# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1g _database_code_depnum_ccdc_archive 'CCDC 896146' #TrackingRef 'cgyan-wl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H24 N2 O3, C2 H6 O' _chemical_formula_sum 'C31 H30 N2 O4' _chemical_formula_weight 494.57 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 14.1251(19) _cell_length_b 11.6285(15) _cell_length_c 16.905(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.455(2) _cell_angle_gamma 90.00 _cell_volume 2721.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6394 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 26.33 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 23209 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 27.57 _reflns_number_total 6298 _reflns_number_gt 4327 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1017P)^2^+0.6055P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.026(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6261 _refine_ls_number_parameters 339 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1948 _refine_ls_wR_factor_gt 0.1709 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.26503(13) 1.07194(15) 0.09386(10) 0.0411(4) Uani 1 1 d . . . C2 C 0.18860(15) 1.14457(17) 0.10096(12) 0.0504(5) Uani 1 1 d . . . H2 H 0.1303 1.1136 0.1085 0.061 Uiso 1 1 calc R . . C3 C 0.19931(18) 1.26274(19) 0.09681(15) 0.0650(6) Uani 1 1 d . . . H3 H 0.1478 1.3104 0.1014 0.078 Uiso 1 1 calc R . . C4 C 0.2853(2) 1.3111(2) 0.08595(17) 0.0736(7) Uani 1 1 d . . . H4 H 0.2918 1.3905 0.0832 0.088 Uiso 1 1 calc R . . C5 C 0.36132(18) 1.2392(2) 0.07929(15) 0.0656(6) Uani 1 1 d . . . H5 H 0.4192 1.2714 0.0719 0.079 Uiso 1 1 calc R . . C6 C 0.35369(14) 1.12009(17) 0.08331(12) 0.0501(5) Uani 1 1 d . . . C7 C 0.43302(14) 1.04304(19) 0.07709(13) 0.0548(5) Uani 1 1 d . . . H7 H 0.4913 1.0744 0.0700 0.066 Uiso 1 1 calc R . . C8 C 0.42508(13) 0.92985(19) 0.08120(12) 0.0514(5) Uani 1 1 d . . . H8 H 0.4779 0.8843 0.0766 0.062 Uiso 1 1 calc R . . C9 C 0.33428(12) 0.87291(16) 0.09299(11) 0.0410(4) Uani 1 1 d . . . H9 H 0.3483 0.8295 0.1437 0.049 Uiso 1 1 calc R . . C10 C 0.16678(12) 0.89249(15) 0.08870(11) 0.0399(4) Uani 1 1 d . . . H10 H 0.1153 0.9362 0.0541 0.048 Uiso 1 1 calc R . . C11 C 0.13905(13) 0.86975(16) 0.17110(11) 0.0425(4) Uani 1 1 d . . . C12 C 0.05315(13) 0.79512(17) 0.17263(12) 0.0471(4) Uani 1 1 d . . . C13 C 0.05744(18) 0.7208(2) 0.23744(15) 0.0676(6) Uani 1 1 d . . . H13 H 0.1117 0.7206 0.2789 0.081 Uiso 1 1 calc R . . C14 C -0.0182(2) 0.6472(3) 0.24073(19) 0.0864(9) Uani 1 1 d . . . H14 H -0.0142 0.5968 0.2839 0.104 Uiso 1 1 calc R . . C15 C -0.0989(2) 0.6480(3) 0.18081(18) 0.0848(9) Uani 1 1 d . . . H15 H -0.1498 0.5982 0.1833 0.102 Uiso 1 1 calc R . . C16 C -0.10488(18) 0.7225(3) 0.11690(16) 0.0803(8) Uani 1 1 d . . . H16 H -0.1604 0.7243 0.0768 0.096 Uiso 1 1 calc R . . C17 C -0.02835(15) 0.7950(2) 0.11213(14) 0.0616(6) Uani 1 1 d . . . H17 H -0.0319 0.8437 0.0680 0.074 Uiso 1 1 calc R . . C18 C 0.18360(12) 0.77679(16) 0.04680(11) 0.0407(4) Uani 1 1 d . . . H18 H 0.1869 0.7145 0.0863 0.049 Uiso 1 1 calc R . . C19 C 0.10627(15) 0.7473(2) -0.02635(14) 0.0601(6) Uani 1 1 d . . . C20 C 0.1059(3) 0.6254(3) -0.0573(2) 0.1056(11) Uani 1 1 d . . . H20A H 0.0545 0.6165 -0.1034 0.158 Uiso 1 1 calc R . . H20B H 0.0965 0.5730 -0.0157 0.158 Uiso 1 1 calc R . . H20C H 0.1666 0.6094 -0.0724 0.158 Uiso 1 1 calc R . . C21 C 0.28488(12) 0.78980(15) 0.02399(10) 0.0386(4) Uani 1 1 d . . . C22 C 0.34010(13) 0.67582(16) 0.02732(11) 0.0433(4) Uani 1 1 d . . . C23 C 0.34184(13) 0.75675(17) -0.09536(11) 0.0443(4) Uani 1 1 d . . . C24 C 0.35999(16) 0.7745(2) -0.17180(12) 0.0573(5) Uani 1 1 d . . . H24 H 0.3963 0.7224 -0.1950 0.069 Uiso 1 1 calc R . . C25 C 0.32233(18) 0.8722(2) -0.21240(13) 0.0658(6) Uani 1 1 d . . . H25 H 0.3338 0.8858 -0.2639 0.079 Uiso 1 1 calc R . . C26 C 0.26717(19) 0.9518(2) -0.17848(13) 0.0641(6) Uani 1 1 d . . . C27 C 0.2246(3) 1.0558(3) -0.2261(2) 0.1133(13) Uani 1 1 d . . . H27A H 0.2371 1.1231 -0.1929 0.170 Uiso 1 1 calc R . . H27B H 0.1561 1.0457 -0.2433 0.170 Uiso 1 1 calc R . . H27C H 0.2535 1.0646 -0.2726 0.170 Uiso 1 1 calc R . . C28 C 0.25039(16) 0.93159(18) -0.10110(12) 0.0526(5) Uani 1 1 d . . . H28 H 0.2144 0.9836 -0.0775 0.063 Uiso 1 1 calc R . . C29 C 0.28756(12) 0.83383(15) -0.05971(10) 0.0398(4) Uani 1 1 d . . . C30 C 0.5836(3) 0.5453(3) 0.1893(2) 0.1181(13) Uani 1 1 d D . . H30A H 0.6435 0.5031 0.2059 0.142 Uiso 1 1 calc R . . H30B H 0.5457 0.5356 0.2308 0.142 Uiso 1 1 calc R . . C31 C 0.6059(4) 0.6710(4) 0.1815(4) 0.187(3) Uani 1 1 d D . . H31A H 0.6285 0.6834 0.1322 0.280 Uiso 1 1 calc R . . H31B H 0.6548 0.6943 0.2265 0.280 Uiso 1 1 calc R . . H31C H 0.5484 0.7155 0.1807 0.280 Uiso 1 1 calc R . . N1 N 0.25721(10) 0.95415(13) 0.09708(10) 0.0442(4) Uani 1 1 d . . . N2 N 0.37237(12) 0.66469(14) -0.04207(10) 0.0509(4) Uani 1 1 d . . . H2A H 0.4073 0.6083 -0.0526 0.061 Uiso 1 1 calc R . . O1 O 0.18855(11) 0.90645(14) 0.23257(9) 0.0632(4) Uani 1 1 d . . . O2 O 0.04946(12) 0.81811(19) -0.05900(10) 0.0783(5) Uani 1 1 d . . . O3 O 0.35361(11) 0.60886(12) 0.08473(9) 0.0565(4) Uani 1 1 d . . . O4 O 0.53138(15) 0.4988(2) 0.11479(14) 0.1034(8) Uani 1 1 d . . . H4A H 0.4779 0.5289 0.1035 0.155 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0468(9) 0.0419(9) 0.0355(9) -0.0053(7) 0.0100(7) -0.0041(7) C2 0.0526(11) 0.0462(11) 0.0528(11) -0.0088(8) 0.0113(9) 0.0010(8) C3 0.0717(14) 0.0484(12) 0.0707(15) -0.0104(10) 0.0040(12) 0.0077(11) C4 0.0921(19) 0.0415(12) 0.0824(18) -0.0053(11) 0.0056(14) -0.0100(12) C5 0.0697(14) 0.0561(13) 0.0716(15) -0.0046(11) 0.0160(12) -0.0205(11) C6 0.0548(11) 0.0495(11) 0.0474(11) -0.0077(8) 0.0138(9) -0.0117(9) C7 0.0452(10) 0.0645(13) 0.0592(12) -0.0121(10) 0.0213(9) -0.0152(9) C8 0.0366(9) 0.0623(13) 0.0583(12) -0.0108(9) 0.0170(8) -0.0020(8) C9 0.0382(9) 0.0450(10) 0.0418(9) -0.0026(7) 0.0129(7) 0.0015(7) C10 0.0353(8) 0.0430(9) 0.0441(9) -0.0011(7) 0.0146(7) 0.0002(7) C11 0.0395(9) 0.0480(10) 0.0418(10) -0.0040(8) 0.0125(7) 0.0028(7) C12 0.0435(10) 0.0585(11) 0.0439(10) -0.0021(8) 0.0194(8) -0.0021(8) C13 0.0602(13) 0.0907(17) 0.0546(13) 0.0156(12) 0.0180(10) -0.0058(12) C14 0.0876(19) 0.098(2) 0.0804(18) 0.0258(16) 0.0334(16) -0.0195(16) C15 0.0817(18) 0.099(2) 0.0830(19) -0.0081(16) 0.0382(16) -0.0387(16) C16 0.0578(14) 0.122(2) 0.0624(15) -0.0053(15) 0.0154(12) -0.0307(14) C17 0.0477(11) 0.0888(16) 0.0503(12) 0.0063(11) 0.0148(9) -0.0106(10) C18 0.0398(9) 0.0428(9) 0.0428(9) -0.0031(7) 0.0158(7) -0.0016(7) C19 0.0418(10) 0.0789(16) 0.0622(13) -0.0205(11) 0.0166(10) -0.0108(10) C20 0.093(2) 0.101(2) 0.120(3) -0.057(2) 0.0128(19) -0.0294(18) C21 0.0375(8) 0.0408(9) 0.0400(9) -0.0004(7) 0.0136(7) 0.0019(7) C22 0.0415(9) 0.0418(10) 0.0482(10) -0.0030(8) 0.0129(8) 0.0015(7) C23 0.0423(9) 0.0505(10) 0.0424(10) -0.0063(8) 0.0135(7) -0.0019(8) C24 0.0591(12) 0.0728(14) 0.0449(11) -0.0096(10) 0.0226(9) -0.0018(10) C25 0.0780(15) 0.0839(16) 0.0399(11) 0.0016(11) 0.0223(10) -0.0127(13) C26 0.0860(16) 0.0597(13) 0.0480(12) 0.0095(10) 0.0168(11) -0.0028(11) C27 0.181(4) 0.090(2) 0.075(2) 0.0365(17) 0.039(2) 0.027(2) C28 0.0660(12) 0.0483(11) 0.0459(11) 0.0024(8) 0.0172(9) 0.0028(9) C29 0.0415(9) 0.0432(9) 0.0361(9) -0.0014(7) 0.0115(7) -0.0025(7) C30 0.121(3) 0.114(3) 0.106(3) -0.016(2) -0.011(2) 0.029(2) C31 0.165(5) 0.139(4) 0.221(7) 0.014(4) -0.048(4) -0.018(4) N1 0.0368(7) 0.0404(8) 0.0598(10) -0.0060(7) 0.0208(7) -0.0022(6) N2 0.0531(9) 0.0516(9) 0.0521(9) -0.0057(7) 0.0203(8) 0.0129(7) O1 0.0605(9) 0.0827(11) 0.0477(8) -0.0133(7) 0.0138(7) -0.0136(8) O2 0.0498(9) 0.1250(16) 0.0572(10) -0.0143(10) 0.0031(8) 0.0064(10) O3 0.0662(9) 0.0499(8) 0.0564(9) 0.0096(6) 0.0192(7) 0.0140(7) O4 0.0771(13) 0.1108(16) 0.1109(16) -0.0559(13) -0.0087(11) 0.0410(11) _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 1.376(2) . ? C1 C2 1.394(3) . ? C1 C6 1.415(3) . ? C2 C3 1.386(3) . ? C2 H2 0.9300 . ? C3 C4 1.383(4) . ? C3 H3 0.9300 . ? C4 C5 1.383(4) . ? C4 H4 0.9300 . ? C5 C6 1.392(3) . ? C5 H5 0.9300 . ? C6 C7 1.455(3) . ? C7 C8 1.324(3) . ? C7 H7 0.9300 . ? C8 C9 1.492(2) . ? C8 H8 0.9300 . ? C9 N1 1.453(2) . ? C9 C21 1.568(2) . ? C9 H9 0.9800 . ? C10 N1 1.447(2) . ? C10 C11 1.543(2) . ? C10 C18 1.561(2) . ? C10 H10 0.9800 . ? C11 O1 1.209(2) . ? C11 C12 1.496(3) . ? C12 C17 1.380(3) . ? C12 C13 1.387(3) . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 C15 1.367(4) . ? C14 H14 0.9300 . ? C15 C16 1.374(4) . ? C15 H15 0.9300 . ? C16 C17 1.386(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.518(3) . ? C18 C21 1.561(2) . ? C18 H18 0.9800 . ? C19 O2 1.205(3) . ? C19 C20 1.510(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C29 1.512(2) . ? C21 C22 1.533(2) . ? C22 O3 1.229(2) . ? C22 N2 1.346(2) . ? C23 C24 1.382(3) . ? C23 C29 1.392(2) . ? C23 N2 1.410(3) . ? C24 C25 1.378(3) . ? C24 H24 0.9300 . ? C25 C26 1.404(3) . ? C25 H25 0.9300 . ? C26 C28 1.395(3) . ? C26 C27 1.510(4) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.383(3) . ? C28 H28 0.9300 . ? C30 O4 1.433(4) . ? C30 C31 1.507(2) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? N2 H2A 0.8600 . ? O4 H4A 0.8200 . ? 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 122.00(16) . . ? N1 C1 C6 118.61(16) . . ? C2 C1 C6 119.39(18) . . ? C3 C2 C1 120.1(2) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 121.2(2) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 118.8(2) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C4 C5 C6 121.9(2) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C5 C6 C1 118.61(19) . . ? C5 C6 C7 122.76(18) . . ? C1 C6 C7 118.62(18) . . ? C8 C7 C6 122.28(17) . . ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? C7 C8 C9 122.17(17) . . ? C7 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? N1 C9 C8 112.95(16) . . ? N1 C9 C21 102.07(13) . . ? C8 C9 C21 116.22(14) . . ? N1 C9 H9 108.4 . . ? C8 C9 H9 108.4 . . ? C21 C9 H9 108.4 . . ? N1 C10 C11 111.97(15) . . ? N1 C10 C18 105.10(13) . . ? C11 C10 C18 110.54(14) . . ? N1 C10 H10 109.7 . . ? C11 C10 H10 109.7 . . ? C18 C10 H10 109.7 . . ? O1 C11 C12 121.49(17) . . ? O1 C11 C10 120.54(16) . . ? C12 C11 C10 117.85(15) . . ? C17 C12 C13 118.9(2) . . ? C17 C12 C11 123.22(18) . . ? C13 C12 C11 117.81(19) . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 120.3(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.9(2) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 120.2(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 120.2(2) . . ? C12 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C10 114.51(16) . . ? C19 C18 C21 111.55(15) . . ? C10 C18 C21 104.96(13) . . ? C19 C18 H18 108.5 . . ? C10 C18 H18 108.5 . . ? C21 C18 H18 108.5 . . ? O2 C19 C20 121.8(2) . . ? O2 C19 C18 121.7(2) . . ? C20 C19 C18 116.5(2) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C29 C21 C22 102.70(14) . . ? C29 C21 C18 117.28(15) . . ? C22 C21 C18 113.05(14) . . ? C29 C21 C9 113.40(14) . . ? C22 C21 C9 110.95(14) . . ? C18 C21 C9 99.81(13) . . ? O3 C22 N2 126.91(17) . . ? O3 C22 C21 125.07(16) . . ? N2 C22 C21 108.00(15) . . ? C24 C23 C29 121.93(19) . . ? C24 C23 N2 128.38(17) . . ? C29 C23 N2 109.69(15) . . ? C25 C24 C23 117.66(19) . . ? C25 C24 H24 121.2 . . ? C23 C24 H24 121.2 . . ? C24 C25 C26 122.05(19) . . ? C24 C25 H25 119.0 . . ? C26 C25 H25 119.0 . . ? C28 C26 C25 118.9(2) . . ? C28 C26 C27 120.7(2) . . ? C25 C26 C27 120.3(2) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C26 119.66(19) . . ? C29 C28 H28 120.2 . . ? C26 C28 H28 120.2 . . ? C28 C29 C23 119.78(17) . . ? C28 C29 C21 132.40(16) . . ? C23 C29 C21 107.78(15) . . ? O4 C30 C31 111.6(4) . . ? O4 C30 H30A 109.3 . . ? C31 C30 H30A 109.3 . . ? O4 C30 H30B 109.3 . . ? C31 C30 H30B 109.3 . . ? H30A C30 H30B 108.0 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C1 N1 C10 124.44(15) . . ? C1 N1 C9 125.33(14) . . ? C10 N1 C9 109.16(14) . . ? C22 N2 C23 111.72(15) . . ? C22 N2 H2A 124.1 . . ? C23 N2 H2A 124.1 . . ? C30 O4 H4A 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A O4 0.86 1.94 2.763(2) 159.6 3_665 O4 H4A O3 0.82 1.96 2.774(2) 175.1 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.651 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.061 data_1i _database_code_depnum_ccdc_archive 'CCDC 896147' #TrackingRef 'cgyan-wl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H24 Cl2 N2 O3' _chemical_formula_sum 'C34 H24 Cl2 N2 O3' _chemical_formula_weight 579.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7306(18) _cell_length_b 12.134(2) _cell_length_c 15.316(3) _cell_angle_alpha 79.865(3) _cell_angle_beta 75.145(3) _cell_angle_gamma 70.894(2) _cell_volume 1643.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2305 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 21.00 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600.0 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_T_max 0.946 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 12026 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0767 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5780 _reflns_number_gt 3492 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1095P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5738 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1955 _refine_ls_wR_factor_gt 0.1721 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _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 0.1533(3) 0.1353(2) 0.54323(18) 0.0465(7) Uani 1 1 d . . . C2 C 0.0510(4) 0.1214(3) 0.5011(2) 0.0596(8) Uani 1 1 d . . . H2 H 0.0817 0.0777 0.4517 0.072 Uiso 1 1 calc R . . C3 C -0.0983(4) 0.1743(3) 0.5347(3) 0.0669(9) Uani 1 1 d . . . H3 H -0.1679 0.1650 0.5071 0.080 Uiso 1 1 calc R . . C4 C -0.1490(3) 0.2411(3) 0.6082(2) 0.0590(8) Uani 1 1 d . . . C5 C -0.3097(4) 0.2992(4) 0.6397(3) 0.0865(12) Uani 1 1 d . . . H5A H -0.3657 0.2733 0.6086 0.130 Uiso 1 1 calc R . . H5B H -0.3293 0.3826 0.6271 0.130 Uiso 1 1 calc R . . H5C H -0.3384 0.2795 0.7039 0.130 Uiso 1 1 calc R . . C6 C -0.0429(3) 0.2541(2) 0.6495(2) 0.0511(7) Uani 1 1 d . . . H6 H -0.0730 0.2988 0.6983 0.061 Uiso 1 1 calc R . . C7 C 0.1069(3) 0.2004(2) 0.61726(17) 0.0420(6) Uani 1 1 d . . . C8 C 0.2435(3) 0.2000(2) 0.64651(17) 0.0404(6) Uani 1 1 d . . . C9 C 0.3701(3) 0.1235(2) 0.58035(18) 0.0454(7) Uani 1 1 d . . . C10 C 0.2609(3) 0.3245(2) 0.64242(18) 0.0468(7) Uani 1 1 d . . . H10 H 0.3644 0.3164 0.6426 0.056 Uiso 1 1 calc R . . C11 C 0.2169(4) 0.4082(3) 0.56343(19) 0.0549(8) Uani 1 1 d . . . H11 H 0.2690 0.3900 0.5052 0.066 Uiso 1 1 calc R . . C12 C 0.1074(4) 0.5065(3) 0.5729(2) 0.0589(8) Uani 1 1 d . . . H12 H 0.0850 0.5552 0.5211 0.071 Uiso 1 1 calc R . . C13 C 0.0204(3) 0.5417(3) 0.6611(2) 0.0560(8) Uani 1 1 d . . . C14 C -0.0971(4) 0.6449(3) 0.6721(3) 0.0756(10) Uani 1 1 d . . . H14 H -0.1226 0.6932 0.6208 0.091 Uiso 1 1 calc R . . C15 C -0.1768(5) 0.6773(3) 0.7569(3) 0.0880(12) Uani 1 1 d . . . H15 H -0.2543 0.7469 0.7628 0.106 Uiso 1 1 calc R . . C16 C -0.1394(4) 0.6046(3) 0.8329(3) 0.0848(11) Uani 1 1 d . . . H16 H -0.1923 0.6254 0.8904 0.102 Uiso 1 1 calc R . . C17 C -0.0245(4) 0.5015(3) 0.8242(2) 0.0656(9) Uani 1 1 d . . . H17 H 0.0001 0.4542 0.8761 0.079 Uiso 1 1 calc R . . C18 C 0.0550(3) 0.4672(2) 0.7395(2) 0.0509(7) Uani 1 1 d . . . C19 C 0.1853(3) 0.2658(2) 0.79976(17) 0.0438(7) Uani 1 1 d . . . H19 H 0.0884 0.2670 0.8395 0.053 Uiso 1 1 calc R . . C20 C 0.2926(3) 0.2699(3) 0.85599(19) 0.0506(7) Uani 1 1 d . . . C21 C 0.3019(3) 0.1946(2) 0.94364(17) 0.0461(7) Uani 1 1 d . . . C22 C 0.2004(3) 0.1335(3) 0.98535(19) 0.0553(8) Uani 1 1 d . . . H22 H 0.1240 0.1381 0.9575 0.066 Uiso 1 1 calc R . . C23 C 0.2105(4) 0.0658(3) 1.0675(2) 0.0601(8) Uani 1 1 d . . . H23 H 0.1431 0.0238 1.0941 0.072 Uiso 1 1 calc R . . C24 C 0.3217(3) 0.0617(3) 1.10909(19) 0.0541(8) Uani 1 1 d . . . C25 C 0.4254(4) 0.1223(3) 1.0689(2) 