# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_1 #TrackingRef 'AS-05-03-2013-5d.CIF' #============================================================= _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _journal_coeditor_?tes ; ? ; _iucr_compatibility_tag ACTA95 loop_ _publ_author_foot?te ; ? ; ; to whom correspondence should be addressed ; ; ? ; ; to whom correspondence should be addressed ; # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 N2 O Se' _chemical_formula_sum 'C26 H24 N2 O Se' _chemical_formula_weight 459.43 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' Se Se -0.0929 2.2259 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.598(2) _cell_length_b 16.561(3) _cell_length_c 13.354(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.05(3) _cell_angle_gamma 90.00 _cell_volume 2101.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 1.807 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.232 _exptl_absorpt_correction_T_max 0.527 _exptl_absorpt_process_details difabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4' _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.09 _diffrn_reflns_number 3830 _diffrn_reflns_av_R_equivalents 0.0949 _diffrn_reflns_av_sigmaI/netI 0.1718 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3669 _reflns_number_gt 1552 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM-4 Software (Kuma Diffraction, 1989)' _computing_cell_refinement 'KM-4 Software' _computing_data_reduction 'KM-4 Software' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _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^)+(0.0893P)^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 3669 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1979 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1581 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_restrained_S_all 0.952 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3293(5) 0.1564(3) 0.8844(4) 0.0315(12) Uani 1 1 d . . . C2 C 0.4558(7) 0.1125(4) 0.8641(6) 0.0474(18) Uani 1 1 d . . . H2A H 0.4331 0.0817 0.8022 0.057 Uiso 1 1 calc R . . H2B H 0.4828 0.0744 0.9186 0.057 Uiso 1 1 calc R . . C3 C 0.5765(8) 0.1655(4) 0.8543(6) 0.055(2) Uani 1 1 d . . . H3A H 0.5860 0.1707 0.7832 0.066 Uiso 1 1 calc R . . H3B H 0.6615 0.1402 0.8880 0.066 Uiso 1 1 calc R . . C4 C 0.5643(8) 0.2484(4) 0.8979(6) 0.053(2) Uani 1 1 d . . . H4A H 0.5656 0.2450 0.9706 0.064 Uiso 1 1 calc R . . H4B H 0.6428 0.2817 0.8845 0.064 Uiso 1 1 calc R . . C4A C 0.4283(7) 0.2846(4) 0.8494(4) 0.0326(14) Uani 1 1 d . . . C5 C 0.4136(7) 0.3624(4) 0.8143(5) 0.0409(17) Uani 1 1 d . . . H5A H 0.4907 0.3970 0.8215 0.049 Uiso 1 1 calc R . . C6 C 0.2855(8) 0.3891(4) 0.7687(5) 0.0468(19) Uani 1 1 d . . . H6A H 0.2754 0.4430 0.7495 0.056 Uiso 1 1 calc R . . C6A C 0.1703(8) 0.3382(4) 0.7502(5) 0.0405(17) Uani 1 1 d . B . C7 C 0.0308(8) 0.3675(5) 0.7026(7) 0.065(2) Uani 1 1 d . . . H7B H 0.0220 0.3599 0.6299 0.078 Uiso 1 1 calc R A 1 H7A H 0.0226 0.4248 0.7158 0.078 Uiso 1 1 calc R A 1 C8 C -0.0921(17) 0.3198(10) 0.746(3) 0.054(9) Uani 0.44(4) 1 d P B 1 H8A H -0.1089 0.3454 0.8086 0.065 Uiso 0.44(4) 1 calc PR B 1 H8B H -0.1776 0.3250 0.6983 0.065 Uiso 0.44(4) 1 calc PR B 1 C8A C -0.0761(15) 0.3134(8) 0.6835(16) 0.034(4) Uiso 0.56(4) 1 d P B 2 H8C H -0.0749 0.2906 0.6168 0.041 Uiso 0.56(4) 1 calc PR B 2 H8D H -0.1648 0.3416 0.6830 0.041 Uiso 0.56(4) 1 calc PR B 2 C9 C -0.0679(7) 0.2417(4) 0.7642(5) 0.0408(17) Uani 1 1 d . . . H9B H -0.1351 0.2122 0.7168 0.049 Uiso 1 1 calc R B 1 H9A H -0.0919 0.2309 0.8311 0.049 Uiso 1 1 calc R B 1 N10 N 