# Electronic Supplementary Material (ESI) for Chemical Communications # 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_a11924 _database_code_depnum_ccdc_archive 'CCDC 865909' #TrackingRef '- 4a (CCDC 865909).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H20 O3' _chemical_formula_sum 'C29 H20 O3' _chemical_formula_weight 416.45 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2326(10) _cell_length_b 11.4464(15) _cell_length_c 12.2568(14) _cell_angle_alpha 97.004(8) _cell_angle_beta 104.823(7) _cell_angle_gamma 103.450(8) _cell_volume 1065.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9739 _exptl_absorpt_correction_T_max 0.9909 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 8225 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3672 _reflns_number_gt 2579 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0729P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3672 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.5505(3) 0.25761(19) 0.77669(17) 0.0292(5) Uani 1 1 d . . . C2 C 0.6654(3) 0.20560(18) 0.85874(16) 0.0274(5) Uani 1 1 d . . . C3 C 0.8363(3) 0.2183(2) 0.85562(19) 0.0342(5) Uani 1 1 d . . . H3 H 0.8765 0.2575 0.7997 0.041 Uiso 1 1 calc R . . C4 C 0.9470(3) 0.1737(2) 0.9341(2) 0.0424(6) Uani 1 1 d . . . H4 H 1.0627 0.1807 0.9307 0.051 Uiso 1 1 calc R . . C5 C 0.8916(3) 0.1193(2) 1.0174(2) 0.0429(6) Uani 1 1 d . . . H5 H 0.9696 0.0905 1.0721 0.052 Uiso 1 1 calc R . . C6 C 0.7228(3) 0.1068(2) 1.02081(18) 0.0425(6) Uani 1 1 d . . . H6 H 0.6840 0.0688 1.0778 0.051 Uiso 1 1 calc R . . C7 C 0.6096(3) 0.1491(2) 0.94174(17) 0.0354(6) Uani 1 1 d . . . H7 H 0.4929 0.1395 0.9441 0.043 Uiso 1 1 calc R . . C8 C 0.2597(3) 0.2673(2) 0.70434(17) 0.0299(5) Uani 1 1 d . . . C9 C 0.2146(3) 0.36842(19) 0.76407(17) 0.0301(5) Uani 1 1 d . . . C10 C 0.2777(3) 0.4059(2) 0.88314(18) 0.0370(6) Uani 1 1 d . . . H10 H 0.3579 0.3688 0.9263 0.044 Uiso 1 1 calc R . . C11 C 0.2260(3) 0.4960(2) 0.9395(2) 0.0457(6) Uani 1 1 d . . . H11 H 0.2704 0.5201 1.0208 0.055 Uiso 1 1 calc R . . C12 C 0.1106(3) 0.5511(2) 0.8787(2) 0.0486(7) Uani 1 1 d . . . H12 H 0.0743 0.6125 0.9179 0.058 Uiso 1 1 calc R . . C13 C 0.0476(3) 0.5172(2) 0.7605(2) 0.0453(6) Uani 1 1 d . . . H13 H -0.0318 0.5554 0.7183 0.054 Uiso 1 1 calc R . . C14 C 0.0998(3) 0.4275(2) 0.70331(19) 0.0367(6) Uani 1 1 d . . . H14 H 0.0573 0.4057 0.6218 0.044 Uiso 1 1 calc R . . C15 C 0.1958(3) 0.2133(2) 0.59388(18) 0.0326(5) Uani 1 1 d . . . H15 H 0.1154 0.2462 0.5454 0.039 Uiso 1 1 calc R . . C16 C 0.2392(3) 0.10753(19) 0.54088(17) 0.0304(5) Uani 1 1 d . . . C17 C 0.2858(2) 0.09592(19) 0.44226(17) 0.0294(5) Uani 1 1 d . . . C18 C 0.3220(3) 0.1795(2) 0.36455(17) 0.0321(5) Uani 1 1 d . . . C19 C 0.3527(3) 0.3051(2) 0.3994(2) 0.0420(6) Uani 1 1 d . . . H19 H 0.3477 0.3364 0.4736 0.050 Uiso 1 1 calc R . . C20 C 0.3901(3) 0.3843(2) 0.3279(2) 0.0510(7) Uani 1 1 d . . . H20 H 0.4093 0.4696 0.3526 0.061 Uiso 1 1 calc R . . C21 C 0.4000(3) 0.3408(3) 0.2208(2) 0.0547(7) Uani 1 1 d . . . H21 H 0.4267 0.3957 0.1716 0.066 Uiso 1 1 calc R . . C22 C 0.3708(3) 0.2169(3) 0.1855(2) 0.0513(7) Uani 1 1 d . . . H22 H 0.3773 0.1865 0.1115 0.062 Uiso 1 1 calc R . . C23 C 0.3324(3) 0.1367(2) 0.25610(18) 0.0411(6) Uani 1 1 d . . . H23 H 0.3128 0.0515 0.2306 0.049 Uiso 1 1 calc R . . C24 C 0.2253(3) -0.00882(19) 0.57580(17) 0.0301(5) Uani 1 1 d . . . C25 C 0.1747(3) -0.0595(2) 0.66530(18) 0.0379(6) Uani 1 1 d . . . H25 H 0.1430 -0.0123 0.7216 0.045 Uiso 1 1 calc R . . C26 C 0.1729(3) -0.1800(2) 0.66839(19) 0.0405(6) Uani 1 1 d . . . H26 H 0.1384 -0.2163 0.7276 0.049 Uiso 1 1 calc R . . C27 C 0.2202(3) -0.2493(2) 0.58709(19) 0.0401(6) Uani 1 1 d . . . H27 H 0.2207 -0.3311 0.5934 0.048 Uiso 1 1 calc R . . C28 C 0.2661(3) -0.2032(2) 0.49773(19) 0.0368(6) Uani 1 1 d . . . H28 H 0.2962 -0.2511 0.4411 0.044 Uiso 1 1 calc R . . C29 C 0.2662(3) -0.0837(2) 0.49496(17) 0.0293(5) Uani 1 1 d . . . O1 O 0.59725(19) 0.32581(14) 0.71674(13) 0.0432(4) Uani 1 1 d . . . O2 O 0.38121(17) 0.22083(13) 0.77772(11) 0.0317(4) Uani 1 1 d . . . O3 O 0.30373(18) -0.02009(13) 0.41150(12) 0.0345(4) 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 0.0286(12) 0.0272(12) 0.0296(11) 0.0013(10) 0.0075(9) 0.0069(10) C2 0.0309(12) 0.0213(11) 0.0290(11) 0.0014(9) 0.0085(9) 0.0078(9) C3 0.0321(12) 0.0315(13) 0.0423(13) 0.0092(10) 0.0143(10) 0.0102(10) C4 0.0309(13) 0.0401(15) 0.0549(15) 0.0079(12) 0.0075(11) 0.0137(11) C5 0.0446(15) 0.0344(14) 0.0444(14) 0.0076(11) 0.0009(11) 0.0140(11) C6 0.0502(15) 0.0395(15) 0.0346(12) 0.0138(11) 0.0089(11) 0.0070(12) C7 0.0348(12) 0.0371(14) 0.0331(12) 0.0055(10) 0.0106(10) 0.0075(10) C8 0.0259(11) 0.0348(13) 0.0307(11) 0.0074(10) 0.0079(9) 0.0113(10) C9 0.0274(11) 0.0280(12) 0.0352(12) 0.0039(10) 0.0123(9) 0.0056(9) C10 0.0377(13) 0.0358(14) 0.0353(12) 0.0022(10) 0.0107(10) 0.0084(11) C11 0.0565(16) 0.0382(15) 0.0400(13) -0.0032(11) 0.0173(12) 0.0105(13) C12 0.0563(16) 0.0320(14) 0.0592(17) -0.0044(12) 0.0270(13) 0.0110(12) C13 0.0462(14) 0.0294(14) 0.0604(16) 0.0063(12) 0.0145(12) 0.0129(11) C14 0.0399(13) 0.0304(13) 0.0383(12) 0.0036(10) 0.0111(10) 0.0086(11) C15 0.0291(11) 0.0384(13) 0.0316(11) 0.0061(10) 0.0078(9) 0.0131(10) C16 0.0277(11) 0.0329(13) 0.0300(11) 0.0049(10) 0.0064(9) 0.0102(10) C17 0.0270(11) 0.0260(12) 0.0339(12) 0.0028(9) 0.0066(9) 0.0087(9) C18 0.0264(11) 0.0368(14) 0.0318(11) 0.0090(10) 0.0058(9) 0.0079(10) C19 0.0479(15) 0.0413(15) 0.0413(13) 0.0085(12) 0.0152(11) 0.0183(12) C20 0.0576(17) 0.0377(15) 0.0619(17) 0.0170(13) 0.0163(14) 0.0183(13) C21 0.0584(17) 0.0571(19) 0.0518(16) 0.0302(15) 0.0165(13) 0.0115(14) C22 0.0572(17) 0.0626(19) 0.0330(13) 0.0124(13) 0.0149(12) 0.0108(14) C23 0.0444(14) 0.0391(14) 0.0365(13) 0.0047(11) 0.0101(11) 0.0089(11) C24 0.0261(11) 0.0324(13) 0.0287(11) 0.0040(10) 0.0042(9) 0.0071(9) C25 0.0385(13) 0.0443(15) 0.0278(11) 0.0032(10) 0.0076(10) 0.0099(11) C26 0.0454(14) 0.0405(15) 0.0322(12) 0.0129(11) 0.0082(10) 0.0056(11) C27 0.0394(13) 0.0359(14) 0.0415(13) 0.0117(11) 0.0040(11) 0.0100(11) C28 0.0316(12) 0.0373(14) 0.0401(13) 0.0053(11) 0.0083(10) 0.0104(10) C29 0.0241(11) 0.0340(13) 0.0296(11) 0.0084(10) 0.0083(9) 0.0060(9) O1 0.0376(9) 0.0468(11) 0.0525(10) 0.0255(9) 0.0163(8) 0.0141(8) O2 0.0268(8) 0.0376(9) 0.0307(8) 0.0070(7) 0.0073(6) 0.0097(7) O3 0.0379(9) 0.0333(9) 0.0340(8) 0.0040(7) 0.0138(7) 0.0105(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.201(2) . ? C1 O2 1.363(2) . ? C1 C2 1.477(3) . ? C2 C7 1.388(3) . ? C2 C3 1.391(3) . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C5 1.378(3) . ? C4 H4 0.9500 . ? C5 C6 1.376(3) . ? C5 H5 0.9500 . ? C6 C7 1.380(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C15 1.331(3) . ? C8 O2 1.413(2) . ? C8 C9 1.465(3) . ? C9 C10 1.393(3) . ? C9 C14 1.402(3) . ? C10 C11 1.380(3) . ? C10 H10 0.9500 . ? C11 C12 1.373(3) . ? C11 H11 0.9500 . ? C12 C13 1.380(3) . ? C12 H12 0.9500 . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.464(3) . ? C15 H15 0.9500 . ? C16 C17 1.359(3) . ? C16 C24 1.436(3) . ? C17 O3 1.387(2) . ? C17 C18 1.465(3) . ? C18 C23 1.390(3) . ? C18 C19 1.393(3) . ? C19 C20 1.373(3) . ? C19 H19 0.9500 . ? C20 C21 1.376(4) . ? C20 H20 0.9500 . ? C21 C22 1.376(4) . ? C21 H21 0.9500 . ? C22 C23 1.375(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C29 1.389(3) . ? C24 C25 1.410(3) . ? C25 C26 1.382(3) . ? C25 H25 0.9500 . ? C26 C27 1.386(3) . ? C26 H26 0.9500 . ? C27 C28 1.372(3) . ? C27 H27 0.9500 . ? C28 C29 1.372(3) . ? C28 H28 0.9500 . ? C29 O3 1.383(2) . ? 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 O2 122.76(19) . . ? O1 C1 C2 125.4(2) . . ? O2 C1 C2 111.79(18) . . ? C7 C2 C3 119.27(19) . . ? C7 C2 C1 121.71(19) . . ? C3 C2 C1 118.96(19) . . ? C4 C3 C2 119.7(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 120.8(2) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 119.6(2) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 120.3(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 120.3(2) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? C15 C8 O2 118.20(19) . . ? C15 C8 C9 128.25(19) . . ? O2 C8 C9 113.49(17) . . ? C10 C9 C14 117.6(2) . . ? C10 C9 C8 121.54(19) . . ? C14 C9 C8 120.83(18) . . ? C11 C10 C9 121.2(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 120.3(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.8(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 120.1(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C9 120.9(2) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C8 C15 C16 125.46(19) . . ? C8 C15 H15 117.3 . . ? C16 C15 H15 117.3 . . ? C17 C16 C24 105.92(19) . . ? C17 C16 C15 126.62(19) . . ? C24 C16 C15 127.22(19) . . ? C16 C17 O3 111.55(18) . . ? C16 C17 C18 133.6(2) . . ? O3 C17 C18 114.83(18) . . ? C23 C18 C19 118.2(2) . . ? C23 C18 C17 121.3(2) . . ? C19 C18 C17 120.5(2) . . ? C20 C19 C18 120.8(2) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 120.4(2) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C22 119.4(2) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 120.7(2) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C22 C23 C18 120.5(2) . . ? C22 C23 H23 119.8 . . ? C18 C23 H23 119.8 . . ? C29 C24 C25 118.1(2) . . ? C29 C24 C16 106.87(18) . . ? C25 C24 C16 134.9(2) . . ? C26 C25 C24 117.8(2) . . ? C26 C25 H25 121.1 . . ? C24 C25 H25 121.1 . . ? C25 C26 C27 121.5(2) . . ? C25 C26 H26 119.3 . . ? C27 C26 H26 119.3 . . ? C28 C27 C26 121.9(2) . . ? C28 C27 H27 119.0 . . ? C26 C27 H27 119.0 . . ? C29 C28 C27 116.1(2) . . ? C29 C28 H28 122.0 . . ? C27 C28 H28 122.0 . . ? C28 C29 O3 125.8(2) . . ? C28 C29 C24 124.6(2) . . ? O3 C29 C24 109.64(18) . . ? C1 O2 C8 116.83(16) . . ? C29 O3 C17 106.01(16) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.259 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.099 data_a11925 _database_code_depnum_ccdc_archive 'CCDC 865910' #TrackingRef '- 8 (CCDC 865910).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H50 Cl O5 P' _chemical_formula_sum 'C41 H50 Cl O5 P' _chemical_formula_weight 689.23 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' 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 'P 21/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 8.6928(9) _cell_length_b 27.828(3) _cell_length_c 15.9755(17) _cell_angle_alpha 90.00 _cell_angle_beta 93.278(2) _cell_angle_gamma 90.00 _cell_volume 3858.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9611 _exptl_absorpt_correction_T_max 0.9803 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 22879 _diffrn_reflns_av_R_equivalents 0.0695 _diffrn_reflns_av_sigmaI/netI 0.0856 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.05 _reflns_number_total 6803 _reflns_number_gt 3958 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1462P)^2^+4.3827P] 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 6803 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1390 _refine_ls_R_factor_gt 0.0792 _refine_ls_wR_factor_ref 0.2599 _refine_ls_wR_factor_gt 0.2126 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.002 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 0.3125(5) 0.27915(15) 0.7383(3) 0.0326(11) Uani 1 1 d . . . C2 C 0.2526(6) 0.25865(16) 0.8157(3) 0.0358(11) Uani 1 1 d . . . C3 C 0.1193(6) 0.23142(18) 0.8088(3) 0.0442(13) Uani 1 1 d . . . H3 H 0.0686 0.2261 0.7554 0.053 Uiso 1 1 calc R . . C4 C 0.0595(7) 0.2118(2) 0.8802(4) 0.0587(17) Uani 1 1 d . . . H4 H -0.0313 0.1928 0.8755 0.070 Uiso 1 1 calc R . . C5 C 0.1332(8) 0.2202(2) 0.9586(4) 0.0635(17) Uani 1 1 d . . . H5 H 0.0922 0.2071 1.0076 0.076 Uiso 1 1 calc R . . C6 C 0.2639(7) 0.2470(2) 0.9648(4) 0.0615(16) Uani 1 1 d . . . H6 H 0.3137 0.2526 1.0184 0.074 Uiso 1 1 calc R . . C7 C 0.3256(6) 0.26626(19) 0.8944(3) 0.0478(13) Uani 1 1 d . . . H7 H 0.4177 0.2847 0.8997 0.057 Uiso 1 1 calc R . . C8 C 0.5186(5) 0.32316(16) 0.6839(3) 0.0298(10) Uani 1 1 d . . . C9 C 0.5914(5) 0.28790(17) 0.6303(3) 0.0405(12) Uani 1 1 d . . . C10 C 0.6203(7) 0.2415(2) 0.6569(4) 0.0613(17) Uani 1 1 d . . . H10 H 0.5915 0.2318 0.7108 0.074 Uiso 1 1 calc R . . C11 C 0.6913(8) 0.2086(2) 0.6058(5) 0.086(2) Uani 1 1 d . . . H11 H 0.7109 0.1768 0.6253 0.103 Uiso 1 1 calc R . . C12 C 0.7325(9) 0.2218(3) 0.5280(6) 0.091(3) Uani 1 1 d . . . H12 H 0.7807 0.1993 0.4933 0.110 Uiso 1 1 calc R . . C13 C 0.7039(7) 0.2681(3) 0.5001(4) 0.0722(19) Uani 1 1 d . . . H13 H 0.7314 0.2774 0.4457 0.087 Uiso 1 1 calc R . . C14 C 0.6347(6) 0.3010(2) 0.5515(3) 0.0498(14) Uani 1 1 d . . . H14 H 0.6169 0.3329 0.5323 0.060 Uiso 1 1 calc R . . C15 C 0.5277(5) 0.36996(16) 0.6776(3) 0.0299(10) Uani 1 1 d . . . H15 H 0.5846 0.3825 0.6335 0.036 Uiso 1 1 calc R . . C16 C 0.4555(5) 0.40530(15) 0.7343(3) 0.0286(10) Uani 1 1 d . . . H16 H 0.4111 0.3865 0.7805 0.034 Uiso 1 1 calc R . . C17 C 0.5697(5) 0.44128(15) 0.7753(3) 0.0289(10) Uani 1 1 d . . . C18 C 0.6854(5) 0.46265(16) 0.7317(3) 0.0325(11) Uani 1 1 d . . . H18 H 0.6967 0.4542 0.6747 0.039 Uiso 1 1 calc R . . C19 C 0.7844(5) 0.49592(17) 0.7698(3) 0.0411(12) Uani 1 1 d . . . H19 H 0.8615 0.5105 0.7386 0.049 Uiso 1 1 calc R . . C20 C 0.7724(6) 0.50797(19) 0.8516(3) 0.0481(13) Uani 1 1 d . . . H20 H 0.8412 0.5309 0.8772 0.058 Uiso 1 1 calc R . . C21 C 0.6601(6) 0.48694(19) 0.8977(3) 0.0462(13) Uani 1 1 d . . . H21 H 0.6522 0.4947 0.9552 0.055 Uiso 1 1 calc R . . C22 C 0.5600(5) 0.45448(17) 0.8586(3) 0.0371(11) Uani 1 1 d . A . C23 C 0.4650(8) 0.4068(2) 0.9684(4) 0.0645(18) Uani 1 1 d . A . C24 C 0.3241(9) 0.3922(2) 1.0077(4) 0.070(2) Uani 1 1 d . . . C25 C 0.1956(13) 0.3975(4) 0.9816(6) 0.043(3) Uiso 0.600(15) 1 d P A 1 H25 H 0.1787 0.4131 0.9290 0.051 Uiso 0.600(15) 1 calc PR A 1 C26 C 0.0639(14) 0.3821(5) 1.0235(8) 0.060(3) Uiso 0.600(15) 1 d P A 1 H26 H -0.0378 0.3885 1.0013 0.072 Uiso 0.600(15) 1 calc PR A 1 C27 C 0.0901(19) 0.3581(5) 1.0957(8) 0.058(3) Uiso 0.600(15) 1 d P A 1 H27 H 0.0046 0.3456 1.1231 0.070 Uiso 0.600(15) 1 calc PR A 1 C28 C 0.2406(14) 0.3506(4) 1.1329(8) 0.059(3) Uiso 0.600(15) 1 d P A 1 H28 H 0.2551 0.3344 1.1852 0.071 Uiso 0.600(15) 1 calc PR A 1 C29 C 0.3634(14) 0.3669(4) 1.0924(7) 0.055(3) Uiso 0.600(15) 1 d P A 1 H29 H 0.4664 0.3631 1.1146 0.066 Uiso 0.600(15) 1 calc PR A 1 C25' C 0.1560(15) 0.4165(6) 0.9711(8) 0.035(4) Uiso 0.400(15) 1 d P A 2 H25' H 0.1540 0.4381 0.9249 0.042 Uiso 0.400(15) 1 calc PR A 2 C26' C 0.0213(19) 0.4053(7) 1.0082(10) 0.057(5) Uiso 0.400(15) 1 d P A 2 H26' H -0.0740 0.4193 0.9894 0.069 Uiso 0.400(15) 1 calc PR A 2 C27' C 0.030(2) 0.3721(7) 1.0751(13) 0.064(6) Uiso 0.400(15) 1 d P A 2 H27' H -0.0617 0.3657 1.1029 0.077 Uiso 0.400(15) 1 calc PR A 2 C28' C 0.162(3) 0.3484(6) 1.1027(12) 0.057(5) Uiso 0.400(15) 1 d P A 2 H28' H 0.1635 0.3254 1.1467 0.068 Uiso 0.400(15) 1 calc PR A 2 C29' C 0.298(3) 0.3613(7) 1.0593(14) 0.074(6) Uiso 0.400(15) 1 d P A 2 H29' H 0.3841 0.3416 1.0741 0.089 Uiso 0.400(15) 1 calc PR A 2 C30 C 0.2377(5) 0.48795(17) 0.7355(3) 0.0391(12) Uani 1 1 d . . . H30A H 0.1258 0.4930 0.7238 0.047 Uiso 1 1 calc R . . H30B H 0.2539 0.4805 0.7959 0.047 Uiso 1 1 calc R . . C31 C 0.3199(6) 0.53530(17) 0.7188(4) 0.0468(13) Uani 1 1 d . . . H31A H 0.4285 0.5331 0.7407 0.056 Uiso 1 1 calc R . . H31B H 0.3193 0.5409 0.6576 0.056 Uiso 1 1 calc R . . C32 C 0.2411(10) 0.5778(2) 0.7609(5) 0.089(2) Uani 1 1 d . . . H32A H 0.2742 0.5785 0.8212 0.107 Uiso 1 1 calc R . . H32B H 0.1280 0.5730 0.7562 0.107 Uiso 1 1 calc R . . C33 C 0.2806(11) 0.6263(3) 0.7204(5) 0.0988(19) Uani 1 1 d . . . H33A H 0.2286 0.6524 0.7488 0.148 Uiso 1 1 calc R . . H33B H 0.2462 0.6259 0.6609 0.148 Uiso 1 1 calc R . . H33C H 0.3923 0.6314 0.7258 0.148 Uiso 1 1 calc R . . C34 C 0.3486(5) 0.45210(17) 0.5732(3) 0.0334(11) Uani 1 1 d . . . H34A H 0.2958 0.4824 0.5560 0.040 Uiso 1 1 calc R . . H34B H 0.4610 0.4583 0.5753 0.040 Uiso 1 1 calc R . . C35 C 0.3099(5) 0.41360(18) 0.5065(3) 0.0370(11) Uani 1 1 d . . . H35A H 0.1967 0.4099 0.4991 0.044 Uiso 1 1 calc R . . H35B H 0.3541 0.3824 0.5255 0.044 Uiso 1 1 calc R . . C36 C 0.3744(6) 0.42745(19) 0.4226(3) 0.0450(13) Uani 1 1 d . . . H36A H 0.3386 0.4601 0.4067 0.054 Uiso 1 1 calc R . . H36B H 0.4884 0.4281 0.4289 0.054 Uiso 1 1 calc R . . C37 C 0.3241(10) 0.3925(3) 0.3534(5) 0.0988(19) Uani 1 1 d . . . H37A H 0.3681 0.4023 0.3010 0.148 Uiso 1 1 calc R . . H37B H 0.2114 0.3924 0.3460 0.148 Uiso 1 1 calc R . . H37C