0.0614(8) Uani 1 1 d . . . H25 H 0.5013 0.1182 1.0970 0.074 Uiso 1 1 calc R . . C26 C 0.4131(3) 0.1882(3) 0.98703(19) 0.0554(8) Uani 1 1 d . . . H26 H 0.4812 0.2296 0.9601 0.066 Uiso 1 1 calc R . . C27 C 0.2482(3) 0.1539(2) 0.74845(17) 0.0446(7) Uani 1 1 d . . . H27 H 0.3522 0.1166 0.7531 0.054 Uiso 1 1 calc R . . C28 C 0.1642(3) 0.0638(2) 0.78115(18) 0.0469(7) Uani 1 1 d . . . C29 C 0.2282(3) -0.0515(2) 0.74198(19) 0.0502(7) Uani 1 1 d . . . C30 C 0.3810(3) -0.1050(3) 0.7153(2) 0.0579(8) Uani 1 1 d . . . H30 H 0.4478 -0.0683 0.7214 0.069 Uiso 1 1 calc R . . C31 C 0.4341(4) -0.2121(3) 0.6797(2) 0.0672(9) Uani 1 1 d . . . H31 H 0.5361 -0.2477 0.6629 0.081 Uiso 1 1 calc R . . C32 C 0.3358(4) -0.2651(3) 0.6696(3) 0.0724(10) Uani 1 1 d . . . C33 C 0.1847(4) -0.2148(3) 0.6958(3) 0.0725(10) Uani 1 1 d . . . H33 H 0.1190 -0.2527 0.6899 0.087 Uiso 1 1 calc R . . C34 C 0.1314(4) -0.1082(3) 0.7308(2) 0.0628(9) Uani 1 1 d . . . H34 H 0.0292 -0.0735 0.7473 0.075 Uiso 1 1 calc R . . Cl1 Cl 0.33396(11) -0.02047(8) 1.21319(6) 0.0780(3) Uani 1 1 d . . . Cl2 Cl 0.40205(14) -0.39812(10) 0.62405(11) 0.1223(5) Uani 1 1 d . . . N1 N 0.3096(3) 0.0930(2) 0.52208(15) 0.0500(6) Uani 1 1 d . . . H1 H 0.3603 0.0526 0.4774 0.060 Uiso 1 1 calc R . . N2 N 0.1668(3) 0.36259(19) 0.72864(14) 0.0484(6) Uani 1 1 d . . . O1 O 0.5031(2) 0.09691(18) 0.58152(14) 0.0575(6) Uani 1 1 d . . . O2 O 0.0452(3) 0.08654(19) 0.83326(15) 0.0651(6) Uani 1 1 d . . . O3 O 0.3748(3) 0.3320(2) 0.82681(15) 0.0762(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0456(17) 0.0442(16) 0.0507(15) -0.0017(12) -0.0129(13) -0.0143(13) C2 0.071(2) 0.0562(19) 0.0634(18) -0.0064(15) -0.0286(17) -0.0228(17) C3 0.063(2) 0.062(2) 0.091(2) 0.0033(18) -0.0396(19) -0.0250(18) C4 0.0425(18) 0.0542(18) 0.079(2) 0.0086(16) -0.0186(16) -0.0169(15) C5 0.046(2) 0.086(3) 0.120(3) 0.004(2) -0.021(2) -0.0145(19) C6 0.0461(18) 0.0464(16) 0.0603(17) -0.0039(13) -0.0116(14) -0.0135(14) C7 0.0391(16) 0.0418(15) 0.0455(14) -0.0055(12) -0.0073(12) -0.0133(12) C8 0.0357(15) 0.0460(15) 0.0413(14) -0.0111(11) -0.0032(11) -0.0148(12) C9 0.0383(17) 0.0497(16) 0.0453(15) -0.0094(12) -0.0022(12) -0.0120(13) C10 0.0460(17) 0.0503(17) 0.0460(15) -0.0114(12) -0.0046(13) -0.0174(14) C11 0.070(2) 0.0577(19) 0.0417(15) -0.0055(13) -0.0035(14) -0.0318(18) C12 0.076(2) 0.0495(18) 0.0607(19) 0.0046(15) -0.0242(17) -0.0289(18) C13 0.0551(19) 0.0460(17) 0.072(2) -0.0015(15) -0.0200(16) -0.0193(15) C14 0.078(3) 0.049(2) 0.101(3) 0.0003(19) -0.038(2) -0.0106(18) C15 0.067(3) 0.060(2) 0.118(3) -0.021(2) -0.013(2) 0.0065(19) C16 0.073(3) 0.070(2) 0.097(3) -0.032(2) -0.004(2) -0.001(2) C17 0.070(2) 0.0545(19) 0.0613(19) -0.0192(15) -0.0071(17) -0.0024(17) C18 0.0479(18) 0.0415(16) 0.0651(18) -0.0143(13) -0.0158(15) -0.0080(14) C19 0.0432(16) 0.0442(15) 0.0418(14) -0.0072(12) -0.0038(12) -0.0125(13) C20 0.0544(19) 0.0493(17) 0.0486(16) -0.0116(13) -0.0096(14) -0.0138(15) C21 0.0455(17) 0.0479(16) 0.0423(14) -0.0136(12) -0.0045(13) -0.0093(13) C22 0.0465(18) 0.071(2) 0.0516(17) -0.0065(15) -0.0111(14) -0.0215(16) C23 0.058(2) 0.071(2) 0.0523(17) -0.0057(15) -0.0037(15) -0.0271(17) C24 0.0500(18) 0.0583(18) 0.0470(16) -0.0030(14) -0.0093(14) -0.0089(15) C25 0.056(2) 0.070(2) 0.0588(18) -0.0035(16) -0.0223(16) -0.0141(17) C26 0.0539(19) 0.0590(19) 0.0535(17) -0.0099(14) -0.0074(14) -0.0178(15) C27 0.0403(16) 0.0434(15) 0.0484(15) -0.0078(12) -0.0110(12) -0.0074(13) C28 0.0456(18) 0.0476(16) 0.0455(15) -0.0028(12) -0.0101(14) -0.0120(14) C29 0.0566(19) 0.0431(16) 0.0533(16) -0.0016(13) -0.0167(14) -0.0156(14) C30 0.053(2) 0.0495(18) 0.074(2) -0.0070(15) -0.0176(16) -0.0151(15) C31 0.058(2) 0.0459(18) 0.097(3) -0.0118(17) -0.0218(19) -0.0072(16) C32 0.080(3) 0.054(2) 0.090(2) -0.0188(18) -0.021(2) -0.0212(19) C33 0.070(2) 0.063(2) 0.095(3) -0.0290(19) -0.017(2) -0.0224(19) C34 0.055(2) 0.069(2) 0.070(2) -0.0150(17) -0.0107(16) -0.0242(17) Cl1 0.0798(7) 0.0853(7) 0.0621(5) 0.0125(4) -0.0231(4) -0.0196(5) Cl2 0.1076(10) 0.0765(7) 0.1915(14) -0.0688(8) -0.0177(9) -0.0215(7) N1 0.0475(15) 0.0565(15) 0.0461(12) -0.0200(11) -0.0025(11) -0.0137(12) N2 0.0523(15) 0.0468(14) 0.0399(12) -0.0094(10) -0.0066(11) -0.0064(12) O1 0.0400(13) 0.0653(13) 0.0675(13) -0.0253(10) -0.0033(10) -0.0126(10) O2 0.0634(15) 0.0684(14) 0.0641(13) -0.0158(11) 0.0038(12) -0.0289(12) O3 0.0974(19) 0.0834(17) 0.0702(14) 0.0119(12) -0.0334(13) -0.0548(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.384(4) . ? C1 C7 1.390(4) . ? C1 N1 1.406(4) . ? C2 C3 1.382(5) . ? C2 H2 0.9300 . ? C3 C4 1.394(5) . ? C3 H3 0.9300 . ? C4 C6 1.402(4) . ? C4 C5 1.479(5) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.384(4) . ? C6 H6 0.9300 . ? C7 C8 1.506(4) . ? C8 C9 1.533(4) . ? C8 C10 1.564(4) . ? C8 C27 1.570(3) . ? C9 O1 1.230(3) . ? C9 N1 1.344(3) . ? C10 N2 1.454(3) . ? C10 C11 1.492(4) . ? C10 H10 0.9800 . ? C11 C12 1.315(4) . ? C11 H11 0.9300 . ? C12 C13 1.451(4) . ? C12 H12 0.9300 . ? C13 C14 1.393(4) . ? C13 C18 1.414(4) . ? C14 C15 1.381(5) . ? C14 H14 0.9300 . ? C15 C16 1.382(6) . ? C15 H15 0.9300 . ? C16 C17 1.378(5) . ? C16 H16 0.9300 . ? C17 C18 1.385(4) . ? C17 H17 0.9300 . ? C18 N2 1.379(3) . ? C19 N2 1.453(3) . ? C19 C20 1.532(4) . ? C19 C27 1.556(4) . ? C19 H19 0.9800 . ? C20 O3 1.225(4) . ? C20 C21 1.491(4) . ? C21 C26 1.384(4) . ? C21 C22 1.386(4) . ? C22 C23 1.383(4) . ? C22 H22 0.9300 . ? C23 C24 1.374(4) . ? C23 H23 0.9300 . ? C24 C25 1.395(5) . ? C24 Cl1 1.735(3) . ? C25 C26 1.374(4) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.515(4) . ? C27 H27 0.9800 . ? C28 O2 1.204(3) . ? C28 C29 1.496(4) . ? C29 C34 1.391(4) . ? C29 C30 1.396(4) . ? C30 C31 1.384(4) . ? C30 H30 0.9300 . ? C31 C32 1.366(5) . ? C31 H31 0.9300 . ? C32 C33 1.375(5) . ? C32 Cl2 1.730(3) . ? C33 C34 1.376(4) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? N1 H1 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C7 120.8(3) . . ? C2 C1 N1 129.5(3) . . ? C7 C1 N1 109.7(2) . . ? C3 C2 C1 118.0(3) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 122.8(3) . . ? C2 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? C3 C4 C6 118.0(3) . . ? C3 C4 C5 120.7(3) . . ? C6 C4 C5 121.2(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C4 119.8(3) . . ? C7 C6 H6 120.1 . . ? C4 C6 H6 120.1 . . ? C6 C7 C1 120.6(3) . . ? C6 C7 C8 131.5(2) . . ? C1 C7 C8 107.9(2) . . ? C7 C8 C9 102.7(2) . . ? C7 C8 C10 114.2(2) . . ? C9 C8 C10 111.9(2) . . ? C7 C8 C27 115.3(2) . . ? C9 C8 C27 112.5(2) . . ? C10 C8 C27 100.69(19) . . ? O1 C9 N1 127.3(3) . . ? O1 C9 C8 124.8(2) . . ? N1 C9 C8 107.9(2) . . ? N2 C10 C11 112.5(2) . . ? N2 C10 C8 101.4(2) . . ? C11 C10 C8 115.5(2) . . ? N2 C10 H10 109.0 . . ? C11 C10 H10 109.0 . . ? C8 C10 H10 109.0 . . ? C12 C11 C10 122.6(3) . . ? C12 C11 H11 118.7 . . ? C10 C11 H11 118.7 . . ? C11 C12 C13 122.4(3) . . ? C11 C12 H12 118.8 . . ? C13 C12 H12 118.8 . . ? C14 C13 C18 118.4(3) . . ? C14 C13 C12 123.0(3) . . ? C18 C13 C12 118.6(3) . . ? C15 C14 C13 121.9(3) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C14 C15 C16 118.8(3) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C17 C16 C15 120.6(4) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 121.1(3) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? N2 C18 C17 122.4(3) . . ? N2 C18 C13 118.5(3) . . ? C17 C18 C13 119.1(3) . . ? N2 C19 C20 111.9(2) . . ? N2 C19 C27 104.6(2) . . ? C20 C19 C27 110.8(2) . . ? N2 C19 H19 109.8 . . ? C20 C19 H19 109.8 . . ? C27 C19 H19 109.8 . . ? O3 C20 C21 120.2(3) . . ? O3 C20 C19 119.6(3) . . ? C21 C20 C19 120.1(3) . . ? C26 C21 C22 118.4(3) . . ? C26 C21 C20 118.9(3) . . ? C22 C21 C20 122.7(3) . . ? C23 C22 C21 121.4(3) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C24 C23 C22 118.9(3) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? C23 C24 C25 121.1(3) . . ? C23 C24 Cl1 119.6(2) . . ? C25 C24 Cl1 119.4(2) . . ? C26 C25 C24 118.7(3) . . ? C26 