223(7) 0.0216(6) 0.0012(5) -0.0010(5) -0.0007(5) C3 0.0167(6) 0.0192(6) 0.0187(6) -0.0008(5) -0.0015(5) -0.0040(5) C4 0.0220(7) 0.0200(6) 0.0208(6) 0.0016(5) 0.0001(5) -0.0014(5) C5 0.0215(7) 0.0239(7) 0.0268(7) -0.0026(6) 0.0023(5) -0.0002(6) C6 0.0210(7) 0.0224(7) 0.0181(6) 0.0005(5) 0.0003(5) 0.0023(5) C7 0.0157(6) 0.0189(6) 0.0206(6) -0.0027(5) 0.0027(5) 0.0012(5) C8 0.0170(6) 0.0189(6) 0.0199(6) -0.0018(5) 0.0039(5) 0.0029(5) C9 0.0180(6) 0.0239(7) 0.0227(7) -0.0042(5) 0.0013(5) 0.0019(5) C10 0.0222(7) 0.0310(8) 0.0198(6) -0.0026(6) -0.0013(5) 0.0068(6) C11 0.0262(7) 0.0281(7) 0.0199(6) 0.0032(6) 0.0044(5) 0.0079(6) C12 0.0227(7) 0.0205(6) 0.0230(6) 0.0001(5) 0.0062(5) 0.0022(6) C13 0.0163(6) 0.0190(6) 0.0190(6) -0.0026(5) 0.0027(5) 0.0016(5) C14 0.0177(6) 0.0181(6) 0.0198(6) -0.0016(5) 0.0036(5) 0.0008(5) _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 C1 1.341(2) . ? N1 C5 1.3416(19) . ? N2 C14 1.3964(17) . ? N2 C7 1.3992(16) . ? N2 C6 1.4504(16) . ? O1 C7 1.2075(16) . ? O2 C14 1.2122(16) . ? C1 C2 1.383(2) . ? C1 H2B 0.9933 . ? C2 C3 1.3905(18) . ? C2 H2A 0.9504 . ? C3 C4 1.3874(19) . ? C3 C6 1.5115(19) . ? C4 C5 1.386(2) . ? C4 H4 0.9696 . ? C5 H5 0.9738 . ? C6 H6 0.9936 . ? C6 H14 0.9870 . ? C7 C8 1.4895(18) . ? C8 C9 1.3820(17) . ? C8 C13 1.3914(18) . ? C9 C10 1.393(2) . ? C9 H9 0.9577 . ? C10 C11 1.390(2) . ? C10 H10 0.9632 . ? C11 C12 1.3966(19) . ? C11 H11 0.9490 . ? C12 C13 1.3791(19) . ? C12 H12 0.9467 . ? C13 C14 1.4896(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 115.97(13) . . ? C14 N2 C7 112.44(10) . . ? C14 N2 C6 124.35(11) . . ? C7 N2 C6 123.13(11) . . ? N1 C1 C2 124.02(13) . . ? N1 C1 H2B 115.7 . . ? C2 C1 H2B 120.3 . . ? C1 C2 C3 119.23(13) . . ? C1 C2 H2A 121.3 . . ? C3 C2 H2A 119.4 . . ? C4 C3 C2 117.59(13) . . ? C4 C3 C6 123.08(12) . . ? C2 C3 C6 119.27(12) . . ? C5 C4 C3 118.96(12) . . ? C5 C4 H4 118.0 . . ? C3 C4 H4 123.1 . . ? N1 C5 C4 124.23(13) . . ? N1 C5 H5 116.0 . . ? C4 C5 H5 119.8 . . ? N2 C6 C3 113.86(11) . . ? N2 C6 H6 107.6 . . ? C3 C6 H6 111.5 . . ? N2 C6 H14 106.4 . . ? C3 C6 H14 109.8 . . ? H6 C6 H14 107.3 . . ? O1 C7 N2 124.64(12) . . ? O1 C7 C8 129.83(12) . . ? N2 C7 C8 105.53(11) . . ? C9 C8 C13 121.73(12) . . ? C9 C8 C7 130.06(13) . . ? C13 C8 C7 108.20(11) . . ? C8 C9 C10 116.92(13) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 122.3 . . ? C11 C10 C9 121.45(12) . . ? C11 C10 H10 118.1 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 121.22(13) . . ? C10 C11 H11 118.4 . . ? C12 C11 H11 120.4 . . ? C13 C12 C11 117.07(13) . . ? C13 C12 H12 121.4 . . ? C11 C12 H12 121.6 . . ? C12 C13 C8 121.60(12) . . ? C12 C13 C14 130.13(12) . . ? C8 C13 C14 108.27(11) . . ? O2 C14 N2 124.50(12) . . ? O2 C14 C13 129.94(12) . . ? N2 C14 C13 105.56(11) . . ? 