H 0.3603 0.3601 0.3687 0.148 Uiso 1 1 calc R . . C38 C 0.1345(5) 0.39453(17) 0.6690(3) 0.0326(11) Uani 1 1 d . . . H38A H 0.0524 0.4084 0.6310 0.039 Uiso 1 1 calc R . . H38B H 0.1698 0.3645 0.6429 0.039 Uiso 1 1 calc R . . C39 C 0.0652(5) 0.38183(17) 0.7521(3) 0.0362(11) Uani 1 1 d . . . H39A H 0.1460 0.3675 0.7906 0.043 Uiso 1 1 calc R . . H39B H 0.0280 0.4115 0.7785 0.043 Uiso 1 1 calc R . . C40 C -0.0678(5) 0.34660(18) 0.7393(3) 0.0403(12) Uani 1 1 d . . . H40A H -0.0297 0.3167 0.7142 0.048 Uiso 1 1 calc R . . H40B H -0.1469 0.3606 0.6995 0.048 Uiso 1 1 calc R . . C41 C -0.1411(6) 0.3345(2) 0.8206(3) 0.0484(13) Uani 1 1 d . . . H41A H -0.2253 0.3116 0.8093 0.073 Uiso 1 1 calc R . . H41B H -0.1818 0.3639 0.8449 0.073 Uiso 1 1 calc R . . H41C H -0.0636 0.3203 0.8600 0.073 Uiso 1 1 calc R . . O1 O 0.4462(4) 0.30389(11) 0.75441(19) 0.0342(7) Uani 1 1 d . . . O2 O 0.2506(4) 0.27573(13) 0.6688(2) 0.0438(9) Uani 1 1 d . . . O3 O 0.4352(4) 0.43616(13) 0.9026(2) 0.0453(9) Uani 1 1 d . . . O4 O 0.5946(7) 0.3959(2) 0.9910(4) 0.130(3) Uani 1 1 d . . . O5 O 0.9857(5) 0.51622(18) 0.6028(2) 0.0723(13) Uani 1 1 d . . . H5A H 1.0390 0.5334 0.5607 0.087 Uiso 1 1 d R . . H5B H 0.9225 0.4930 0.5666 0.087 Uiso 1 1 d R . . P1 P 0.29403(13) 0.43618(4) 0.67709(7) 0.0298(3) Uani 1 1 d . . . Cl1 Cl 0.20324(15) 0.57173(5) 0.47849(9) 0.0533(4) 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) 0.028(2) 0.034(3) -0.002(2) 0.009(2) 0.006(2) C2 0.042(3) 0.031(2) 0.036(3) 0.002(2) 0.012(2) 0.008(2) C3 0.053(3) 0.041(3) 0.039(3) -0.003(2) 0.016(3) 0.004(2) C4 0.051(3) 0.046(3) 0.083(5) 0.007(3) 0.035(3) 0.001(3) C5 0.080(5) 0.069(4) 0.044(4) 0.016(3) 0.027(3) 0.013(4) C6 0.068(4) 0.082(4) 0.035(3) 0.012(3) 0.011(3) 0.000(4) C7 0.053(3) 0.051(3) 0.040(3) 0.004(3) 0.006(3) 0.000(3) C8 0.022(2) 0.037(3) 0.031(2) -0.004(2) 0.0054(19) -0.0014(19) C9 0.032(3) 0.037(3) 0.054(3) -0.007(2) 0.008(2) -0.002(2) C10 0.054(4) 0.044(3) 0.088(5) -0.003(3) 0.025(3) 0.008(3) C11 0.079(5) 0.054(4) 0.129(7) -0.008(4) 0.046(5) 0.017(4) C12 0.073(5) 0.078(5) 0.128(7) -0.032(5) 0.050(5) 0.008(4) C13 0.067(4) 0.082(5) 0.072(4) -0.017(4) 0.036(4) -0.001(4) C14 0.049(3) 0.052(3) 0.050(3) -0.010(3) 0.020(3) -0.002(3) C15 0.024(2) 0.039(3) 0.027(2) 0.002(2) 0.0041(19) -0.0002(19) C16 0.025(2) 0.033(2) 0.028(2) 0.007(2) 0.0080(19) 0.0028(19) C17 0.024(2) 0.029(2) 0.034(3) 0.004(2) 0.0046(19) 0.0004(18) C18 0.031(2) 0.037(3) 0.030(2) 0.006(2) 0.005(2) 0.003(2) C19 0.032(3) 0.039(3) 0.054(3) 0.001(2) 0.009(2) -0.006(2) C20 0.044(3) 0.052(3) 0.049(3) -0.008(3) 0.002(3) -0.016(3) C21 0.050(3) 0.053(3) 0.036(3) -0.009(3) 0.006(2) -0.013(3) C22 0.037(3) 0.041(3) 0.034(3) 0.006(2) 0.009(2) -0.006(2) C23 0.080(5) 0.046(3) 0.072(4) 0.011(3) 0.037(4) 0.005(3) C24 0.108(6) 0.050(4) 0.057(4) -0.007(3) 0.049(4) -0.023(4) C30 0.032(2) 0.044(3) 0.042(3) 0.004(2) 0.009(2) 0.005(2) C31 0.051(3) 0.037(3) 0.055(3) -0.001(3) 0.018(3) 0.002(2) C32 0.121(6) 0.052(4) 0.098(6) -0.022(4) 0.047(5) -0.012(4) C33 0.131(5) 0.087(4) 0.080(4) -0.009(3) 0.014(4) -0.018(4) C34 0.033(2) 0.037(2) 0.031(3) 0.012(2) 0.002(2) -0.001(2) C35 0.039(3) 0.045(3) 0.028(3) 0.010(2) 0.000(2) -0.004(2) C36 0.051(3) 0.051(3) 0.034(3) 0.008(2) 0.008(2) -0.014(3) C37 0.131(5) 0.087(4) 0.080(4) -0.009(3) 0.014(4) -0.018(4) C38 0.024(2) 0.045(3) 0.029(2) 0.008(2) -0.0004(19) -0.005(2) C39 0.027(2) 0.044(3) 0.038(3) 0.011(2) 0.006(2) 0.000(2) C40 0.030(2) 0.051(3) 0.040(3) 0.012(2) 0.007(2) -0.005(2) C41 0.037(3) 0.058(3) 0.051(3) 0.012(3) 0.012(2) -0.005(3) O1 0.0378(17) 0.0355(17) 0.0294(17) 0.0041(14) 0.0025(14) -0.0041(14) O2 0.0398(19) 0.062(2) 0.0303(19) -0.0054(17) 0.0052(16) -0.0036(17) O3 0.047(2) 0.061(2) 0.0290(18) 0.0014(17) 0.0144(16) -0.0169(17) O4 0.110(5) 0.133(5) 0.153(6) 0.105(5) 0.066(4) 0.047(4) O5 0.059(2) 0.114(4) 0.045(2) 0.016(2) 0.0089(19) -0.026(3) P1 0.0236(6) 0.0361(7) 0.0300(6) 0.0074(5) 0.0043(5) 0.0012(5) Cl1 0.0490(8) 0.0656(9) 0.0459(8) 0.0154(7) 0.0077(6) -0.0034(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.210(5) . ? C1 O1 1.363(5) . ? C1 C2 1.483(6) . ? C2 C3 1.384(7) . ? C2 C7 1.392(7) . ? C3 C4 1.391(7) . ? C3 H3 0.9500 . ? C4 C5 1.394(9) . ? C4 H4 0.9500 . ? C5 C6 1.358(9) . ? C5 H5 0.9500 . ? C6 C7 1.381(7) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C15 1.309(6) . ? C8 O1 1.426(5) . ? C8 C9 1.469(6) . ? C9 C14 1.383(7) . ? C9 C10 1.378(7) . ? C10 C11 1.394(8) . ? C10 H10 0.9500 . ? C11 C12 1.363(10) . ? C11 H11 0.9500 . ? C12 C13 1.382(10) . ? C12 H12 0.9500 . ? C13 C14 1.390(8) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.499(6) . ? C15 H15 0.9500 . ? C16 C17 1.531(6) . ? C16 P1 1.843(4) . ? C16 H16 1.0000 . ? C17 C18 1.390(6) . ? C17 C22 1.387(6) . ? C18 C19 1.381(6) . ? C18 H18 0.9500 . ? C19 C20 1.358(7) . ? C19 H19 0.9500 . ? C20 C21 1.386(7) . ? C20 H20 0.9500 . ? C21 C22 1.379(7) . ? C21 H21 0.9500 . ? C22 O3 1.420(5) . ? C23 O4 1.202(8) . ? C23 O3 1.346(7) . ? C23 C24 1.465(8) . ? C24 C25 1.179(12) . ? C24 C29' 1.222(19) . ? C24 C29 1.545(14) . ? C24 C25' 1.686(17) . ? C25 C26 1.425(15) . ? C25 H25 0.9500 . ? C26 C27 1.341(17) . ? C26 H26 0.9500 . ? C27 C28 1.421(18) . ? C27 H27 0.9500 . ? C28 C29 1.358(14) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C25' C26' 1.378(19) . ? C25' H25' 0.9500 . ? C26' C27' 1.41(3) . ? C26' H26' 0.9500 . ? C27' C28' 1.37(3) . ? C27' H27' 0.9500 . ? C28' C29' 1.45(3) . ? C28' H28' 0.9500 . ? C29' H29' 0.9500 . ? C30 C31 1.529(7) . ? C30 P1 1.799(5) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.540(8) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.544(10) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.535(7) . ? C34 P1 1.808(4) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.532(6) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.518(8) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 C39 1.530(6) . ? C38 P1 1.806(4) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.521(6) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.516(6) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? O5 H5A 0.9650 . ? O5 H5B 1.0096 . ? 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 O2 C1 O1 122.9(4) . . ? O2 C1 C2 125.2(4) . . ? O1 C1 C2 111.9(4) . . ? C3 C2 C7 119.5(5) . . ? C3 C2 C1 118.5(4) . . ? C7 C2 C1 122.1(5) . . ? C2 C3 C4 120.0(5) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 119.8(6) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.7(5) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 121.2(6) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C6 C7 C2 119.8(5) . . ? C6 C7 H7 120.1 . . ? C2 C7 H7 120.1 . . ? C15 C8 O1 117.8(4) . . ? C15 C8 C9 126.1(4) . . ? O1 C8 C9 115.7(4) . . ? C14 C9 C10 118.2(5) . . ? C14 C9 C8 120.2(5) . . ? C10 C9 C8 121.6(5) . . ? C9 C10 C11 121.0(6) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C12 C11 C10 120.3(7) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 119.6(6) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 119.9(6) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.1 . . ? C9 C14 C13 121.0(6) . . ? C9 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C8 C15 C16 125.2(4) . . ? C8 C15 H15 117.4 . . ? C16 C15 H15 117.4 . . ? C15 C16 C17 113.8(3) . . ? C15 C16 P1 109.8(3) . . ? C17 C16 P1 111.4(3) . . ? C15 C16 H16 107.2 . . ? C17 C16 H16 107.2 . . ? P1 C16 H16 107.2 . . ? C18 C17 C22 116.9(4) . . ? C18 C17 C16 122.4(4) . . ? C22 C17 C16 120.7(4) . . ? C19 C18 C17 121.1(4) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C20 C19 C18 120.6(5) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 120.1(5) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 C20 118.8(5) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C17 122.5(4) . . ? C21 C22 O3 119.4(4) . . ? C17 C22 O3 118.0(4) . . ? O4 C23 O3 121.5(5) . . ? O4 C23 C24 126.4(7) . . ? O3 C23 C24 112.0(6) . . ? C25 C24 C29' 96.6(13) . . ? C25 C24 C23 127.7(8) . . ? C29' C24 C23 132.8(13) . . ? C25 C24 C29 121.6(8) . . ? C29' C24 C29 29.6(11) . . ? C23 C24 C29 110.7(8) . . ? C25 C24 C25' 16.6(7) . . ? C29' C24 C25' 108.8(13) . . ? C23 C24 C25' 118.0(7) . . ? C29 C24 C25' 129.1(7) . . ? C24 C25 C26 124.5(11) . . ? C24 C25 H25 117.8 . . ? C26 C25 H25 117.8 . . ? C27 C26 C25 116.9(12) . . ? C27 C26 H26 121.7 . . ? C25 C26 H26 121.4 . . ? C26 C27 C28 122.7(12) . . ? C26 C27 H27 118.5 . . ? C28 C27 H27 118.8 . . ? C29 C28 C27 118.7(11) . . ? C29 C28 H28 120.7 . . ? C27 C28 H28 120.6 . . ? C28 C29 C24 115.5(10) . . ? C28 C29 H29 122.2 . . ? C24 C29 H29 122.3 . . ? C26' C25' C24 120.0(12) . . ? C26' C25' H25' 120.0 . . ? C24 C25' H25' 120.0 . . ? C27' C26' C25' 117.8(16) . . ? C27' C26' H26' 121.2 . . ? C25' C26' H26' 121.1 . . ? C26' C27' C28' 124.3(18) . . ? C26' C27' H27' 117.7 . . ? C28' C27' H27' 118.0 . . ? C27' C28' C29' 114.6(17) . . ? C27' C28' H28' 122.5 . . ? C29' C28' H28' 122.9 . . ? C24 C29' C28' 133(2) . . ? C24 C29' H29' 113.3 . . ? C28' C29' H29' 113.2 . . ? C31 C30 P1 117.2(3) . . ? C31 C30 H30A 108.0 . . ? P1 C30 H30A 108.0 . . ? C31 C30 H30B 108.0 . . ? P1 C30 H30B 108.0 . . ? H30A C30 H30B 107.3 . . ? C32 C31 C30 111.2(4) . . ? C32 C31 H31A 109.4 . . ? C30 C31 H31A 109.4 . . ? C32 C31 H31B 109.4 . . ? C30 C31 H31B 109.4 . . ? H31A C31 H31B 108.0 . . ? C31 C32 C33 111.9(6) . . ? C31 C32 H32A 109.2 . . ? C33 C32 H32A 109.2 . . ? C31 C32 H32B 109.2 . . ? C33 C32 H32B 109.2 . . ? H32A C32 H32B 107.9 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 P1 114.1(3) . . ? C35 C34 H34A 108.7 . . ? P1 C34 H34A 108.7 . . ? C35 C34 H34B 108.7 . . ? P1 C34 H34B 108.7 . . ? H34A C34 H34B 107.6 . . ? C34 C35 C36 110.8(4) . . ? C34 C35 H35A 109.5 . . ? C36 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? C36 C35 H35B 109.5 . . ? H35A C35 H35B 108.1 . . ? C37 C36 C35 111.8(5) . . ? C37 C36 H36A 109.3 . . ? C35 C36 H36A 109.3 . . ? C37 C36 H36B 109.3 . . ? C35 C36 H36B 109.3 . . ? H36A C36 H36B 107.9 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C39 C38 P1 115.2(3) . . ? C39 C38 H38A 108.5 . . ? P1 C38 H38A 108.5 . . ? C39 C38 H38B 108.5 . . ? P1 C38 H38B 108.5 . . ? H38A C38 H38B 107.5 . . ? C40 C39 C38 111.5(4) . . ? C40 C39 H39A 109.3 . . ? C38 C39 H39A 109.3 . . ? C40 C39 H39B 109.3 . . ? C38 C39 H39B 109.3 . . ? H39A C39 H39B 108.0 . . ? C39 C40 C41 112.4(4) . . ? C39 C40 H40A 109.1 . . ? C41 C40 H40A 109.1 . . ? C39 C40 H40B 109.1 . . ? C41 C40 H40B 109.1 . . ? H40A C40 H40B 107.8 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C1 O1 C8 116.8(3) . . ? C23 O3 C22 119.1(4) . . ? H5A O5 H5B 100.6 . . ? C30 P1 C38 108.7(2) . . ? C30 P1 C34 111.9(2) . . ? C38 P1 C34 109.4(2) . . ? C30 P1 C16 109.8(2) . . ? C38 P1 C16 107.2(2) . . ? C34 P1 C16 109.7(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.967 _refine_diff_density_min -1.030 _refine_diff_density_rms 0.075 data_a13063b _database_code_depnum_ccdc_archive 'CCDC 865911' #TrackingRef '- 4q (CCDC 865911).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H23 N O5' _chemical_formula_sum 'C27 H23 N O5' _chemical_formula_weight 441.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.0371(10) _cell_length_b 18.781(3) _cell_length_c 34.661(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.200(2) _cell_angle_gamma 90.00 _cell_volume 4580.9(12) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9671 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 26368 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 25.03 _reflns_number_total 8007 _reflns_number_gt 4563 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0853P)^2^+1.4729P] 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 8007 _refine_ls_number_parameters 594 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1182 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1714 _refine_ls_wR_factor_gt 0.1373 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _refine_ls_shift/su_max 0.008 _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 0.4444(5) 0.60584(16) -0.00787(10) 0.0521(8) Uani 1 1 d . . . C2 C 0.5937(5) 0.61289(18) -0.03326(10) 0.0616(9) Uani 1 1 d . . . H2 H 0.5850 0.5937 -0.0586 0.074 Uiso 1 1 calc R . . C3 C 0.7563(5) 0.64829(17) -0.02147(9) 0.0541(9) Uani 1 1 d . . . H3 H 0.8608 0.6530 -0.0386 0.065 Uiso 1 1 calc R . . C4 C 0.7662(4) 0.67704(15) 0.01551(8) 0.0428(7) Uani 1 1 d . . . C5 C 0.6108(5) 0.66872(16) 0.04038(9) 0.0498(8) Uani 1 1 d . . . H5 H 0.6163 0.6883 0.0656 0.060 Uiso 1 1 calc R . . C6 C 0.4496(5) 0.63241(16) 0.02866(9) 0.0514(8) Uani 1 1 d . . . H6 H 0.3453 0.6262 0.0457 0.062 Uiso 1 1 calc R . . C7 C 0.9331(4) 0.71722(15) 0.02697(8) 0.0412(7) Uani 1 1 d . . . C8 C 1.0049(4) 0.74465(14) 0.06038(8) 0.0387(7) Uani 1 1 d . . . C9 C 1.1735(4) 0.78248(14) 0.04970(8) 0.0412(7) Uani 1 1 d . . . H9 H 1.2551 0.8076 0.0668 0.049 Uiso 1 1 calc R . . C10 C 1.1970(4) 0.77635(14) 0.01120(8) 0.0400(7) Uani 1 1 d . . . C11 C 1.3425(4) 0.79982(14) -0.01629(8) 0.0391(7) Uani 1 1 d . . . C12 C 1.3167(5) 0.79088(15) -0.05560(8) 0.0452(8) Uani 1 1 d . . . H12 H 1.2019 0.7705 -0.0650 0.054 Uiso 1 1 calc R . . C13 C 1.4565(5) 0.81139(16) -0.08155(9) 0.0533(8) Uani 1 1 d . . . H13 H 1.4355 0.8059 -0.1085 0.064 Uiso 1 1 calc R . . C14 C 1.6257(5) 0.83975(16) -0.06845(9) 0.0551(9) Uani 1 1 d . . . H14 H 1.7226 0.8527 -0.0861 0.066 Uiso 1 1 calc R . . C15 C 1.6522(5) 0.84899(17) -0.02946(9) 0.0574(9) Uani 1 1 d . . . H15 H 1.7679 0.8688 -0.0202 0.069 Uiso 1 1 calc R . . C16 C 1.5112(5) 0.82964(16) -0.00351(9) 0.0504(8) Uani 1 1 d . . . H16 H 1.5308 0.8370 0.0233 0.060 Uiso 1 1 calc R . . C17 C 0.9342(4) 0.73366(15) 0.10041(8) 0.0400(7) Uani 1 1 d . . . C18 C 0.9091(4) 0.66532(17) 0.11556(9) 0.0505(8) Uani 1 1 d . . . H18 H 0.9327 0.6249 0.0998 0.061 Uiso 1 1 calc R . . C19 C 0.8499(4) 0.65599(18) 0.15345(9) 0.0539(9) Uani 1 1 d . . . H19 H 0.8340 0.6092 0.1634 0.065 Uiso 1 1 calc R . . C20 C 0.8142(4) 0.71360(19) 0.17659(9) 0.0543(9) Uani 1 1 d . . . H20 H 0.7727 0.7066 0.2024 0.065 Uiso 1 1 calc R . . C21 C 0.8383(4) 0.78154(18) 0.16257(9) 0.0504(8) Uani 1 1 d . . . H21 H 0.8131 0.8216 0.1785 0.060 Uiso 1 1 calc R . . C22 C 0.8996(4) 0.79063(15) 0.12504(8) 0.0397(7) Uani 1 1 d . . . C23 C 0.7973(5) 0.89327(16) 0.09198(8) 0.0451(8) Uani 1 1 d . . . C24 C 0.8504(5) 0.96839(17) 0.08144(10) 0.0607(9) Uani 1 1 d . . . C25 C 1.0442(8) 0.9699(2) 0.06193(16) 0.1208(19) Uani 1 1 d . . . H25A H 1.0765 1.0191 0.0551 0.181 Uiso 1 1 calc R . . H25B H 1.0401 0.9408 0.0385 0.181 Uiso 1 1 calc R . . H25C H 1.1405 0.9509 0.0796 0.181 Uiso 1 1 calc R . . C26 C 0.7002(8) 0.9999(2) 0.05495(14) 0.1119(17) Uani 1 1 d . . . H26A H 0.7357 1.0488 0.0482 0.168 Uiso 1 1 calc R . . H26B H 0.5773 1.0002 0.0681 0.168 Uiso 1 1 calc R . . H26C H 0.6908 0.9712 0.0314 0.168 Uiso 1 1 calc R . . C27 C 0.8584(7) 1.0114(2) 0.11894(13) 0.1023(15) Uani 1 1 d . . . H27A H 0.8922 1.0608 0.1131 0.154 Uiso 1 1 calc R . . H27B H 0.9543 0.9908 0.1362 0.154 Uiso 1 1 calc R . . H27C H 0.7339 1.0101 0.1315 0.154 Uiso 1 1 calc R . . C28 C 0.8158(4) 0.78104(16) 0.33222(9) 0.0484(8) Uani 1 1 d . B . C29 C 0.6890(5) 0.80683(17) 0.35890(9) 0.0547(9) Uani 1 1 d . . . H29 H 0.7189 0.8048 0.3856 0.066 Uiso 1 1 calc R . . C30 C 0.5200(4) 0.83537(16) 0.34696(8) 0.0468(8) Uani 1 1 d . . . H30 H 0.4313 0.8526 0.3653 0.056 Uiso 1 1 calc R . . C31 C 0.4790(4) 0.83897(14) 0.30766(8) 0.0386(7) Uani 1 1 d . . . C32 C 0.6121(4) 0.81322(15) 0.28099(8) 0.0416(7) Uani 1 1 d . . . H32 H 0.5857 0.8165 0.2542 0.050 Uiso 1 1 calc R . . C33 C 0.7800(4) 0.78333(15) 0.29323(9) 0.0449(8) Uani 1 1 d . . . H33 H 0.8688 0.7648 0.2753 0.054 Uiso 1 1 calc R . . C34 C 0.3017(4) 0.87100(14) 0.29473(8) 0.0377(7) Uani 1 1 d . . . C35 C 0.2065(4) 0.87447(13) 0.26051(7) 0.0354(7) Uani 1 1 d . . . C36 C 0.0419(4) 0.91644(14) 0.26757(8) 0.0389(7) Uani 1 1 d . . . H36 H -0.0512 0.9294 0.2489 0.047 Uiso 1 1 calc R . . C37 C 0.0402(4) 0.93489(14) 0.30549(8) 0.0387(7) Uani 1 1 d . . . C38 C -0.0956(4) 0.97035(14) 0.33081(8) 0.0409(7) Uani 1 1 d . . . C39 C -0.0640(5) 0.97610(16) 0.37021(8) 0.0496(8) Uani 1 1 d . . . H39 H 0.0513 0.9589 0.3811 0.060 Uiso 1 1 calc R . . C40 C -0.2012(6) 1.00708(18) 0.39387(10) 0.0610(9) Uani 1 1 d . . . H40 H -0.1777 1.0112 0.4208 0.073 Uiso 1 1 calc R . . C41 C -0.3691(6) 1.03167(18) 0.37890(11) 0.0650(10) Uani 1 1 d . . . H41 H -0.4628 1.0517 0.3953 0.078 