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? C25 C26 C21 121.6(3) . . ? C25 C26 H26 119.2 . . ? C21 C26 H26 119.2 . . ? C28 C27 C19 115.4(2) . . ? C28 C27 C8 110.1(2) . . ? C19 C27 C8 104.98(19) . . ? C28 C27 H27 108.7 . . ? C19 C27 H27 108.7 . . ? C8 C27 H27 108.7 . . ? O2 C28 C29 120.7(3) . . ? O2 C28 C27 121.0(3) . . ? C29 C28 C27 118.2(3) . . ? C34 C29 C30 118.1(3) . . ? C34 C29 C28 118.8(3) . . ? C30 C29 C28 123.1(3) . . ? C31 C30 C29 120.7(3) . . ? C31 C30 H30 119.7 . . ? C29 C30 H30 119.7 . . ? C32 C31 C30 119.6(3) . . ? C32 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? C31 C32 C33 121.0(3) . . ? C31 C32 Cl2 119.6(3) . . ? C33 C32 Cl2 119.4(3) . . ? C32 C33 C34 119.6(3) . . ? C32 C33 H33 120.2 . . ? C34 C33 H33 120.2 . . ? C33 C34 C29 121.0(3) . . ? C33 C34 H34 119.5 . . ? C29 C34 H34 119.5 . . ? C9 N1 C1 111.7(2) . . ? C9 N1 H1 124.1 . . ? C1 N1 H1 124.1 . . ? C18 N2 C19 123.3(2) . . ? C18 N2 C10 125.3(2) . . ? C19 N2 C10 110.3(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.86 2.06 2.864(3) 154.9 2_656 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.222 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.057 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.500 1.000 337 33 ' ' _platon_squeeze_details ; ; data_2d _database_code_depnum_ccdc_archive 'CCDC 896148' #TrackingRef 'cgyan-wl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H25 F N2 O3 ' _chemical_formula_sum 'C34 H25 F N2 O3 ' _chemical_formula_weight 528.56 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' F F 0.0171 0.0103 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.5214(14) _cell_length_b 9.2191(12) _cell_length_c 32.976(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.588(4) _cell_angle_gamma 90.00 _cell_volume 3049.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3809 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 20.74 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 0.9830 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 26244 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.63 _reflns_number_total 7088 _reflns_number_gt 3611 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1016P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7040 _refine_ls_number_parameters 362 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.2059 _refine_ls_wR_factor_gt 0.1838 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5427(2) -0.0658(2) 0.86110(6) 0.0582(6) Uani 1 1 d . . . H1 H 0.5952 -0.1553 0.8650 0.070 Uiso 1 1 calc R . . C2 C 0.4496(3) -0.0754(3) 0.88821(8) 0.0691(7) Uani 1 1 d . . . C3 C 0.5022(3) -0.1179(3) 0.93041(9) 0.0905(9) Uani 1 1 d . . . H3 H 0.5915 -0.1444 0.9408 0.109 Uiso 1 1 calc R . . C4 C 0.4240(5) -0.1212(4) 0.95664(12) 0.1178(13) Uani 1 1 d . . . H4 H 0.4591 -0.1523 0.9846 0.141 Uiso 1 1 calc R . . C5 C 0.2927(5) -0.0784(4) 0.94155(16) 0.1186(13) Uani 1 1 d . . . H5 H 0.2404 -0.0760 0.9598 0.142 Uiso 1 1 calc R . . C6 C 0.2385(4) -0.0393(4) 0.89962(15) 0.1089(11) Uani 1 1 d . . . H6 H 0.1491 -0.0129 0.8896 0.131 Uiso 1 1 calc R . . C7 C 0.3165(3) -0.0386(3) 0.87172(10) 0.0819(8) Uani 1 1 d . . . C8 C 0.2655(3) 0.0026(4) 0.82704(11) 0.0982(10) Uani 1 1 d . . . H8 H 0.1776 0.0333 0.8160 0.118 Uiso 1 1 calc R . . C9 C 0.3426(3) -0.0033(3) 0.80217(9) 0.0806(8) Uani 1 1 d . . . H9 H 0.3068 0.0247 0.7739 0.097 Uiso 1 1 calc R . . C10 C 0.5681(2) -0.0021(2) 0.79485(6) 0.0580(6) Uani 1 1 d . . . H10 H 0.5241 0.0605 0.7707 0.070 Uiso 1 1 calc R . . C11 C 0.6382(2) -0.1260(3) 0.77997(6) 0.0620(6) Uani 1 1 d . . . C12 C 0.7311(3) -0.0865(3) 0.75558(7) 0.0667(6) Uani 1 1 d . . . C13 C 0.8390(3) -0.1755(3) 0.75781(10) 0.0896(8) Uani 1 1 d . . . H13 H 0.8502 -0.2603 0.7737 0.107 Uiso 1 1 calc R . . C14 C 0.9291(4) -0.1410(5) 0.73708(14) 0.1189(12) Uani 1 1 d . . . H14 H 1.0010 -0.2022 0.7391 0.143 Uiso 1 1 calc R . . C15 C 0.9146(5) -0.0174(5) 0.71340(12) 0.1182(12) Uani 1 1 d . . . H15 H 0.9764 0.0056 0.6993 0.142 Uiso 1 1 calc R . . C16 C 0.8062(5) 0.0746(4) 0.71034(10) 0.1108(11) Uani 1 1 d . . . H16 H 0.7959 0.1592 0.6943 0.133 Uiso 1 1 calc R . . C17 C 0.7143(3) 0.0392(3) 0.73135(8) 0.0828(8) Uani 1 1 d . . . H17 H 0.6416 0.0995 0.7292 0.099 Uiso 1 1 calc R . . C18 C 0.6760(2) 0.0865(2) 0.82873(6) 0.0515(5) Uani 1 1 d . . . H18 H 0.7632 0.0422 0.8319 0.062 Uiso 1 1 calc R . . C19 C 0.6836(2) 0.2463(2) 0.81759(6) 0.0589(6) Uani 1 1 d . . . C20 C 0.8005(2) 0.3320(2) 0.84273(6) 0.0575(6) Uani 1 1 d . . . C21 C 0.7841(3) 0.4798(3) 0.84778(8) 0.0771(7) Uani 1 1 d . . . H21 H 0.7016 0.5229 0.8353 0.093 Uiso 1 1 calc R . . C22 C 0.8888(4) 0.5620(3) 0.87106(10) 0.0919(9) Uani 1 1 d . . . H22 H 0.8754 0.6603 0.8746 0.110 Uiso 1 1 calc R . . C23 C 1.0135(4) 0.5039(3) 0.88946(9) 0.0860(9) Uani 1 1 d . . . C24 C 1.1294(4) 0.5975(4) 0.91457(14) 0.1349(15) Uani 1 1 d . . . H24A H 1.2083 0.5390 0.9242 0.202 Uiso 1 1 calc R . . H24B H 1.1092 0.6388 0.9386 0.202 Uiso 1 1 calc R . . H24C H 1.1441 0.6739 0.8967 0.202 Uiso 1 1 calc R . . C25 C 1.0311(3) 0.3583(3) 0.88379(9) 0.0827(8) Uani 1 1 d . . . H25 H 1.1151 0.3173 0.8954 0.099 Uiso 1 1 calc R . . C26 C 0.9254(2) 0.2710(3) 0.86102(8) 0.0697(6) Uani 1 1 d . . . H26 H 0.9386 0.1723 0.8581 0.084 Uiso 1 1 calc R . . C27 C 0.6429(2) 0.0679(2) 0.87154(6) 0.0517(5) Uani 1 1 d . . . C28 C 0.7688(2) 0.0288(2) 0.90806(6) 0.0544(5) Uani 1 1 d . . . C29 C 0.6755(2) 0.2249(3) 0.93021(7) 0.0614(6) Uani 1 1 d . . . C30 C 0.6568(3) 0.3375(3) 0.95484(8) 0.0848(8) Uani 1 1 d . . . H30 H 0.7136 0.3520 0.9822 0.102 Uiso 1 1 calc R . . C31 C 0.5504(4) 0.4286(3) 0.93741(11) 0.0997(10) Uani 1 1 d . . . H31 H 0.5335 0.5059 0.9532 0.120 Uiso 1 1 calc R . . C32 C 0.4703(3) 0.4049(3) 0.89709(10) 0.0922(9) Uani 1 1 d . . . C33 C 0.4871(2) 0.2931(3) 0.87171(8) 0.0724(7) Uani 1 1 d . . . H33 H 0.4298 0.2803 0.8443 0.087 Uiso 1 1 calc R . . C34 C 0.5935(2) 0.2002(2) 0.88888(6) 0.0562(5) Uani 1 1 d . . . F1 F 0.3681(2) 0.5001(3) 0.88008(7) 0.1469(9) Uani 1 1 d . . . N1 N 0.47281(18) -0.0484(2) 0.81562(5) 0.0630(5) Uani 1 1 d . . . N2 N 0.77700(19) 0.1197(2) 0.94068(5) 0.0642(5) Uani 1 1 d . . . H2 H 0.8371 0.1140 0.9650 0.077 Uiso 1 1 d R . . O1 O 0.62668(17) -0.25158(18) 0.79065(5) 0.0770(5) Uani 1 1 d . . . O2 O 0.59325(19) 0.30406(19) 0.79037(5) 0.0858(6) Uani 1 1 d . . . O3 O 0.84515(16) -0.07059(18) 0.90778(5) 0.0694(5) 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 0.0608(13) 0.0572(13) 0.0463(11) -0.0025(9) 0.0007(10) -0.0041(10) C2 0.0822(18) 0.0598(14) 0.0636(14) -0.0066(11) 0.0196(13) -0.0187(13) C3 0.110(2) 0.095(2) 0.0683(16) 0.0016(14) 0.0300(16) -0.0350(17) C4 0.166(4) 0.117(3) 0.083(2) -0.0182(19) 0.056(3) -0.066(3) C5 0.149(4) 0.107(3) 0.125(3) -0.025(2) 0.081(3) -0.048(3) C6 0.108(3) 0.082(2) 0.155(4) -0.009(2) 0.067(3) -0.0168(18) C7 0.085(2) 0.0683(17) 0.097(2) -0.0043(14) 0.0352(17) -0.0049(14) C8 0.0619(17) 0.111(2) 0.114(3) 0.014(2) 0.0138(18) 0.0061(16) C9 0.0628(16) 0.0910(19) 0.0728(16) 0.0093(14) -0.0024(14) -0.0014(14) C10 0.0645(13) 0.0577(13) 0.0406(10) 0.0026(9) -0.0012(9) -0.0026(11) C11 0.0706(15) 0.0580(14) 0.0428(11) -0.0067(10) -0.0047(10) -0.0009(12) C12 0.0797(16) 0.0639(15) 0.0507(12) -0.0134(11) 0.0110(11) -0.0045(13) C13 0.096(2) 0.085(2) 0.0846(19) -0.0123(15) 0.0228(17) -0.0003(17) C14 0.109(3) 0.133(3) 0.124(3) -0.022(3) 0.048(2) 0.001(2) C15 0.138(3) 0.130(3) 0.101(3) -0.024(2) 0.057(2) -0.027(3) C16 0.155(3) 0.102(3) 0.082(2) -0.0062(17) 0.045(2) -0.027(3) C17 0.106(2) 0.0791(18) 0.0645(15) -0.0041(13) 0.0268(15) -0.0033(16) C18 0.0572(12) 0.0491(12) 0.0383(10) -0.0017(8) -0.0006(9) 0.0015(9) C19 0.0741(14) 0.0541(13) 0.0405(10) 0.0063(9) 0.0052(10) 0.0049(11) C20 0.0814(16) 0.0467(12) 0.0441(11) 0.0012(9) 0.0183(11) -0.0031(11) C21 0.105(2) 0.0528(14) 0.0752(16) -0.0003(12) 0.0303(15) 0.0000(14) C22 0.137(3) 0.0500(16) 0.099(2) -0.0145(14) 0.051(2) -0.0224(18) C23 0.111(2) 0.078(2) 0.0792(18) -0.0292(15) 0.0446(17) -0.0404(18) C24 0.144(3) 0.126(3) 