0.0682(5) 0.2052(3) 0.7603(4) 0.0303(12) Uani 1 1 d . B . C10A C 0.1875(6) 0.2576(3) 0.7828(4) 0.0276(14) Uani 1 1 d . . . C10B C 0.3110(6) 0.2340(3) 0.8377(4) 0.0288(14) Uani 1 1 d . B . C11 C 0.2434(6) 0.1265(4) 0.9465(4) 0.0306(14) Uani 1 1 d . . . C12 C 0.1409(6) 0.1800(4) 0.9863(4) 0.0319(15) Uani 1 1 d . . . C13 C 0.0125(7) 0.1466(5) 1.0067(5) 0.0430(17) Uani 1 1 d . . . H13A H -0.0072 0.0925 0.9928 0.052 Uiso 1 1 calc R . . C14 C -0.0838(8) 0.1940(5) 1.0472(5) 0.056(2) Uani 1 1 d . . . H14A H -0.1695 0.1721 1.0583 0.067 Uiso 1 1 calc R . . C15 C -0.0543(8) 0.2725(6) 1.0708(6) 0.063(2) Uani 1 1 d . . . H15A H -0.1202 0.3040 1.0977 0.076 Uiso 1 1 calc R . . C16 C 0.0725(8) 0.3058(5) 1.0552(5) 0.054(2) Uani 1 1 d . . . H16 H 0.0931 0.3592 1.0728 0.064 Uiso 1 1 calc R . . C17 C 0.1681(8) 0.2596(4) 1.0137(5) 0.0415(17) Uani 1 1 d . . . H17A H 0.2536 0.2824 1.0037 0.050 Uiso 1 1 calc R . . Se18 Se 0.25763(8) 0.02178(4) 0.98784(6) 0.0489(3) Uani 1 1 d . . . C19 C 0.0851(6) 0.1358(4) 0.7054(5) 0.0323(14) Uani 1 1 d . . . C20 C -0.0407(7) 0.0839(3) 0.6771(5) 0.0335(15) Uani 1 1 d . B . C21 C -0.1149(7) 0.0503(4) 0.7479(5) 0.0398(16) Uani 1 1 d . . . H21A H -0.0890 0.0621 0.8161 0.048 Uiso 1 1 calc R B . C22 C -0.2279(8) -0.0011(4) 0.7190(6) 0.055(2) Uani 1 1 d . B . H22A H -0.2771 -0.0239 0.7672 0.066 Uiso 1 1 calc R . . C23 C -0.2656(7) -0.0174(5) 0.6180(6) 0.0554(19) Uani 1 1 d . . . H23A H -0.3415 -0.0513 0.5975 0.066 Uiso 1 1 calc R B . C24 C -0.1918(7) 0.0159(5) 0.5467(6) 0.0556(19) Uani 1 1 d . B . H24A H -0.2178 0.0043 0.4785 0.067 Uiso 1 1 calc R . . C25 C -0.0809(7) 0.0659(4) 0.5764(5) 0.0425(17) Uani 1 1 d . . . H25A H -0.0315 0.0881 0.5279 0.051 Uiso 1 1 calc R B . O26 O 0.2008(5) 0.1159(3) 0.6790(4) 0.0474(12) Uani 1 1 d . B . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.025(3) 0.032(3) 0.038(3) 0.010(2) 0.008(2) 0.008(2) C2 0.028(4) 0.039(4) 0.076(5) 0.009(4) 0.007(3) 0.011(3) C3 0.046(4) 0.053(5) 0.068(5) -0.003(4) 0.007(4) 0.007(4) C4 0.041(5) 0.066(5) 0.051(5) 0.002(4) 0.005(4) -0.017(4) C4A 0.035(4) 0.035(3) 0.030(4) -0.002(3) 0.010(3) 0.000(3) C5 0.046(4) 0.037(4) 0.041(4) -0.002(3) 0.010(3) -0.012(3) C6 0.072(6) 0.028(3) 0.045(4) 0.007(3) 0.024(4) -0.003(4) C6A 0.060(5) 0.033(3) 0.031(4) 0.009(3) 0.013(3) 0.004(3) C7 0.055(5) 0.061(5) 0.080(6) 0.036(5) 0.016(5) 0.027(4) C8 0.034(10) 0.044(11) 0.09(2) 0.007(10) 0.010(10) 0.023(8) C9 0.034(4) 0.054(4) 0.035(4) -0.004(3) 0.005(3) 0.010(3) N10 0.025(3) 0.030(3) 0.038(3) 0.002(2) 0.011(2) 0.005(2) C10A 0.030(4) 0.026(3) 0.029(3) 0.002(3) 0.011(3) 0.001(3) C10B 0.031(4) 0.023(3) 0.035(3) 0.008(3) 0.012(3) 0.004(3) C11 0.029(4) 0.032(3) 0.030(3) 0.003(3) 0.000(3) -0.002(3) C12 0.028(4) 0.040(4) 0.026(3) 0.007(3) -0.002(3) -0.004(3) C13 0.041(4) 0.048(4) 0.040(4) 0.005(3) 0.009(3) -0.009(3) C14 0.034(4) 0.090(6) 0.048(5) -0.016(4) 0.025(4) -0.004(4) C15 0.053(5) 0.091(6) 0.049(5) -0.015(5) 0.022(4) 0.018(5) C16 0.071(6) 0.049(4) 0.045(4) -0.014(4) 0.024(4) 0.000(4) C17 0.044(4) 0.042(4) 0.040(4) -0.011(3) 0.010(3) -0.010(3) Se18 0.0596(5) 0.0311(3) 0.0558(5) 0.0109(4) 0.0071(3) -0.0027(4) C19 0.027(4) 0.032(3) 0.039(4) -0.001(3) 0.008(3) -0.003(3) C20 0.043(4) 0.028(3) 0.030(4) 0.001(3) 0.010(3) 0.007(3) C21 0.045(4) 0.041(4) 0.036(4) -0.011(3) 0.016(3) -0.011(3) C22 0.060(5) 0.048(5) 0.061(5) 0.002(3) 0.026(4) -0.009(4) C23 0.041(4) 0.054(4) 0.073(6) -0.015(5) 0.011(4) -0.005(4) C24 0.049(4) 0.063(5) 0.050(4) -0.021(4) -0.008(4) 0.004(4) C25 0.042(4) 0.055(4) 0.031(4) 0.002(3) 0.010(3) 0.002(3) O26 0.039(3) 0.045(3) 0.061(3) -0.015(2) 