Uiso 1 1 calc R . . C42 C -0.4002(5) 1.02693(17) 0.33992(10) 0.0598(9) Uani 1 1 d . . . H42 H -0.5156 1.0445 0.3293 0.072 Uiso 1 1 calc R . . C43 C -0.2648(5) 0.99660(15) 0.31569(9) 0.0506(8) Uani 1 1 d . . . H43 H -0.2882 0.9939 0.2887 0.061 Uiso 1 1 calc R . . C44 C 0.2566(4) 0.83692(14) 0.22422(7) 0.0342(7) Uani 1 1 d . . . C45 C 0.2567(4) 0.76285(14) 0.22241(8) 0.0423(7) Uani 1 1 d . . . H45 H 0.2241 0.7360 0.2447 0.051 Uiso 1 1 calc R . . C46 C 0.3036(4) 0.72783(16) 0.18866(9) 0.0473(8) Uani 1 1 d . . . H46 H 0.3044 0.6773 0.1880 0.057 Uiso 1 1 calc R . . C47 C 0.3489(4) 0.76573(17) 0.15599(9) 0.0478(8) Uani 1 1 d . . . H47 H 0.3799 0.7413 0.1329 0.057 Uiso 1 1 calc R . . C48 C 0.3495(4) 0.83916(16) 0.15676(8) 0.0425(7) Uani 1 1 d . . . H48 H 0.3821 0.8657 0.1344 0.051 Uiso 1 1 calc R . . C49 C 0.3017(4) 0.87349(14) 0.19071(8) 0.0367(7) Uani 1 1 d . A . C50 C 0.4440(5) 0.98392(16) 0.20572(8) 0.0481(8) Uani 1 1 d . A . C51 C 0.4074(5) 1.06350(16) 0.20620(9) 0.0592(10) Uani 1 1 d . . . C52 C 0.6200(11) 1.0980(4) 0.2119(2) 0.060(2) Uiso 0.546(11) 1 d P A 1 H52A H 0.6969 1.0881 0.1890 0.090 Uiso 0.546(11) 1 calc PR A 1 H52B H 0.6810 1.0768 0.2346 0.090 Uiso 0.546(11) 1 calc PR A 1 H52C H 0.6091 1.1496 0.2155 0.090 Uiso 0.546(11) 1 calc PR A 1 C53 C 0.2979(14) 1.0783(4) 0.2393(2) 0.074(3) Uiso 0.546(11) 1 d P A 1 H53A H 0.3587 1.0570 0.2620 0.111 Uiso 0.546(11) 1 calc PR A 1 H53B H 0.1702 1.0583 0.2360 0.111 Uiso 0.546(11) 1 calc PR A 1 H53C H 0.2886 1.1300 0.2428 0.111 Uiso 0.546(11) 1 calc PR A 1 C52' C 0.5362(17) 1.1063(5) 0.2271(3) 0.080(3) Uiso 0.454(11) 1 d P A 2 H52D H 0.5593 1.0850 0.2525 0.120 Uiso 0.454(11) 1 calc PR A 2 H52E H 0.4826 1.1541 0.2303 0.120 Uiso 0.454(11) 1 calc PR A 2 H52F H 0.6563 1.1095 0.2130 0.120 Uiso 0.454(11) 1 calc PR A 2 C53' C 0.1944(14) 1.0796(4) 0.2279(2) 0.059(3) Uiso 0.454(11) 1 d P A 2 H53D H 0.0951 1.0511 0.2154 0.089 Uiso 0.454(11) 1 calc PR A 2 H53E H 0.1629 1.1303 0.2255 0.089 Uiso 0.454(11) 1 calc PR A 2 H53F H 0.2027 1.0668 0.2553 0.089 Uiso 0.454(11) 1 calc PR A 2 C54 C 0.3543(6) 1.08866(18) 0.16660(10) 0.0784(12) Uani 1 1 d . A . H54A H 0.3320 1.1402 0.1671 0.118 Uiso 1 1 calc R . . H54B H 0.2383 1.0643 0.1581 0.118 Uiso 1 1 calc R . . H54C H 0.4578 1.0780 0.1487 0.118 Uiso 1 1 calc R . . N1 N 0.2711(5) 0.56989(17) -0.02122(12) 0.0751(9) Uani 1 1 d . . . N2 N 0.9962(5) 0.74898(19) 0.34429(10) 0.0727(9) Uani 1 1 d . . . O1 O 0.2619(5) 0.5512(2) -0.05456(10) 0.1260(13) Uani 1 1 d . . . O2 O 0.1426(4) 0.56075(15) 0.00225(10) 0.0906(9) Uani 1 1 d . . . O3 O 1.0517(3) 0.73670(10) -0.00343(5) 0.0437(5) Uani 1 1 d . . . O4 O 0.9361(3) 0.86018(10) 0.11215(5) 0.0452(5) Uani 1 1 d . . . O5 O 0.6490(3) 0.86395(12) 0.08488(6) 0.0592(6) Uani 1 1 d . . . O6 O 1.0998(4) 0.72047(16) 0.32126(9) 0.0859(9) Uani 1 1 d . B . O7 O 1.0440(7) 0.7722(5) 0.37943(15) 0.073(3) Uiso 0.557(16) 1 d P B 3 O7' O 1.0188(9) 0.7323(6) 0.37653(19) 0.075(3) Uiso 0.443(16) 1 d P B 4 O8 O 0.1996(3) 0.90755(10) 0.32261(5) 0.0417(5) Uani 1 1 d . . . O9 O 0.2938(3) 0.94861(9) 0.19065(5) 0.0413(5) Uani 1 1 d . . . O10 O 0.5831(3) 0.95406(12) 0.21696(7) 0.0653(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 0.045(2) 0.0505(19) 0.061(2) 0.0047(16) -0.0138(17) -0.0044(15) C2 0.058(2) 0.074(2) 0.053(2) -0.0126(18) -0.0131(18) -0.0037(19) C3 0.048(2) 0.067(2) 0.047(2) -0.0093(16) -0.0014(15) -0.0067(17) C4 0.044(2) 0.0436(17) 0.0407(18) -0.0002(13) -0.0068(14) 0.0001(14) C5 0.050(2) 0.0518(19) 0.0470(19) 0.0037(15) -0.0031(16) -0.0025(16) C6 0.048(2) 0.0526(19) 0.054(2) 0.0118(16) -0.0002(16) -0.0036(16) C7 0.0451(19) 0.0430(17) 0.0355(17) 0.0024(13) 0.0013(14) -0.0001(14) C8 0.0444(18) 0.0366(15) 0.0350(17) 0.0008(13) -0.0022(13) 0.0022(13) C9 0.0457(19) 0.0423(16) 0.0355(17) -0.0011(13) -0.0065(13) -0.0035(14) C10 0.0446(19) 0.0389(16) 0.0365(17) -0.0006(13) -0.0059(14) -0.0011(14) C11 0.0482(19) 0.0354(15) 0.0337(17) 0.0031(12) -0.0022(14) 0.0001(13) C12 0.050(2) 0.0460(18) 0.0396(19) -0.0033(14) -0.0022(15) -0.0027(15) C13 0.068(2) 0.055(2) 0.0373(18) 0.0003(15) 0.0032(17) -0.0031(17) C14 0.065(2) 0.054(2) 0.047(2) 0.0072(16) 0.0098(17) -0.0034(17) C15 0.056(2) 0.063(2) 0.053(2) 0.0107(17) -0.0004(17) -0.0138(17) C16 0.062(2) 0.0548(19) 0.0347(17) 0.0066(14) -0.0090(16) -0.0091(17) C17 0.0370(18) 0.0459(18) 0.0371(17) 0.0052(14) -0.0067(13) -0.0034(13) C18 0.054(2) 0.0486(18) 0.049(2) 0.0034(15) -0.0081(16) 0.0027(15) C19 0.046(2) 0.061(2) 0.055(2) 0.0210(18) -0.0064(16) -0.0069(16) C20 0.045(2) 0.080(2) 0.0383(19) 0.0134(18) -0.0012(14) 0.0005(17) C21 0.043(2) 0.068(2) 0.0399(19) -0.0023(16) -0.0023(14) 0.0015(16) C22 0.0349(17) 0.0451(18) 0.0390(17) 0.0029(14) -0.0061(13) -0.0017(13) C23 0.053(2) 0.0517(19) 0.0305(17) -0.0038(14) -0.0024(15) 0.0068(16) C24 0.081(3) 0.0438(19) 0.058(2) -0.0006(16) 0.0010(19) 0.0059(18) C25 0.134(5) 0.059(3) 0.170(5) 0.038(3) 0.067(4) -0.004(3) C26 0.160(5) 0.061(3) 0.114(4) 0.015(3) -0.053(3) 0.016(3) C27 0.148(5) 0.059(3) 0.100(3) -0.027(2) -0.017(3) 0.000(3) C28 0.042(2) 0.0491(18) 0.054(2) 0.0177(16) -0.0164(16) -0.0063(15) C29 0.059(2) 0.065(2) 0.0400(19) 0.0150(16) -0.0168(17) -0.0103(18) C30 0.050(2) 0.0523(18) 0.0385(18) 0.0048(14) -0.0072(15) -0.0025(15) C31 0.0460(19) 0.0358(15) 0.0338(17) 0.0052(13) -0.0082(14) -0.0069(13) C32 0.0463(19) 0.0410(16) 0.0374(17) 0.0016(13) -0.0098(14) -0.0035(14) C33 0.0434(19) 0.0406(17) 0.051(2) 0.0045(14) -0.0068(15) -0.0055(14) C34 0.0452(19) 0.0342(15) 0.0337(16) 0.0001(12) -0.0003(14) -0.0021(13) C35 0.0432(18) 0.0315(15) 0.0316(16) 0.0025(12) -0.0048(13) -0.0027(13) C36 0.0432(18) 0.0337(15) 0.0396(17) 0.0043(13) -0.0046(13) -0.0023(13) C37 0.0455(19) 0.0331(15) 0.0376(17) 0.0033(13) -0.0043(14) -0.0035(13) C38 0.052(2) 0.0315(15) 0.0397(18) 0.0014(13) 0.0037(14) -0.0043(14) C39 0.060(2) 0.0480(18) 0.0410(19) -0.0033(15) 0.0040(16) -0.0056(16) C40 0.078(3) 0.059(2) 0.046(2) -0.0112(17) 0.0094(19) -0.0083(19) C41 0.069(3) 0.062(2) 0.065(3) -0.0156(19) 0.021(2) 0.000(2) C42 0.063(2) 0.051(2) 0.066(2) -0.0076(17) 0.0080(18) 0.0083(17) C43 0.061(2) 0.0408(17) 0.050(2) -0.0012(15) 0.0049(17) 0.0013(16) C44 0.0350(17) 0.0355(15) 0.0320(16) -0.0009(12) -0.0100(12) 0.0014(12) C45 0.0452(19) 0.0353(17) 0.0464(19) 0.0021(14) -0.0123(14) 0.0001(13) C46 0.046(2) 0.0393(17) 0.057(2) -0.0110(16) -0.0128(16) 0.0068(14) C47 0.0429(19) 0.056(2) 0.0441(19) -0.0157(16) -0.0087(15) 0.0066(15) C48 0.0425(19) 0.0507(19) 0.0341(17) -0.0023(14) -0.0074(13) -0.0003(14) C49 0.0401(18) 0.0335(15) 0.0366(17) -0.0010(13) -0.0105(13) -0.0008(13) C50 0.065(2) 0.0485(19) 0.0302(17) 0.0047(14) -0.0102(16) -0.0138(17) C51 0.101(3) 0.0388(18) 0.0377(19) 0.0000(14) -0.0043(18) -0.0148(18) C54 0.125(4) 0.045(2) 0.065(2) 0.0145(18) -0.003(2) 0.013(2) N1 0.063(2) 0.073(2) 0.089(3) 0.0086(19) -0.025(2) -0.0178(18) N2 0.061(2) 0.098(3) 0.059(2) 0.033(2) -0.0117(17) -0.0080(19) O1 0.102(3) 0.182(4) 0.094(2) -0.033(2) -0.0323(19) -0.053(2) O2 0.065(2) 0.091(2) 0.115(2) 0.0107(17) -0.0138(17) -0.0305(16) O3 0.0457(13) 0.0490(12) 0.0364(11) -0.0022(9) -0.0035(9) -0.0079(10) O4 0.0451(13) 0.0430(12) 0.0474(12) 0.0000(9) -0.0070(10) 0.0000(9) O5 0.0561(16) 0.0734(15) 0.0480(14) 0.0098(11) -0.0144(11) -0.0009(12) O6 0.0577(19) 0.103(2) 0.096(2) 0.0211(17) -0.0058(16) 0.0181(16) O8 0.0502(13) 0.0440(11) 0.0307(11) -0.0008(9) -0.0042(9) 0.0002(10) O9 0.0538(13) 0.0335(11) 0.0366(11) 0.0015(8) -0.0085(9) -0.0017(9) O10 0.0665(17) 0.0562(14) 0.0731(17) 0.0110(12) -0.0267(13) -0.0161(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.361(4) . ? C1 C2 1.379(5) . ? C1 N1 1.468(4) . ? C2 C3 1.384(4) . ? C2 H2 0.9500 . ? C3 C4 1.392(4) . ? C3 H3 0.9500 . ? C4 C5 1.404(4) . ? C4 C7 1.450(4) . ? C5 C6 1.383(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.363(4) . ? C7 O3 1.395(3) . ? C8 C9 1.433(4) . ? C8 C17 1.490(4) . ? C9 C10 1.350(4) . ? C9 H9 0.9500 . ? C10 O3 1.362(3) . ? C10 C11 1.469(4) . ? C11 C16 1.384(4) . ? C11 C12 1.384(4) . ? C12 C13 1.390(4) . ? C12 H12 0.9500 . ? C13 C14 1.380(4) . ? C13 H13 0.9500 . ? C14 C15 1.374(4) . ? C14 H14 0.9500 . ? C15 C16 1.390(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.391(4) . ? C17 C18 1.398(4) . ? C18 C19 1.390(4) . ? C18 H18 0.9500 . ? C19 C20 1.371(4) . ? C19 H19 0.9500 . ? C20 C21 1.376(4) . ? C20 H20 0.9500 . ? C21 C22 1.383(4) . ? C21 H21 0.9500 . ? C22 O4 1.405(3) . ? C23 O5 1.205(4) . ? C23 O4 1.351(3) . ? C23 C24 1.505(4) . ? C24 C26 1.518(5) . ? C24 C27 1.531(5) . ? C24 C25 1.524(5) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.375(4) . ? C28 C33 1.374(4) . ? C28 N2 1.465(4) . ? C29 C30 1.367(4) . ? C29 H29 0.9500 . ? C30 C31 1.393(4) . ? C30 H30 0.9500 . ? C31 C32 1.404(4) . ? C31 C34 1.454(4) . ? C32 C33 1.374(4) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C35 1.362(4) . ? C34 O8 1.388(3) . ? C35 C36 1.423(4) . ? C35 C44 1.486(4) . ? C36 C37 1.359(4) . ? C36 H36 0.9500 . ? C37 O8 1.367(3) . ? C37 C38 1.460(4) . ? C38 C39 1.387(4) . ? C38 C43 1.390(4) . ? C39 C40 1.396(4) . ? C39 H39 0.9500 . ? C40 C41 1.369(5) . ? C40 H40 0.9500 . ? C41 C42 1.371(5) . ? C41 H41 0.9500 . ? C42 C43 1.394(4) . ? C42 H42 0.9500 . ? C43 H43 0.9500 . ? C44 C49 1.387(4) . ? C44 C45 1.392(4) . ? C45 C46 1.383(4) . ? C45 H45 0.9500 . ? C46 C47 1.376(4) . ? C46 H46 0.9500 . ? C47 C48 1.379(4) . ? C47 H47 0.9500 . ? C48 C49 1.384(4) . ? C48 H48 0.9500 . ? C49 O9 1.412(3) . ? C50 O10 1.192(4) . ? C50 O9 1.352(3) . ? C50 C51 1.517(4) . ? C51 C52' 1.409(9) . ? C51 C53 1.411(8) . ? C51 C54 1.498(4) . ? C51 C52 1.642(8) . ? C51 C53' 1.707(9) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C52' H52D 0.9800 . ? C52' H52E 0.9800 . ? C52' H52F 0.9800 . ? C53' H53D 0.9800 . ? C53' H53E 0.9800 . ? C53' H53F 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? N1 O1 1.209(4) . ? N1 O2 1.230(4) . ? N2 O7' 1.171(7) . ? N2 O6 1.208(4) . ? N2 O7 1.336(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 122.7(3) . . ? C6 C1 N1 118.8(3) . . ? C2 C1 N1 118.5(3) . . ? C1 C2 C3 119.3(3) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 119.0(3) . . ? C3 C4 C7 119.5(3) . . ? C5 C4 C7 121.5(3) . . ? C6 C5 C4 121.0(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C1 C6 C5 118.3(3) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? C8 C7 O3 108.8(3) . . ? C8 C7 C4 136.6(3) . . ? O3 C7 C4 114.6(2) . . ? C7 C8 C9 105.8(2) . . ? C7 C8 C17 127.9(3) . . ? C9 C8 C17 126.1(2) . . ? C10 C9 C8 108.5(2) . . ? C10 C9 H9 125.7 . . ? C8 C9 H9 125.7 . . ? C9 C10 O3 108.7(3) . . ? C9 C10 C11 134.7(3) . . ? O3 C10 C11 116.6(2) . . ? C16 C11 C12 118.3(3) . . ? C16 C11 C10 120.9(3) . . ? C12 C11 C10 120.8(3) . . ? C11 C12 C13 120.8(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.1(3) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 120.6(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 120.8(3) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C22 C17 C18 116.9(3) . . ? C22 C17 C8 121.6(2) . . ? C18 C17 C8 121.3(3) . . ? C17 C18 C19 120.6(3) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 120.6(3) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 120.2(3) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C20 C21 C22 119.1(3) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C21 C22 C17 122.6(3) . . ? C21 C22 O4 118.2(3) . . ? C17 C22 O4 119.2(2) . . ? O5 C23 O4 121.3(3) . . ? O5 C23 C24 126.5(3) . . ? O4 C23 C24 112.1(3) . . ? C23 C24 C26 109.9(3) . . ? C23 C24 C27 107.3(3) . . ? C26 C24 C27 109.3(3) . . ? C23 C24 C25 110.4(3) . . ? C26 C24 C25 110.3(4) . . ? C27 C24 C25 109.7(4) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C33 122.2(3) . . ? C29 C28 N2 121.1(3) . . ? C33 C28 N2 116.7(3) . . ? C30 C29 C28 120.0(3) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C31 119.5(3) . . ? C29 C30 H30 120.3 . . ? C31 C30 H30 120.3 . . ? C30 C31 C32 119.4(3) . . ? C30 C31 C34 119.7(3) . . ? C32 C31 C34 120.9(2) . . ? C33 C32 C31 120.8(3) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C32 C33 C28 118.1(3) . . ? C32 C33 H33 121.0 . . ? C28 C33 H33 121.0 . . ? C35 C34 O8 109.2(2) . . ? C35 C34 C31 135.0(3) . . ? O8 C34 C31 115.8(2) . . ? C34 C35 C36 106.0(2) . . ? C34 C35 C44 126.7(3) . . ? C36 C35 C44 127.2(2) . . ? C37 C36 C35 108.5(2) . . ? C37 C36 H36 125.8 . . ? C35 C36 H36 125.8 . . ? C36 C37 O8 108.3(2) . . ? C36 C37 C38 134.8(3) . . ? O8 C37 C38 116.6(2) . . ? C39 C38 C43 118.5(3) . . ? C39 C38 C37 121.6(3) . . ? C43 C38 C37 119.8(3) . . ? C38 C39 C40 120.1(3) . . ? C38 C39 H39 119.9 . . ? C40 C39 H39 119.9 . . ? C41 C40 C39 121.0(3) . . ? C41 C40 H40 119.5 . . ? C39 C40 H40 119.5 . . ? C40 C41 C42 119.1(3) . . ? C40 C41 H41 120.4 . . ? C42 C41 H41 120.4 . . ? C41 C42 C43 120.8(3) . . ? C41 C42 H42 119.6 . . ? C43 C42 H42 119.6 . . ? C42 C43 C38 120.3(3) . . ? C42 C43 H43 119.8 . . ? C38 C43 H43 119.8 . . ? C49 C44 C45 117.2(2) . . ? C49 C44 C35 122.0(2) . . ? C45 C44 C35 120.8(2) . . ? C46 C45 C44 120.9(3) . . ? C46 C45 H45 119.6 . . ? C44 C45 H45 119.6 . . ? C47 C46 C45 120.4(3) . . ? C47 C46 H46 119.8 . . ? C45 C46 H46 119.8 . . ? C48 C47 C46 120.1(3) . . ? C48 C47 H47 119.9 . . ? C46 C47 H47 119.9 . . ? C47 C48 C49 118.8(3) . . ? C47 C48 H48 120.6 . . ? C49 C48 H48 120.6 . . ? C48 C49 C44 122.5(2) . . ? C48 C49 O9 118.3(2) . . ? C44 C49 O9 119.1(2) . . ? O10 C50 O9 122.4(3) . . ? O10 C50 C51 126.8(3) . . ? O9 C50 C51 110.8(3) . . ? C52' C51 C53 79.8(5) . . ? C52' C51 C54 116.6(5) . . ? C53 C51 C54 123.2(5) . . ? C52' C51 C50 117.3(5) . . ? C53 C51 C50 107.2(4) . . ? C54 C51 C50 110.0(3) . . ? C52' C51 C52 29.4(5) . . ? C53 C51 C52 108.9(5) . . ? C54 C51 C52 102.2(4) . . ? C50 C51 C52 103.6(4) . . ? C52' C51 C53' 103.7(6) . . ? C53 C51 C53' 28.8(4) . . ? C54 C51 C53' 97.6(4) . . ? C50 C51 C53' 109.2(3) . . ? C52 C51 C53' 132.7(4) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C51 C53 H53A 109.5 . . ? C51 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C51 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C51 C52' H52D 109.5 . . ? C51 C52' H52E 109.5 . . ? H52D C52' H52E 109.5 . . ? C51 C52' H52F 109.5 . . ? H52D C52' H52F 109.5 . . ? H52E C52' H52F 109.5 . . ? C51 C53' H53D 109.5 . . ? C51 C53' H53E 109.5 . . ? H53D C53' H53E 109.5 . . ? C51 C53' H53F 109.5 . . ? H53D C53' H53F 109.5 . . ? H53E C53' H53F 109.5 . . ? C51 C54 H54A 109.5 . . ? C51 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C51 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? O1 N1 O2 123.7(3) . . ? O1 N1 C1 118.5(4) . . ? O2 N1 C1 117.9(4) . . ? O7' N2 O6 115.5(5) . . ? O7' N2 O7 35.3(4) . . ? O6 N2 O7 126.6(4) . . ? O7' N2 C28 119.8(5) . . ? O6 N2 C28 121.2(3) . . ? O7 N2 C28 110.0(4) . . ? C10 O3 C7 108.2(2) . . ? C23 O4 C22 117.4(2) . . ? C37 O8 C34 108.0(2) . . ? C50 O9 C49 117.3(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.371 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.042 data_12404 _database_code_depnum_ccdc_archive 'CCDC 866846' #TrackingRef '- 20a (CCDC 866846).