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 C5 N1 C1 C2 0.0(2) . . . . ? N1 C1 C2 C3 -0.5(2) . . . . ? C1 C2 C3 C4 0.44(19) . . . . ? C1 C2 C3 C6 -176.87(12) . . . . ? C2 C3 C4 C5 0.10(19) . . . . ? C6 C3 C4 C5 177.30(12) . . . . ? C1 N1 C5 C4 0.6(2) . . . . ? C3 C4 C5 N1 -0.7(2) . . . . ? C14 N2 C6 C3 -94.35(15) . . . . ? C7 N2 C6 C3 89.29(15) . . . . ? C4 C3 C6 N2 25.54(18) . . . . ? C2 C3 C6 N2 -157.31(12) . . . . ? C14 N2 C7 O1 179.33(13) . . . . ? C6 N2 C7 O1 -3.9(2) . . . . ? C14 N2 C7 C8 -0.95(15) . . . . ? C6 N2 C7 C8 175.80(11) . . . . ? O1 C7 C8 C9 -0.3(2) . . . . ? N2 C7 C8 C9 -179.96(13) . . . . ? O1 C7 C8 C13 -179.41(14) . . . . ? N2 C7 C8 C13 0.88(14) . . . . ? C13 C8 C9 C10 -0.43(19) . . . . ? C7 C8 C9 C10 -179.49(13) . . . . ? C8 C9 C10 C11 0.7(2) . . . . ? C9 C10 C11 C12 -0.6(2) . . . . ? C10 C11 C12 C13 0.2(2) . . . . ? C11 C12 C13 C8 0.1(2) . . . . ? C11 C12 C13 C14 179.82(13) . . . . ? C9 C8 C13 C12 0.1(2) . . . . ? C7 C8 C13 C12 179.30(12) . . . . ? C9 C8 C13 C14 -179.75(12) . . . . ? C7 C8 C13 C14 -0.51(14) . . . . ? C7 N2 C14 O2 -179.31(13) . . . . ? C6 N2 C14 O2 4.0(2) . . . . ? C7 N2 C14 C13 0.65(14) . . . . ? C6 N2 C14 C13 -176.05(12) . . . . ? C12 C13 C14 O2 0.1(2) . . . . ? C8 C13 C14 O2 179.90(14) . . . . ? C12 C13 C14 N2 -179.84(14) . . . . ? C8 C13 C14 N2 -0.05(14) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 29.17 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.356 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.047 # Attachment 'L4.cif' data_irl31_0m _database_code_depnum_ccdc_archive 'CCDC 723938' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 N2 O2' _chemical_formula_weight 252.27 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 5.3683(9) _cell_length_b 10.1138(16) _cell_length_c 12.1952(19) _cell_angle_alpha 69.049(11) _cell_angle_beta 87.126(10) _cell_angle_gamma 82.370(9) _cell_volume 612.87(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3208 _cell_measurement_theta_min 3.47 _cell_measurement_theta_max 27.35 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9772 _exptl_absorpt_correction_T_max 0.9945 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Apex 2 Kappa CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11451 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.74 _reflns_number_total 2827 _reflns_number_gt 2080 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex v2.1' _computing_cell_refinement 'Bruker Apex v2.1' _computing_data_reduction 'Bruker Apex