0.014(2) -0.013(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C11 1.342(7) . ? N1 C10B 1.429(7) . ? N1 C2 1.473(8) . ? C2 C3 1.474(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.502(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C4A 1.499(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4A C5 1.372(9) . ? C4A C10B 1.394(8) . ? C5 C6 1.367(10) . ? C5 H5A 0.9300 . ? C6 C6A 1.385(9) . ? C6 H6A 0.9300 . ? C6A C10A 1.407(8) . ? C6A C7 1.480(10) . ? C7 C8A 1.359(14) . ? C7 C8 1.60(3) . ? C7 H7B 0.9700 . ? C7 H7A 0.9700 . ? C8 C9 1.330(17) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8A C9 1.598(16) . ? C8A H8C 0.9700 . ? C8A H8D 0.9700 . ? C9 N10 1.447(8) . ? C9 H9B 0.9700 . ? C9 H9A 0.9700 . ? N10 C19 1.385(8) . ? N10 C10A 1.435(8) . ? C10A C10B 1.361(8) . ? C11 C12 1.477(8) . ? C11 Se18 1.820(6) . ? C12 C17 1.383(8) . ? C12 C13 1.411(8) . ? C13 C14 1.379(10) . ? C13 H13A 0.9300 . ? C14 C15 1.358(11) . ? C14 H14A 0.9300 . ? C15 C16 1.378(10) . ? C15 H15A 0.9300 . ? C16 C17 1.370(9) . ? C16 H16 0.9300 . ? C17 H17A 0.9300 . ? C19 O26 1.256(7) . ? C19 C20 1.488(9) . ? C20 C21 1.378(8) . ? C20 C25 1.380(9) . ? C21 C22 1.389(9) . ? C21 H21A 0.9300 . ? C22 C23 1.374(11) . ? C22 H22A 0.9300 . ? C23 C24 1.379(11) . ? C23 H23A 0.9300 . ? C24 C25 1.363(10) . ? C24 H24A 0.9300 . ? C25 H25A 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 C11 N1 C10B 123.5(5) . . ? C11 N1 C2 121.7(5) . . ? C10B N1 C2 114.7(5) . . ? N1 C2 C3 113.6(5) . . ? N1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? N1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 113.9(6) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C4A C4 C3 107.9(6) . . ? C4A C4 H4A 110.1 . . ? C3 C4 H4A 110.1 . . ? C4A C4 H4B 110.1 . . ? C3 C4 H4B 110.1 . . ? H4A C4 H4B 108.4 . . ? C5 C4A C10B 118.9(6) . . ? C5 C4A C4 124.4(6) . . ? C10B C4A C4 116.7(6) . . ? C6 C5 C4A 120.0(6) . . ? C6 C5 H5A 120.0 . . ? C4A C5 H5A 120.0 . . ? C5 C6 C6A 121.9(6) . . ? C5 C6 H6A 119.1 . . ? C6A C6 H6A 119.1 . . ? C6 C6A C10A 117.8(6) . . ? C6 C6A C7 121.9(6) . . ? C10A C6A C7 120.3(6) . . ? C8A C7 C6A 118.6(8) . . ? C6A C7 C8 110.6(10) . . ? C8A C7 H7B 76.7 . . ? C6A C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? C8A C7 H7A 126.8 . . ? C6A C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? H7B C7 H7A 108.1 . . ? C9 C8 C7 115.3(15) . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8B 108.4 . . ? C7 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C7 C8A C9 113.5(10) . . ? C7 C8A H8C 108.9 . . ? C9 C8A H8C 108.9 . . ? C7 C8A H8D 108.9 . . ? C9 C8A H8D 108.9 . . ? H8C C8A H8D 107.7 . . ? C8 C9 N10 122.4(11) . . ? N10 C9 C8A 104.3(8) . . ? C8 C9 H9B 106.7 . . ? N10 C9 H9B 106.7 . . ? C8A C9 H9B 88.2 . . ? C8 C9 H9A 106.7 . . ? N10 C9 H9A 106.7 . . ? C8A C9 H9A 139.6 . . ? H9B C9 H9A 106.6 . . ? C19 N10 C10A 117.6(5) . . ? C19 N10 C9 122.6(5) . . ? C10A N10 C9 116.0(5) . . ? C10B C10A C6A 119.7(6) . . ? C10B C10A N10 123.3(5) . . ? C6A C10A N10 117.0(6) . . ? C10A C10B C4A 121.1(5) . . ? C10A C10B N1 122.5(5) . . ? C4A C10B N1 116.4(5) . . ? N1 C11 C12 120.0(5) . . ? N1 C11 Se18 120.8(4) . . ? C12 C11 Se18 119.2(4) . . ? C17 C12 C13 117.4(6) . . ? C17 C12 C11 123.8(6) . . ? C13 C12 C11 118.6(6) . . ? C14 C13 C12 120.3(7) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C15 C14 C13 120.4(7) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? C14 C15 C16 120.5(7) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C17 C16 C15 119.6(7) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C12 121.8(7) . . ? C16 C17 H17A 119.1 . . ? C12 C17 H17A 119.1 . . ? O26 C19 N10 122.8(5) . . ? O26 C19 C20 119.7(5) . . ? N10 C19 C20 117.6(5) . . ? C21 C20 C25 118.8(6) . . ? C21 C20 C19 122.6(6) . . ? C25 C20 C19 118.6(6) . . ? C20 C21 C22 121.0(6) . . ? C20 C21 H21A 119.5 . . ? C22 C21 H21A 119.5 . . ? C23 C22 C21 118.8(7) . . ? C23 C22 H22A 120.6 . . ? C21 C22 H22A 120.6 . . ? C22 C23 C24 120.6(7) . . ? C22 C23 H23A 119.7 . . ? C24 C23 H23A 119.7 . . ? C25 C24 C23 119.9(7) . . ? C25 C24 H24A 120.0 . . ? C23 C24 H24A 120.0 . . ? C24 C25 C20 121.0(6) . . ? C24 C25 H25A 119.5 . . ? C20 C25 H25A 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C2 C3 -142.9(6) . . . . ? C10B N1 C2 C3 33.7(9) . . . . ? N1 C2 C3 C4 18.2(10) . . . . ? C2 C3 C4 C4A -55.3(8) . . . . ? C3 C4 C4A C5 -135.7(6) . . . . ? C3 C4 C4A C10B 42.7(8) . . . . ? C10B C4A C5 C6 -0.1(9) . . . . ? C4 C4A C5 C6 178.3(6) . . . . ? C4A C5 C6 C6A -4.5(10) . . . . ? C5 C6 C6A C10A 1.9(9) . . . . ? C5 C6 C6A C7 178.8(7) . . . . ? C6 C6A C7 C8A 177.7(13) . . . . ? C10A C6A C7 C8A -5.5(15) . . . . ? C6 C6A C7 C8 -146.6(14) . . . . ? C10A C6A C7 C8 30.2(16) . . . . ? C8A C7 C8 C9 74(2) . . . . ? C6A C7 C8 C9 -37(3) . . . . ? C6A C7 C8A C9 32(2) . . . . ? C8 C7 C8A C9 -51.9(13) . . . . ? C7 C8 C9 N10 10(3) . . . . ? C7 C8 C9 C8A -55(2) . . . . ? C7 C8A C9 C8 70.9(18) . . . . ? C7 C8A C9 N10 -57.4(16) . . . . ? C8 C9 N10 C19 -130(2) . . . . ? C8A C9 N10 C19 -98.9(9) . . . . ? C8 C9 N10 C10A 28(2) . . . . ? C8A C9 N10 C10A 58.6(9) . . . . ? C6 C6A C10A C10B 5.3(9) . . . . ? C7 C6A C10A C10B -171.7(6) . . . . ? C6 C6A C10A N10 -178.2(5) . . . . ? C7 C6A C10A N10 4.8(9) . . . . ? C19 N10 C10A C10B -60.5(8) . . . . ? C9 N10 C10A C10B 140.9(6) . . . . ? C19 N10 C10A C6A 123.1(6) . . . . ? C9 N10 C10A C6A -35.5(7) . . . . ? C6A C10A C10B C4A -9.9(9) . . . . ? N10 C10A C10B C4A 173.8(5) . . . . ? C6A C10A C10B N1 171.5(5) . . . . ? N10 C10A C10B N1 -4.7(9) . . . . ? C5 C4A C10B C10A 7.3(9) . . . . ? C4 C4A C10B C10A -171.2(6) . . . . ? C5 C4A C10B N1 -174.1(5) . . . . ? C4 C4A C10B N1 7.4(8) . . . . ? C11 N1 C10B C10A -53.1(8) . . . . ? C2 N1 C10B C10A 130.4(6) . . . . ? C11 N1 C10B C4A 128.3(6) . . . . ? C2 N1 C10B C4A -48.2(7) . . . . ? C10B N1 C11 C12 -12.6(9) . . . . ? C2 N1 C11 C12 163.8(6) . . . . ? C10B N1 C11 Se18 170.7(4) . . . . ? C2 N1 C11 Se18 -12.9(8) . . . . ? N1 C11 C12 C17 -37.0(9) . . . . ? Se18 C11 C12 C17 139.7(5) . . . . ? N1 C11 C12 C13 149.1(6) . . . . ? Se18 C11 C12 C13 -34.1(8) . . . . ? C17 C12 C13 C14 3.6(10) . . . . ? C11 C12 C13 C14 177.8(6) . . . . ? C12 C13 C14 C15 -2.1(12) . . . . ? C13 C14 C15 C16 -0.3(13) . . . . ? C14 C15 C16 C17 1.3(12) . . . . ? C15 C16 C17 C12 0.3(11) . . . . ? C13 C12 C17 C16 -2.6(10) . . . . ? C11 C12 C17 C16 -176.6(6) . . . . ? C10A N10 C19 O26 3.1(9) . . . . ? C9 N10 C19 O26 160.2(6) . . . . ? C10A N10 C19 C20 -176.6(5) . . . . ? C9 N10 C19 C20 -19.5(8) . . . . ? O26 C19 C20 C21 121.5(7) . . . . ? N10 C19 C20 C21 -58.8(8) . . . . ? O26 C19 C20 C25 -55.6(9) . . . . ? N10 C19 C20 C25 124.2(6) . . . . ? C25 C20 C21 C22 0.2(10) . . . . ? C19 C20 C21 C22 -176.9(6) . . . . ? C20 C21 C22 C23 -0.5(11) . . . . ? C21 C22 C23 C24 0.6(12) . . . . ? C22 C23 C24 C25 -0.3(12) . . . . ? C23 C24 C25 C20 -0.1(11) . . . . ? C21 C20 C25 C24 0.1(10) . . . . ? C19 C20 C25 C24 177.