0.143(3) -0.062(2) 0.057(3) -0.077(3) C25 0.0791(17) 0.0839(19) 0.0825(18) -0.0125(15) 0.0205(14) -0.0195(15) C26 0.0741(16) 0.0591(14) 0.0711(15) -0.0032(11) 0.0146(12) -0.0089(13) C27 0.0575(12) 0.0499(12) 0.0383(10) 0.0013(8) 0.0002(9) -0.0008(10) C28 0.0619(13) 0.0517(12) 0.0413(10) 0.0047(9) 0.0032(9) -0.0016(11) C29 0.0707(14) 0.0625(14) 0.0465(11) -0.0046(10) 0.0111(10) -0.0061(12) C30 0.105(2) 0.0835(19) 0.0583(14) -0.0197(13) 0.0129(14) -0.0011(17) C31 0.125(3) 0.085(2) 0.091(2) -0.0207(16) 0.035(2) 0.025(2) C32 0.099(2) 0.083(2) 0.0860(19) -0.0086(15) 0.0148(16) 0.0334(17) C33 0.0714(15) 0.0732(16) 0.0632(14) -0.0050(12) 0.0061(12) 0.0105(13) C34 0.0601(13) 0.0555(13) 0.0455(11) -0.0016(9) 0.0047(9) -0.0022(11) F1 0.1429(17) 0.1416(18) 0.1374(17) -0.0238(14) 0.0141(14) 0.0809(15) N1 0.0572(11) 0.0691(12) 0.0493(10) -0.0015(8) -0.0039(8) -0.0039(10) N2 0.0745(12) 0.0626(12) 0.0394(9) -0.0009(8) -0.0070(8) -0.0007(10) O1 0.0987(13) 0.0562(10) 0.0654(10) -0.0001(8) 0.0088(9) -0.0035(9) O2 0.1106(14) 0.0656(10) 0.0574(10) 0.0112(8) -0.0106(9) 0.0100(10) O3 0.0736(10) 0.0679(11) 0.0524(9) 0.0057(7) -0.0025(7) 0.0121(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.466(3) . ? C1 C2 1.516(3) . ? C1 C27 1.590(3) . ? C1 H1 0.9800 . ? C2 C7 1.382(4) . ? C2 C3 1.390(4) . ? C3 C4 1.363(5) . ? C3 H3 0.9300 . ? C4 C5 1.377(6) . ? C4 H4 0.9300 . ? C5 C6 1.375(5) . ? C5 H5 0.9300 . ? C6 C7 1.406(5) . ? C6 H6 0.9300 . ? C7 C8 1.458(4) . ? C8 C9 1.318(4) . ? C8 H8 0.9300 . ? C9 N1 1.370(3) . ? C9 H9 0.9300 . ? C10 N1 1.439(3) . ? C10 C11 1.519(3) . ? C10 C18 1.562(3) . ? C10 H10 0.9800 . ? C11 O1 1.227(3) . ? C11 C12 1.487(4) . ? C12 C13 1.384(4) . ? C12 C17 1.388(4) . ? C13 C14 1.363(5) . ? C13 H13 0.9300 . ? C14 C15 1.363(6) . ? C14 H14 0.9300 . ? C15 C16 1.400(5) . ? C15 H15 0.9300 . ? C16 C17 1.388(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.526(3) . ? C18 C27 1.562(3) . ? C18 H18 0.9800 . ? C19 O2 1.215(2) . ? C19 C20 1.486(3) . ? C20 C26 1.388(3) . ? C20 C21 1.390(3) . ? C21 C22 1.365(4) . ? C21 H21 0.9300 . ? C22 C23 1.377(4) . ? C22 H22 0.9300 . ? C23 C25 1.375(4) . ? C23 C24 1.519(4) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.394(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C34 1.505(3) . ? C27 C28 1.540(3) . ? C28 O3 1.220(3) . ? C28 N2 1.345(3) . ? C29 C30 1.368(3) . ? C29 C34 1.394(3) . ? C29 N2 1.406(3) . ? C30 C31 1.379(4) . ? C30 H30 0.9300 . ? C31 C32 1.360(4) . ? C31 H31 0.9300 . ? C32 F1 1.370(3) . ? C32 C33 1.372(4) . ? C33 C34 1.388(3) . ? C33 H33 0.9300 . ? N2 H2 0.8599 . ? 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 113.32(18) . . ? N1 C1 C27 103.39(16) . . ? C2 C1 C27 114.96(17) . . ? N1 C1 H1 108.3 . . ? C2 C1 H1 108.3 . . ? C27 C1 H1 108.3 . . ? C7 C2 C3 120.9(3) . . ? C7 C2 C1 120.8(2) . . ? C3 C2 C1 118.3(2) . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.8(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.3(4) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.8(4) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C2 C7 C6 117.6(3) . . ? C2 C7 C8 118.8(3) . . ? C6 C7 C8 123.5(3) . . ? C9 C8 C7 120.7(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 N1 123.7(3) . . ? C8 C9 H9 118.2 . . ? N1 C9 H9 118.2 . . ? N1 C10 C11 114.02(19) . . ? N1 C10 C18 105.97(17) . . ? C11 C10 C18 107.78(17) . . ? N1 C10 H10 109.6 . . ? C11 C10 H10 109.6 . . ? C18 C10 H10 109.6 . . ? O1 C11 C12 121.6(2) . . ? O1 C11 C10 121.1(2) . . ? C12 C11 C10 117.0(2) . . ? C13 C12 C17 119.0(3) . . ? C13 C12 C11 119.3(2) . . ? C17 C12 C11 121.7(2) . . ? C14 C13 C12 121.2(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C13 120.5(4) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.7(4) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 119.8(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C12 119.8(3) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? C19 C18 C10 114.36(16) . . ? C19 C18 C27 111.46(16) . . ? C10 C18 C27 106.02(17) . . ? C19 C18 H18 108.3 . . ? C10 C18 H18 108.3 . . ? C27 C18 H18 108.3 . . ? O2 C19 C20 120.7(2) . . ? O2 C19 C18 121.0(2) . . ? C20 C19 C18 118.25(17) . . ? C26 C20 C21 118.7(2) . . ? C26 C20 C19 122.9(2) . . ? C21 C20 C19 118.4(2) . . ? C22 C21 C20 120.2(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 122.1(3) . . ? C21 C22 H22 119.0 . . ? C23 C22 H22 119.0 . . ? C25 C23 C22 118.0(3) . . ? C25 C23 C24 120.6(4) . . ? C22 C23 C24 121.4(3) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 C26 121.2(3) . . ? C23 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C20 C26 C25 119.8(2) . . ? C20 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C34 C27 C28 101.92(16) . . ? C34 C27 C18 116.81(16) . . ? C28 C27 C18 110.99(17) . . ? C34 C27 C1 115.34(18) . . ? C28 C27 C1 110.22(16) . . ? C18 C27 C1 101.78(15) . . ? O3 C28 N2 126.18(19) . . ? O3 C28 C27 125.61(19) . . ? N2 C28 C27 108.17(19) . . ? C30 C29 C34 123.2(2) . . ? C30 C29 N2 127.8(2) . . ? C34 C29 N2 109.07(19) . . ? C29 C30 C31 117.3(2) . . ? C29 C30 H30 121.3 . . ? C31 C30 H30 121.3 . . ? C32 C31 C30 119.7(3) . . ? C32 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? C31 C32 F1 118.4(3) . . ? C31 C32 C33 124.1(3) . . ? F1 C32 C33 117.5(3) . . ? C32 C33 C34 116.8(2) . . ? C32 C33 H33 121.6 . . ? C34 C33 H33 121.6 . . ? C33 C34 C29 118.9(2) . . ? C33 C34 C27 132.40(18) . . ? C29 C34 C27 108.74(18) . . ? C9 N1 C10 121.9(2) . . ? C9 N1 C1 120.5(2) . . ? C10 N1 C1 108.24(16) . . ? C28 N2 C29 111.90(17) . . ? C28 N2 H2 124.0 . . ? C29 N2 H2 124.1 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.498 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.042 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.500 192 36 ' ' 2 1.000 0.500 1.000 192 36 ' ' _platon_squeeze_details ; ; data_2n _database_code_depnum_ccdc_archive 'CCDC 896149' #TrackingRef 'cgyan-wl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H25 F N2 O3 ' _chemical_formula_sum 'C34 H25 F N2 O3 ' _chemical_formula_weight 528.56 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' F F 0.0171 0.0103 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.5214(14) _cell_length_b 9.2191(12) _cell_length_c 32.976(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.588(4) _cell_angle_gamma 90.00 _cell_volume 3049.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3809 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 20.74 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 0.9830 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 26244 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.63 _reflns_number_total 7088 _reflns_number_gt 3611 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1016P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7040 _refine_ls_number_parameters 362 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.2059 _refine_ls_wR_factor_gt 0.1838 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5427(2) -0.0658(2) 0.86110(6) 0.0582(6) Uani 1 1 d . . . H1 H 0.5952 -0.1553 0.8650 0.070 Uiso 1 1 calc R . . C2 C 0.4496(3) -0.0754(3) 0.88821(8) 0.0691(7) Uani 1 1 d . . . C3 C 0.5022(3) -0.1179(3) 0.93041(9) 0.0905(9) Uani 1 1 d . . . H3 H 0.5915 -0.1444 0.9408 0.109 Uiso 1 1 calc R . . C4 C 0.4240(5) -0.1212(4) 0.95664(12) 0.1178(13) Uani 1 1 d . . . H4 H 0.4591 -0.1523 0.9846 0.141 Uiso 1 1 calc R . . C5 C 0.2927(5) -0.0784(4) 0.94155(16) 0.1186(13) Uani 1 1 d . . . H5 H 0.2404 -0.0760 0.9598 0.142 Uiso 1 1 calc R . . C6 C 0.2385(4) -0.0393(4) 0.89962(15) 0.1089(11) Uani 1 1 d . . . H6 H 0.1491 -0.0129 0.8896 0.131 Uiso 1 1 calc R . . C7 C 0.3165(3) -0.0386(3) 0.87172(10) 0.0819(8) Uani 1 1 d . . . C8 C 0.2655(3) 0.0026(4) 0.82704(11) 0.0982(10) Uani 1 1 d . . . H8 H 0.1776 0.0333 0.8160 0.118 Uiso 1 1 calc R . . C9 C 0.3426(3) -0.0033(3) 0.80217(9) 0.0806(8) Uani 1 1 d . . . H9 H 0.3068 0.0247 0.7739 0.097 Uiso 1 1 calc R . . C10 C 0.5681(2) -0.0021(2) 0.79485(6) 0.0580(6) Uani 