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H27 N1 O2' _chemical_formula_sum 'C36 H27 N O2' _chemical_formula_weight 505.59 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/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 10.6388(2) _cell_length_b 17.7523(4) _cell_length_c 14.6042(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.6850(10) _cell_angle_gamma 90.00 _cell_volume 2679.89(10) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 14841 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9267 _exptl_absorpt_correction_T_max 1.0296 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22582 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_sigmaI/netI 0.0753 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4725 _reflns_number_gt 2696 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1600P)^2^+0.0775P] 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 4725 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1566 _refine_ls_R_factor_gt 0.0849 _refine_ls_wR_factor_ref 0.3100 _refine_ls_wR_factor_gt 0.2605 _refine_ls_goodness_of_fit_ref 1.233 _refine_ls_restrained_S_all 1.233 _refine_ls_shift/su_max 0.032 _refine_ls_shift/su_mean 0.021 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.9402(3) 0.18756(16) 0.2026(2) 0.0470(8) Uani 1 1 d . . . O2 O 1.0447(4) 0.2700(2) 0.3097(3) 0.0856(13) Uani 1 1 d . . . N1 N 0.6443(3) 0.15938(19) 0.3650(2) 0.0374(9) Uani 1 1 d . . . C1 C 0.9697(5) 0.2578(3) 0.2357(3) 0.0528(13) Uani 1 1 d . . . C2 C 0.9033(4) 0.3167(2) 0.1679(3) 0.0440(11) Uani 1 1 d . . . C3 C 0.8356(4) 0.2986(3) 0.0772(3) 0.0489(12) Uani 1 1 d . . . H3 H 0.8270 0.2475 0.0575 0.059 Uiso 1 1 calc R . . C4 C 0.7805(5) 0.3553(3) 0.0152(4) 0.0559(13) Uani 1 1 d . . . H4 H 0.7332 0.3431 -0.0467 0.067 Uiso 1 1 calc R . . C5 C 0.7946(5) 0.4288(3) 0.0438(4) 0.0657(15) Uani 1 1 d . . . H5 H 0.7600 0.4678 0.0006 0.079 Uiso 1 1 calc R . . C6 C 0.8584(5) 0.4467(3) 0.1345(4) 0.0716(16) Uani 1 1 d . . . H6 H 0.8653 0.4978 0.1544 0.086 Uiso 1 1 calc R . . C7 C 0.9129(5) 0.3900(3) 0.1971(4) 0.0606(14) Uani 1 1 d . . . H7 H 0.9567 0.4022 0.2599 0.073 Uiso 1 1 calc R . . C8 C 1.0082(4) 0.1278(2) 0.2578(3) 0.0425(11) Uani 1 1 d . . . C9 C 1.1250(4) 0.1054(2) 0.2293(3) 0.0435(11) Uani 1 1 d . . . C10 C 1.1587(5) 0.1384(3) 0.1517(4) 0.0605(14) Uani 1 1 d . . . H10 H 1.1068 0.1775 0.1177 0.073 Uiso 1 1 calc R . . C11 C 1.2682(5) 0.1139(4) 0.1242(4) 0.0725(18) Uani 1 1 d . . . H11 H 1.2913 0.1368 0.0717 0.087 Uiso 1 1 calc R . . C12 C 1.3423(5) 0.0578(3) 0.1714(4) 0.0653(16) Uani 1 1 d . . . H12 H 1.4167 0.0414 0.1517 0.078 Uiso 1 1 calc R . . C13 C 1.3110(5) 0.0253(3) 0.2459(4) 0.0609(14) Uani 1 1 d . . . H13 H 1.3635 -0.0139 0.2789 0.073 Uiso 1 1 calc R . . C14 C 1.2041(4) 0.0484(2) 0.2742(3) 0.0481(12) Uani 1 1 d . . . H14 H 1.1832 0.0243 0.3268 0.058 Uiso 1 1 calc R . . C15 C 0.9564(4) 0.0963(2) 0.3225(3) 0.0414(11) Uani 1 1 d . . . H15 H 0.9989 0.0524 0.3518 0.050 Uiso 1 1 calc R . . C16 C 0.8433(4) 0.1197(2) 0.3547(3) 0.0395(11) Uani 1 1 d . . . C17 C 0.8387(4) 0.1232(2) 0.4523(3) 0.0405(11) Uani 1 1 d . . . C18 C 0.9302(4) 0.1085(2) 0.5369(3) 0.0489(12) Uani 1 1 d . . . H18 H 1.0144 0.0911 0.5364 0.059 Uiso 1 1 calc R . . C19 C 0.8946(5) 0.1200(3) 0.6216(3) 0.0542(13) Uani 1 1 d . . . H19 H 0.9555 0.1101 0.6793 0.065 Uiso 1 1 calc R . . C20 C 0.7724(5) 0.1456(3) 0.6235(3) 0.0570(14) Uani 1 1 d . . . H20 H 0.7515 0.1532 0.6825 0.068 Uiso 1 1 calc R . . C21 C 0.6791(5) 0.1604(3) 0.5406(3) 0.0493(12) Uani 1 1 d . . . H21 H 0.5948 0.1773 0.5419 0.059 Uiso 1 1 calc R . . C22 C 0.7158(4) 0.1491(2) 0.4556(3) 0.0395(11) Uani 1 1 d . . . C23 C 0.5146(4) 0.1906(2) 0.3439(3) 0.0422(11) Uani 1 1 d . . . H23A H 0.4633 0.1645 0.3827 0.051 Uiso 1 1 calc R . . H23B H 0.4729 0.1809 0.2769 0.051 Uiso 1 1 calc R . . C24 C 0.5125(5) 0.2739(2) 0.3622(3) 0.0475(12) Uani 1 1 d . . . C25 C 0.6201(6) 0.3179(3) 0.3678(4) 0.0708(17) Uani 1 1 d . . . H25 H 0.6988 0.2963 0.3603 0.085 Uiso 1 1 calc R . . C26 C 0.6117(8) 0.3983(4) 0.3854(4) 0.100(2) Uani 1 1 d . . . H26 H 0.6830 0.4314 0.3898 0.120 Uiso 1 1 calc R . . C27 C 0.4979(7) 0.4216(5) 0.3947(5) 0.098(2) Uani 1 1 d . . . H27 H 0.4937 0.4741 0.4066 0.117 Uiso 1 1 calc R . . C28 C 0.3925(9) 0.3862(5) 0.3907(5) 0.118(3) Uani 1 1 d . . . H28 H 0.3160 0.4105 0.3981 0.142 Uiso 1 1 calc R . . C29 C 0.3986(6) 0.3068(4) 0.3739(4) 0.085(2) Uani 1 1 d . . . H29 H 0.3242 0.2764 0.3708 0.102 Uiso 1 1 calc R . . C30 C 0.7219(4) 0.1415(2) 0.3031(3) 0.0372(10) Uani 1 1 d . . . C31 C 0.6710(4) 0.1392(2) 0.1997(3) 0.0378(10) Uani 1 1 d . . . C32 C 0.6919(4) 0.0748(3) 0.1514(3) 0.0461(12) Uani 1 1 d . . . H32 H 0.7387 0.0337 0.1848 0.055 Uiso 1 1 calc R . . C33 C 0.6449(5) 0.0702(3) 0.0548(3) 0.0607(14) Uani 1 1 d . . . H33 H 0.6601 0.0260 0.0225 0.073 Uiso 1 1 calc R . . C34 C 0.5759(5) 0.1290(3) 0.0046(3) 0.0604(14) Uani 1 1 d . . . H34 H 0.5431 0.1251 -0.0616 0.072 Uiso 1 1 calc R . . C35 C 0.5556(5) 0.1934(3) 0.0521(3) 0.0561(13) Uani 1 1 d . . . H35 H 0.5093 0.2344 0.0181 0.067 Uiso 1 1 calc R . . C36 C 0.6020(4) 0.1988(2) 0.1483(3) 0.0443(11) Uani 1 1 d . . . H36 H 0.5869 0.2433 0.1801 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0492(18) 0.0387(18) 0.0496(19) 0.0054(14) 0.0050(15) -0.0020(14) O2 0.115(3) 0.066(3) 0.057(2) -0.0032(19) -0.017(2) -0.004(2) N1 0.041(2) 0.041(2) 0.030(2) -0.0029(15) 0.0080(17) 0.0036(16) C1 0.068(3) 0.046(3) 0.041(3) -0.004(2) 0.007(3) -0.006(2) C2 0.047(3) 0.041(3) 0.046(3) 0.003(2) 0.015(2) -0.003(2) C3 0.047(3) 0.049(3) 0.051(3) 0.000(2) 0.013(2) 0.000(2) C4 0.059(3) 0.054(3) 0.052(3) 0.009(2) 0.009(3) 0.012(2) C5 0.071(4) 0.051(3) 0.073(4) 0.016(3) 0.014(3) 0.014(3) C6 0.082(4) 0.045(3) 0.081(4) -0.001(3) 0.007(3) 0.003(3) C7 0.081(4) 0.037(3) 0.060(3) -0.004(2) 0.008(3) 0.000(3) C8 0.043(3) 0.042(3) 0.043(3) 0.008(2) 0.013(2) 0.008(2) C9 0.044(3) 0.044(3) 0.042(3) -0.003(2) 0.010(2) -0.006(2) C10 0.050(3) 0.081(4) 0.050(3) 0.012(3) 0.011(3) 0.001(3) C11 0.055(3) 0.123(5) 0.045(3) -0.012(3) 0.021(3) -0.032(4) C12 0.035(3) 0.090(4) 0.068(4) -0.040(3) 0.007(3) -0.007(3) C13 0.048(3) 0.060(3) 0.079(4) -0.010(3) 0.023(3) -0.003(3) C14 0.044(3) 0.047(3) 0.056(3) 0.000(2) 0.015(2) 0.003(2) C15 0.043(3) 0.038(2) 0.043(3) 0.004(2) 0.010(2) 0.006(2) C16 0.043(3) 0.037(2) 0.039(3) 0.0050(19) 0.012(2) 0.002(2) C17 0.050(3) 0.033(2) 0.036(3) 0.0009(18) 0.006(2) -0.007(2) C18 0.046(3) 0.047(3) 0.049(3) 0.007(2) 0.002(2) -0.003(2) C19 0.063(3) 0.062(3) 0.032(3) 0.010(2) 0.000(2) -0.011(3) C20 0.077(4) 0.059(3) 0.036(3) 0.003(2) 0.015(3) -0.004(3) C21 0.058(3) 0.052(3) 0.041(3) -0.003(2) 0.017(2) 0.002(2) C22 0.049(3) 0.034(2) 0.036(3) -0.0028(18) 0.011(2) -0.003(2) C23 0.040(3) 0.049(3) 0.039(3) -0.002(2) 0.011(2) 0.001(2) C24 0.070(3) 0.043(3) 0.026(2) -0.0016(19) 0.006(2) 0.016(3) C25 0.108(5) 0.036(3) 0.052(3) -0.003(2) -0.013(3) -0.010(3) C26 0.124 0.099(5) 0.050(4) 0.016(3) -0.032(4) -0.049(4) C27 0.071 0.156(7) 0.053 -0.010(4) -0.010(4) 0.043(5) C28 0.151(7) 0.155(8) 0.049(4) 0.017(4) 0.023(5) 0.121(7) C29 0.123(5) 0.093(5) 0.047(3) 0.019(3) 0.034(3) 0.072(4) C30 0.045(3) 0.033(2) 0.035(2) -0.0009(18) 0.010(2) 0.0033(19) C31 0.034(2) 0.045(3) 0.035(2) -0.001(2) 0.0095(19) -0.0010(19) C32 0.051(3) 0.048(3) 0.039(3) -0.003(2) 0.010(2) 0.008(2) C33 0.074(4) 0.064(3) 0.043(3) -0.017(3) 0.012(3) 0.000(3) C34 0.059(3) 0.082(4) 0.035(3) 0.000(3) 0.003(2) -0.005(3) C35 0.059(3) 0.062(3) 0.044(3) 0.009(2) 0.005(2) 0.002(3) C36 0.042(3) 0.044(3) 0.045(3) -0.001(2) 0.008(2) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.347(5) . ? O1 C8 1.423(5) . ? O2 C1 1.201(6) . ? N1 C22 1.373(5) . ? N1 C30 1.397(5) . ? N1 C23 1.451(5) . ? C1 C2 1.497(6) . ? C2 C7 1.366(6) . ? C2 C3 1.387(6) . ? C3 C4 1.386(6) . ? C3 H3 0.9500 . ? C4 C5 1.367(7) . ? C4 H4 0.9500 . ? C5 C6 1.375(7) . ? C5 H5 0.9500 . ? C6 C7 1.391(7) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C15 1.325(6) . ? C8 C9 1.456(6) . ? C9 C14 1.378(6) . ? C9 C10 1.397(6) . ? C10 C11 1.388(7) . ? C10 H10 0.9500 . ? C11 C12 1.353(8) . ? C11 H11 0.9500 . ? C12 C13 1.341(7) . ? C12 H12 0.9500 . ? C13 C14 1.362(7) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.452(6) . ? C15 H15 0.9500 . ? C16 C30 1.388(6) . ? C16 C17 1.439(6) . ? C17 C22 1.398(6) . ? C17 C18 1.405(6) . ? C18 C19 1.391(7) . ? C18 H18 0.9500 . ? C19 C20 1.383(7) . ? C19 H19 0.9500 . ? C20 C21 1.396(6) . ? C20 H20 0.9500 . ? C21 C22 1.401(6) . ? C21 H21 0.9500 . ? C23 C24 1.504(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.372(7) . ? C24 C29 1.392(7) . ? C25 C26 1.456(8) . ? C25 H25 0.9500 . ? C26 C27 1.317(9) . ? C26 H26 0.9500 . ? C27 C28 1.274(11) . ? C27 H27 0.9500 . ? C28 C29 1.436(10) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C31 1.479(6) . ? C31 C32 1.390(6) . ? C31 C36 1.399(6) . ? C32 C33 1.382(6) . ? C32 H32 0.9500 . ? C33 C34 1.382(7) . ? C33 H33 0.9500 . ? C34 C35 1.381(7) . ? C34 H34 0.9500 . ? C35 C36 1.378(6) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C8 116.3(4) . . ? C22 N1 C30 108.4(3) . . ? C22 N1 C23 122.5(3) . . ? C30 N1 C23 128.8(3) . . ? O2 C1 O1 122.6(4) . . ? O2 C1 C2 125.3(4) . . ? O1 C1 C2 112.1(4) . . ? C7 C2 C3 120.1(4) . . ? C7 C2 C1 118.0(4) . . ? C3 C2 C1 121.8(4) . . ? C4 C3 C2 120.0(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 119.6(5) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.6(5) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C7 120.0(5) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C2 C7 C6 119.7(5) . . ? C2 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C15 C8 O1 118.5(4) . . ? C15 C8 C9 128.0(4) . . ? O1 C8 C9 113.3(4) . . ? C14 C9 C10 116.7(4) . . ? C14 C9 C8 122.1(4) . . ? C10 C9 C8 121.2(4) . . ? C9 C10 C11 119.8(5) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.7(5) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 120.2(5) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.1(5) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C9 122.4(5) . . ? C13 C14 H14 118.8 . . ? C9 C14 H14 118.8 . . ? C8 C15 C16 128.8(4) . . ? C8 C15 H15 115.6 . . ? C16 C15 H15 115.6 . . ? C30 C16 C17 106.3(4) . . ? C30 C16 C15 129.8(4) . . ? C17 C16 C15 123.9(4) . . ? C22 C17 C18 119.3(4) . . ? C22 C17 C16 107.4(4) . . ? C18 C17 C16 133.2(4) . . ? C19 C18 C17 118.5(4) . . ? C19 C18 H18 120.8 . . ? C17 C18 H18 120.8 . . ? C20 C19 C18 121.4(4) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C21 C20 C19 121.5(5) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? C20 C21 C22 116.8(4) . . ? C20 C21 H21 121.6 . . ? C22 C21 H21 121.6 . . ? N1 C22 C17 108.7(4) . . ? N1 C22 C21 128.9(4) . . ? C17 C22 C21 122.4(4) . . ? N1 C23 C24 113.1(4) . . ? N1 C23 H23A 109.0 . . ? C24 C23 H23A 109.0 . . ? N1 C23 H23B 109.0 . . ? C24 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C25 C24 C29 119.5(5) . . ? C25 C24 C23 121.5(4) . . ? C29 C24 C23 119.0(5) . . ? C24 C25 C26 118.8(6) . . ? C24 C25 H25 120.6 . . ? C26 C25 H25 120.5 . . ? C27 C26 C25 115.0(7) . . ? C27 C26 H26 122.4 . . ? C25 C26 H26 122.6 . . ? C28 C27 C26 131.3(9) . . ? C28 C27 H27 114.2 . . ? C26 C27 H27 114.4 . . ? C27 C28 C29 114.7(7) . . ? C27 C28 H28 122.7 . . ? C29 C28 H28 122.6 . . ? C28 C29 C24 120.5(7) . . ? C28 C29 H29 119.8 . . ? C24 C29 H29 119.7 . . ? C16 C30 N1 109.2(4) . . ? C16 C30 C31 128.0(4) . . ? N1 C30 C31 122.5(4) . . ? C32 C31 C36 118.4(4) . . ? C32 C31 C30 118.5(4) . . ? C36 C31 C30 123.1(4) . . ? C33 C32 C31 120.2(4) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C34 C33 C32 121.1(5) . . ? C34 C33 H33 119.4 . . ? C32 C33 H33 119.4 . . ? C33 C34 C35 119.0(5) . . ? C33 C34 H34 120.5 . . ? C35 C34 H34 120.5 . . ? C36 C35 C34 120.6(5) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C31 120.7(4) . . ? C35 C36 H36 119.6 . . ? C31 C36 H36 119.6 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.724 _refine_diff_density_min -0.723 _refine_diff_density_rms 0.130 data_12694 _database_code_depnum_ccdc_archive 'CCDC 866847' #TrackingRef '- 20b (CCDC 866847).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H29 N O3' _chemical_formula_sum 'C37 H29 N O3' _chemical_formula_weight 535.61 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' 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 14.8668(3) _cell_length_b 11.2853(3) _cell_length_c 18.3823(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.5910(10) _cell_angle_gamma 90.00 _cell_volume 2905.57(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11611 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_T_max 1.0569 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24498 _diffrn_reflns_av_R_equivalents 0.1020 _diffrn_reflns_av_sigmaI/netI 0.1086 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4948 _reflns_number_gt 2285 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0909P)^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 4948 _refine_ls_number_parameters 368 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1750 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.2022 _refine_ls_wR_factor_gt 0.1365 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1788(2) 0.3352(3) 0.32244(19) 0.0920(11) Uani 1 1 d . . . O2 O 0.13077(17) 0.1578(2) 0.26759(13) 0.0571(7) Uani 1 1 d . . . O3 O 0.6755(2) 0.3835(3) 0.52173(18) 0.0863(10) Uani 1 1 d . . . N1 N 0.3127(2) 0.0704(3) 0.53442(16) 0.0513(8) Uani 1 1 d . . . C1 C 0.1184(3) 0.2614(5) 0.3011(2) 0.0618(12) Uani 1 1 d . . . C2 C 0.0214(3) 0.2669(4) 0.3079(2) 0.0684(13) Uani 1 1 d . . . C3 C -0.0472(3) 0.1818(5) 0.2774(3) 0.0859(15) Uani 1 1 d . . . H3 H -0.0340 0.1179 0.2507 0.103 Uiso 1 1 calc R . . C4 C -0.1364(4) 0.1908(6) 0.2864(3) 0.1095(18) Uani 1 1 d . . . H4 H -0.1829 0.1335 0.2660 0.131 Uiso 1 1 calc R . . C5 C -0.1538(5) 0.2850(7) 0.3254(4) 0.118(2) Uani 1 1 d . . . H5 H -0.2131 0.2900 0.3318 0.142 Uiso 1 1 calc R . . C6 C -0.0897(5) 0.3720(6) 0.3555(3) 0.1133(19) Uani 1 1 d . . . H6 H -0.1046 0.4360 0.3812 0.136 Uiso 1 1 calc R . . C7 C 0.0002(4) 0.3625(4) 0.3466(3) 0.0899(15) Uani 1 1 d . . . H7 H 0.0459 0.4209 0.3669 0.108 Uiso 1 1 calc R . . C8 C 0.2227(3) 0.1328(3) 0.2650(2) 0.0505(10) Uani 1 1 d . . . C9 C 0.2279(3) 0.1373(3) 0.1872(2) 0.0508(10) Uani 1 1 d . . . C10 C 0.1549(3) 0.1874(4) 0.1269(2) 0.0668(12) Uani 1 1 d . . . H10 H 0.1031 0.2215 0.1366 0.080 Uiso 1 1 calc R . . C11 C 0.1580(3) 0.1875(4) 0.0526(2) 0.0776(13) Uani 1 1 d . . . H11 H 0.1083 0.2214 0.0129 0.093 Uiso 1 1 calc R . . C12 C 0.2334(4) 0.1381(4) 0.0370(3) 0.0775(13) Uani 1 1 d . . . H12 H 0.2350 0.1374 -0.0132 0.093 Uiso 1 1 calc R . . C13 C 0.3065(3) 0.0898(4) 0.0962(3) 0.0746(13) Uani 1 1 d . . . H13 H 0.3587 0.0572 0.0862 0.090 Uiso 1 1 calc R . . C14 C 0.3042(3) 0.0885(3) 0.1701(2) 0.0614(11) Uani 1 1 d . . . H14 H 0.3544 0.0545 0.2093 0.074 Uiso 1 1 calc R . . C15 C 0.2904(3) 0.1015(3) 0.3300(2) 0.0508(10) Uani 1 1 d . . . H15 H 0.3513 0.0910 0.3275 0.061 Uiso 1 1 calc R . . C16 C 0.2791(2) 0.0816(3) 0.4051(2) 0.0498(10) Uani 1 1 d . . . C17 C 0.3446(3) 0.1127(3) 0.47546(19) 0.0468(9) Uani 1 1 d . . . C18 C 0.4327(3) 0.1803(3) 0.49075(19) 0.0462(9) Uani 1 1 d . . . C19 C 0.4301(3) 0.2876(4) 0.4524(2) 0.0567(11) Uani 1 1 d . . . H19 H 0.3724 0.3160 0.4188 0.068 Uiso 1 1 calc R . . C20 C 0.5124(3) 0.3514(4) 0.4642(2) 0.0625(11) Uani 1 1 d . . . H20 H 0.5097 0.4227 0.4382 0.075 Uiso 1 1 calc R . . C21 C 0.5993(3) 0.3117(4) 0.5140(2) 0.0562(11) Uani 1 1 d . . . C22 C 0.7678(3) 0.3386(5) 0.5600(3) 0.120(2) Uani 1 1 d . . . H22A H 0.8143 0.3983 0.5615 0.180 Uiso 1 1 calc R . . H22B H 0.7786 0.2704 0.5328 0.180 Uiso 1 1 calc R . . H22C H 0.7733 0.3164 0.6117 0.180 Uiso 1 1 calc R . . C23 C 0.6031(3) 0.2059(3) 0.5519(2) 0.0530(10) Uani 1 1 d . . . H23 H 0.6611 0.1775 0.5850 0.064 Uiso 1 1 calc R . . C24 C 0.5201(3) 0.1419(3) 0.54072(19) 0.0497(10) Uani 1 1 d . . . H24 H 0.5231 0.0712 0.5674 0.060 Uiso 1 1 calc R . . C25 C 0.3496(3) 0.1028(3) 0.6159(2) 0.0616(11) Uani 1 1 d . . . H25A H 0.3006 0.1466 0.6284 0.074 Uiso 1 1 calc R . . H25B H 0.4037 0.1553 0.6241 0.074 Uiso 1 1 calc R . . C26 C 0.3801(3) 0.0002(4) 0.6702(2) 0.0549(10) Uani 1 1 d . . . C27 C 0.4150(3) -0.1031(4) 0.6507(2) 0.0734(13) Uani 1 1 d . . . H27 H 0.4214 -0.1099 0.6023 0.088 Uiso 1 1 calc R . . C28 C 0.4407(3) -0.1973(5) 0.7015(3) 0.0948(16) Uani 1 1 d . . . H28 H 0.4633 -0.2673 0.6872 0.114 Uiso 1 1 calc R . . C29 C 0.4327(4) -0.1863(6) 0.7733(3) 0.1013(18) Uani 1 1 d . . . H29 H 0.4500 -0.2489 0.8081 0.122 Uiso 1 1 calc R . . C30 C 0.3994(4) -0.0840(6) 0.7937(3) 0.0951(17) Uani 1 1 d . . . H30 H 0.3948 -0.0767 0.8427 0.114 Uiso 1 1 calc R . . C31 C 0.3724(3) 0.0092(4) 0.7425(2) 0.0805(14) Uani 1 1 d . . . H31 H 0.3488 0.0784 0.7569 0.097 Uiso 1 1 calc R . . C32 C 0.2268(3) 0.0137(3) 0.5009(2) 0.0554(10) Uani 1 1 d . . . C33 C 0.1679(3) -0.0405(4) 0.5364(3) 0.0743(13) Uani 1 1 d . . . H33 H 0.1836 -0.0411 0.5898 0.089 Uiso 1 1 calc R . . C34 C 0.0860(4) -0.0928(4) 0.4891(3) 0.0907(15) Uani 1 1 d . . . H34 H 0.0446 -0.1283 0.5109 0.109 Uiso 1 1 calc R . . C35 C 0.0631(3) -0.0942(4) 0.4087(3) 0.0931(16) Uani 1 1 d . . . H35 H 0.0075 -0.1316 0.3783 0.112 Uiso 1 1 calc R . . C36 C 0.1214(3) -0.0411(4) 0.3739(2) 0.0719(12) Uani 1 1 d . . . H36 H 0.1063 -0.0437 0.3206 0.086 Uiso 1 1 calc R . . C37 C 0.2033(3) 0.0166(3) 0.4203(2) 0.0540(10) 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 O1 0.077(2) 0.080(2) 0.115(3) -0.0207(19) 0.028(2) -0.0035(19) O2 0.0501(17) 0.073(2) 0.0485(15) -0.0009(14) 0.0176(13) 0.0009(14) O3 0.064(2) 0.076(2) 0.111(3) 0.0154(18) 0.0186(19) -0.0187(18) N1 0.058(2) 0.056(2) 0.0410(18) 0.0033(15) 0.0178(16) -0.0045(17) C1 0.061(3) 0.073(4) 0.050(3) 