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.487 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.096 _database_code_depnum_ccdc_archive 'CCDC 927852' ####################################################################### # # 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_2 #TrackingRef 'AS-05-03-2013-5b.CIF' #============================================================= _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _journal_coeditor_?tes ; ? ; _iucr_compatibility_tag ACTA95 loop_ _publ_author_foot?te ; ? ; ; to whom correspondence should be addressed ; ; ? ; ; to whom correspondence should be addressed ; # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 N2 S2' _chemical_formula_sum 'C26 H24 N2 S2' _chemical_formula_weight 428.59 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.197(2) _cell_length_b 13.572(3) _cell_length_c 13.886(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.67(3) _cell_angle_gamma 90.00 _cell_volume 2150.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4' _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.03 _diffrn_reflns_number 1906 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1821 _reflns_number_gt 1085 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM-4 Software (Kuma Diffraction, 1989)' _computing_cell_refinement 'KM-4 Software' _computing_data_reduction 'KM-4 Software' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _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^)+(0.0778P)^2^+4.9971P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0050(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1821 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1125 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1814 _refine_ls_wR_factor_gt 0.1311 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.1293(3) 0.2607(2) 0.2979(2) 0.0374(7) Uani 1 1 d . . . C2 C 0.2324(4) 0.2557(3) 0.2647(3) 0.0521(11) Uani 1 1 d . . . H2A H 0.2940 0.2183 0.3152 0.062 Uiso 1 1 calc R . . H2B H 0.2104 0.2206 0.1998 0.062 Uiso 1 1 calc R . . C3 C 0.2784(4) 0.3531(4) 0.2523(4) 0.0648(13) Uani 1 1 d . . . H3A H 0.2440 0.3736 0.1810 0.078 Uiso 1 1 calc R . . H3B H 0.3626 0.3490 0.2697 0.078 Uiso 1 1 calc R . . C4A C 0.1218(4) 0.4354(3) 0.2870(3) 0.0460(10) Uani 1 1 d . . . C4 C 0.2507(4) 0.4289(3) 0.3207(3) 0.0599(12) Uani 1 1 d . . . H4A H 0.2834 0.4087 0.3923 0.072 Uiso 1 1 calc R . . H4B H 0.2837 0.4924 0.3137 0.072 Uiso 1 1 calc R . . C5 C 0.0596(4) 0.5218(3) 0.2664(3) 0.0589(12) Uani 1 1 d . . . H5A H 0.0995 0.5814 0.2748 0.071 Uiso 1 1 calc R . . C10B C 0.0603(3) 0.3473(2) 0.2713(3) 0.0349(8) Uani 1 1 d . . . C11 C 0.1140(3) 0.1888(3) 0.3585(3) 0.0391(9) Uani 1 1 d . . . C12 C 0.0387(3) 0.2088(3) 0.4195(3) 0.0381(9) Uani 1 1 d . . . C13 C -0.0269(4) 0.1330(3) 0.4379(3) 0.0537(11) Uani 1 1 d . . . H13A H -0.0274 0.0715 0.4082 0.064 Uiso 1 1 calc R . . C14 C -0.0914(4) 0.1482(4) 0.4999(4) 0.0693(14) Uani 1 1 d . . . H14A H -0.1365 0.0974 0.5112 0.083 Uiso 1 1 calc R . . C15 C -0.0896(5) 0.2370(5) 0.5447(4) 0.0744(15) Uani 1 1 d . . . H15A H -0.1331 0.2467 0.5870 0.089 Uiso 1 1 calc R . . C16 C -0.0241(4) 0.3122(4) 0.5283(3) 0.0642(13) Uani 1 1 d . . . H16A H -0.0240 0.3734 0.5586 0.077 Uiso 1 1 calc R . . C17 C 0.0416(4) 0.2976(3) 0.4669(3) 0.0479(10) Uani 1 1 d . . . H17A H 0.0882 0.3483 0.4575 0.057 Uiso 1 1 calc R . . S18 S 0.18143(12) 0.08243(8) 0.37035(10) 0.0630(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 N1 0.0378(17) 0.0379(16) 0.0389(16) -0.0009(13) 0.0163(14) -0.0022(14) C2 0.040(2) 0.069(3) 0.053(2) 0.001(2) 0.025(2) 0.002(2) C3 0.053(3) 0.080(3) 0.070(3) 0.002(3) 0.033(2) -0.011(2) C4A 0.065(3) 0.044(2) 0.037(2) -0.0024(16) 0.027(2) -0.0106(19) C4 0.065(3) 0.066(3) 0.050(2) -0.004(2) 0.022(2) -0.028(2) C5 0.095(3) 0.035(2) 0.059(3) -0.0037(19) 0.043(3) -0.011(2) C10B 0.047(2) 