v2.1' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0409P)^2^+0.2547P] 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 2827 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.20714(19) 0.71340(11) 0.48481(9) 0.0230(2) Uani 1 1 d . . . O2 O 0.52806(19) 0.80833(11) 0.24311(9) 0.0238(3) Uani 1 1 d . . . N1 N 0.8418(2) 0.78756(13) 0.37432(10) 0.0180(3) Uani 1 1 d . . . N2 N 0.6327(2) 1.18043(14) 0.19003(11) 0.0231(3) Uani 1 1 d . . . C1 C 1.0682(3) 0.70024(15) 0.41506(12) 0.0182(3) Uani 1 1 d . . . C2 C 1.0938(3) 0.59324(15) 0.35557(12) 0.0184(3) Uani 1 1 d . . . C3 C 1.2811(3) 0.48243(16) 0.36308(13) 0.0224(3) Uani 1 1 d . . . H3 H 1.4285 0.4631 0.4121 0.017(4) Uiso 1 1 d R . . C4 C 1.2535(3) 0.39978(16) 0.29512(14) 0.0253(3) Uani 1 1 d . . . H4 H 1.3790 0.3242 0.2964 0.030(5) Uiso 1 1 d R . . C5 C 1.0445(3) 0.42760(17) 0.22345(14) 0.0258(4) Uani 1 1 d . . . H5 H 1.0314 0.3687 0.1776 0.023(4) Uiso 1 1 d R . . C6 C 0.8560(3) 0.53922(16) 0.21659(13) 0.0224(3) Uani 1 1 d . . . H6 H 0.7034 0.5648 0.1670 0.029(5) Uiso 1 1 d R . . C7 C 0.8856(3) 0.62134(15) 0.28354(12) 0.0185(3) Uani 1 1 d . . . C8 C 0.7233(3) 0.74844(16) 0.29337(12) 0.0184(3) Uani 1 1 d . . . C9 C 0.7440(3) 0.90588(15) 0.41273(13) 0.0198(3) Uani 1 1 d . . . H9B H 0.5632 0.9331 0.3891 0.018(4) Uiso 1 1 d R . . H9A H 0.7503 0.8729 0.4998 0.026(4) Uiso 1 1 d R . . C10 C 0.8890(3) 1.03493(16) 0.35814(13) 0.0209(3) Uani 1 1 d . . . H10B H 1.0762 1.0040 0.3777 0.025(4) Uiso 1 1 d R . . H10A H 0.8191 1.1101 0.3949 0.026(4) Uiso 1 1 d R . . C11 C 0.8553(3) 1.10136(15) 0.22684(13) 0.0183(3) Uani 1 1 d . . . C12 C 1.0424(3) 1.08130(16) 0.14967(13) 0.0223(3) Uani 1 1 d . . . H12 H 1.2011 1.0266 0.1793 0.023(4) Uiso 1 1 d R . . C13 C 1.0000(3) 1.14586(17) 0.02981(14) 0.0254(3) Uani 1 1 d . . . H13 H 1.1247 1.1331 -0.0271 0.035(5) Uiso 1 1 d R . . C14 C 0.7720(3) 1.22765(18) -0.00926(14) 0.0263(4) Uani 1 1 d . . . H14 H 0.7296 1.2729 -0.0925 0.030(5) Uiso 1 1 d R . . C15 C 0.5965(3) 1.24162(17) 0.07391(14) 0.0261(4) Uani 1 1 d . . . H15 H 0.4382 1.3027 0.0506 0.033(5) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0206(6) 0.0256(6) 0.0214(5) -0.0069(5) -0.0044(4) -0.0007(4) O2 0.0203(6) 0.0242(6) 0.0252(6) -0.0075(5) -0.0064(4) 0.0020(4) N1 0.0174(6) 0.0168(6) 0.0191(6) -0.0064(5) -0.0014(5) 0.0008(5) N2 0.0213(7) 0.0223(7) 0.0231(6) -0.0055(6) -0.0018(5) -0.0005(5) C1 0.0166(7) 0.0177(7) 0.0168(7) -0.0020(6) 0.0008(5) -0.0023(6) C2 0.0179(7) 0.0161(7) 0.0190(7) -0.0035(6) 0.0022(5) -0.0034(5) C3 0.0183(7) 0.0195(8) 0.0246(8) -0.0030(6) 0.0027(6) -0.0004(6) C4 0.0254(8) 0.0159(8) 0.0307(8) -0.0055(7) 0.0094(7) -0.0003(6) C5 0.0322(9) 0.0194(8) 