0.003(2) 0.017(2) 0.009(3) C2 0.063(3) 0.096(4) 0.047(3) 0.018(2) 0.019(2) 0.029(3) C3 0.056(3) 0.125(4) 0.079(3) 0.016(3) 0.026(3) 0.004(3) C4 0.074(4) 0.139(5) 0.117(5) 0.026(4) 0.034(3) 0.002(4) C5 0.127(6) 0.114 0.137(6) 0.046(5) 0.076(5) 0.041(5) C6 0.148(6) 0.116 0.099(4) 0.034(4) 0.072(4) 0.072(4) C7 0.095(4) 0.102(4) 0.076(3) 0.019(3) 0.033(3) 0.043(3) C8 0.045(2) 0.062(3) 0.045(2) -0.0012(19) 0.016(2) 0.000(2) C9 0.055(2) 0.057(3) 0.043(2) 0.0007(19) 0.020(2) -0.004(2) C10 0.064(3) 0.089(3) 0.046(3) 0.007(2) 0.017(2) 0.011(2) C11 0.087(3) 0.095(4) 0.041(3) 0.008(2) 0.009(2) 0.003(3) C12 0.100(4) 0.092(4) 0.048(3) -0.014(3) 0.036(3) -0.019(3) C13 0.078(3) 0.091(4) 0.061(3) -0.009(3) 0.030(3) 0.004(3) C14 0.069(3) 0.072(3) 0.046(2) 0.000(2) 0.021(2) 0.006(2) C15 0.047(2) 0.063(3) 0.045(2) 0.0047(19) 0.0179(19) 0.001(2) C16 0.045(2) 0.059(3) 0.042(2) 0.0056(19) 0.0106(19) -0.001(2) C17 0.050(2) 0.049(2) 0.042(2) 0.0045(18) 0.017(2) 0.003(2) C18 0.054(3) 0.050(3) 0.036(2) -0.0008(18) 0.016(2) -0.002(2) C19 0.056(3) 0.065(3) 0.049(2) 0.010(2) 0.017(2) 0.003(2) C20 0.066(3) 0.053(3) 0.069(3) 0.013(2) 0.023(2) 0.000(3) C21 0.058(3) 0.054(3) 0.055(3) -0.002(2) 0.017(2) -0.008(2) C22 0.063(4) 0.112(4) 0.165(6) 0.032(4) 0.011(4) -0.018(3) C23 0.055(3) 0.053(3) 0.045(2) 0.002(2) 0.0081(19) 0.001(2) C24 0.063(3) 0.050(2) 0.036(2) 0.0011(18) 0.016(2) 0.000(2) C25 0.079(3) 0.067(3) 0.044(2) -0.004(2) 0.028(2) -0.006(2) C26 0.058(3) 0.068(3) 0.039(2) 0.006(2) 0.0154(19) -0.002(2) C27 0.080(3) 0.085(4) 0.062(3) 0.023(3) 0.033(3) 0.015(3) C28 0.101(4) 0.096(4) 0.095(4) 0.042(3) 0.043(3) 0.030(3) C29 0.089(4) 0.141(6) 0.069(4) 0.056(4) 0.021(3) 0.021(4) C30 0.103(4) 0.140(5) 0.042(3) 0.019(3) 0.023(3) -0.023(4) C31 0.104(4) 0.098(4) 0.043(3) 0.002(3) 0.030(2) -0.014(3) C32 0.058(3) 0.057(3) 0.055(3) 0.009(2) 0.024(2) 0.001(2) C33 0.068(3) 0.089(3) 0.073(3) 0.018(3) 0.033(3) -0.002(3) C34 0.071(3) 0.104(4) 0.105(4) 0.031(3) 0.040(3) -0.010(3) C35 0.067(3) 0.107(4) 0.097(4) 0.024(3) 0.016(3) -0.026(3) C36 0.059(3) 0.082(3) 0.065(3) 0.012(2) 0.007(2) -0.015(3) C37 0.047(2) 0.060(3) 0.053(2) 0.010(2) 0.014(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.192(5) . ? O2 C1 1.362(5) . ? O2 C8 1.411(4) . ? O3 C21 1.361(4) . ? O3 C22 1.409(5) . ? N1 C32 1.376(4) . ? N1 C17 1.404(4) . ? N1 C25 1.458(4) . ? C1 C2 1.489(6) . ? C2 C3 1.376(6) . ? C2 C7 1.386(6) . ? C3 C4 1.393(6) . ? C3 H3 0.9300 . ? C4 C5 1.355(8) . ? C4 H4 0.9300 . ? C5 C6 1.351(8) . ? C5 H5 0.9300 . ? C6 C7 1.404(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C15 1.326(4) . ? C8 C9 1.458(5) . ? C9 C10 1.386(5) . ? C9 C14 1.388(5) . ? C10 C11 1.382(5) . ? C10 H10 0.9300 . ? C11 C12 1.366(6) . ? C11 H11 0.9300 . ? C12 C13 1.368(6) . ? C12 H12 0.9300 . ? C13 C14 1.370(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.462(5) . ? C15 H15 0.9300 . ? C16 C17 1.378(4) . ? C16 C37 1.448(5) . ? C17 C18 1.460(5) . ? C18 C24 1.386(5) . ? C18 C19 1.395(5) . ? C19 C20 1.373(5) . ? C19 H19 0.9300 . ? C20 C21 1.383(5) . ? C20 H20 0.9300 . ? C21 C23 1.375(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.384(5) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.497(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.372(5) . ? C26 C31 1.375(5) . ? C27 C28 1.382(5) . ? C27 H27 0.9300 . ? C28 C29 1.370(7) . ? C28 H28 0.9300 . ? C29 C30 1.357(7) . ? C29 H29 0.9300 . ? C30 C31 1.378(6) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 C33 1.397(5) . ? C32 C37 1.404(5) . ? C33 C34 1.369(6) . ? C33 H33 0.9300 . ? C34 C35 1.402(6) . ? C34 H34 0.9300 . ? C35 C36 1.373(5) . ? C35 H35 0.9300 . ? C36 C37 1.392(5) . ? C36 H36 0.9300 . ? 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 O2 C8 117.7(3) . . ? C21 O3 C22 118.4(3) . . ? C32 N1 C17 108.3(3) . . ? C32 N1 C25 123.3(3) . . ? C17 N1 C25 126.9(3) . . ? O1 C1 O2 123.2(4) . . ? O1 C1 C2 126.0(5) . . ? O2 C1 C2 110.8(4) . . ? C3 C2 C7 119.1(5) . . ? C3 C2 C1 122.9(5) . . ? C7 C2 C1 118.0(5) . . ? C4 C3 C2 120.4(6) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 118.6(6) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C6 C5 C4 123.6(6) . . ? C6 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C5 C6 C7 117.7(6) . . ? C5 C6 H6 121.1 . . ? C7 C6 H6 121.1 . . ? C6 C7 C2 120.6(6) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? C15 C8 O2 118.3(3) . . ? C15 C8 C9 128.2(3) . . ? O2 C8 C9 113.4(3) . . ? C10 C9 C14 117.4(3) . . ? C10 C9 C8 120.8(3) . . ? C14 C9 C8 121.7(4) . . ? C11 C10 C9 120.9(4) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C10 120.7(4) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 119.0(4) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C12 C13 C14 121.0(4) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C9 121.0(4) . . ? C13 C14 H14 119.5 . . ? C9 C14 H14 119.5 . . ? C8 C15 C16 126.8(3) . . ? C8 C15 H15 116.6 . . ? C16 C15 H15 116.6 . . ? C17 C16 C37 107.3(3) . . ? C17 C16 C15 125.4(3) . . ? C37 C16 C15 127.0(3) . . ? C16 C17 N1 108.9(3) . . ? C16 C17 C18 128.3(3) . . ? N1 C17 C18 122.8(3) . . ? C24 C18 C19 117.9(3) . . ? C24 C18 C17 123.1(3) . . ? C19 C18 C17 119.0(3) . . ? C20 C19 C18 120.2(4) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 121.3(4) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? O3 C21 C23 124.9(4) . . ? O3 C21 C20 115.9(4) . . ? C23 C21 C20 119.2(4) . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 C24 119.7(4) . . ? C21 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C23 C24 C18 121.7(3) . . ? C23 C24 H24 119.1 . . ? C18 C24 H24 119.1 . . ? N1 C25 C26 114.6(3) . . ? N1 C25 H25A 108.6 . . ? C26 C25 H25A 108.6 . . ? N1 C25 H25B 108.6 . . ? C26 C25 H25B 108.6 . . ? H25A C25 H25B 107.6 . . ? C27 C26 C31 118.5(4) . . ? C27 C26 C25 122.6(3) . . ? C31 C26 C25 118.9(4) . . ? C26 C27 C28 121.3(4) . . ? C26 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C29 C28 C27 119.2(5) . . ? C29 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? C30 C29 C28 120.0(5) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C31 120.8(5) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? C26 C31 C30 120.2(5) . . ? C26 C31 H31 119.9 . . ? C30 C31 H31 119.9 . . ? N1 C32 C33 128.9(4) . . ? N1 C32 C37 109.1(3) . . ? C33 C32 C37 122.0(4) . . ? C34 C33 C32 117.1(4) . . ? C34 C33 H33 121.4 . . ? C32 C33 H33 121.4 . . ? C33 C34 C35 121.6(4) . . ? C33 C34 H34 119.2 . . ? C35 C34 H34 119.2 . . ? C36 C35 C34 121.2(4) . . ? C36 C35 H35 119.4 . . ? C34 C35 H35 119.4 . . ? C35 C36 C37 118.6(4) . . ? C35 C36 H36 120.7 . . ? C37 C36 H36 120.7 . . ? C36 C37 C32 119.4(4) . . ? C36 C37 C16 134.2(4) . . ? C32 C37 C16 106.3(3) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.259 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.104 data_a13435 _database_code_depnum_ccdc_archive 'CCDC 869630' #TrackingRef '- 19a (CCDC 869630).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H27 N O4 S' _chemical_formula_sum 'C36 H27 N O4 S' _chemical_formula_weight 569.65 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.443(4) _cell_length_b 17.398(8) _cell_length_c 19.970(9) _cell_angle_alpha 66.139(11) _cell_angle_beta 78.522(7) _cell_angle_gamma 76.820(7) _cell_volume 2900(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9314 _exptl_absorpt_correction_T_max 0.9939 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 22189 _diffrn_reflns_av_R_equivalents 0.0697 _diffrn_reflns_av_sigmaI/netI 0.1021 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 25.04 _reflns_number_total 9779 _reflns_number_gt 6099 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1728P)^2^+4.6887P] 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 9779 _refine_ls_number_parameters 757 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1482 _refine_ls_R_factor_gt 0.0994 _refine_ls_wR_factor_ref 0.2963 _refine_ls_wR_factor_gt 0.2563 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.003 _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 0.1056(6) 0.8865(3) 0.5110(3) 0.0301(12) Uani 1 1 d . A 1 C2 C 0.0007(7) 0.8772(4) 0.5709(3) 0.0435(15) Uani 1 1 d . A 1 H2 H -0.0850 0.8557 0.5737 0.052 Uiso 1 1 calc R A 1 C3 C 0.0206(7) 0.8994(4) 0.6270(4) 0.0497(17) Uani 1 1 d . A 1 H3 H -0.0536 0.8943 0.6677 0.060 Uiso 1 1 calc R A 1 C4 C 0.1450(7) 0.9286(4) 0.6253(3) 0.0374(13) Uani 1 1 d . A 1 C5 C 0.1649(8) 0.9528(4) 0.6873(4) 0.0524(17) Uani 1 1 d . A 1 H5A H 0.2592 0.9725 0.6766 0.079 Uiso 1 1 calc R A 1 H5B H 0.1630 0.9030 0.7337 0.079 Uiso 1 1 calc R A 1 H5C H 0.0855 0.9985 0.6917 0.079 Uiso 1 1 calc R A 1 C6 C 0.2482(7) 0.9390(4) 0.5635(3) 0.0462(15) Uani 1 1 d . A 1 H6 H 0.3326 0.9621 0.5600 0.055 Uiso 1 1 calc R A 1 C7 C 0.2315(7) 0.9166(4) 0.5075(3) 0.0426(15) Uani 1 1 d . A 1 H7 H 0.3056 0.9217 0.4667 0.051 Uiso 1 1 calc R A 1 C8 C 0.0781(6) 0.6940(3) 0.5270(3) 0.0289(12) Uani 1 1 d . A 1 C9 C -0.0718(6) 0.6947(4) 0.5482(3) 0.0364(13) Uani 1 1 d . A 1 H9 H -0.1418 0.7409 0.5228 0.044 Uiso 1 1 calc R A 1 C10 C -0.1143(6) 0.6250(4) 0.6078(3) 0.0394(14) Uani 1 1 d . A 1 H10 H -0.2155 0.6242 0.6248 0.047 Uiso 1 1 calc R A 1 C11 C -0.0123(6) 0.5564(4) 0.6431(3) 0.0405(14) Uani 1 1 d . A 1 H11 H -0.0454 0.5088 0.6830 0.049 Uiso 1 1 calc R A 1 C12 C 0.1355(6) 0.5554(3) 0.6220(3) 0.0329(13) Uani 1 1 d . A 1 H12 H 0.2044 0.5080 0.6468 0.040 Uiso 1 1 calc R A 1 C13 C 0.1817(6) 0.6256(3) 0.5631(3) 0.0282(12) Uani 1 1 d . A 1 C14 C 0.3255(6) 0.6436(3) 0.5247(3) 0.0296(12) Uani 1 1 d . A 1 C15 C 0.3069(6) 0.7214(3) 0.4672(3) 0.0284(12) Uani 1 1 d . A 1 C16 C 0.4197(6) 0.7632(3) 0.4111(3) 0.0302(12) Uani 1 1 d . A 1 C17 C 0.5418(7) 0.7744(4) 0.4336(4) 0.0446(15) Uani 1 1 d . A 1 H17 H 0.5495 0.7551 0.4847 0.054 Uiso 1 1 calc R A 1 C18 C 0.6513(8) 0.8129(5) 0.3828(4) 0.061(2) Uani 1 1 d . A 1 H18 H 0.7331 0.8209 0.3989 0.073 Uiso 1 1 calc R A 1 C19 C 0.6412(8) 0.8402(4) 0.3075(4) 0.0576(19) Uani 1 1 d . A 1 H19 H 0.7161 0.8670 0.2721 0.069 Uiso 1 1 calc R A 1 C20 C 0.5239(7) 0.8281(4) 0.2850(4) 0.0471(16) Uani 1 1 d . A 1 H20 H 0.5179 0.8466 0.2338 0.056 Uiso 1 1 calc R A 1 C21 C 0.4131(7) 0.7895(3) 0.3354(3) 0.0368(13) Uani 1 1 d . A 1 H21 H 0.3328 0.7808 0.3187 0.044 Uiso 1 1 calc R A 1 C22 C 0.4658(6) 0.5863(3) 0.5375(3) 0.0311(12) Uani 1 1 d . A 1 H22 H 0.5278 0.5801 0.4957 0.037 Uiso 1 1 calc R A 1 C23 C 0.5132(5) 0.5427(3) 0.6027(3) 0.0279(12) Uani 1 1 d . A 1 C24 C 0.6495(6) 0.4804(3) 0.6200(3) 0.0298(12) Uani 1 1 d . A 1 C25 C 0.7613(6) 0.4736(4) 0.5645(3) 0.0390(14) Uani 1 1 d . A 1 H25 H 0.7502 0.5097 0.5146 0.047 Uiso 1 1 calc R A 1 C26 C 0.8877(7) 0.4153(4) 0.5808(4) 0.0475(16) Uani 1 1 d . A 1 H26 H 0.9642 0.4120 0.5427 0.057 Uiso 1 1 calc R A 1 C27 C 0.9023(7) 0.3612(4) 0.6537(4) 0.0485(17) Uani 1 1 d . A 1 H27 H 0.9879 0.3195 0.6651 0.058 Uiso 1 1 calc R A 1 C28 C 0.7936(7) 0.3676(4) 0.7095(4) 0.0481(16) Uani 1 1 d . A 1 H28 H 0.8052 0.3310 0.7592 0.058 Uiso 1 1 calc R A 1 C29 C 0.6678(6) 0.4269(3) 0.6934(3) 0.0379(13) Uani 1 1 d . A 1 H29 H 0.5936 0.4316 0.7321 0.045 Uiso 1 1 calc R A 1 C30 C 0.4136(6) 0.6258(3) 0.6751(3) 0.0331(13) Uani 1 1 d . A 1 C31 C 0.3030(6) 0.6312(3) 0.7373(3) 0.0306(12) Uani 1 1 d . A 1 C32 C 0.2597(7) 0.7092(4) 0.7446(4) 0.0453(15) Uani 1 1 d . A 1 H32 H 0.3011 0.7573 0.7102 0.054 Uiso 1 1 calc R A 1 C33 C 0.1552(8) 0.7171(4) 0.8024(4) 0.0552(18) Uani 1 1 d . A 1 H33 H 0.1248 0.7708 0.8070 0.066 Uiso 1 1 calc R A 1 C34 C 0.0965(7) 0.6488(4) 0.8522(4) 0.0501(16) Uani 1 1 d . A 1 H34 H 0.0262 0.6545 0.8918 0.060 Uiso 1 1 calc R A 1 C35 C 0.1394(7) 0.5699(4) 0.8451(3) 0.0466(15) Uani 1 1 d . A 1 H35 H 0.0973 0.5222 0.8796 0.056 Uiso 1 1 calc R A 1 C36 C 0.2430(6) 0.5610(4) 0.7879(3) 0.0387(14) Uani 1 1 d . A 1 H36 H 0.2728 0.5072 0.7833 0.046 Uiso 1 1 calc R A 1 C37 C 0.4827(6) 0.3816(3) 0.0086(3) 0.0294(12) Uani 1 1 d . B 1 C38 C 0.3353(6) 0.4145(4) 0.0037(3) 0.0452(15) Uani 1 1 d . B 1 H38 H 0.2912 0.4199 -0.0371 0.054 Uiso 1 1 calc R B 1 C39 C 0.2537(7) 0.4393(4) 0.0590(4) 0.0496(16) Uani 1 1 d . B 1 H39 H 0.1538 0.4643 0.0546 0.060 Uiso 1 1 calc R B 1 C40 C 0.3126(7) 0.4291(4) 0.1207(3) 0.0384(14) Uani 1 1 d . B 1 C41 C 0.2220(8) 0.4543(4) 0.1822(4) 0.0549(18) Uani 1 1 d . B 1 H41A H 0.1206 0.4760 0.1711 0.082 Uiso 1 1 calc R B 1 H41B H 0.2623 0.4988 0.1869 0.082 Uiso 1 1 calc R B 1 H41C H 0.2242 0.4045 0.2287 0.082 Uiso 1 1 calc R B 1 C42 C 0.4594(8) 0.3972(5) 0.1236(3) 0.0523(17) Uani 1 1 d . B 1 H42 H 0.5033 0.3918 0.1645 0.063 Uiso 1 1 calc R B 1 C43 C 0.5452(7) 0.3726(4) 0.0681(4) 0.0500(17) Uani 1 1 d . B 1 H43 H 0.6462 0.3498 0.0716 0.060 Uiso 1 1 calc R B 1 C44 C 0.6591(6) 0.1879(3) 0.0230(3) 0.0315(12) Uani 1 1 d . B 1 C45 C 0.7898(6) 0.1886(4) 0.0456(3) 0.0368(13) Uani 1 1 d . B 1 H45 H 0.8406 0.2357 0.0219 0.044 Uiso 1 1 calc R B 1 C46 C 0.8415(7) 0.1181(4) 0.1036(3) 0.0438(15) Uani 1 1 d . B 1 H46 H 0.9281 0.1174 0.1213 0.053 Uiso 1 1 calc R B 1 C47 C 0.7706(6) 0.0478(4) 0.1370(3) 0.0413(14) Uani 1 1 d . B 1 H47 H 0.8116 -0.0007 0.1757 0.050 Uiso 1 1 calc R B 1 C48 C 0.6401(6) 0.0472(3) 0.1147(3) 0.0355(13) Uani 1 1 d . B 1 H48 H 0.5910 -0.0007 0.1382 0.043 Uiso 1 1 calc R B 1 C49 C 0.5839(6) 0.1185(3) 0.0572(3) 0.0323(12) Uani 1 1 d . B 1 C50 C 0.4567(6) 0.1369(3) 0.0190(3) 0.0338(13) Uani 1 1 d . B 1 C51 C 0.4576(6) 0.2155(3) -0.0363(3) 0.0297(12) Uani 1 1 d . B 1 C52 C 0.3524(6) 0.2597(3) -0.0905(3) 0.0319(12) Uani 1 1 d . B 1 C53 C 0.2035(6) 0.2747(4) -0.0675(4) 0.0425(15) Uani 1 1 d . B 1 H53 H 0.1711 0.2558 -0.0161 0.051 Uiso 1 1 calc R B 1 C54 C 0.1016(7) 0.3158(4) -0.1162(4) 0.0529(17) Uani 1 1 d . B 1 H54 H 0.0005 0.3258 -0.0990 0.063 Uiso 1 1 calc R B 1 C55 C 0.1491(8) 0.3426(4) -0.1916(4) 0.0539(18) Uani 1 1 d . B 1 H55 H 0.0802 0.3713 -0.2262 0.065 Uiso 1 1 calc R B 1 C56 C 0.2967(8) 0.3273(4) -0.2160(4) 0.0482(16) Uani 1 1 d . B 1 H56 H 0.3284 0.3455 -0.2674 0.058 Uiso 1 1 calc R B 1 C57 C 0.3983(7) 0.2858(4) -0.1664(3) 0.0390(14) Uani 1 1 d . B 1 H57 H 0.4992 0.2750 -0.1837 0.047 Uiso 1 1 calc R B 1 C58 C 0.3523(6) 0.0794(3) 0.0342(3) 0.0327(12) Uani 1 1 d . B 1 H58 H 0.3287 0.0717 -0.0065 0.039 Uiso 1 1 calc R B 1 C59 C 0.2880(6) 0.0369(3) 0.1013(3) 0.0304(12) Uani 1 1 d . B 1 C60 C 0.1928(6) -0.0277(3) 0.1236(3) 0.0300(12) Uani 1 1 d . B 1 C61 C 0.1479(7) -0.0511(4) 0.0733(3) 0.0414(15) Uani 1 1 d . B 1 H61 H 0.1796 -0.0248 0.0223 0.050 Uiso 1 1 calc R B 1 C62 C 0.0580(7) -0.1119(4) 0.0961(4) 0.0512(17) Uani 1 1 d . B 1 H62 H 0.0261 -0.1255 0.0606 0.061 Uiso 1 1 calc R B 1 C63 C 0.0149(7) -0.1526(4) 0.1696(4) 0.0459(16) Uani 1 1 d . B 1 H63 H -0.0451 -0.1952 0.1855 0.055 Uiso 1 1 calc R B 1 C64 C 0.0598(7) -0.1308(4) 0.2205(4) 0.0435(15) Uani 1 1 d . B 1 H64 H 0.0299 -0.1585 0.2716 0.052 Uiso 1 1 calc R B 1 C65 C 0.1478(6) -0.0691(3) 0.1978(3) 0.0362(13) Uani 1 1 d . B 1 H65 H 0.1778 -0.0549 0.2334 0.043 Uiso 1 1 calc R B 1 C66 C 0.2576(6) 0.1243(4) 0.1702(3) 0.0342(13) Uani 1 1 d . B 1 C67 C 0.3098(6) 0.1306(3) 0.2330(3) 0.0320(12) Uani 1 1 d . B 1 C68 C 0.2807(7) 0.2096(4) 0.2394(4) 0.0464(16) Uani 1 1 d . B 1 H68 H 0.2301 0.2576 0.2039 0.056 Uiso 1 1 calc R B 1 C69 C 0.3253(8) 0.2182(5) 0.2973(4) 0.0557(18) Uani 1 1 d . B 1 H69 H 0.3036 0.2719 0.3022 0.067 Uiso 1 1 calc R B 1 C70 C 0.4008(8) 0.1494(4) 0.3478(4) 0.0525(17) Uani 1 1 d . B 1 H70 H 0.4333 0.1559 0.3870 0.063 Uiso 1 1 calc R B 1 C71 C 0.4299(7) 0.0708(4) 0.3420(3) 0.0438(15) Uani 1 1 d . B 1 H71 H 0.4802 0.0232 0.3779 0.053 Uiso 1 1 calc R B 1 C72 C 0.3859(6) 0.0609(4) 0.2838(3) 0.0381(14) Uani 1 1 d . B 1 H72 H 0.4079 0.0072 0.2790 0.046 Uiso 1 1 calc R B 1 N1 N 0.1530(5) 0.7537(3) 0.4655(2) 0.0280(10) Uani 1 1 d . A 1 N2 N 0.5845(5) 0.2476(3) -0.0367(2) 0.0301(10) Uani 1 1 d . B 1 O1 O 0.1746(4) 0.9016(2) 0.3743(2) 0.0383(9) Uani 1 1 d . A 1 O2 O -0.0677(4) 0.8635(2) 0.4367(2) 0.0350(9) Uani 1 1 d . A 1 O3 O 0.4235(4) 0.5510(2) 0.66559(19) 0.0301(8) Uani 1 1 d . A 1 O4 O 0.4884(5) 0.6786(3) 0.6379(2) 0.0489(11) Uani 1 1 d . A 1 O5 O 0.7385(4) 0.3576(2) -0.0647(2) 0.0320(9) Uani 1 1 d . B 1 O6 O 0.5167(4) 0.3963(2) -0.1282(2) 0.0408(10) Uani 1 1 d . B 1 O7 O 0.3217(4) 0.0497(2) 0.16138(19) 0.0319(9) Uani 1 1 d . B 1 O8 O 0.1700(5) 0.1758(3) 0.1323(2) 0.0496(11) Uani 1 1 d . B 1 S1 S 0.08517(15) 0.85831(8) 0.43892(7) 0.0298(4) Uani 1 1 d . A 1 S2 S 0.58730(15) 0.35276(8) -0.06316(8) 0.0319(4) Uani 1 1 d . B 1 