0.0324(17) 0.0306(17) -0.0011(14) 0.0205(17) -0.0031(15) C11 0.040(2) 0.0387(19) 0.0365(18) -0.0030(16) 0.0113(16) -0.0078(17) C12 0.037(2) 0.043(2) 0.0305(17) 0.0055(15) 0.0065(16) -0.0002(17) C13 0.057(3) 0.050(2) 0.055(2) 0.012(2) 0.021(2) -0.004(2) C14 0.056(3) 0.087(4) 0.073(3) 0.027(3) 0.032(3) -0.005(3) C15 0.068(3) 0.113(5) 0.055(3) 0.005(3) 0.038(3) -0.004(3) C16 0.078(3) 0.077(3) 0.044(2) -0.006(2) 0.030(2) 0.004(3) C17 0.059(3) 0.052(2) 0.0367(19) 0.0015(17) 0.0219(19) -0.003(2) S18 0.0761(9) 0.0465(6) 0.0717(8) 0.0078(5) 0.0326(7) 0.0138(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 N1 C11 1.344(4) . ? N1 C10B 1.416(4) . ? N1 C2 1.486(5) . ? C2 C3 1.470(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.518(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4A C5 1.371(6) . ? C4A C10B 1.388(5) . ? C4A C4 1.476(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 1.362(10) 2 ? C5 H5A 0.9300 . ? C10B C10B 1.379(7) 2 ? C11 C12 1.479(5) . ? C11 S18 1.641(4) . ? C12 C17 1.367(5) . ? C12 C13 1.382(5) . ? C13 C14 1.371(6) . ? C13 H13A 0.9300 . ? C14 C15 1.352(7) . ? C14 H14A 0.9300 . ? C15 C16 1.364(7) . ? C15 H15A 0.9300 . ? C16 C17 1.376(6) . ? C16 H16A 0.9300 . ? C17 H17A 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 C11 N1 C10B 124.4(3) . . ? C11 N1 C2 118.7(3) . . ? C10B N1 C2 116.6(3) . . ? C3 C2 N1 113.2(3) . . ? C3 C2 H2A 108.9 . . ? N1 C2 H2A 108.9 . . ? C3 C2 H2B 108.9 . . ? N1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 111.0(3) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4A C10B 118.4(4) . . ? C5 C4A C4 124.5(4) . . ? C10B C4A C4 117.0(4) . . ? C4A C4 C3 106.8(4) . . ? C4A C4 H4A 110.4 . . ? C3 C4 H4A 110.4 . . ? C4A C4 H4B 110.4 . . ? C3 C4 H4B 110.4 . . ? H4A C4 H4B 108.6 . . ? C5 C5 C4A 121.1(2) 2 . ? C5 C5 H5A 119.4 2 . ? C4A C5 H5A 119.4 . . ? C10B C10B C4A 120.2(2) 2 . ? C10B C10B N1 123.92(18) 2 . ? C4A C10B N1 115.8(3) . . ? N1 C11 C12 118.5(3) . . ? N1 C11 S18 121.8(3) . . ? C12 C11 S18 119.6(3) . . ? C17 C12 C13 119.1(4) . . ? C17 C12 C11 121.4(3) . . ? C13 C12 C11 119.1(3) . . ? C14 C13 C12 120.1(4) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C15 C14 C13 120.2(4) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C14 C15 C16 120.4(4) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C15 C16 C17 119.9(5) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C12 C17 C16 120.2(4) . . ? C12 C17 H17A 119.9 . . ? C16 C17 H17A 119.9 . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.286 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 927853' ####################################################################### # # 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_3 #TrackingRef 'AS-05-03-2013-5D-6A.CIF' #============================================================= _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _journal_coeditor_?tes ; ? ; _iucr_compatibility_tag ACTA95 loop_ _publ_author_foot?te ; ? ; ; to whom correspondence should be addressed ; ; ? ; ; to whom correspondence should be addressed ; # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C31 H30 O4), C26 H24 N2 O Se' _chemical_formula_sum 'C88 H84 N2 O9 Se' _chemical_formula_weight 1392.53 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.364(3) _cell_length_b 9.393(2) _cell_length_c 23.502(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.82(3) _cell_angle_gamma 90.00 _cell_volume 3507.8(12) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3324 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 25.00 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464.0 _exptl_absorpt_coefficient_mu 0.599 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.897 _exptl_absorpt_correction_T_max 0.927 _exptl_absorpt_process_details difabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4' _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.15 _diffrn_reflns_number 3324 _diffrn_reflns_av_R_equivalents 0.0690 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3324 _reflns_number_gt 2131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM-4 Software (Kuma Diffraction, 1989)' _computing_cell_refinement 'KM-4 Software' _computing_data_reduction 'KM-4 Software' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _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^)+(0.1208P)^2^+3.8739P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.17(3) _chemical_absolute_configuration rm _refine_ls_number_reflns 3324 _refine_ls_number_parameters 457 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1224 _refine_ls_R_factor_gt 0.0739 _refine_ls_wR_factor_ref 0.2140 _refine_ls_wR_factor_gt 0.1891 _refine_ls_goodness_of_fit_ref 1.184 _refine_ls_restrained_S_all 1.183 _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 Se18 Se 0.46066(14) 0.7090(3) 0.58952(12) 0.0537(8) Uani 0.50 1 d P . . O18 O 0.4432(13) 0.646(3) 0.5870(11) 0.067(7) Uiso 0.50 1 d P . . N1 N 0.4997(4) 0.4385(8) 0.5632(4) 0.040(3) Uani 1 1 d . . . C2 C 0.5636(6) 0.4274(12) 0.6195(5) 0.053(3) Uani 1 1 d . . . H2B H 0.6188 0.4161 0.6117 0.064 Uiso 1 1 calc R . . H2A H 0.5638 0.5148 0.6415 0.064 Uiso 1 1 calc R . . C3 C 0.5466(8) 0.3061(13) 0.6548(6) 0.070(4) Uani 1 1 d . . . H3B H 0.5209 0.3416 0.6852 0.084 Uiso 1 1 calc R . . H3A H 0.5997 0.2621 0.6739 0.084 Uiso 1 1 calc R . . C4A C 0.4964(5) 0.1844(12) 0.5583(5) 0.051(4) Uani 1 1 d . . . C4 C 0.4913(7) 0.1967(15) 0.6207(5) 0.068(4) Uani 1 1 d . . . H4B H 0.4336 0.2181 0.6215 0.082 Uiso 1 1 calc R . . H4A H 0.5055 0.1053 0.6397 0.082 Uiso 1 1 calc R . . C5 C 0.4987(7) 0.0595(12) 0.5295(6) 0.059(4) Uani 1 1 d . . . H5 H 0.4986 -0.0264 0.5491 0.070 Uiso 1 1 calc R . . C10B C 0.4960(5) 0.3152(10) 0.5289(4) 0.031(3) Uani 1 1 d . . . C11 C 0.4437(5) 0.5468(10) 0.5536(5) 0.042(3) Uani 1 1 d . . . C12 C 0.3678(5) 0.5285(9) 0.5035(5) 0.042(3) Uani 1 1 d . . . C13 C 0.3446(6) 0.6356(12) 0.4625(5) 0.053(4) Uani 1 1 d . . . H13 H 0.3787 0.7150 0.4630 0.064 Uiso 1 1 calc R . . C14 C 0.2699(6) 0.6225(13) 0.4208(6) 0.058(4) Uani 1 1 d . . . H14 H 0.2531 0.6958 0.3940 0.069 Uiso 1 1 calc R . . C15 C 0.2207(6) 0.5068(12) 0.4177(6) 0.053(3) Uani 1 1 d . . . H15 H 0.1709 0.5006 0.3888 0.063 Uiso 1 1 calc R . . C16 C 0.2435(6) 0.3988(13) 0.4568(5) 0.058(4) Uani 1 1 d . . . H16 H 0.2105 0.3175 0.4544 0.069 Uiso 1 1 calc R . . C17 C 0.3180(5) 0.4124(13) 0.5010(6) 0.055(4) Uani 1 1 d . . . H17 H 0.3332 0.3409 0.5288 0.066 Uiso 1 1 calc R . . C19 C 0.5884(5) 0.5538(11) 0.8406(5) 0.050(4) Uani 1 1 d . . . C20 C 0.5109(5) 0.6469(10) 0.8405(5) 0.040(3) Uani 1 1 d . . . H20 H 0.5194 0.7419 0.8256 0.048 Uiso 1 1 calc R . . C21 C 0.4216(6) 0.5887(10) 0.8070(5) 0.041(3) Uani 1 1 d . . . H21 H 0.4235 0.4844 0.8063 0.049 Uiso 1 1 calc R . . C22 C 0.3886(5) 0.6456(11) 0.7417(5) 0.045(3) Uani 1 1 d . . . O23 O 0.6050(4) 0.5712(8) 0.7836(3) 0.052(2) Uani 1 1 d . . . H23 H 0.5607 0.5865 0.7595 0.078 Uiso 1 1 calc R . . O24 O 0.4523(4) 0.5991(9) 0.7138(3) 0.059(3) Uani 1 1 d . . . H24 H 0.4429 0.6316 0.6805 0.089 Uiso 1 1 calc R . . O25 O 0.4997(4) 0.6589(7) 0.8981(3) 0.045(2) Uani 1 1 d . . . C26 C 0.4153(5) 0.6987(12) 0.8945(4) 0.043(3) Uani 1 1 d . . . O27 O 