0.0279(8) -0.0106(7) 0.0102(7) -0.0082(6) C6 0.0233(8) 0.0218(8) 0.0221(7) -0.0066(6) 0.0036(6) -0.0073(6) C7 0.0182(7) 0.0167(7) 0.0192(7) -0.0045(6) 0.0019(6) -0.0034(6) C8 0.0179(7) 0.0182(7) 0.0171(7) -0.0034(6) 0.0012(5) -0.0041(6) C9 0.0208(7) 0.0177(7) 0.0202(7) -0.0072(6) 0.0004(6) 0.0011(6) C10 0.0227(8) 0.0195(8) 0.0212(7) -0.0083(6) -0.0043(6) -0.0004(6) C11 0.0198(7) 0.0148(7) 0.0215(7) -0.0072(6) -0.0024(6) -0.0031(5) C12 0.0203(8) 0.0189(8) 0.0272(8) -0.0078(7) -0.0018(6) -0.0009(6) C13 0.0257(8) 0.0259(8) 0.0256(8) -0.0103(7) 0.0041(6) -0.0053(6) C14 0.0281(9) 0.0276(9) 0.0206(7) -0.0036(7) -0.0029(6) -0.0077(7) C15 0.0198(8) 0.0270(9) 0.0252(8) -0.0023(7) -0.0045(6) 0.0002(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 O1 C1 1.2119(17) . ? O2 C8 1.2129(17) . ? N1 C8 1.3947(18) . ? N1 C1 1.4018(18) . ? N1 C9 1.4616(18) . ? N2 C15 1.340(2) . ? N2 C11 1.3460(19) . ? C1 C2 1.493(2) . ? C2 C3 1.382(2) . ? C2 C7 1.392(2) . ? C3 C4 1.396(2) . ? C3 H3 0.9720 . ? C4 C5 1.393(2) . ? C4 H4 0.9457 . ? C5 C6 1.394(2) . ? C5 H5 0.9618 . ? C6 C7 1.384(2) . ? C6 H6 0.9925 . ? C7 C8 1.493(2) . ? C9 C10 1.532(2) . ? C9 H9B 1.0010 . ? C9 H9A 0.9931 . ? C10 C11 1.508(2) . ? C10 H10B 1.0260 . ? C10 H10A 1.0343 . ? C11 C12 1.387(2) . ? C12 C13 1.388(2) . ? C12 H12 0.9618 . ? C13 C14 1.384(2) . ? C13 H13 0.9707 . ? C14 C15 1.381(2) . ? C14 H14 0.9768 . ? C15 H15 0.9712 . ? 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 C8 N1 C1 112.18(12) . . ? C8 N1 C9 124.44(12) . . ? C1 N1 C9 123.37(12) . . ? C15 N2 C11 117.37(13) . . ? O1 C1 N1 124.87(13) . . ? O1 C1 C2 129.38(13) . . ? N1 C1 C2 105.75(12) . . ? C3 C2 C7 121.53(14) . . ? C3 C2 C1 130.46(14) . . ? C7 C2 C1 108.01(12) . . ? C2 C3 C4 117.29(14) . . ? C2 C3 H3 122.0 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 121.13(14) . . ? C5 C4 H4 118.8 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 121.26(15) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 117.26(14) . . ? C7 C6 H6 117.6 . . ? C5 C6 H6 125.1 . . ? C6 C7 C2 121.52(14) . . ? C6 C7 C8 130.23(13) . . ? C2 C7 C8 108.25(12) . . ? O2 C8 N1 125.43(13) . . ? O2 C8 C7 128.79(13) . . ? N1 C8 C7 105.79(12) . . ? N1 C9 C10 112.13(12) . . ? N1 C9 H9B 107.4 . . ? C10 C9 H9B 109.9 . . ? N1 C9 H9A 109.3 . . ? C10 C9 H9A 110.3 . . ? H9B C9 H9A 107.6 . . ? C11 C10 C9 112.28(12) . . ? C11 C10 H10B 109.7 . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10A 107.4 . . ? H10B C10 H10A 109.7 . . ? N2 C11 C12 122.54(14) . . ? N2 C11 C10 115.70(13) . . ? C12 C11 C10 121.76(13) . . ? C11 C12 C13 118.91(14) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.9 . . ? C14 C13 C12 119.15(15) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 121.5 . . ? C15 C14 C13 117.96(15) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 122.7 . . ? N2 C15 C14 124.07(15) . . ? N2 C15 H15 115.1 . . ? C14 C15 H15 120.