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 0.032(3) 0.024(3) 0.030(3) -0.008(2) -0.005(2) -0.003(2) C2 0.037(3) 0.050(4) 0.050(4) -0.028(3) 0.011(3) -0.018(3) C3 0.054(4) 0.057(4) 0.044(4) -0.030(3) 0.015(3) -0.018(3) C4 0.048(4) 0.033(3) 0.030(3) -0.012(3) -0.009(3) -0.001(3) C5 0.068(5) 0.052(4) 0.046(4) -0.028(3) -0.015(3) 0.000(3) C6 0.045(4) 0.058(4) 0.045(4) -0.024(3) -0.010(3) -0.013(3) C7 0.041(4) 0.062(4) 0.035(3) -0.026(3) 0.002(3) -0.020(3) C8 0.028(3) 0.028(3) 0.035(3) -0.015(3) -0.003(2) -0.007(2) C9 0.032(3) 0.036(3) 0.044(4) -0.020(3) -0.001(3) -0.003(2) C10 0.035(3) 0.039(3) 0.053(4) -0.027(3) 0.001(3) -0.011(3) C11 0.042(4) 0.038(3) 0.045(4) -0.018(3) 0.006(3) -0.018(3) C12 0.041(3) 0.027(3) 0.029(3) -0.008(3) 0.001(2) -0.011(2) C13 0.034(3) 0.026(3) 0.027(3) -0.012(2) -0.002(2) -0.006(2) C14 0.032(3) 0.028(3) 0.035(3) -0.016(3) -0.004(2) -0.009(2) C15 0.028(3) 0.031(3) 0.027(3) -0.010(2) -0.008(2) -0.003(2) C16 0.032(3) 0.024(3) 0.031(3) -0.007(2) -0.003(2) -0.003(2) C17 0.049(4) 0.040(3) 0.044(4) -0.005(3) -0.018(3) -0.015(3) C18 0.049(4) 0.058(4) 0.069(5) -0.007(4) -0.006(4) -0.026(3) C19 0.048(4) 0.046(4) 0.063(5) -0.004(4) 0.005(3) -0.018(3) C20 0.059(4) 0.037(3) 0.039(4) -0.011(3) 0.006(3) -0.010(3) C21 0.047(4) 0.030(3) 0.034(3) -0.012(3) -0.002(3) -0.007(2) C22 0.030(3) 0.029(3) 0.035(3) -0.014(3) -0.001(2) -0.004(2) C23 0.026(3) 0.028(3) 0.031(3) -0.012(2) 0.000(2) -0.007(2) C24 0.029(3) 0.026(3) 0.038(3) -0.016(3) -0.008(2) -0.001(2) C25 0.039(3) 0.046(3) 0.037(3) -0.023(3) -0.005(3) -0.002(3) C26 0.035(4) 0.058(4) 0.060(4) -0.041(4) -0.008(3) 0.008(3) C27 0.038(4) 0.037(3) 0.077(5) -0.030(4) -0.019(3) 0.006(3) C28 0.051(4) 0.033(3) 0.054(4) -0.007(3) -0.015(3) -0.004(3) C29 0.039(3) 0.030(3) 0.039(3) -0.007(3) -0.009(3) -0.002(2) C30 0.033(3) 0.036(3) 0.036(3) -0.019(3) -0.005(3) -0.005(2) C31 0.029(3) 0.036(3) 0.031(3) -0.017(3) -0.005(2) -0.002(2) C32 0.051(4) 0.035(3) 0.050(4) -0.020(3) -0.001(3) -0.003(3) C33 0.061(5) 0.049(4) 0.060(5) -0.036(4) -0.002(4) 0.007(3) C34 0.044(4) 0.052(4) 0.047(4) -0.022(3) 0.006(3) 0.004(3) C35 0.042(4) 0.054(4) 0.041(4) -0.019(3) 0.001(3) -0.005(3) C36 0.034(3) 0.040(3) 0.044(4) -0.021(3) -0.005(3) 0.000(2) C37 0.027(3) 0.030(3) 0.028(3) -0.008(2) -0.001(2) -0.006(2) C38 0.031(3) 0.065(4) 0.039(4) -0.023(3) -0.010(3) 0.004(3) C39 0.036(4) 0.062(4) 0.044(4) -0.020(3) -0.001(3) 0.002(3) C40 0.045(4) 0.037(3) 0.033(3) -0.015(3) 0.005(3) -0.013(3) C41 0.064(5) 0.053(4) 0.049(4) -0.026(4) 0.011(3) -0.016(3) C42 0.059(5) 0.075(5) 0.035(4) -0.034(4) -0.011(3) -0.003(4) C43 0.037(4) 0.065(4) 0.057(4) -0.036(4) -0.010(3) 0.001(3) C44 0.029(3) 0.030(3) 0.031(3) -0.009(3) -0.003(2) -0.001(2) C45 0.031(3) 0.036(3) 0.043(4) -0.016(3) -0.009(3) 0.000(2) C46 0.037(3) 0.047(4) 0.049(4) -0.020(3) -0.011(3) -0.002(3) C47 0.037(3) 0.043(3) 0.040(4) -0.013(3) -0.013(3) 0.005(3) C48 0.036(3) 0.027(3) 0.036(3) -0.006(3) -0.002(3) -0.003(2) C49 0.028(3) 0.034(3) 0.037(3) -0.019(3) 0.000(2) -0.002(2) C50 0.040(3) 0.030(3) 0.032(3) -0.013(3) -0.003(2) -0.006(2) C51 0.031(3) 0.030(3) 0.024(3) -0.007(2) -0.002(2) -0.004(2) C52 0.033(3) 0.025(3) 0.033(3) -0.007(2) -0.001(2) -0.006(2) C53 0.032(3) 0.039(3) 0.045(4) -0.010(3) 0.004(3) -0.002(3) C54 0.036(4) 0.045(4) 0.067(5) -0.010(4) -0.013(3) -0.004(3) C55 0.059(5) 0.031(3) 0.069(5) -0.003(3) -0.035(4) -0.007(3) C56 0.064(5) 0.037(3) 0.041(4) -0.005(3) -0.018(3) -0.011(3) C57 0.042(4) 0.038(3) 0.035(3) -0.012(3) -0.003(3) -0.007(3) C58 0.037(3) 0.028(3) 0.035(3) -0.013(3) -0.003(2) -0.006(2) C59 0.034(3) 0.028(3) 0.033(3) -0.015(3) -0.008(2) -0.003(2) C60 0.029(3) 0.025(3) 0.033(3) -0.010(2) -0.003(2) -0.002(2) C61 0.050(4) 0.051(4) 0.035(3) -0.025(3) 0.004(3) -0.021(3) C62 0.055(4) 0.061(4) 0.057(4) -0.041(4) 0.002(3) -0.020(3) C63 0.046(4) 0.035(3) 0.062(4) -0.023(3) -0.001(3) -0.015(3) C64 0.045(4) 0.030(3) 0.046(4) -0.004(3) -0.005(3) -0.010(3) C65 0.042(3) 0.028(3) 0.038(3) -0.009(3) -0.007(3) -0.008(2) C66 0.031(3) 0.034(3) 0.041(3) -0.020(3) -0.001(3) -0.005(2) C67 0.031(3) 0.035(3) 0.034(3) -0.016(3) 0.001(2) -0.012(2) C68 0.057(4) 0.034(3) 0.055(4) -0.023(3) -0.007(3) -0.007(3) C69 0.069(5) 0.052(4) 0.061(5) -0.036(4) -0.006(4) -0.011(3) C70 0.062(5) 0.061(4) 0.045(4) -0.021(4) -0.010(3) -0.025(4) C71 0.047(4) 0.048(4) 0.040(4) -0.017(3) -0.007(3) -0.012(3) C72 0.041(3) 0.037(3) 0.038(3) -0.015(3) -0.003(3) -0.011(3) N1 0.028(2) 0.025(2) 0.029(2) -0.007(2) -0.0049(19) -0.0043(18) N2 0.028(2) 0.033(2) 0.028(2) -0.008(2) 0.0012(19) -0.0108(19) O1 0.054(3) 0.029(2) 0.026(2) -0.0047(18) -0.0074(18) -0.0047(18) O2 0.031(2) 0.031(2) 0.045(2) -0.0138(19) -0.0194(17) 0.0025(16) O3 0.039(2) 0.0245(18) 0.028(2) -0.0128(17) -0.0010(16) -0.0041(15) O4 0.054(3) 0.049(3) 0.055(3) -0.030(2) 0.013(2) -0.027(2) O5 0.0202(19) 0.0296(19) 0.041(2) -0.0098(18) 0.0061(16) -0.0097(15) O6 0.050(3) 0.034(2) 0.031(2) -0.0070(19) 0.0001(18) -0.0070(18) O7 0.039(2) 0.030(2) 0.030(2) -0.0139(17) -0.0067(16) -0.0057(16) O8 0.048(3) 0.050(3) 0.056(3) -0.032(2) -0.015(2) 0.012(2) S1 0.0339(8) 0.0247(7) 0.0315(8) -0.0097(6) -0.0114(6) -0.0014(5) S2 0.0317(8) 0.0288(7) 0.0321(8) -0.0094(6) 0.0021(6) -0.0079(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.372(8) . ? C1 C7 1.383(8) . ? C1 S1 1.754(5) . ? C2 C3 1.380(8) . ? C2 H2 0.9500 . ? C3 C4 1.373(9) . ? C3 H3 0.9500 . ? C4 C6 1.388(8) . ? C4 C5 1.514(8) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.371(8) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.394(7) . ? C8 C13 1.396(7) . ? C8 N1 1.429(7) . ? C9 C10 1.382(8) . ? C9 H9 0.9500 . ? C10 C11 1.384(9) . ? C10 H10 0.9500 . ? C11 C12 1.374(8) . ? C11 H11 0.9500 . ? C12 C13 1.394(7) . ? C12 H12 0.9500 . ? C13 C14 1.454(7) . ? C14 C15 1.377(7) . ? C14 C22 1.463(7) . ? C15 N1 1.436(6) . ? C15 C16 1.462(7) . ? C16 C17 1.396(8) . ? C16 C21 1.400(8) . ? C17 C18 1.376(9) . ? C17 H17 0.9500 . ? C18 C19 1.399(10) . ? C18 H18 0.9500 . ? C19 C20 1.361(9) . ? C19 H19 0.9500 . ? C20 C21 1.383(8) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.322(7) . ? C22 H22 0.9500 . ? C23 O3 1.409(6) . ? C23 C24 1.479(7) . ? C24 C25 1.394(8) . ? C24 C29 1.404(8) . ? C25 C26 1.376(8) . ? C25 H25 0.9500 . ? C26 C27 1.392(9) . ? C26 H26 0.9500 . ? C27 C28 1.379(9) . ? C27 H27 0.9500 . ? C28 C29 1.380(8) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 O4 1.195(6) . ? C30 O3 1.371(6) . ? C30 C31 1.475(8) . ? C31 C32 1.383(8) . ? C31 C36 1.386(8) . ? C32 C33 1.393(9) . ? C32 H32 0.9500 . ? C33 C34 1.353(9) . ? C33 H33 0.9500 . ? C34 C35 1.395(9) . ? C34 H34 0.9500 . ? C35 C36 1.383(8) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 C43 1.370(8) . ? C37 C38 1.386(8) . ? C37 S2 1.753(5) . ? C38 C39 1.376(8) . ? C38 H38 0.9500 . ? C39 C40 1.381(9) . ? C39 H39 0.9500 . ? C40 C42 1.374(9) . ? C40 C41 1.510(8) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.391(9) . ? C42 H42 0.9500 . ? C43 H43 0.9500 . ? C44 C45 1.400(7) . ? C44 C49 1.401(7) . ? C44 N2 1.412(7) . ? C45 C46 1.373(8) . ? C45 H45 0.9500 . ? C46 C47 1.387(9) . ? C46 H46 0.9500 . ? C47 C48 1.395(8) . ? C47 H47 0.9500 . ? C48 C49 1.389(8) . ? C48 H48 0.9500 . ? C49 C50 1.455(8) . ? C50 C51 1.367(7) . ? C50 C58 1.467(7) . ? C51 N2 1.430(7) . ? C51 C52 1.469(8) . ? C52 C53 1.389(8) . ? C52 C57 1.400(8) . ? C53 C54 1.371(9) . ? C53 H53 0.9500 . ? C54 C55 1.394(10) . ? C54 H54 0.9500 . ? C55 C56 1.384(10) . ? C55 H55 0.9500 . ? C56 C57 1.381(9) . ? C56 H56 0.9500 . ? C57 H57 0.9500 . ? C58 C59 1.338(7) . ? C58 H58 0.9500 . ? C59 O7 1.411(6) . ? C59 C60 1.472(7) . ? C60 C65 1.386(8) . ? C60 C61 1.389(7) . ? C61 C62 1.383(8) . ? C61 H61 0.9500 . ? C62 C63 1.369(9) . ? C62 H62 0.9500 . ? C63 C64 1.383(9) . ? C63 H63 0.9500 . ? C64 C65 1.383(8) . ? C64 H64 0.9500 . ? C65 H65 0.9500 . ? C66 O8 1.193(7) . ? C66 O7 1.366(6) . ? C66 C67 1.487(8) . ? C67 C72 1.383(8) . ? C67 C68 1.392(8) . ? C68 C69 1.377(9) . ? C68 H68 0.9500 . ? C69 C70 1.371(10) . ? C69 H69 0.9500 . ? C70 C71 1.380(9) . ? C70 H70 0.9500 . ? C71 C72 1.393(8) . ? C71 H71 0.9500 . ? C72 H72 0.9500 . ? N1 S1 1.682(4) . ? N2 S2 1.692(4) . ? O1 S1 1.420(4) . ? O2 S1 1.434(4) . ? O5 S2 1.443(4) . ? O6 S2 1.422(4) . ? 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 120.2(5) . . ? C2 C1 S1 121.0(4) . . ? C7 C1 S1 118.8(4) . . ? C1 C2 C3 119.6(6) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 121.5(6) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C6 117.7(5) . . ? C3 C4 C5 120.8(6) . . ? C6 C4 C5 121.3(6) . . ? 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 121.7(6) . . ? C7 C6 H6 119.2 . . ? C4 C6 H6 119.2 . . ? C6 C7 C1 119.2(5) . . ? C6 C7 H7 120.4 . . ? C1 C7 H7 120.4 . . ? C9 C8 C13 121.9(5) . . ? C9 C8 N1 129.4(5) . . ? C13 C8 N1 108.5(4) . . ? C10 C9 C8 117.1(5) . . ? C10 C9 H9 121.5 . . ? C8 C9 H9 121.5 . . ? C9 C10 C11 121.3(6) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C12 C11 C10 121.7(6) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 118.3(5) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C12 C13 C8 119.7(5) . . ? C12 C13 C14 132.7(5) . . ? C8 C13 C14 107.5(5) . . ? C15 C14 C13 108.2(5) . . ? C15 C14 C22 124.3(5) . . ? C13 C14 C22 127.2(5) . . ? C14 C15 N1 108.8(4) . . ? C14 C15 C16 127.6(5) . . ? N1 C15 C16 123.3(4) . . ? C17 C16 C21 118.5(5) . . ? C17 C16 C15 118.9(5) . . ? C21 C16 C15 122.6(5) . . ? C18 C17 C16 121.1(6) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 119.5(6) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C20 C19 C18 119.8(6) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 121.3(6) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C16 119.8(6) . . ? C20 C21 H21 120.1 . . ? C16 C21 H21 120.1 . . ? C23 C22 C14 125.2(5) . . ? C23 C22 H22 117.4 . . ? C14 C22 H22 117.4 . . ? C22 C23 O3 118.5(5) . . ? C22 C23 C24 128.0(5) . . ? O3 C23 C24 113.4(4) . . ? C25 C24 C29 118.9(5) . . ? C25 C24 C23 121.2(5) . . ? C29 C24 C23 120.0(5) . . ? C26 C25 C24 121.0(6) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 C27 119.4(6) . . ? C25 C26 H26 120.3 . . ? C27 C26 H26 120.3 . . ? C28 C27 C26 120.5(6) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C27 C28 C29 120.2(6) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C28 C29 C24 120.0(6) . . ? C28 C29 H29 120.0 . . ? C24 C29 H29 120.0 . . ? O4 C30 O3 123.2(5) . . ? O4 C30 C31 125.2(5) . . ? O3 C30 C31 111.6(5) . . ? C32 C31 C36 119.9(5) . . ? C32 C31 C30 118.0(5) . . ? C36 C31 C30 122.1(5) . . ? C31 C32 C33 119.9(6) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C34 C33 C32 120.6(6) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C35 119.9(6) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C36 C35 C34 120.3(6) . . ? C36 C35 H35 119.9 . . ? C34 C35 H35 119.9 . . ? C35 C36 C31 119.5(5) . . ? C35 C36 H36 120.2 . . ? C31 C36 H36 120.2 . . ? C43 C37 C38 120.4(5) . . ? C43 C37 S2 120.8(4) . . ? C38 C37 S2 118.8(4) . . ? C39 C38 C37 118.9(6) . . ? C39 C38 H38 120.5 . . ? C37 C38 H38 120.5 . . ? C38 C39 C40 122.1(6) . . ? C38 C39 H39 118.9 . . ? C40 C39 H39 118.9 . . ? C42 C40 C39 117.6(5) . . ? C42 C40 C41 120.3(6) . . ? C39 C40 C41 122.1(6) . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C40 C42 C43 121.6(6) . . ? C40 C42 H42 119.2 . . ? C43 C42 H42 119.2 . . ? C37 C43 C42 119.3(6) . . ? C37 C43 H43 120.3 . . ? C42 C43 H43 120.3 . . ? C45 C44 C49 122.0(5) . . ? C45 C44 N2 130.3(5) . . ? C49 C44 N2 107.6(5) . . ? C46 C45 C44 117.1(5) . . ? C46 C45 H45 121.4 . . ? C44 C45 H45 121.4 . . ? C45 C46 C47 121.8(6) . . ? C45 C46 H46 119.1 . . ? C47 C46 H46 119.1 . . ? C46 C47 C48 121.1(5) . . ? C46 C47 H47 119.5 . . ? C48 C47 H47 119.5 . . ? C49 C48 C47 118.2(5) . . ? C49 C48 H48 120.9 . . ? C47 C48 H48 120.9 . . ? C48 C49 C44 119.8(5) . . ? C48 C49 C50 132.1(5) . . ? C44 C49 C50 108.0(5) . . ? C51 C50 C49 107.4(5) . . ? C51 C50 C58 126.3(5) . . ? C49 C50 C58 126.2(5) . . ? C50 C51 N2 109.1(5) . . ? C50 C51 C52 126.9(5) . . ? N2 C51 C52 123.9(5) . . ? C53 C52 C57 118.2(5) . . ? C53 C52 C51 120.5(5) . . ? C57 C52 C51 121.3(5) . . ? C54 C53 C52 122.4(6) . . ? C54 C53 H53 118.8 . . ? C52 C53 H53 118.8 . . ? C53 C54 C55 118.8(6) . . ? C53 C54 H54 120.6 . . ? C55 C54 H54 120.6 . . ? C56 C55 C54 120.0(6) . . ? C56 C55 H55 120.0 . . ? C54 C55 H55 120.0 . . ? C57 C56 C55 120.7(6) . . ? C57 C56 H56 119.6 . . ? C55 C56 H56 119.6 . . ? C56 C57 C52 119.9(6) . . ? C56 C57 H57 120.0 . . ? C52 C57 H57 120.0 . . ? C59 C58 C50 124.7(5) . . ? C59 C58 H58 117.7 . . ? C50 C58 H58 117.7 . . ? C58 C59 O7 117.4(5) . . ? C58 C59 C60 129.2(5) . . ? O7 C59 C60 113.3(5) . . ? C65 C60 C61 117.8(5) . . ? C65 C60 C59 119.4(5) . . ? C61 C60 C59 122.8(5) . . ? C62 C61 C60 121.4(5) . . ? C62 C61 H61 119.3 . . ? C60 C61 H61 119.3 . . ? C63 C62 C61 120.3(6) . . ? C63 C62 H62 119.9 . . ? C61 C62 H62 119.9 . . ? C62 C63 C64 119.2(6) . . ? C62 C63 H63 120.4 . . ? C64 C63 H63 120.4 . . ? C65 C64 C63 120.7(6) . . ? C65 C64 H64 119.7 . . ? C63 C64 H64 119.7 . . ? C64 C65 C60 120.7(5) . . ? C64 C65 H65 119.6 . . ? C60 C65 H65 119.6 . . ? O8 C66 O7 123.2(5) . . ? O8 C66 C67 125.8(5) . . ? O7 C66 C67 111.0(5) . . ? C72 C67 C68 120.2(5) . . ? C72 C67 C66 121.8(5) . . ? C68 C67 C66 118.0(5) . . ? C69 C68 C67 120.0(6) . . ? C69 C68 H68 120.0 . . ? C67 C68 H68 120.0 . . ? C70 C69 C68 120.1(6) . . ? C70 C69 H69 119.9 . . ? C68 C69 H69 119.9 . . ? C69 C70 C71 120.3(6) . . ? C69 C70 H70 119.9 . . ? C71 C70 H70 119.9 . . ? C70 C71 C72 120.4(6) . . ? C70 C71 H71 119.8 . . ? C72 C71 H71 119.8 . . ? C67 C72 C71 118.9(5) . . ? C67 C72 H72 120.5 . . ? C71 C72 H72 120.5 . . ? C8 N1 C15 107.0(4) . . ? C8 N1 S1 119.5(3) . . ? C15 N1 S1 122.5(3) . . ? C44 N2 C51 107.8(4) . . ? C44 N2 S2 119.7(3) . . ? C51 N2 S2 122.8(4) . . ? C30 O3 C23 116.8(4) . . ? C66 O7 C59 117.3(4) . . ? O1 S1 O2 120.2(2) . . ? O1 S1 N1 107.5(2) . . ? O2 S1 N1 104.5(2) . . ? O1 S1 C1 109.2(2) . . ? O2 S1 C1 109.2(2) . . ? N1 S1 C1 105.1(2) . . ? O6 S2 O5 120.2(2) . . ? O6 S2 N2 107.5(2) . . ? O5 S2 N2 104.5(2) . . ? O6 S2 C37 109.4(2) . . ? O5 S2 C37 108.7(2) . . ? N2 S2 C37 105.5(2) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 1.285 _refine_diff_density_min -0.569 _refine_diff_density_rms 0.105 data_ch13611 _database_code_depnum_ccdc_archive 'CCDC 874692' #TrackingRef '- 18d (CCDC 874692).