1 1 d . . . H10 H 0.5241 0.0605 0.7707 0.070 Uiso 1 1 calc R . . C11 C 0.6382(2) -0.1260(3) 0.77997(6) 0.0620(6) Uani 1 1 d . . . C12 C 0.7311(3) -0.0865(3) 0.75558(7) 0.0667(6) Uani 1 1 d . . . C13 C 0.8390(3) -0.1755(3) 0.75781(10) 0.0896(8) Uani 1 1 d . . . H13 H 0.8502 -0.2603 0.7737 0.107 Uiso 1 1 calc R . . C14 C 0.9291(4) -0.1410(5) 0.73708(14) 0.1189(12) Uani 1 1 d . . . H14 H 1.0010 -0.2022 0.7391 0.143 Uiso 1 1 calc R . . C15 C 0.9146(5) -0.0174(5) 0.71340(12) 0.1182(12) Uani 1 1 d . . . H15 H 0.9764 0.0056 0.6993 0.142 Uiso 1 1 calc R . . C16 C 0.8062(5) 0.0746(4) 0.71034(10) 0.1108(11) Uani 1 1 d . . . H16 H 0.7959 0.1592 0.6943 0.133 Uiso 1 1 calc R . . C17 C 0.7143(3) 0.0392(3) 0.73135(8) 0.0828(8) Uani 1 1 d . . . H17 H 0.6416 0.0995 0.7292 0.099 Uiso 1 1 calc R . . C18 C 0.6760(2) 0.0865(2) 0.82873(6) 0.0515(5) Uani 1 1 d . . . H18 H 0.7632 0.0422 0.8319 0.062 Uiso 1 1 calc R . . C19 C 0.6836(2) 0.2463(2) 0.81759(6) 0.0589(6) Uani 1 1 d . . . C20 C 0.8005(2) 0.3320(2) 0.84273(6) 0.0575(6) Uani 1 1 d . . . C21 C 0.7841(3) 0.4798(3) 0.84778(8) 0.0771(7) Uani 1 1 d . . . H21 H 0.7016 0.5229 0.8353 0.093 Uiso 1 1 calc R . . C22 C 0.8888(4) 0.5620(3) 0.87106(10) 0.0919(9) Uani 1 1 d . . . H22 H 0.8754 0.6603 0.8746 0.110 Uiso 1 1 calc R . . C23 C 1.0135(4) 0.5039(3) 0.88946(9) 0.0860(9) Uani 1 1 d . . . C24 C 1.1294(4) 0.5975(4) 0.91457(14) 0.1349(15) Uani 1 1 d . . . H24A H 1.2083 0.5390 0.9242 0.202 Uiso 1 1 calc R . . H24B H 1.1092 0.6388 0.9386 0.202 Uiso 1 1 calc R . . H24C H 1.1441 0.6739 0.8967 0.202 Uiso 1 1 calc R . . C25 C 1.0311(3) 0.3583(3) 0.88379(9) 0.0827(8) Uani 1 1 d . . . H25 H 1.1151 0.3173 0.8954 0.099 Uiso 1 1 calc R . . C26 C 0.9254(2) 0.2710(3) 0.86102(8) 0.0697(6) Uani 1 1 d . . . H26 H 0.9386 0.1723 0.8581 0.084 Uiso 1 1 calc R . . C27 C 0.6429(2) 0.0679(2) 0.87154(6) 0.0517(5) Uani 1 1 d . . . C28 C 0.7688(2) 0.0288(2) 0.90806(6) 0.0544(5) Uani 1 1 d . . . C29 C 0.6755(2) 0.2249(3) 0.93021(7) 0.0614(6) Uani 1 1 d . . . C30 C 0.6568(3) 0.3375(3) 0.95484(8) 0.0848(8) Uani 1 1 d . . . H30 H 0.7136 0.3520 0.9822 0.102 Uiso 1 1 calc R . . C31 C 0.5504(4) 0.4286(3) 0.93741(11) 0.0997(10) Uani 1 1 d . . . H31 H 0.5335 0.5059 0.9532 0.120 Uiso 1 1 calc R . . C32 C 0.4703(3) 0.4049(3) 0.89709(10) 0.0922(9) Uani 1 1 d . . . C33 C 0.4871(2) 0.2931(3) 0.87171(8) 0.0724(7) Uani 1 1 d . . . H33 H 0.4298 0.2803 0.8443 0.087 Uiso 1 1 calc R . . C34 C 0.5935(2) 0.2002(2) 0.88888(6) 0.0562(5) Uani 1 1 d . . . F1 F 0.3681(2) 0.5001(3) 0.88008(7) 0.1469(9) Uani 1 1 d . . . N1 N 0.47281(18) -0.0484(2) 0.81562(5) 0.0630(5) Uani 1 1 d . . . N2 N 0.77700(19) 0.1197(2) 0.94068(5) 0.0642(5) Uani 1 1 d . . . H2 H 0.8371 0.1140 0.9650 0.077 Uiso 1 1 d R . . O1 O 0.62668(17) -0.25158(18) 0.79065(5) 0.0770(5) Uani 1 1 d . . . O2 O 0.59325(19) 0.30406(19) 0.79037(5) 0.0858(6) Uani 1 1 d . . . O3 O 0.84515(16) -0.07059(18) 0.90778(5) 0.0694(5) 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 0.0608(13) 0.0572(13) 0.0463(11) -0.0025(9) 0.0007(10) -0.0041(10) C2 0.0822(18) 0.0598(14) 0.0636(14) -0.0066(11) 0.0196(13) -0.0187(13) C3 0.110(2) 0.095(2) 0.0683(16) 0.0016(14) 0.0300(16) -0.0350(17) C4 0.166(4) 0.117(3) 0.083(2) -0.0182(19) 0.056(3) -0.066(3) C5 0.149(4) 0.107(3) 0.125(3) -0.025(2) 0.081(3) -0.048(3) C6 0.108(3) 0.082(2) 0.155(4) -0.009(2) 0.067(3) -0.0168(18) C7 0.085(2) 0.0683(17) 0.097(2) -0.0043(14) 0.0352(17) -0.0049(14) C8 0.0619(17) 0.111(2) 0.114(3) 0.014(2) 0.0138(18) 0.0061(16) C9 0.0628(16) 0.0910(19) 0.0728(16) 0.0093(14) -0.0024(14) -0.0014(14) C10 0.0645(13) 0.0577(13) 0.0406(10) 0.0026(9) -0.0012(9) -0.0026(11) C11 0.0706(15) 0.0580(14) 0.0428(11) -0.0067(10) -0.0047(10) -0.0009(12) C12 0.0797(16) 0.0639(15) 0.0507(12) -0.0134(11) 0.0110(11) -0.0045(13) C13 0.096(2) 0.085(2) 0.0846(19) -0.0123(15) 0.0228(17) -0.0003(17) C14 0.109(3) 0.133(3) 0.124(3) -0.022(3) 0.048(2) 0.001(2) C15 0.138(3) 0.130(3) 0.101(3) -0.024(2) 0.057(2) -0.027(3) C16 0.155(3) 0.102(3) 0.082(2) -0.0062(17) 0.045(2) -0.027(3) C17 0.106(2) 0.0791(18) 0.0645(15) -0.0041(13) 0.0268(15) -0.0033(16) C18 0.0572(12) 0.0491(12) 0.0383(10) -0.0017(8) -0.0006(9) 0.0015(9) C19 0.0741(14) 0.0541(13) 0.0405(10) 0.0063(9) 0.0052(10) 0.0049(11) C20 0.0814(16) 0.0467(12) 0.0441(11) 0.0012(9) 0.0183(11) -0.0031(11) C21 0.105(2) 0.0528(14) 0.0752(16) -0.0003(12) 0.0303(15) 0.0000(14) C22 0.137(3) 0.0500(16) 0.099(2) -0.0145(14) 0.051(2) -0.0224(18) C23 0.111(2) 0.078(2) 0.0792(18) -0.0292(15) 0.0446(17) -0.0404(18) C24 0.144(3) 0.126(3) 0.143(3) -0.062(2) 0.057(3) -0.077(3) C25 0.0791(17) 0.0839(19) 0.0825(18) -0.0125(15) 0.0205(14) -0.0195(15) C26 0.0741(16) 0.0591(14) 0.0711(15) -0.0032(11) 0.0146(12) -0.0089(13) C27 0.0575(12) 0.0499(12) 0.0383(10) 0.0013(8) 0.0002(9) -0.0008(10) C28 0.0619(13) 0.0517(12) 0.0413(10) 0.0047(9) 0.0032(9) -0.0016(11) C29 0.0707(14) 0.0625(14) 0.0465(11) -0.0046(10) 0.0111(10) -0.0061(12) C30 0.105(2) 0.0835(19) 0.0583(14) -0.0197(13) 0.0129(14) -0.0011(17) C31 0.125(3) 0.085(2) 0.091(2) -0.0207(16) 0.035(2) 0.025(2) C32 0.099(2) 0.083(2) 0.0860(19) -0.0086(15) 0.0148(16) 0.0334(17) C33 0.0714(15) 0.0732(16) 0.0632(14) -0.0050(12) 0.0061(12) 0.0105(13) C34 0.0601(13) 0.0555(13) 0.0455(11) -0.0016(9) 0.0047(9) -0.0022(11) F1 0.1429(17) 0.1416(18) 0.1374(17) -0.0238(14) 0.0141(14) 0.0809(15) N1 0.0572(11) 0.0691(12) 0.0493(10) -0.0015(8) -0.0039(8) -0.0039(10) N2 0.0745(12) 0.0626(12) 0.0394(9) -0.0009(8) -0.0070(8) -0.0007(10) O1 0.0987(13) 0.0562(10) 0.0654(10) -0.0001(8) 0.0088(9) -0.0035(9) O2 0.1106(14) 0.0656(10) 0.0574(10) 0.0112(8) -0.0106(9) 0.0100(10) O3 0.0736(10) 0.0679(11) 0.0524(9) 0.0057(7) -0.0025(7) 0.0121(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.466(3) . ? C1 C2 1.516(3) . ? C1 C27 1.590(3) . ? C1 H1 0.9800 . ? C2 C7 1.382(4) . ? C2 C3 1.390(4) . ? C3 C4 1.363(5) . ? C3 H3 0.9300 . ? C4 C5 1.377(6) . ? C4 H4 0.9300 . ? C5 C6 1.375(5) . ? C5 H5 0.9300 . ? C6 C7 1.406(5) . ? C6 H6 0.9300 . ? C7 C8 1.458(4) . ? C8 C9 1.318(4) . ? C8 H8 0.9300 . ? C9 N1 1.370(3) . ? C9 H9 0.9300 . ? C10 N1 1.439(3) . ? C10 C11 1.519(3) . ? C10 C18 1.562(3) . ? C10 H10 0.9800 . ? C11 O1 1.227(3) . ? C11 C12 1.487(4) . ? C12 C13 1.384(4) . ? C12 C17 1.388(4) . ? C13 C14 1.363(5) . ? C13 H13 0.9300 . ? C14 C15 1.363(6) . ? C14 H14 0.9300 . ? C15 C16 1.400(5) . ? C15 H15 0.9300 . ? C16 C17 1.388(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.526(3) . ? C18 C27 1.562(3) . ? C18 H18 0.9800 . ? C19 O2 1.215(2) . ? C19 C20 1.486(3) . ? C20 C26 1.388(3) . ? C20 C21 1.390(3) . ? C21 C22 1.365(4) . ? C21 H21 0.9300 . ? C22 C23 1.377(4) . ? C22 H22 0.9300 . ? C23 C25 1.375(4) . ? C23 C24 1.519(4) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.394(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C34 1.505(3) . ? C27 C28 1.540(3) . ? C28 O3 1.220(3) . ? C28 N2 1.345(3) . ? C29 C30 1.368(3) . ? C29 C34 1.394(3) . ? C29 N2 1.406(3) . ? C30 C31 1.379(4) . ? C30 H30 0.9300 . ? C31 C32 1.360(4) . ? C31 H31 0.9300 . ? C32 F1 1.370(3) . ? C32 C33 1.372(4) . ? C33 C34 1.388(3) . ? C33 H33 0.9300 . ? N2 H2 0.8599 . ? 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 113.32(18) . . ? N1 C1 C27 103.39(16) . . ? C2 C1 C27 114.96(17) . . ? N1 C1 H1 108.3 . . ? C2 C1 H1 108.3 . . ? C27 C1 H1 108.3 . . ? C7 C2 C3 120.9(3) . . ? C7 C2 C1 120.8(2) . . ? C3 C2 C1 118.3(2) . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.8(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.3(4) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.8(4) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C2 C7 C6 117.6(3) . . ? C2 C7 C8 118.8(3) . . ? C6 C7 C8 123.5(3) . . ? C9 C8 C7 120.7(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 N1 123.7(3) . . ? C8 C9 H9 118.2 . . ? N1 C9 H9 118.2 . . ? N1 C10 C11 114.02(19) . . ? N1 C10 C18 105.97(17) . . ? C11 C10 C18 107.78(17) . . ? N1 C10 H10 109.6 . . ? C11 C10 H10 109.6 . . ? C18 C10 H10 109.6 . . ? O1 C11 C12 121.6(2) . . ? O1 C11 C10 121.1(2) . . ? C12 C11 C10 117.0(2) . . ? C13 C12 C17 119.0(3) . . ? C13 C12 C11 119.3(2) . . ? C17 C12 C11 121.7(2) . . ? C14 C13 C12 121.2(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C13 120.5(4) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.7(4) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 119.8(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C12 119.8(3) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? C19 C18 C10 114.36(16) . . ? C19 C18 C27 111.46(16) . . ? C10 C18 C27 106.02(17) . . ? C19 C18 H18 108.3 . . ? C10 C18 H18 108.3 . . ? C27 C18 H18 108.3 . . ? O2 C19 C20 120.7(2) . . ? O2 C19 C18 121.0(2) . . ? C20 C19 C18 118.25(17) . . ? C26 C20 C21 118.7(2) . . ? C26 C20 C19 122.9(2) . . ? C21 C20 C19 118.4(2) . . ? C22 C21 C20 120.2(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 122.1(3) . . ? C21 C22 H22 119.0 . . ? C23 C22 H22 119.0 . . ? C25 C23 C22 118.0(3) . . ? C25 C23 C24 120.6(4) . . ? C22 C23 C24 121.4(3) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 C26 121.2(3) . . ? C23 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C20 C26 C25 119.8(2) . . ? C20 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C34 C27 C28 101.92(16) . . ? C34 C27 C18 116.81(16) . . ? C28 C27 C18 110.99(17) . . ? C34 C27 C1 115.34(18) . . ? C28 C27 C1 110.22(16) . . ? C18 C27 C1 101.78(15) . . ? O3 C28 N2 126.18(19) . . ? O3 C28 C27 125.61(19) . . ? N2 C28 C27 108.17(19) . . ? C30 C29 C34 123.2(2) . . ? C30 C29 N2 127.8(2) . . ? C34 C29 N2 109.07(19) . . ? C29 C30 C31 117.3(2) . . ? C29 C30 H30 121.3 . . ? C31 C30 H30 121.3 . . ? C32 C31 C30 119.7(3) . . ? C32 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? C31 C32 F1 118.4(3) . . ? C31 C32 C33 124.1(3) . . ? F1 C32 C33 117.5(3) . . ? C32 C33 C34 116.8(2) . . ? C32 C33 H33 121.6 . . ? C34 C33 H33 121.6 . . ? C33 C34 C29 118.9(2) . . ? C33 C34 C27 132.40(18) . . ? C29 C34 C27 108.74(18) . . ? C9 N1 C10 121.9(2) . . ? C9 N1 C1 120.5(2) . . ? C10 N1 C1 108.24(16) . . ? C28 N2 C29 111.90(17) . . ? C28 N2 H2 124.0 . . ? C29 N2 H2 124.1 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.498 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.042 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.500 192 36 ' ' 2 1.000 0.500 1.000 192 36 ' ' _platon_squeeze_details ; ; data_3e _database_code_depnum_ccdc_archive 'CCDC 896150' #TrackingRef 'cgyan-wl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H26 Cl N3 O3' _chemical_formula_sum 'C37 H26 Cl N3 O3' _chemical_formula_weight 596.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7989(14) _cell_length_b 11.8637(19) _cell_length_c 15.562(3) _cell_angle_alpha 88.053(2) _cell_angle_beta 74.732(2) _cell_angle_gamma 69.982(2) _cell_volume 1469.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2750 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 23.00 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620.0 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 0.959 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 10720 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5188 _reflns_number_gt 3640 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0740P)^2^+0.4007P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5135 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1583 _refine_ls_wR_factor_gt 0.1385 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0934(4) 1.0777(3) 0.2041(2) 0.0676(8) Uani 1 1 d . . . H1 H -0.1539 1.0765 0.2627 0.081 Uiso 1 1 calc R . . C2 C -0.1512(5) 1.1743(3) 0.1550(2) 0.0812(10) Uani 1 1 d . . . H2 H -0.2502 1.2373 0.1799 0.097 Uiso 1 1 calc R . . C3 C -0.0603(5) 1.1760(3) 0.0684(2) 0.0687(9) Uani 1 1 d . . . C4 C 0.0852(4) 1.0838(3) 0.0304(2) 0.0633(8) Uani 1 1 d . . . H4 H 0.1455 1.0866 -0.0281 0.076 Uiso 1 1 calc R . . C5 C 0.1424(3) 0.9856(2) 0.08004(17) 0.0524(7) Uani 1 1 d . . . H5 H 0.2404 0.9221 0.0543 0.063 Uiso 1 1 calc R . . C6 C 0.0537(3) 0.9821(2) 0.16766(16) 0.0459(6) Uani 1 1 d . . . C8 C 0.1109(3) 0.8808(2) 0.22467(16) 0.0418(6) Uani 1 1 d . . . C9 C 0.2967(3) 0.8012(2) 0.19993(14) 0.0375(5) Uani 1 1 d . . . H9 H 0.3283 0.7656 0.1391 0.045 Uiso 1 1 calc R . . C10 C 0.3372(3) 0.6984(2) 0.26498(15) 0.0399(5) Uani 1 1 d . . . H10 H 0.2355 0.7054 0.3126 0.048 Uiso 1 1 calc R . . C11 C 0.4040(4) 0.5755(2) 0.21482(17) 0.0503(6) Uani 1 1 d . . . C12 C 0.2823(4) 0.5358(2) 0.18218(17) 0.0528(7) Uani 1 1 d . . . C13 C 0.3431(5) 0.4588(2) 0.10633(19) 0.0712(9) Uani 1 1 d . . . H13 H 0.4569 0.4323 0.0769 0.085 Uiso 1 1 calc R . . C14 C 0.2336(7) 0.4212(3) 0.0742(3) 0.0941(13) Uani 1 1 d . . . H14 H 0.2740 0.3700 0.0231 0.113 Uiso 1 1 calc R . . C15 C 0.0647(7) 0.4602(4) 0.1187(3) 0.0963(14) Uani 1 1 d . . . H15 H -0.0082 0.4350 0.0971 0.116 Uiso 1 1 calc R . . C16 C 0.0039(5) 0.5351(3) 0.1935(2) 0.0791(10) Uani 1 1 d . . . H16 H -0.1097 0.5598 0.2234 0.095 Uiso 1 1 calc R . . C17 C 0.1112(4) 0.5746(3) 0.2253(2) 0.0604(7) Uani 1 1 d . . . H17 H 0.0688 0.6274 0.2757 0.073 Uiso 1 1 calc R . . C18 C 0.4106(3) 0.8749(2) 0.20491(14) 0.0374(5) Uani 1 1 d . . . C19 C 0.4822(3) 0.9176(2) 0.11428(15) 0.0427(6) Uani 1 1 d . . . C20 C 0.3563(3) 1.0835(2) 0.21165(15) 0.0433(6) Uani 1 1 d . . . C21 C 0.2952(4) 1.1999(2) 0.24720(18) 0.0573(7) Uani 1 1 d . . . H21 H 0.3163 1.2615 0.2132 0.069 Uiso 1 1 calc R . . C22 C 0.2007(4) 1.2222(2) 0.33574(19) 0.0603(7) Uani 1 1 d . . . H22 H 0.1576 1.3006 0.3607 0.072 Uiso 1 1 calc R . . C23 C 0.1681(3) 1.1316(2) 0.38850(16) 0.0472(6) Uani 1 1 d . . . C24 C 0.0644(4) 1.1577(3) 0.48426(18) 0.0658(8) Uani 1 1 d . . . H24A H -0.0491 1.1652 0.4876 0.099 Uiso 1 1 calc R . . H24B H 0.0660 1.2315 0.5069 0.099 Uiso 1 1 calc R . . H24C H 0.1104 1.0933 0.5193 0.099 Uiso 1 1 calc R . . C25 C 0.2331(3) 1.0142(2) 0.35050(15) 0.0408(5) Uani 1 1 d . . . H25 H 0.2136 0.9520 0.3845 0.049 Uiso 1 1 calc R . . C26 C 0.3263(3) 0.9905(2) 0.26245(14) 0.0364(5) Uani 1 1 d . . . C27 C 0.5533(3) 0.7801(2) 0.23909(16) 0.0437(6) Uani 1 1 d . . . H27 H 0.6292 0.7233 0.1890 0.052 Uiso 1 1 calc R . . C28 C 0.6536(3) 0.8328(3) 0.27717(19) 0.0551(7) Uani 1 1 d . . . H28 H 0.7294 0.8631 0.2392 0.066 Uiso 1 1 calc R . . C29 C 0.6375(3) 0.8376(3) 0.36391(19) 0.0574(7) Uani 1 1 d . . . H29 H 0.6961 0.8769 0.3857 0.069 Uiso 1 1 calc R . . C30 C 0.5318(3) 0.7838(2) 0.42662(17) 0.0476(6) Uani 1 1 d . . . C31 C 0.5154(4) 0.7904(3) 0.51953(19) 0.0602(7) Uani 1 1 d . . . H31 H 0.5669 0.8356 0.5412 0.072 Uiso 1 1 calc R . . C32 C 0.4277(4) 0.7333(3) 0.57772(18) 0.0631(8) Uani 1 1 d . . . H32 H 0.4160 0.7420 0.6385 0.076 Uiso 1 1 calc R . . C33 C 0.3540(3) 0.6607(2) 0.54648(16) 0.0523(7) Uani 1 1 d . . . C34 C 0.3652(3) 0.6520(2) 0.45386(15) 0.0420(6) Uani 1 1 d . . . C35 C 0.4498(3) 0.7198(2) 0.39356(15) 0.0398(5) Uani 1 1 d . . . C36 C 0.2698(4) 0.5917(3) 0.60275(19) 0.0645(8) Uani 1 1 d . . . H36 H 0.2581 0.5953 0.6638 0.077 Uiso 1 1 calc R . . C37 C 0.2067(4) 0.5210(3) 0.5682(2) 0.0668(8) Uani 1 1 d . . . H37 H 0.1503 0.4762 0.6049 0.080 Uiso 1 1 calc R . . C38 C 0.2273(3) 0.5159(2) 0.47581(19) 0.0577(7) Uani 1 1 d . . . H38 H 0.1845 0.4657 0.4528 0.069 Uiso 1 1 calc R . . Cl1 Cl -0.13442(16) 1.29461(8) 0.00432(7) 0.1044(4) Uani 1 1 d . . . N1 N 0.4531(3) 1.03693(19) 0.12450(13) 0.0476(5) Uani 1 1 d . . . H1A H 0.4890 1.0788 0.0831 0.057 Uiso 1 1 calc R . . N2 N 0.4619(2) 0.71682(18) 0.30289(12) 0.0420(5) Uani 1 1 d . . . N3 N 0.3034(3) 0.57753(18) 0.41957(14) 0.0483(5) Uani 1 1 d . . . O1 O 0.0126(2) 0.86542(17) 0.29110(13) 0.0568(5) Uani 1 1 d . . . O2 O 0.5535(2) 0.85375(16) 0.04472(11) 0.0542(5) Uani 1 1 d . . . O3 O 0.5510(3) 0.51369(19) 0.19839(15) 0.0781(6) 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 0.071(2) 0.0600(18) 0.0596(18) 0.0023(14) -0.0229(15) -0.0030(15) C2 0.098(3) 0.0563(19) 0.075(2) -0.0005(16) -0.039(2) 0.0034(18) C3 0.099(3) 0.0480(17) 0.079(2) 0.0164(15) -0.057(2) -0.0260(17) C4 