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 O1 179.19(14) . . . . ? C9 N1 C1 O1 -0.6(2) . . . . ? C8 N1 C1 C2 -1.06(15) . . . . ? C9 N1 C1 C2 179.12(12) . . . . ? O1 C1 C2 C3 -0.5(3) . . . . ? N1 C1 C2 C3 179.74(15) . . . . ? O1 C1 C2 C7 179.75(15) . . . . ? N1 C1 C2 C7 0.01(15) . . . . ? C7 C2 C3 C4 0.2(2) . . . . ? C1 C2 C3 C4 -179.50(14) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? C3 C4 C5 C6 0.3(2) . . . . ? C4 C5 C6 C7 0.2(2) . . . . ? C5 C6 C7 C2 -0.5(2) . . . . ? C5 C6 C7 C8 178.41(14) . . . . ? C3 C2 C7 C6 0.3(2) . . . . ? C1 C2 C7 C6 -179.94(13) . . . . ? C3 C2 C7 C8 -178.81(13) . . . . ? C1 C2 C7 C8 0.94(16) . . . . ? C1 N1 C8 O2 -178.38(14) . . . . ? C9 N1 C8 O2 1.4(2) . . . . ? C1 N1 C8 C7 1.61(15) . . . . ? C9 N1 C8 C7 -178.57(12) . . . . ? C6 C7 C8 O2 -0.6(3) . . . . ? C2 C7 C8 O2 178.44(15) . . . . ? C6 C7 C8 N1 179.43(14) . . . . ? C2 C7 C8 N1 -1.56(16) . . . . ? C8 N1 C9 C10 -105.41(15) . . . . ? C1 N1 C9 C10 74.39(17) . . . . ? N1 C9 C10 C11 65.74(16) . . . . ? C15 N2 C11 C12 -0.5(2) . . . . ? C15 N2 C11 C10 179.72(13) . . . . ? C9 C10 C11 N2 75.59(16) . . . . ? C9 C10 C11 C12 -104.23(16) . . . . ? N2 C11 C12 C13 0.4(2) . . . . ? C10 C11 C12 C13 -179.74(13) . . . . ? C11 C12 C13 C14 -0.3(2) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? C11 N2 C15 C14 0.4(2) . . . . ? C13 C14 C15 N2 -0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.74 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.218 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.046 # Attachment 'L6b.cif' data_irl33_0m _database_code_depnum_ccdc_archive 'CCDC 723939' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H10 N2 O2' _chemical_formula_weight 274.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(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 7.9097(4) _cell_length_b 16.4710(8) _cell_length_c 10.1089(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.700(3) _cell_angle_gamma 90.00 _cell_volume 1298.17(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7127 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 30.29 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9814 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details 'Bruker Apex v2.1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22786 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 31.17 _reflns_number_total 4003 _reflns_number_gt 3203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex v2.1' _computing_cell_refinement 'Bruker Apex v2.1' _computing_data_reduction 'Bruker Apex v2.1' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0616P)^2^+0.3144P] 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 4003 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1148 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 N1 N 0.09939(12) 0.12500(5) 0.11647(9) 0.01751(19) Uani 1 1 d . . . N2 N 0.18208(11) 0.09141(5) 0.38973(9) 0.01653(19) Uani 1 1 d . . . O1 O 0.44710(10) 0.15142(5) 0.46021(8) 0.01911(17) Uani 1 1 d . . . O2 O -0.10811(11) 0.06006(5) 0.36576(8) 0.02491(19) Uani 1 1 d . . . C1 C 0.06874(15) 0.14149(7) -0.01327(11) 0.0201(2) Uani 1 1 d . . . H1 H 0.0022 0.1930 -0.0415 0.026(4) Uiso 1 1 d R . . C2 C 0.12421(15) 0.09319(7) -0.11314(11) 0.0218(2) Uani 1 1 d . . . H2 H 0.0921 0.1091 -0.2073 0.033(4) Uiso 1 1 d R . . C3 C 0.21672(14) 0.02452(7) -0.07550(11) 0.0199(2) Uani 1 1 d . . . H3 H 0.2518 -0.0136 -0.1413 0.027(4) Uiso 1 1 d R . . C4 C 0.25528(14) 0.00407(6) 0.06231(10) 0.0169(2) Uani 1 1 d . . . C5 C 0.35117(15) -0.06591(7) 0.10970(11) 0.0210(2) Uani 1 1 d . . . H5 H 0.3907 -0.1033 0.0424 0.027(4) Uiso 1 1 d R . . C6 C 0.38511(16) -0.08328(7) 0.24386(12) 0.0244(2) Uani 1 1 d . . . H6 H 0.4532 -0.1312 0.2777 0.032(4) Uiso 1 1 d R . . C7 C 0.32623(15) -0.03101(7) 0.33737(11) 0.0216(2) Uani 1 1 d . . . H7 H 0.3577 -0.0436 0.4365 0.029(4) Uiso 1 1 d R . . C8 C 0.23311(14) 0.03684(6) 0.29388(10) 0.0165(2) Uani 1 1 d . . . C9 C 0.19313(13) 0.05652(6) 0.15493(10) 0.0154(2) Uani 1 1 d . . . C10 C 0.29574(14) 0.14590(6) 0.46480(10) 0.0154(2) Uani 1 1 d . . . C11 C 0.19163(14) 0.19400(6) 0.54623(10) 0.0156(2) Uani 1 1 d . . . C12 C 0.24091(15) 0.25509(6) 0.63897(11) 0.0181(2) Uani 1 1 d . . . H12 H 0.3562 0.2743 0.6620 0.024(4) Uiso 1 1 d R . . C13 C 0.11221(15) 0.28945(7) 0.70037(11) 0.0205(2) Uani 1 1 d . . . H13 H 0.1417 0.3326 0.7686 0.019(3) Uiso 1 1 d R . . C14 C -0.05767(15) 0.26383(7) 0.66743(11) 0.0212(2) Uani 1 1 d . . . H14 H -0.1479 0.2909 0.7135 0.031(4) Uiso 1 1 d R . . C15 C -0.10670(14) 0.20302(7) 0.57225(11) 0.0201(2) Uani 1 1 d . . . H15 H -0.2232 0.1839 0.5486 0.022(3) Uiso 1 1 d R . . C16 C 0.02212(14) 0.16824(6) 0.51400(10) 0.0169(2) Uani 1 1 d . . . C17 C 0.01339(14) 0.10072(7) 0.41458(10) 0.0176(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0177(4) 0.0179(4) 0.0171(4) -0.0002(3) 0.0031(3) -0.0007(3) N2 0.0171(4) 0.0194(4) 0.0134(4) -0.0029(3) 0.0031(3) 0.0004(3) O1 0.0182(4) 0.0221(4) 0.0179(4) 0.0008(3) 0.0054(3) -0.0004(3) O2 0.0204(4) 0.0330(5) 0.0211(4) -0.0088(3) 0.0027(3) -0.0042(3) C1 0.0203(5) 0.0211(5) 0.0188(5) 