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H26 Cl N O4' _chemical_formula_sum 'C37 H26 Cl N O4' _chemical_formula_weight 584.04 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 monoclinic _symmetry_space_group_name_H-M 'P 21/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 14.182(6) _cell_length_b 11.626(5) _cell_length_c 17.884(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.334(8) _cell_angle_gamma 90.00 _cell_volume 2946(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9343 _exptl_absorpt_correction_T_max 0.9598 _exptl_absorpt_process_details ? _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 ? _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 18046 _diffrn_reflns_av_R_equivalents 0.0821 _diffrn_reflns_av_sigmaI/netI 0.0890 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.14 _reflns_number_total 5216 _reflns_number_gt 2491 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1261P)^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 5216 _refine_ls_number_parameters 387 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1549 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.2330 _refine_ls_wR_factor_gt 0.1568 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.062 _refine_ls_shift/su_mean 0.010 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 0.2389(3) 0.8100(4) -0.0615(3) 0.0535(11) Uani 1 1 d . . . C2 C 0.2887(4) 0.9754(4) 0.0066(3) 0.0725(14) Uani 1 1 d . . . H2A H 0.2390 1.0329 0.0052 0.087 Uiso 1 1 calc R . . H2B H 0.3276 0.9874 -0.0361 0.087 Uiso 1 1 calc R . . C3 C 0.3471(3) 0.9860(4) 0.0775(2) 0.0512(11) Uani 1 1 d . . . C4 C 0.3174(3) 0.9402(4) 0.1438(3) 0.0601(12) Uani 1 1 d . . . H4 H 0.2596 0.9025 0.1444 0.072 Uiso 1 1 calc R . . C5 C 0.3709(4) 0.9494(4) 0.2080(3) 0.0750(15) Uani 1 1 d . . . H5 H 0.3496 0.9188 0.2523 0.090 Uiso 1 1 calc R . . C6 C 0.4560(4) 1.0036(5) 0.2075(3) 0.0813(16) Uani 1 1 d . . . H6 H 0.4936 1.0078 0.2513 0.098 Uiso 1 1 calc R . . C7 C 0.4865(4) 1.0520(5) 0.1428(4) 0.0780(15) Uani 1 1 d . . . H7 H 0.5438 1.0909 0.1430 0.094 Uiso 1 1 calc R . . C8 C 0.4322(3) 1.0428(4) 0.0779(3) 0.0649(13) Uani 1 1 d . . . H8 H 0.4530 1.0750 0.0339 0.078 Uiso 1 1 calc R . . C9 C 0.2102(3) 0.6114(4) -0.1083(2) 0.0503(11) Uani 1 1 d . . . C10 C 0.2444(4) 0.6157(5) -0.1803(3) 0.0712(14) Uani 1 1 d . . . H10 H 0.2679 0.6835 -0.1999 0.085 Uiso 1 1 calc R . . C11 C 0.2419(4) 0.5150(6) -0.2211(3) 0.0854(17) Uani 1 1 d . . . H11 H 0.2643 0.5148 -0.2693 0.103 Uiso 1 1 calc R . . C12 C 0.2071(4) 0.4151(5) -0.1922(3) 0.0814(16) Uani 1 1 d . . . H12 H 0.2046 0.3495 -0.2220 0.098 Uiso 1 1 calc R . . C13 C 0.1755(3) 0.4089(4) -0.1201(3) 0.0631(13) Uani 1 1 d . . . H13 H 0.1529 0.3403 -0.1010 0.076 Uiso 1 1 calc R . . C14 C 0.1787(3) 0.5091(4) -0.0770(2) 0.0473(10) Uani 1 1 d . . . C15 C 0.1492(3) 0.5347(3) -0.0027(2) 0.0434(10) Uani 1 1 d . . . C16 C 0.1598(3) 0.6499(4) 0.0086(2) 0.0438(10) Uani 1 1 d . . . C17 C 0.1234(3) 0.7155(4) 0.0720(2) 0.0464(10) Uani 1 1 d . . . C18 C 0.1541(3) 0.6906(4) 0.1449(2) 0.0603(12) Uani 1 1 d . . . H18 H 0.2016 0.6366 0.1539 0.072 Uiso 1 1 calc R . . C19 C 0.1143(4) 0.7457(5) 0.2040(3) 0.0734(15) Uani 1 1 d . . . H19 H 0.1367 0.7307 0.2526 0.088 Uiso 1 1 calc R . . C20 C 0.0425(4) 0.8221(5) 0.1919(3) 0.0759(15) Uani 1 1 d . . . H20 H 0.0147 0.8574 0.2321 0.091 Uiso 1 1 calc R . . C21 C 0.0110(3) 0.8469(4) 0.1199(3) 0.0676(14) Uani 1 1 d . . . C22 C 0.0518(3) 0.7950(4) 0.0595(2) 0.0560(12) Uani 1 1 d . . . H22 H 0.0313 0.8134 0.0110 0.067 Uiso 1 1 calc R . . C23 C 0.1081(3) 0.4554(3) 0.0508(2) 0.0449(10) Uani 1 1 d . . . H23 H 0.0520 0.4776 0.0718 0.054 Uiso 1 1 calc R . . C24 C 0.1441(3) 0.3544(3) 0.0718(2) 0.0429(10) Uani 1 1 d . . . C25 C 0.1070(3) 0.2731(3) 0.1254(2) 0.0432(10) Uani 1 1 d . . . C26 C 0.0155(3) 0.2820(4) 0.1483(2) 0.0538(11) Uani 1 1 d . . . H26 H -0.0242 0.3374 0.1266 0.065 Uiso 1 1 calc R . . C27 C -0.0181(3) 0.2111(4) 0.2025(3) 0.0674(13) Uani 1 1 d . . . H27 H -0.0802 0.2183 0.2167 0.081 Uiso 1 1 calc R . . C28 C 0.0396(4) 0.1296(4) 0.2358(3) 0.0685(14) Uani 1 1 d . . . H28 H 0.0175 0.0831 0.2736 0.082 Uiso 1 1 calc R . . C29 C 0.1297(4) 0.1171(4) 0.2132(3) 0.0691(14) Uani 1 1 d . . . H29 H 0.1685 0.0608 0.2349 0.083 Uiso 1 1 calc R . . C30 C 0.1637(3) 0.1876(4) 0.1580(2) 0.0577(12) Uani 1 1 d . . . H30 H 0.2250 0.1778 0.1426 0.069 Uiso 1 1 calc R . . C31 C 0.3102(3) 0.3670(4) 0.0712(3) 0.0521(11) Uani 1 1 d . . . C32 C 0.3935(3) 0.3396(4) 0.0276(3) 0.0596(12) Uani 1 1 d . . . C33 C 0.4802(3) 0.3760(5) 0.0557(4) 0.0858(17) Uani 1 1 d . . . H33 H 0.4864 0.4141 0.1014 0.103 Uiso 1 1 calc R . . C34 C 0.5584(4) 0.3536(6) 0.0130(5) 0.112(2) Uani 1 1 d . . . H34 H 0.6179 0.3751 0.0318 0.134 Uiso 1 1 calc R . . C35 C 0.5507(5) 0.3021(7) -0.0540(4) 0.106(2) Uani 1 1 d . . . H35 H 0.6040 0.2914 -0.0818 0.128 Uiso 1 1 calc R . . C36 C 0.4655(5) 0.2656(6) -0.0812(3) 0.0943(19) Uani 1 1 d . . . H36 H 0.4603 0.2274 -0.1269 0.113 Uiso 1 1 calc R . . C37 C 0.3860(4) 0.2857(5) -0.0404(3) 0.0736(15) Uani 1 1 d . . . H37 H 0.3271 0.2624 -0.0595 0.088 Uiso 1 1 calc R . . N1 N 0.1997(2) 0.7003(3) -0.05493(17) 0.0447(8) Uani 1 1 d . . . O1 O 0.2477(2) 0.8599(3) 0.00384(17) 0.0653(9) Uani 1 1 d . . . O2 O 0.2637(2) 0.8477(3) -0.11951(18) 0.0767(10) Uani 1 1 d . . . O3 O 0.22955(18) 0.3208(2) 0.04030(15) 0.0491(7) Uani 1 1 d . . . O4 O 0.3109(2) 0.4228(3) 0.1273(2) 0.0807(11) Uani 1 1 d . . . Cl1 Cl -0.08200(12) 0.93920(17) 0.10381(11) 0.1291(8) 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 0.054(3) 0.061(3) 0.046(3) 0.008(3) 0.005(2) -0.001(2) C2 0.104(4) 0.044(3) 0.068(3) 0.012(2) -0.010(3) -0.019(3) C3 0.060(3) 0.042(3) 0.052(3) 0.004(2) 0.003(2) 0.001(2) C4 0.060(3) 0.056(3) 0.064(3) 0.010(2) 0.003(2) -0.006(2) C5 0.099(4) 0.068(4) 0.058(3) 0.009(3) 0.001(3) -0.006(3) C6 0.086(4) 0.073(4) 0.084(4) -0.004(3) -0.019(3) 0.003(3) C7 0.060(3) 0.076(4) 0.097(5) -0.010(3) 0.003(3) -0.014(3) C8 0.074(3) 0.056(3) 0.066(3) 0.000(2) 0.018(3) -0.009(3) C9 0.051(3) 0.057(3) 0.043(3) -0.004(2) 0.003(2) 0.007(2) C10 0.091(4) 0.074(4) 0.050(3) 0.003(3) 0.026(3) 0.002(3) C11 0.121(5) 0.092(5) 0.045(3) -0.009(3) 0.024(3) 0.018(4) C12 0.117(5) 0.071(4) 0.056(3) -0.018(3) 0.009(3) 0.019(3) C13 0.080(3) 0.055(3) 0.054(3) -0.010(2) 0.001(2) 0.011(2) C14 0.045(2) 0.051(3) 0.046(2) -0.003(2) 0.0024(19) 0.010(2) C15 0.042(2) 0.047(3) 0.042(2) 0.002(2) 0.0016(18) 0.0062(19) C16 0.042(2) 0.050(3) 0.040(2) 0.003(2) 0.0024(18) 0.0027(19) C17 0.052(2) 0.043(3) 0.045(3) 0.002(2) 0.0065(19) -0.006(2) C18 0.084(3) 0.052(3) 0.046(3) 0.004(2) 0.009(2) 0.005(2) C19 0.113(4) 0.068(4) 0.040(3) 0.001(3) 0.014(3) 0.002(3) C20 0.092(4) 0.072(4) 0.066(4) -0.021(3) 0.028(3) -0.007(3) C21 0.062(3) 0.061(3) 0.080(4) -0.028(3) 0.008(3) 0.006(2) C22 0.058(3) 0.050(3) 0.059(3) -0.009(2) -0.005(2) 0.004(2) C23 0.042(2) 0.047(3) 0.046(2) -0.007(2) 0.0060(18) 0.004(2) C24 0.043(2) 0.043(3) 0.043(2) -0.005(2) -0.0001(18) 0.0010(19) C25 0.047(2) 0.042(3) 0.041(2) -0.0063(19) 0.0006(19) -0.0027(19) C26 0.053(3) 0.055(3) 0.054(3) 0.003(2) 0.001(2) -0.002(2) C27 0.068(3) 0.068(3) 0.068(3) 0.004(3) 0.019(3) -0.009(3) C28 0.097(4) 0.050(3) 0.059(3) 0.008(2) 0.008(3) -0.009(3) C29 0.092(4) 0.052(3) 0.064(3) 0.011(3) 0.005(3) 0.007(3) C30 0.063(3) 0.047(3) 0.063(3) -0.001(2) 0.004(2) 0.004(2) C31 0.047(3) 0.053(3) 0.056(3) 0.002(2) 0.000(2) 0.005(2) C32 0.052(3) 0.059(3) 0.069(3) 0.014(3) 0.009(2) 0.019(2) C33 0.049(3) 0.084(4) 0.124(5) 0.016(3) 0.001(3) 0.012(3) C34 0.052(4) 0.114(6) 0.170(8) 0.053(5) 0.007(4) 0.022(3) C35 0.095(5) 0.116(6) 0.111 0.041(5) 0.040(4) 0.050(4) C36 0.090(5) 0.101(5) 0.094(4) 0.030(4) 0.030(4) 0.035(4) C37 0.071(3) 0.077(4) 0.075(4) 0.014(3) 0.021(3) 0.027(3) N1 0.051(2) 0.043(2) 0.041(2) 0.0006(17) 0.0068(15) -0.0020(16) O1 0.087(2) 0.057(2) 0.052(2) 0.0012(16) 0.0053(16) -0.0206(17) O2 0.104(3) 0.074(2) 0.053(2) 0.0113(18) 0.0133(18) -0.0241(19) O3 0.0452(17) 0.0487(17) 0.0535(18) -0.0041(14) 0.0040(13) 0.0043(13) O4 0.060(2) 0.104(3) 0.077(3) -0.029(2) -0.0008(18) -0.0051(18) Cl1 0.1085(12) 0.1366(17) 0.1404(16) -0.0608(12) -0.0188(11) 0.0656(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 O2 1.192(5) . ? C1 O1 1.307(5) . ? C1 N1 1.398(5) . ? C2 O1 1.463(5) . ? C2 C3 1.491(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C8 1.376(6) . ? C3 C4 1.381(6) . ? C4 C5 1.355(6) . ? C4 H4 0.9300 . ? C5 C6 1.361(7) . ? C5 H5 0.9300 . ? C6 C7 1.372(7) . ? C6 H6 0.9300 . ? C7 C8 1.371(7) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.395(6) . ? C9 C14 1.396(6) . ? C9 N1 1.419(5) . ? C10 C11 1.380(7) . ? C10 H10 0.9300 . ? C11 C12 1.371(7) . ? C11 H11 0.9300 . ? C12 C13 1.384(7) . ? C12 H12 0.9300 . ? C13 C14 1.397(6) . ? C13 H13 0.9300 . ? C14 C15 1.441(5) . ? C15 C16 1.362(5) . ? C15 C23 1.466(5) . ? C16 N1 1.417(5) . ? C16 C17 1.476(5) . ? C17 C22 1.384(6) . ? C17 C18 1.390(6) . ? C18 C19 1.376(6) . ? C18 H18 0.9300 . ? C19 C20 1.363(7) . ? C19 H19 0.9300 . ? C20 C21 1.376(7) . ? C20 H20 0.9300 . ? C21 C22 1.383(6) . ? C21 Cl1 1.716(5) . ? C22 H22 0.9300 . ? C23 C24 1.328(5) . ? C23 H23 0.9300 . ? C24 O3 1.411(4) . ? C24 C25 1.461(6) . ? C25 C26 1.380(5) . ? C25 C30 1.391(6) . ? C26 C27 1.373(6) . ? C26 H26 0.9300 . ? C27 C28 1.372(7) . ? C27 H27 0.9300 . ? C28 C29 1.363(6) . ? C28 H28 0.9300 . ? C29 C30 1.384(6) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 O4 1.194(5) . ? C31 O3 1.360(5) . ? C31 C32 1.477(6) . ? C32 C37 1.368(7) . ? C32 C33 1.377(7) . ? C33 C34 1.396(8) . ? C33 H33 0.9300 . ? C34 C35 1.341(9) . ? C34 H34 0.9300 . ? C35 C36 1.352(9) . ? C35 H35 0.9300 . ? C36 C37 1.388(7) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? 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 O2 C1 O1 126.4(5) . . ? O2 C1 N1 122.8(4) . . ? O1 C1 N1 110.7(4) . . ? O1 C2 C3 108.1(4) . . ? O1 C2 H2A 110.1 . . ? C3 C2 H2A 110.1 . . ? O1 C2 H2B 110.1 . . ? C3 C2 H2B 110.1 . . ? H2A C2 H2B 108.4 . . ? C8 C3 C4 118.6(4) . . ? C8 C3 C2 120.1(4) . . ? C4 C3 C2 121.3(4) . . ? C5 C4 C3 121.1(5) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C6 C5 C4 119.9(5) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 120.3(5) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C8 119.8(5) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C3 120.3(5) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? C10 C9 C14 122.0(4) . . ? C10 C9 N1 130.2(4) . . ? C14 C9 N1 107.8(3) . . ? C11 C10 C9 117.1(5) . . ? C11 C10 H10 121.5 . . ? C9 C10 H10 121.5 . . ? C12 C11 C10 121.4(5) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C13 122.0(5) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C12 C13 C14 117.8(5) . . ? C12 C13 H13 121.1 . . ? C14 C13 H13 121.1 . . ? C9 C14 C13 119.5(4) . . ? C9 C14 C15 107.7(4) . . ? C13 C14 C15 132.7(4) . . ? C16 C15 C14 107.8(4) . . ? C16 C15 C23 124.5(4) . . ? C14 C15 C23 127.5(4) . . ? C15 C16 N1 109.5(3) . . ? C15 C16 C17 125.6(4) . . ? N1 C16 C17 124.4(4) . . ? C22 C17 C18 119.3(4) . . ? C22 C17 C16 120.0(4) . . ? C18 C17 C16 120.4(4) . . ? C19 C18 C17 120.1(5) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 120.6(5) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 119.8(5) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C22 120.6(5) . . ? C20 C21 Cl1 120.3(4) . . ? C22 C21 Cl1 119.0(4) . . ? C17 C22 C21 119.6(4) . . ? C17 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C24 C23 C15 125.5(4) . . ? C24 C23 H23 117.2 . . ? C15 C23 H23 117.2 . . ? C23 C24 O3 117.3(4) . . ? C23 C24 C25 127.8(4) . . ? O3 C24 C25 114.9(3) . . ? C26 C25 C30 117.6(4) . . ? C26 C25 C24 121.0(4) . . ? C30 C25 C24 121.3(4) . . ? C27 C26 C25 121.5(4) . . ? C27 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? C26 C27 C28 120.2(5) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C29 C28 C27 119.7(5) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C28 C29 C30 120.4(5) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C29 C30 C25 120.6(4) . . ? C29 C30 H30 119.7 . . ? C25 C30 H30 119.7 . . ? O4 C31 O3 122.3(4) . . ? O4 C31 C32 125.5(4) . . ? O3 C31 C32 112.1(4) . . ? C37 C32 C33 120.1(5) . . ? C37 C32 C31 122.3(4) . . ? C33 C32 C31 117.5(5) . . ? C34 C33 C32 117.4(6) . . ? C34 C33 H33 121.3 . . ? C32 C33 H33 121.3 . . ? C35 C34 C33 122.4(7) . . ? C35 C34 H34 118.8 . . ? C33 C34 H34 118.8 . . ? C34 C35 C36 120.1(6) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C35 C36 C37 119.4(7) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? C32 C37 C36 120.6(6) . . ? C32 C37 H37 119.7 . . ? C36 C37 H37 119.7 . . ? C1 N1 C16 128.2(3) . . ? C1 N1 C9 123.7(3) . . ? C16 N1 C9 107.2(3) . . ? C1 O1 C2 117.5(4) . . ? C31 O3 C24 116.7(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.486 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.185 data_ch13612 _database_code_depnum_ccdc_archive 'CCDC 874693' #TrackingRef '- 17e (CCDC 874693).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H31 N O4' _chemical_formula_sum 'C31 H31 N O4' _chemical_formula_weight 481.57 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7424(4) _cell_length_b 10.2579(5) _cell_length_c 14.6034(6) _cell_angle_alpha 109.778(2) _cell_angle_beta 98.868(2) _cell_angle_gamma 98.878(2) _cell_volume 1323.02(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9494 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details ? _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 ? _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 11242 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.13 _reflns_number_total 4708 _reflns_number_gt 3252 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1035P)^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 4708 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1767 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 0.1950(2) 0.7386(2) 0.44875(14) 0.0425(5) Uani 1 1 d . . . C2 C -0.0436(2) 0.5961(3) 0.35720(16) 0.0521(6) Uani 1 1 d . . . C3 C -0.1621(3) 0.5294(3) 0.3938(2) 0.0707(8) Uani 1 1 d . . . H3A H -0.1917 0.6026 0.4426 0.106 Uiso 1 1 calc R . . H3B H -0.1287 0.4665 0.4235 0.106 Uiso 1 1 calc R . . H3C H -0.2414 0.4768 0.3386 0.106 Uiso 1 1 calc R . . C4 C -0.0847(3) 0.7103(3) 0.3224(2) 0.0746(8) Uani 1 1 d . . . H4A H -0.1146 0.7781 0.3745 0.112 Uiso 1 1 calc R . . H4B H -0.1613 0.6681 0.2643 0.112 Uiso 1 1 calc R . . H4C H -0.0041 0.7573 0.3062 0.112 Uiso 1 1 calc R . . C5 C 0.0053(3) 0.4838(3) 0.2797(2) 0.0814(9) Uani 1 1 d . . . H5A H 0.0805 0.5286 0.2576 0.122 Uiso 1 1 calc R . . H5B H -0.0732 0.4315 0.2239 0.122 Uiso 1 1 calc R . . H5C H 0.0395 0.4202 0.3083 0.122 Uiso 1 1 calc R . . C6 C 0.2145(2) 0.8782(2) 0.63043(14) 0.0415(5) Uani 1 1 d . . . C7 C 0.0749(2) 0.8666(3) 0.64168(16) 0.0537(6) Uani 1 1 d . . . H7 H -0.0007 0.8088 0.5893 0.064 Uiso 1 1 calc R . . C8 C 0.0527(3) 0.9440(3) 0.73346(18) 0.0628(7) Uani 1 1 d . . . H8 H -0.0400 0.9382 0.7429 0.075 Uiso 1 1 calc R . . C9 C 0.1650(3) 1.0307(3) 0.81234(17) 0.0611(7) Uani 1 1 d . . . H9 H 0.1464 1.0812 0.8735 0.073 Uiso 1 1 calc R . . C10 C 0.3032(3) 1.0428(2) 0.80088(16) 0.0539(6) Uani 1 1 d . . . H10 H 0.3782 1.1010 0.8536 0.065 Uiso 1 1 calc R . . C11 C 0.3288(2) 0.9657(2) 0.70826(14) 0.0416(5) Uani 1 1 d . . . C12 C 0.4589(2) 0.9591(2) 0.67191(14) 0.0404(5) Uani 1 1 d . . . C13 C 0.4229(2) 0.8705(2) 0.57395(14) 0.0387(5) Uani 1 1 d . . . C14 C 0.5152(2) 0.8119(2) 0.50304(15) 0.0464(5) Uani 1 1 d . . . H14 H 0.4800 0.8226 0.4400 0.056 Uiso 1 1 calc R . . C15 C 0.6713(2) 0.8873(3) 0.54060(18) 0.0589(7) Uani 1 1 d . . . H15A H 0.7237 0.8462 0.4918 0.088 Uiso 1 1 calc R . . H15B H 0.7084 0.8770 0.6020 0.088 Uiso 1 1 calc R . . H15C H 0.6806 0.9863 0.5518 0.088 Uiso 1 1 calc R . . C16 C 0.5012(3) 0.6535(3) 0.4821(2) 0.0683(7) Uani 1 1 d . . . H16A H 0.5594 0.6162 0.4365 0.103 Uiso 1 1 calc R . . H16B H 0.4035 0.6045 0.4532 0.103 Uiso 1 1 calc R . . H16C H 0.5319 0.6403 0.5434 0.103 Uiso 1 1 calc R . . C17 C 0.5976(2) 1.0444(2) 0.73450(14) 0.0450(5) Uani 1 1 d . . . H17 H 0.6457 1.1112 0.7138 0.054 Uiso 1 1 calc R . . C18 C 0.6606(2) 1.0343(2) 0.81857(14) 0.0429(5) Uani 1 1 d . . . C19 C 0.7930(2) 1.1250(2) 0.88902(14) 0.0433(5) Uani 1 1 d . . . C20 C 0.8695(3) 1.2371(3) 0.87108(16) 0.0543(6) Uani 1 1 d . . . H20 H 0.8360 1.2542 0.8140 0.065 Uiso 1 1 calc R . . C21 C 0.9931(3) 1.3224(3) 0.93621(17) 0.0636(7) Uani 1 1 d . . . H21 H 1.0434 1.3959 0.9226 0.076 Uiso 1 1 calc R . . C22 C 1.0431(3) 1.2995(3) 1.02191(18) 0.0667(8) Uani 1 1 d . . . H22 H 1.1264 1.3580 1.0665 0.080 Uiso 1 1 calc R . . C23 C 0.9695(3) 1.1904(3) 1.04086(17) 0.0658(7) Uani 1 1 d . . . H23 H 1.0034 1.1744 1.0983 0.079 Uiso 1 1 calc R . . C24 C 0.8454(3) 1.1037(3) 0.97533(16) 0.0563(6) Uani 1 1 d . . . H24 H 0.7962 1.0301 0.9893 0.068 Uiso 1 1 calc R . . C25 C 0.6251(3) 0.7977(2) 0.81017(16) 0.0499(6) Uani 1 1 d . . . C26 C 0.5426(2) 0.6903(2) 0.84013(15) 0.0496(6) Uani 1 1 d . . . C27 C 0.5669(3) 0.5538(3) 0.80677(19) 0.0625(7) Uani 1 1 d . . . H27 H 0.6326 0.5321 0.7671 0.075 Uiso 1 1 calc R . . C28 C 0.4930(3) 0.4503(3) 0.8328(2) 0.0729(8) Uani 1 1 d . . . H28 H 0.5094 0.3590 0.8111 0.087 Uiso 1 1 calc R . . C29 C 0.3954(3) 0.4825(3) 0.8906(2) 0.0757(8) Uani 1 1 d . . . H29 H 0.3456 0.4125 0.9078 0.091 Uiso 1 1 calc R . . C30 C 0.3709(3) 0.6160(3) 0.9230(2) 0.0723(8) Uani 1 1 d . . . H30 H 0.3048 0.6367 0.9625 0.087 Uiso 1 1 calc R . . C31 C 0.4434(3) 0.7204(3) 0.89782(18) 0.0611(7) Uani 1 1 d . . . H31 H 0.4255 0.8111 0.9196 0.073 Uiso 1 1 calc R . . N1 N 0.27337(17) 0.81786(18) 0.54652(11) 0.0405(4) Uani 1 1 d . . . O1 O 0.07072(15) 0.66689(15) 0.45044(9) 0.0472(4) Uani 1 1 d . . . O2 O 0.23732(17) 0.73716(18) 0.37564(10) 0.0590(5) Uani 1 1 d . . . O3 O 0.59206(16) 0.92665(15) 0.84742(10) 0.0476(4) Uani 1 1 d . . . O4 O 0.7122(2) 0.77628(19) 0.76072(14) 0.0752(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 0.0425(13) 0.0444(13) 0.0403(11) 0.0159(10) 0.0094(10) 0.0075(10) C2 0.0427(13) 0.0582(15) 0.0444(11) 0.0135(11) 0.0006(10) 0.0019(11) C3 0.0493(16) 0.0780(19) 0.0723(16) 0.0237(15) 0.0068(13) -0.0048(14) C4 0.0647(18) 0.093(2) 0.0711(16) 0.0417(16) 0.0038(14) 0.0164(16) C5 0.075(2) 0.0715(19) 0.0663(16) -0.0062(14) 0.0133(15) 0.0030(16) C6 0.0449(13) 0.0449(12) 0.0385(10) 0.0172(9) 0.0136(10) 0.0124(10) C7 0.0468(14) 0.0609(15) 0.0526(12) 0.0178(11) 0.0176(11) 0.0107(12) C8 0.0569(16) 0.0739(18) 0.0628(15) 