0.075(2) 0.079(2) 0.0591(17) 0.0249(16) -0.0370(16) -0.0430(18) C5 0.0544(15) 0.0618(17) 0.0528(16) 0.0162(13) -0.0284(13) -0.0255(13) C6 0.0476(14) 0.0486(14) 0.0482(14) 0.0065(11) -0.0208(12) -0.0194(12) C8 0.0425(13) 0.0478(14) 0.0429(14) 0.0057(11) -0.0163(11) -0.0218(11) C9 0.0409(13) 0.0416(13) 0.0321(11) 0.0041(10) -0.0101(10) -0.0168(10) C10 0.0421(13) 0.0436(13) 0.0369(12) 0.0058(10) -0.0121(10) -0.0176(11) C11 0.0590(17) 0.0445(14) 0.0450(14) 0.0073(12) -0.0125(13) -0.0165(13) C12 0.080(2) 0.0404(14) 0.0467(15) 0.0111(12) -0.0248(14) -0.0259(14) C13 0.116(3) 0.0431(16) 0.0563(18) 0.0060(13) -0.0297(18) -0.0256(17) C14 0.181(5) 0.0506(19) 0.077(2) 0.0066(17) -0.070(3) -0.046(3) C15 0.159(4) 0.073(2) 0.111(3) 0.033(2) -0.090(3) -0.068(3) C16 0.105(3) 0.072(2) 0.097(3) 0.0289(19) -0.058(2) -0.055(2) C17 0.078(2) 0.0572(17) 0.0617(17) 0.0124(14) -0.0293(16) -0.0362(16) C18 0.0374(12) 0.0422(13) 0.0332(12) 0.0077(10) -0.0071(10) -0.0166(10) C19 0.0400(13) 0.0515(15) 0.0358(13) 0.0094(11) -0.0077(11) -0.0175(11) C20 0.0491(14) 0.0477(14) 0.0385(13) 0.0077(11) -0.0148(11) -0.0214(12) C21 0.0752(19) 0.0464(15) 0.0558(17) 0.0108(13) -0.0191(15) -0.0273(14) C22 0.0734(19) 0.0454(15) 0.0620(18) -0.0040(13) -0.0244(15) -0.0154(14) C23 0.0455(14) 0.0533(15) 0.0427(14) 0.0001(12) -0.0167(11) -0.0131(12) C24 0.0606(18) 0.075(2) 0.0489(16) -0.0090(14) -0.0105(13) -0.0091(15) C25 0.0377(12) 0.0482(14) 0.0379(13) 0.0065(11) -0.0114(10) -0.0161(11) C26 0.0370(12) 0.0416(12) 0.0352(12) 0.0079(10) -0.0122(10) -0.0180(10) C27 0.0354(12) 0.0494(14) 0.0456(14) 0.0102(11) -0.0097(11) -0.0153(11) C28 0.0448(15) 0.0692(18) 0.0638(18) 0.0235(14) -0.0227(13) -0.0309(13) C29 0.0525(16) 0.0651(18) 0.0711(19) 0.0171(14) -0.0313(14) -0.0310(14) C30 0.0462(14) 0.0487(14) 0.0513(15) 0.0073(12) -0.0213(12) -0.0147(12) C31 0.0627(18) 0.0658(18) 0.0596(17) -0.0010(14) -0.0302(15) -0.0206(15) C32 0.0650(18) 0.080(2) 0.0406(15) 0.0003(14) -0.0174(14) -0.0183(16) C33 0.0478(15) 0.0603(16) 0.0408(14) 0.0097(12) -0.0116(12) -0.0097(13) C34 0.0365(13) 0.0427(13) 0.0416(13) 0.0096(11) -0.0106(10) -0.0077(11) C35 0.0373(12) 0.0392(12) 0.0410(13) 0.0077(10) -0.0136(10) -0.0089(10) C36 0.0592(18) 0.079(2) 0.0441(15) 0.0183(15) -0.0085(14) -0.0155(16) C37 0.0598(18) 0.072(2) 0.0632(19) 0.0311(16) -0.0088(15) -0.0238(16) C38 0.0548(16) 0.0521(16) 0.0670(18) 0.0194(14) -0.0154(14) -0.0217(13) Cl1 0.1668(10) 0.0607(5) 0.1187(8) 0.0367(5) -0.0974(8) -0.0389(6) N1 0.0577(13) 0.0505(12) 0.0378(11) 0.0121(9) -0.0074(10) -0.0277(10) N2 0.0442(11) 0.0499(12) 0.0392(11) 0.0120(9) -0.0152(9) -0.0232(9) N3 0.0502(12) 0.0434(12) 0.0539(13) 0.0145(10) -0.0161(10) -0.0190(10) O1 0.0417(10) 0.0660(12) 0.0615(12) 0.0152(9) -0.0094(9) -0.0216(9) O2 0.0581(11) 0.0578(11) 0.0359(9) 0.0037(8) -0.0009(8) -0.0153(9) O3 0.0636(14) 0.0630(13) 0.0931(16) -0.0126(12) -0.0141(12) -0.0075(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.379(4) . ? C1 C6 1.391(4) . ? C1 H1 0.9300 . ? C2 C3 1.377(5) . ? C2 H2 0.9300 . ? C3 C4 1.368(4) . ? C3 Cl1 1.738(3) . ? C4 C5 1.397(4) . ? C4 H4 0.9300 . ? C5 C6 1.388(4) . ? C5 H5 0.9300 . ? C6 C8 1.495(3) . ? C8 O1 1.214(3) . ? C8 C9 1.533(3) . ? C9 C18 1.556(3) . ? C9 C10 1.565(3) . ? C9 H9 0.9800 . ? C10 N2 1.454(3) . ? C10 C11 1.526(3) . ? C10 H10 0.9800 . ? C11 O3 1.210(3) . ? C11 C12 1.508(4) . ? C12 C13 1.386(4) . ? C12 C17 1.394(4) . ? C13 C14 1.392(5) . ? C13 H13 0.9300 . ? C14 C15 1.383(6) . ? C14 H14 0.9300 . ? C15 C16 1.360(5) . ? C15 H15 0.9300 . ? C16 C17 1.386(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C26 1.506(3) . ? C18 C19 1.531(3) . ? C18 C27 1.571(3) . ? C19 O2 1.229(3) . ? C19 N1 1.357(3) . ? C20 C21 1.374(3) . ? C20 C26 1.394(3) . ? C20 N1 1.411(3) . ? C21 C22 1.390(4) . ? C21 H21 0.9300 . ? C22 C23 1.393(4) . ? C22 H22 0.9300 . ? C23 C25 1.396(3) . ? C23 C24 1.507(4) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.381(3) . ? C25 H25 0.9300 . ? C27 N2 1.462(3) . ? C27 C28 1.483(3) . ? C27 H27 0.9800 . ? C28 C29 1.321(4) . ? C28 H28 0.9300 . ? C29 C30 1.452(4) . ? C29 H29 0.9300 . ? C30 C35 1.400(3) . ? C30 C31 1.417(4) . ? C31 C32 1.350(4) . ? C31 H31 0.9300 . ? C32 C33 1.405(4) . ? C32 H32 0.9300 . ? C33 C36 1.418(4) . ? C33 C34 1.423(3) . ? C34 N3 1.370(3) . ? C34 C35 1.439(3) . ? C35 N2 1.387(3) . ? C36 C37 1.345(4) . ? C36 H36 0.9300 . ? C37 C38 1.401(4) . ? C37 H37 0.9300 . ? C38 N3 1.316(3) . ? C38 H38 0.9300 . ? N1 H1A 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.3(3) . . ? C2 C1 H1 119.3 . . ? C6 C1 H1 119.3 . . ? C3 C2 C1 119.1(3) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C4 C3 C2 121.3(3) . . ? C4 C3 Cl1 118.9(3) . . ? C2 C3 Cl1 119.7(3) . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 120.3(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 118.5(2) . . ? C5 C6 C8 122.7(2) . . ? C1 C6 C8 118.7(2) . . ? O1 C8 C6 120.2(2) . . ? O1 C8 C9 121.1(2) . . ? C6 C8 C9 118.6(2) . . ? C8 C9 C18 111.32(18) . . ? C8 C9 C10 112.80(18) . . ? C18 C9 C10 105.29(17) . . ? C8 C9 H9 109.1 . . ? C18 C9 H9 109.1 . . ? C10 C9 H9 109.1 . . ? N2 C10 C11 111.3(2) . . ? N2 C10 C9 105.82(17) . . ? C11 C10 C9 110.61(18) . . ? N2 C10 H10 109.7 . . ? C11 C10 H10 109.7 . . ? C9 C10 H10 109.7 . . ? O3 C11 C12 120.8(2) . . ? O3 C11 C10 121.4(2) . . ? C12 C11 C10 117.7(2) . . ? C13 C12 C17 119.1(3) . . ? C13 C12 C11 118.6(3) . . ? C17 C12 C11 122.3(2) . . ? C12 C13 C14 120.0(4) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 119.8(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 120.8(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 120.0(4) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 120.4(3) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? C26 C18 C19 102.41(18) . . ? C26 C18 C9 115.91(18) . . ? C19 C18 C9 112.91(18) . . ? C26 C18 C27 113.39(18) . . ? C19 C18 C27 111.16(18) . . ? C9 C18 C27 101.44(17) . . ? O2 C19 N1 126.5(2) . . ? O2 C19 C18 125.3(2) . . ? N1 C19 C18 108.2(2) . . ? C21 C20 C26 121.5(2) . . ? C21 C20 N1 129.2(2) . . ? C26 C20 N1 109.3(2) . . ? C20 C21 C22 117.7(2) . . ? C20 C21 H21 121.2 . . ? C22 C21 H21 121.2 . . ? C21 C22 C23 122.4(2) . . ? C21 C22 H22 118.8 . . ? C23 C22 H22 118.8 . . ? C22 C23 C25 118.4(2) . . ? C22 C23 C24 121.6(2) . . ? C25 C23 C24 119.9(2) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C23 119.9(2) . . ? C26 C25 H25 120.0 . . ? C23 C25 H25 120.0 . . ? C25 C26 C20 120.1(2) . . ? C25 C26 C18 131.4(2) . . ? C20 C26 C18 108.51(19) . . ? N2 C27 C28 113.9(2) . . ? N2 C27 C18 102.92(17) . . ? C28 C27 C18 114.3(2) . . ? N2 C27 H27 108.5 . . ? C28 C27 H27 108.5 . . ? C18 C27 H27 108.5 . . ? C29 C28 C27 121.3(2) . . ? C29 C28 H28 119.3 . . ? C27 C28 H28 119.3 . . ? C28 C29 C30 122.5(2) . . ? C28 C29 H29 118.7 . . ? C30 C29 H29 118.7 . . ? C35 C30 C31 119.4(2) . . ? C35 C30 C29 118.8(2) . . ? C31 C30 C29 121.7(2) . . ? C32 C31 C30 122.3(3) . . ? C32 C31 H31 118.9 . . ? C30 C31 H31 118.9 . . ? C31 C32 C33 120.1(2) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? C32 C33 C36 123.3(2) . . ? C32 C33 C34 119.9(2) . . ? C36 C33 C34 116.8(3) . . ? N3 C34 C33 122.0(2) . . ? N3 C34 C35 118.7(2) . . ? C33 C34 C35 119.3(2) . . ? N2 C35 C30 119.2(2) . . ? N2 C35 C34 121.9(2) . . ? C30 C35 C34 118.8(2) . . ? C37 C36 C33 120.3(3) . . ? C37 C36 H36 119.8 . . ? C33 C36 H36 119.8 . . ? C36 C37 C38 118.8(3) . . ? C36 C37 H37 120.6 . . ? C38 C37 H37 120.6 . . ? N3 C38 C37 124.3(3) . . ? N3 C38 H38 117.9 . . ? C37 C38 H38 117.9 . . ? C19 N1 C20 111.34(19) . . ? C19 N1 H1A 124.3 . . ? C20 N1 H1A 124.3 . . ? C35 N2 C10 124.09(19) . . ? C35 N2 C27 123.38(19) . . ? C10 N2 C27 107.78(17) . . ? C38 N3 C34 117.7(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O2 0.86 2.20 2.901(3) 139.2 2_675 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.507 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.056 #======================================================