0.0023(4) 0.0031(4) -0.0012(4) C2 0.0230(5) 0.0279(6) 0.0144(5) 0.0013(4) 0.0030(4) -0.0034(4) C3 0.0206(5) 0.0252(5) 0.0147(5) -0.0038(4) 0.0056(4) -0.0041(4) C4 0.0165(5) 0.0190(5) 0.0156(5) -0.0034(4) 0.0042(4) -0.0026(4) C5 0.0221(5) 0.0220(5) 0.0192(5) -0.0057(4) 0.0049(4) 0.0028(4) C6 0.0285(6) 0.0219(5) 0.0222(5) -0.0018(4) 0.0032(5) 0.0083(5) C7 0.0260(6) 0.0219(5) 0.0166(5) 0.0002(4) 0.0027(4) 0.0039(4) C8 0.0181(5) 0.0180(5) 0.0141(4) -0.0029(4) 0.0042(4) 0.0002(4) C9 0.0154(5) 0.0163(4) 0.0150(4) -0.0012(4) 0.0039(4) -0.0020(4) C10 0.0189(5) 0.0163(4) 0.0110(4) 0.0021(3) 0.0029(4) 0.0015(4) C11 0.0183(5) 0.0166(4) 0.0125(4) 0.0012(4) 0.0040(4) 0.0014(4) C12 0.0212(5) 0.0182(5) 0.0153(5) 0.0000(4) 0.0036(4) -0.0008(4) C13 0.0277(6) 0.0182(5) 0.0158(5) -0.0014(4) 0.0043(4) 0.0031(4) C14 0.0242(6) 0.0241(5) 0.0158(5) -0.0004(4) 0.0049(4) 0.0075(4) C15 0.0180(5) 0.0257(5) 0.0165(5) -0.0006(4) 0.0028(4) 0.0035(4) C16 0.0188(5) 0.0192(5) 0.0126(4) -0.0006(4) 0.0024(4) 0.0017(4) C17 0.0181(5) 0.0218(5) 0.0128(4) -0.0008(4) 0.0021(4) 0.0013(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 N1 C1 1.3212(14) . ? N1 C9 1.3697(13) . ? N2 C10 1.3999(13) . ? N2 C17 1.4071(14) . ? N2 C8 1.4287(13) . ? O1 C10 1.2093(13) . ? O2 C17 1.2066(14) . ? C1 C2 1.4120(16) . ? C1 H1 1.0135 . ? C2 C3 1.3659(16) . ? C2 H2 0.9790 . ? C3 C4 1.4157(15) . ? C3 H3 0.9881 . ? C4 C5 1.4179(15) . ? C4 C9 1.4212(14) . ? C5 C6 1.3677(16) . ? C5 H5 1.0057 . ? C6 C7 1.4142(16) . ? C6 H6 0.9841 . ? C7 C8 1.3696(15) . ? C7 H7 1.0125 . ? C8 C9 1.4242(14) . ? C10 C11 1.4871(14) . ? C11 C12 1.3858(15) . ? C11 C16 1.3916(15) . ? C12 C13 1.3981(15) . ? C12 H12 0.9559 . ? C13 C14 1.3942(17) . ? C13 H13 0.9905 . ? C14 C15 1.3977(16) . ? C14 H14 1.0183 . ? C15 C16 1.3840(15) . ? C15 H15 0.9650 . ? C16 C17 1.4927(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C9 116.82(9) . . ? C10 N2 C17 112.02(8) . . ? C10 N2 C8 122.82(9) . . ? C17 N2 C8 125.06(9) . . ? N1 C1 C2 124.52(10) . . ? N1 C1 H1 116.8 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 118.94(10) . . ? C3 C2 H2 122.1 . . ? C1 C2 H2 118.9 . . ? C2 C3 C4 119.19(10) . . ? C2 C3 H3 122.5 . . ? C4 C3 H3 118.2 . . ? C3 C4 C5 122.69(10) . . ? C3 C4 C9 117.55(10) . . ? C5 C4 C9 119.75(9) . . ? C6 C5 C4 120.63(10) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 118.6 . . ? C5 C6 C7 120.25(11) . . ? C5 C6 H6 121.2 . . ? C7 C6 H6 118.6 . . ? C8 C7 C6 120.14(10) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 118.9 . . ? C7 C8 C9 121.35(9) . . ? C7 C8 N2 119.59(9) . . ? C9 C8 N2 118.98(9) . . ? N1 C9 C4 122.98(9) . . ? N1 C9 C8 119.14(9) . . ? C4 C9 C8 117.87(9) . . ? O1 C10 N2 125.23(9) . . ? O1 C10 C11 128.71(10) . . ? N2 C10 C11 106.06(9) . . ? C12 C11 C16 121.99(10) . . ? C12 C11 C10 129.97(10) . . ? C16 C11 C10 108.03(9) . . ? C11 C12 C13 116.84(10) . . ? C11 C12 H12 123.