0.0221(13) 0.0290(14) 0.0210(14) C9 0.0714(18) 0.0693(17) 0.0478(13) 0.0179(12) 0.0278(13) 0.0251(15) C10 0.0674(16) 0.0523(14) 0.0402(11) 0.0136(10) 0.0132(11) 0.0149(12) C11 0.0470(13) 0.0435(12) 0.0372(10) 0.0177(9) 0.0112(10) 0.0098(10) C12 0.0435(12) 0.0396(12) 0.0388(10) 0.0173(9) 0.0079(9) 0.0061(10) C13 0.0378(12) 0.0396(11) 0.0412(10) 0.0185(9) 0.0091(9) 0.0070(9) C14 0.0429(13) 0.0519(13) 0.0448(11) 0.0171(10) 0.0139(10) 0.0100(11) C15 0.0473(14) 0.0650(16) 0.0659(14) 0.0223(13) 0.0213(12) 0.0130(13) C16 0.0663(18) 0.0513(15) 0.0824(17) 0.0124(13) 0.0246(15) 0.0190(13) C17 0.0455(13) 0.0464(13) 0.0417(11) 0.0183(10) 0.0075(10) 0.0041(10) C18 0.0477(13) 0.0412(12) 0.0402(11) 0.0151(9) 0.0127(10) 0.0080(10) C19 0.0457(13) 0.0428(12) 0.0365(10) 0.0089(9) 0.0084(10) 0.0097(10) C20 0.0546(15) 0.0579(15) 0.0431(11) 0.0159(11) 0.0058(11) 0.0029(12) C21 0.0576(16) 0.0634(16) 0.0531(13) 0.0094(12) 0.0092(13) -0.0028(13) C22 0.0555(16) 0.0659(18) 0.0512(14) -0.0048(13) -0.0012(12) 0.0092(14) C23 0.0733(19) 0.0683(18) 0.0422(12) 0.0100(12) -0.0047(13) 0.0186(16) C24 0.0652(16) 0.0567(15) 0.0434(11) 0.0173(11) 0.0039(12) 0.0139(13) C25 0.0491(14) 0.0508(14) 0.0501(12) 0.0207(11) 0.0082(11) 0.0109(11) C26 0.0469(13) 0.0506(14) 0.0461(11) 0.0201(10) -0.0017(10) 0.0034(11) C27 0.0607(17) 0.0549(16) 0.0658(15) 0.0198(13) 0.0047(13) 0.0101(13) C28 0.077(2) 0.0497(16) 0.0858(19) 0.0304(14) -0.0003(16) 0.0033(15) C29 0.074(2) 0.071(2) 0.0798(18) 0.0418(16) 0.0032(16) -0.0068(16) C30 0.0717(19) 0.075(2) 0.0745(17) 0.0371(15) 0.0195(15) 0.0035(15) C31 0.0617(16) 0.0583(16) 0.0651(14) 0.0261(13) 0.0171(13) 0.0078(13) N1 0.0390(10) 0.0447(10) 0.0357(8) 0.0130(8) 0.0105(8) 0.0058(8) O1 0.0428(9) 0.0532(9) 0.0394(7) 0.0155(7) 0.0069(7) -0.0011(7) O2 0.0576(10) 0.0738(12) 0.0384(8) 0.0178(8) 0.0133(8) -0.0019(9) O3 0.0534(10) 0.0467(9) 0.0479(8) 0.0225(7) 0.0142(7) 0.0112(8) O4 0.0797(13) 0.0662(12) 0.0989(13) 0.0370(11) 0.0499(12) 0.0265(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.199(2) . ? C1 O1 1.324(2) . ? C1 N1 1.403(2) . ? C2 O1 1.495(3) . ? C2 C4 1.508(4) . ? C2 C3 1.510(3) . ? C2 C5 1.512(3) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.387(3) . ? C6 C11 1.395(3) . ? C6 N1 1.423(2) . ? C7 C8 1.377(3) . ? C7 H7 0.9300 . ? C8 C9 1.390(4) . ? C8 H8 0.9300 . ? C9 C10 1.374(3) . ? C9 H9 0.9300 . ? C10 C11 1.399(3) . ? C10 H10 0.9300 . ? C11 C12 1.450(3) . ? C12 C13 1.365(3) . ? C12 C17 1.463(3) . ? C13 N1 1.416(3) . ? C13 C14 1.508(3) . ? C14 C15 1.518(3) . ? C14 C16 1.528(3) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.330(3) . ? C17 H17 0.9300 . ? C18 O3 1.420(2) . ? C18 C19 1.470(3) . ? C19 C24 1.385(3) . ? C19 C20 1.395(3) . ? C20 C21 1.371(3) . ? C20 H20 0.9300 . ? C21 C22 1.381(4) . ? C21 H21 0.9300 . ? C22 C23 1.366(4) . ? C22 H22 0.9300 . ? C23 C24 1.380(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 O4 1.195(3) . ? C25 O3 1.360(3) . ? C25 C26 1.487(3) . ? C26 C31 1.381(3) . ? C26 C27 1.390(3) . ? C27 C28 1.382(4) . ? C27 H27 0.9300 . ? C28 C29 1.371(4) . ? C28 H28 0.9300 . ? C29 C30 1.361(4) . ? C29 H29 0.9300 . ? C30 C31 1.377(4) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? 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 O2 C1 O1 126.18(19) . . ? O2 C1 N1 123.8(2) . . ? O1 C1 N1 110.04(16) . . ? O1 C2 C4 107.72(19) . . ? O1 C2 C3 102.12(17) . . ? C4 C2 C3 111.4(2) . . ? O1 C2 C5 110.74(19) . . ? C4 C2 C5 113.3(2) . . ? C3 C2 C5 111.0(2) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C11 121.77(18) . . ? C7 C6 N1 131.7(2) . . ? C11 C6 N1 106.47(17) . . ? C8 C7 C6 117.4(2) . . ? C8 C7 H7 121.3 . . ? C6 C7 H7 121.3 . . ? C7 C8 C9 121.8(2) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C10 C9 C8 120.7(2) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 118.7(2) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C6 C11 C10 119.6(2) . . ? C6 C11 C12 108.41(16) . . ? C10 C11 C12 131.9(2) . . ? C13 C12 C11 107.81(18) . . ? C13 C12 C17 130.17(18) . . ? C11 C12 C17 121.92(17) . . ? C12 C13 N1 108.52(16) . . ? C12 C13 C14 130.56(19) . . ? N1 C13 C14 120.35(17) . . ? C13 C14 C15 113.66(17) . . ? C13 C14 C16 109.55(18) . . ? C15 C14 C16 109.35(19) . . ? C13 C14 H14 108.0 . . ? C15 C14 H14 108.0 . . ? C16 C14 H14 108.0 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C12 125.4(2) . . ? C18 C17 H17 117.3 . . ? C12 C17 H17 117.3 . . ? C17 C18 O3 117.62(19) . . ? C17 C18 C19 127.9(2) . . ? O3 C18 C19 114.49(17) . . ? C24 C19 C20 117.8(2) . . ? C24 C19 C18 121.7(2) . . ? C20 C19 C18 120.51(19) . . ? C21 C20 C19 121.1(2) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 120.1(3) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 119.7(2) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 120.5(2) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C19 120.9(3) . . ? C23 C24 H24 119.5 . . ? C19 C24 H24 119.5 . . ? O4 C25 O3 123.0(2) . . ? O4 C25 C26 125.1(2) . . ? O3 C25 C26 111.91(18) . . ? C31 C26 C27 119.5(2) . . ? C31 C26 C25 123.0(2) . . ? C27 C26 C25 117.5(2) . . ? C28 C27 C26 119.7(2) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C29 C28 C27 120.0(3) . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? C30 C29 C28 120.5(3) . . ? C30 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C29 C30 C31 120.3(3) . . ? C29 C30 H30 119.8 . . ? C31 C30 H30 119.8 . . ? C26 C31 C30 120.0(2) . . ? C26 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C1 N1 C13 124.95(15) . . ? C1 N1 C6 125.48(17) . . ? C13 N1 C6 108.79(16) . . ? C1 O1 C2 120.47(15) . . ? C25 O3 C18 115.91(15) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.241 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.091 data_a13651 _database_code_depnum_ccdc_archive 'CCDC 876151' #TrackingRef '- 22b (CCDC 876151).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H18 Cl N O4 S' _chemical_formula_sum 'C29 H18 Cl N O4 S' _chemical_formula_weight 511.95 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' S S 0.1246 0.1234 '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 8.1399(2) _cell_length_b 12.4092(3) _cell_length_c 12.5776(4) _cell_angle_alpha 78.4510(10) _cell_angle_beta 87.408(2) _cell_angle_gamma 78.835(2) _cell_volume 1221.15(6) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9234 _exptl_absorpt_correction_T_max 0.9463 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 10643 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.39 _reflns_number_total 4442 _reflns_number_gt 3691 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0663P)^2^+0.2010P] 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 4442 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _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 -0.2357(2) 0.67391(15) 0.07903(15) 0.0357(4) Uani 1 1 d . . . C2 C -0.3144(3) 0.75578(17) 0.13307(18) 0.0425(5) Uani 1 1 d . . . H2 H -0.4315 0.7834 0.1260 0.051 Uiso 1 1 calc R . . C3 C -0.2190(2) 0.79673(16) 0.19784(16) 0.0378(4) Uani 1 1 d . . . H3 H -0.2707 0.8529 0.2364 0.045 Uiso 1 1 calc R . . C4 C -0.0485(2) 0.75656(14) 0.20698(14) 0.0279(4) Uani 1 1 d . . . C5 C 0.0278(2) 0.67563(15) 0.14947(15) 0.0338(4) Uani 1 1 d . . . H5 H 0.1454 0.6494 0.1542 0.041 Uiso 1 1 calc R . . C6 C -0.0670(3) 0.63320(16) 0.08549(15) 0.0371(4) Uani 1 1 d . . . H6 H -0.0162 0.5769 0.0467 0.045 Uiso 1 1 calc R . . C7 C 0.0452(2) 0.79792(14) 0.28427(14) 0.0281(4) Uani 1 1 d . . . C8 C 0.3126(2) 0.79604(15) 0.34771(14) 0.0293(4) Uani 1 1 d . . . C9 C 0.3734(2) 0.90064(15) 0.30387(15) 0.0330(4) Uani 1 1 d . . . C10 C 0.3344(3) 0.95845(17) 0.19977(18) 0.0461(5) Uani 1 1 d . . . H10 H 0.2669 0.9305 0.1560 0.055 Uiso 1 1 calc R . . C11 C 0.3920(3) 1.0567(2) 0.1578(2) 0.0627(7) Uani 1 1 d . . . H11 H 0.3640 1.0953 0.0859 0.075 Uiso 1 1 calc R . . C12 C 0.4897(3) 1.09842(19) 0.2204(2) 0.0626(7) Uani 1 1 d . . . H12 H 0.5285 1.1660 0.1921 0.075 Uiso 1 1 calc R . . C13 C 0.5301(3) 1.0418(2) 0.3232(2) 0.0604(7) Uani 1 1 d . . . H13 H 0.5983 1.0701 0.3662 0.072 Uiso 1 1 calc R . . C14 C 0.4733(3) 0.94377(18) 0.36585(18) 0.0470(5) Uani 1 1 d . . . H14 H 0.5024 0.9056 0.4377 0.056 Uiso 1 1 calc R . . C15 C 0.3417(2) 0.73062(15) 0.44499(14) 0.0306(4) Uani 1 1 d . . . H15 H 0.4105 0.7536 0.4919 0.037 Uiso 1 1 calc R . . C16 C 0.2797(2) 0.62685(14) 0.48828(14) 0.0287(4) Uani 1 1 d . . . C17 C 0.2117(2) 0.60751(14) 0.59034(14) 0.0302(4) Uani 1 1 d . . . C18 C 0.1752(2) 0.68309(15) 0.66817(14) 0.0298(4) Uani 1 1 d . . . C19 C 0.1010(2) 0.79510(15) 0.63530(15) 0.0348(4) Uani 1 1 d . . . H19 H 0.0727 0.8234 0.5612 0.042 Uiso 1 1 calc R . . C20 C 0.0678(3) 0.86590(16) 0.70872(16) 0.0398(5) Uani 1 1 d . . . H20 H 0.0168 0.9422 0.6855 0.048 Uiso 1 1 calc R . . C21 C 0.1098(2) 0.82423(17) 0.81644(16) 0.0377(5) Uani 1 1 d . . . C22 C 0.1820(2) 0.71336(17) 0.85180(15) 0.0377(5) Uani 1 1 d . . . H22 H 0.2096 0.6855 0.9261 0.045 Uiso 1 1 calc R . . C23 C 0.2137(2) 0.64347(16) 0.77771(15) 0.0348(4) Uani 1 1 d . . . H23 H 0.2627 0.5669 0.8017 0.042 Uiso 1 1 calc R . . C24 C 0.2344(2) 0.44188(15) 0.50320(15) 0.0330(4) Uani 1 1 d . . . C25 C 0.2951(2) 0.53117(15) 0.43623(14) 0.0293(4) Uani 1 1 d . . . C26 C 0.3616(2) 0.51618(16) 0.33469(16) 0.0359(4) Uani 1 1 d . . . H26 H 0.4090 0.5733 0.2893 0.043 Uiso 1 1 calc R . . C27 C 0.3575(3) 0.41718(18) 0.30108(17) 0.0430(5) Uani 1 1 d . . . H27 H 0.4011 0.4073 0.2316 0.052 Uiso 1 1 calc R . . C28 C 0.2908(3) 0.33167(17) 0.36707(18) 0.0443(5) Uani 1 1 d . . . H28 H 0.2870 0.2653 0.3413 0.053 Uiso 1 1 calc R . . C29 C 0.2306(2) 0.34209(16) 0.46865(18) 0.0403(5) Uani 1 1 d . . . H29 H 0.1875 0.2831 0.5144 0.048 Uiso 1 1 calc R . . N1 N -0.3374(3) 0.62637(16) 0.01259(15) 0.0505(5) Uani 1 1 d . . . O1 O -0.2699(2) 0.54989(16) -0.03030(14) 0.0668(5) Uani 1 1 d . . . O2 O -0.4853(3) 0.66590(19) 0.0038(2) 0.0995(8) Uani 1 1 d . . . O3 O -0.01812(16) 0.85253(11) 0.34896(11) 0.0385(3) Uani 1 1 d . . . O4 O 0.21294(15) 0.76462(10) 0.27429(9) 0.0296(3) Uani 1 1 d . . . S1 S 0.16393(6) 0.47446(4) 0.62685(4) 0.03629(16) Uani 1 1 d . . . Cl1 Cl 0.07699(8) 0.91348(5) 0.90931(5) 0.0589(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 C1 0.0440(12) 0.0331(10) 0.0311(10) -0.0039(8) -0.0112(8) -0.0096(9) C2 0.0353(11) 0.0383(11) 0.0524(12) -0.0095(9) -0.0130(9) 0.0005(9) C3 0.0363(11) 0.0320(10) 0.0453(11) -0.0138(9) -0.0048(9) 0.0005(8) C4 0.0316(10) 0.0251(9) 0.0271(9) -0.0045(7) -0.0012(7) -0.0060(7) C5 0.0315(10) 0.0353(10) 0.0351(10) -0.0114(8) -0.0001(8) -0.0031(8) C6 0.0441(12) 0.0374(11) 0.0328(10) -0.0143(8) -0.0017(9) -0.0069(9) C7 0.0321(10) 0.0221(9) 0.0294(9) -0.0041(7) 0.0011(8) -0.0046(7) C8 0.0259(9) 0.0329(10) 0.0326(10) -0.0132(8) 0.0019(7) -0.0074(7) C9 0.0291(10) 0.0313(10) 0.0400(10) -0.0108(8) 0.0101(8) -0.0073(8) C10 0.0398(12) 0.0421(12) 0.0532(13) 0.0014(10) -0.0004(10) -0.0109(9) C11 0.0582(15) 0.0459(13) 0.0748(17) 0.0117(12) 0.0076(13) -0.0136(12) C12 0.0588(15) 0.0381(13) 0.092(2) -0.0112(13) 0.0283(14) -0.0207(11) C13 0.0659(16) 0.0561(15) 0.0758(18) -0.0349(14) 0.0260(14) -0.0352(13) C14 0.0567(14) 0.0489(13) 0.0460(12) -0.0216(10) 0.0141(10) -0.0267(11) C15 0.0270(9) 0.0355(10) 0.0326(10) -0.0125(8) -0.0018(8) -0.0076(8) C16 0.0264(9) 0.0305(9) 0.0293(9) -0.0064(7) -0.0059(7) -0.0037(7) C17 0.0307(10) 0.0281(9) 0.0310(9) -0.0050(7) -0.0054(8) -0.0037(7) C18 0.0276(9) 0.0316(10) 0.0311(9) -0.0074(7) -0.0009(7) -0.0066(7) C19 0.0401(11) 0.0326(10) 0.0311(10) -0.0065(8) -0.0045(8) -0.0041(8) C20 0.0446(12) 0.0328(10) 0.0422(11) -0.0124(9) -0.0034(9) -0.0019(9) C21 0.0362(11) 0.0453(12) 0.0370(11) -0.0201(9) 0.0024(8) -0.0088(9) C22 0.0383(11) 0.0464(12) 0.0283(10) -0.0073(8) -0.0003(8) -0.0080(9) C23 0.0370(11) 0.0336(10) 0.0317(10) -0.0041(8) 0.0003(8) -0.0043(8) C24 0.0299(10) 0.0315(10) 0.0368(10) -0.0086(8) -0.0077(8) 0.0002(8) C25 0.0249(9) 0.0302(9) 0.0321(9) -0.0084(7) -0.0082(7) 0.0011(7) C26 0.0301(10) 0.0410(11) 0.0362(10) -0.0116(8) -0.0047(8) -0.0006(8) C27 0.0382(11) 0.0500(13) 0.0414(11) -0.0225(10) -0.0079(9) 0.0059(9) C28 0.0414(12) 0.0362(11) 0.0579(14) -0.0218(10) -0.0132(10) 0.0021(9) C29 0.0394(11) 0.0279(10) 0.0543(13) -0.0121(9) -0.0088(9) -0.0017(8) N1 0.0568(13) 0.0471(11) 0.0494(11) -0.0081(9) -0.0242(9) -0.0105(9) O1 0.0801(13) 0.0724(12) 0.0600(11) -0.0355(9) -0.0180(9) -0.0161(10) O2 0.0617(13) 0.0970(16) 0.153(2) -0.0602(15) -0.0564(13) 0.0035(11) O3 0.0361(8) 0.0409(8) 0.0424(8) -0.0220(6) 0.0001(6) -0.0025(6) O4 0.0285(7) 0.0338(7) 0.0279(6) -0.0095(5) 0.0001(5) -0.0057(5) S1 0.0443(3) 0.0276(3) 0.0358(3) -0.0035(2) -0.0002(2) -0.0067(2) Cl1 0.0697(4) 0.0624(4) 0.0500(3) -0.0339(3) -0.0014(3) -0.0021(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 C6 1.369(3) . ? C1 C2 1.375(3) . ? C1 N1 1.477(2) . ? C2 C3 1.379(3) . ? C2 H2 0.9500 . ? C3 C4 1.382(3) . ? C3 H3 0.9500 . ? C4 C5 1.388(2) . ? C4 C7 1.486(2) . ? C5 C6 1.379(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O3 1.198(2) . ? C7 O4 1.355(2) . ? C8 C15 1.329(3) . ? C8 O4 1.413(2) . ? C8 C9 1.473(2) . ? C9 C10 1.380(3) . ? C9 C14 1.396(3) . ? C10 C11 1.388(3) . ? C10 H10 0.9500 . ? C11 C12 1.377(4) . ? C11 H11 0.9500 . ? C12 C13 1.364(4) . ? C12 H12 0.9500 . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.468(2) . ? C15 H15 0.9500 . ? C16 C17 1.370(2) . ? C16 C25 1.449(2) . ? C17 C18 1.469(3) . ? C17 S1 1.7369(17) . ? C18 C19 1.391(3) . ? C18 C23 1.395(3) . ? C19 C20 1.381(3) . ? C19 H19 0.9500 . ? C20 C21 1.383(3) . ? C20 H20 0.9500 . ? C21 C22 1.379(3) . ? C21 Cl1 1.7428(19) . ? C22 C23 1.379(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C29 1.398(3) . ? C24 C25 1.408(3) . ? C24 S1 1.7300(19) . ? C25 C26 1.397(3) . ? C26 C27 1.383(3) . ? C26 H26 0.9500 . ? C27 C28 1.393(3) . ? C27 H27 0.9500 . ? C28 C29 1.369(3) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? N1 O2 1.210(3) . ? N1 O1 1.212(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 122.73(18) . . ? C6 C1 N1 118.46(18) . . ? C2 C1 N1 118.80(18) . . ? C1 C2 C3 118.26(19) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C2 C3 C4 120.43(18) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C5 119.91(17) . . ? C3 C4 C7 117.82(16) . . ? C5 C4 C7 122.17(16) . . ? C6 C5 C4 120.05(18) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C1 C6 C5 118.59(18) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? O3 C7 O4 123.53(16) . . ? O3 C7 C4 124.76(16) . . ? O4 C7 C4 111.70(14) . . ? C15 C8 O4 118.48(15) . . ? C15 C8 C9 127.82(17) . . ? O4 C8 C9 113.70(15) . . ? C10 C9 C14 117.96(18) . . ? C10 C9 C8 120.90(18) . . ? C14 C9 C8 121.14(17) . . ? C9 C10 C11 121.2(2) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 120.1(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 119.4(2) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 121.0(2) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C9 120.4(2) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? C8 C15 C16 127.46(16) . . ? C8 C15 H15 116.3 . . ? C16 C15 H15 116.3 . . ? C17 C16 C25 112.30(16) . . ? C17 C16 C15 121.44(16) . . ? C25 C16 C15 126.05(15) . . ? C16 C17 C18 128.81(16) . . ? C16 C17 S1 112.64(14) . . ? C18 C17 S1 118.55(13) . . ? C19 C18 C23 118.29(17) . . ? C19 C18 C17 121.31(16) . . ? C23 C18 C17 120.40(16) . . ? C20 C19 C18 121.06(18) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C21 C20 C19 119.14(18) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C22 C21 C20 121.22(18) . . ? C22 C21 Cl1 118.90(15) . . ? C20 C21 Cl1 119.85(16) . . ? C21 C22 C23 119.03(18) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C22 C23 C18 121.26(18) . . ? C22 C23 H23 119.4 . . ? C18 C23 H23 119.4 . . ? C29 C24 C25 121.99(18) . . ? C29 C24 S1 126.40(16) . . ? C25 C24 S1 111.60(14) . . ? C26 C25 C24 118.36(17) . . ? C26 C25 C16 129.94(17) . . ? C24 C25 C16 111.68(16) . . ? C27 C26 C25 119.25(19) . . ? C27 C26 H26 120.4 . . ? C25 C26 H26 120.4 . . ? C26 C27 C28 121.31(19) . . ? C26 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C29 C28 C27 120.82(19) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C24 118.17(19) . . ? C28 C29 H29 120.9 . . ? C24 C29 H29 120.9 . . ? O2 N1 O1 123.05(19) . . ? O2 N1 C1 118.0(2) . . ? O1 N1 C1 118.96(19) . . ? C7 O4 C8 115.85(13) . . ? C24 S1 C17 91.78(9) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.298 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.088