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 121.06(10) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 121.72(10) . . ? C13 C14 H14 118.7 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 116.79(10) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 123.2 . . ? C15 C16 C11 121.57(10) . . ? C15 C16 C17 129.87(10) . . ? C11 C16 C17 108.55(9) . . ? O2 C17 N2 125.47(10) . . ? O2 C17 C16 129.22(10) . . ? N2 C17 C16 105.29(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 C1 C2 0.70(16) . . . . ? N1 C1 C2 C3 -0.26(18) . . . . ? C1 C2 C3 C4 -0.43(16) . . . . ? C2 C3 C4 C5 -179.73(10) . . . . ? C2 C3 C4 C9 0.62(15) . . . . ? C3 C4 C5 C6 -179.91(11) . . . . ? C9 C4 C5 C6 -0.28(17) . . . . ? C4 C5 C6 C7 -0.64(19) . . . . ? C5 C6 C7 C8 0.76(19) . . . . ? C6 C7 C8 C9 0.06(17) . . . . ? C6 C7 C8 N2 -176.72(10) . . . . ? C10 N2 C8 C7 75.74(14) . . . . ? C17 N2 C8 C7 -108.25(13) . . . . ? C10 N2 C8 C9 -101.11(12) . . . . ? C17 N2 C8 C9 74.89(14) . . . . ? C1 N1 C9 C4 -0.47(15) . . . . ? C1 N1 C9 C8 178.64(10) . . . . ? C3 C4 C9 N1 -0.17(15) . . . . ? C5 C4 C9 N1 -179.83(10) . . . . ? C3 C4 C9 C8 -179.29(10) . . . . ? C5 C4 C9 C8 1.05(15) . . . . ? C7 C8 C9 N1 179.90(10) . . . . ? N2 C8 C9 N1 -3.30(15) . . . . ? C7 C8 C9 C4 -0.95(16) . . . . ? N2 C8 C9 C4 175.85(9) . . . . ? C17 N2 C10 O1 -178.62(10) . . . . ? C8 N2 C10 O1 -2.15(16) . . . . ? C17 N2 C10 C11 0.61(11) . . . . ? C8 N2 C10 C11 177.09(9) . . . . ? O1 C10 C11 C12 -1.88(18) . . . . ? N2 C10 C11 C12 178.92(10) . . . . ? O1 C10 C11 C16 177.53(10) . . . . ? N2 C10 C11 C16 -1.67(11) . . . . ? C16 C11 C12 C13 0.67(15) . . . . ? C10 C11 C12 C13 -179.99(10) . . . . ? C11 C12 C13 C14 -0.98(16) . . . . ? C12 C13 C14 C15 0.04(17) . . . . ? C13 C14 C15 C16 1.22(16) . . . . ? C14 C15 C16 C11 -1.55(16) . . . . ? C14 C15 C16 C17 177.35(11) . . . . ? C12 C11 C16 C15 0.63(16) . . . . ? C10 C11 C16 C15 -178.84(10) . . . . ? C12 C11 C16 C17 -178.48(10) . . . . ? C10 C11 C16 C17 2.05(11) . . . . ? C10 N2 C17 O2 -177.94(11) . . . . ? C8 N2 C17 O2 5.68(17) . . . . ? C10 N2 C17 C16 0.59(11) . . . . ? C8 N2 C17 C16 -175.79(9) . . . . ? C15 C16 C17 O2 -2.2(2) . . . . ? C11 C16 C17 O2 176.80(11) . . . . ? C15 C16 C17 N2 179.33(11) . . . . ? C11 C16 C17 N2 -1.66(11) . . . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 31.17 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.459 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.051