0.3678(4) 0.6312(8) 0.8421(3) 0.051(2) Uani 1 1 d . . . C28 C 0.3872(7) 0.6419(14) 0.9463(6) 0.060(4) Uani 1 1 d . . . H28C H 0.4002 0.5423 0.9509 0.091 Uiso 1 1 calc R . . H28B H 0.3275 0.6550 0.9403 0.091 Uiso 1 1 calc R . . H28A H 0.4157 0.6920 0.9810 0.091 Uiso 1 1 calc R . . C29 C 0.4028(6) 0.8570(11) 0.8903(6) 0.058(4) Uani 1 1 d . . . H29C H 0.4292 0.8945 0.8612 0.087 Uiso 1 1 calc R . . H29B H 0.4276 0.8997 0.9276 0.087 Uiso 1 1 calc R . . H29A H 0.3437 0.8779 0.8796 0.087 Uiso 1 1 calc R . . C30 C 0.5803(5) 0.3964(10) 0.8525(5) 0.044(3) Uani 1 1 d . . . C31 C 0.5285(6) 0.3460(12) 0.8866(6) 0.058(4) Uani 1 1 d . . . H31 H 0.4941 0.4079 0.9012 0.070 Uiso 1 1 calc R . . C32 C 0.5288(7) 0.1998(15) 0.8988(6) 0.069(4) Uani 1 1 d . . . H32 H 0.4932 0.1657 0.9212 0.083 Uiso 1 1 calc R . . C33 C 0.5797(8) 0.1051(13) 0.8789(7) 0.069(5) Uani 1 1 d . . . H33 H 0.5788 0.0087 0.8878 0.083 Uiso 1 1 calc R . . C34 C 0.6339(9) 0.1576(15) 0.8445(9) 0.095(7) Uani 1 1 d . . . H34 H 0.6704 0.0974 0.8311 0.114 Uiso 1 1 calc R . . C35 C 0.6301(6) 0.3002(15) 0.8318(6) 0.061(4) Uani 1 1 d . . . H35 H 0.6633 0.3344 0.8077 0.073 Uiso 1 1 calc R . . C36 C 0.6646(5) 0.6190(11) 0.8820(4) 0.037(3) Uani 1 1 d . . . C37 C 0.7032(7) 0.5569(14) 0.9343(6) 0.064(4) Uani 1 1 d . . . H37 H 0.6809 0.4738 0.9459 0.077 Uiso 1 1 calc R . . C38 C 0.7745(6) 0.6156(16) 0.9699(6) 0.065(4) Uani 1 1 d . . . H38 H 0.8014 0.5686 1.0041 0.078 Uiso 1 1 calc R . . C39 C 0.8056(7) 0.7389(14) 0.9561(6) 0.070(4) Uani 1 1 d . . . H39 H 0.8533 0.7782 0.9807 0.083 Uiso 1 1 calc R . . C40 C 0.7659(8) 0.8082(17) 0.9044(7) 0.099(7) Uani 1 1 d . . . H40 H 0.7852 0.8961 0.8949 0.119 Uiso 1 1 calc R . . C41 C 0.6971(7) 0.7434(15) 0.8675(6) 0.079(5) Uani 1 1 d . . . H41 H 0.6725 0.7862 0.8319 0.094 Uiso 1 1 calc R . . C42 C 0.3776(5) 0.8033(12) 0.7398(5) 0.048(3) Uani 1 1 d . . . C43 C 0.4437(6) 0.8912(14) 0.7361(5) 0.055(4) Uani 1 1 d . . . H43 H 0.4935 0.8523 0.7306 0.066 Uiso 1 1 calc R . . C44 C 0.4356(9) 1.0398(16) 0.7407(6) 0.073(5) Uani 1 1 d . . . H44 H 0.4818 1.0983 0.7417 0.088 Uiso 1 1 calc R . . C45 C 0.3627(10) 1.0966(15) 0.7435(8) 0.081(6) Uani 1 1 d . . . H45 H 0.3579 1.1952 0.7440 0.097 Uiso 1 1 calc R . . C46 C 0.2921(8) 1.0123(13) 0.7457(6) 0.065(4) Uani 1 1 d . . . H46 H 0.2408 1.0534 0.7469 0.078 Uiso 1 1 calc R . . C47 C 0.3023(7) 0.8683(12) 0.7461(6) 0.061(4) Uani 1 1 d . . . H47 H 0.2581 0.8107 0.7507 0.073 Uiso 1 1 calc R . . C48 C 0.3046(6) 0.5644(12) 0.7143(5) 0.048(4) Uani 1 1 d . . . C49 C 0.2640(6) 0.4755(12) 0.7406(6) 0.056(4) Uani 1 1 d . . . H49 H 0.2836 0.4592 0.7806 0.068 Uiso 1 1 calc R . . C50 C 0.1922(7) 0.4050(13) 0.7099(6) 0.063(4) Uani 1 1 d . . . H50 H 0.1645 0.3430 0.7298 0.076 Uiso 1 1 calc R . . C51 C 0.1629(8) 0.4239(16) 0.6536(8) 0.086(6) Uani 1 1 d . . . H51 H 0.1156 0.3738 0.6338 0.103 Uiso 1 1 calc R . . C52 C 0.2019(8) 0.5183(18) 0.6233(6) 0.081(5) Uani 1 1 d . . . H52 H 0.1803 0.5341 0.5835 0.098 Uiso 1 1 calc R . . C53 C 0.2748(6) 0.5897(15) 0.6538(5) 0.064(4) Uani 1 1 d . . . H53 H 0.3027 0.6526 0.6344 0.077 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 Se18 0.0484(11) 0.0540(18) 0.0570(16) -0.0281(13) 0.0093(11) 0.0033(12) N1 0.034(4) 0.038(5) 0.044(5) -0.005(4) 0.003(4) 0.002(3) C2 0.040(5) 0.072(8) 0.042(7) 0.001(5) -0.002(6) -0.004(5) C3 0.095(8) 0.055(8) 0.050(7) 0.005(6) -0.003(8) -0.006(6) C4A 0.033(4) 0.050(8) 0.062(8) 0.016(6) -0.002(6) -0.012(4) C4 0.065(6) 0.078(9) 0.060(8) 0.032(7) 0.012(8) -0.010(6) C5 0.050(5) 0.048(8) 0.066(8) 0.005(5) -0.008(8) -0.014(5) C10B 0.026(4) 0.042(6) 0.028(5) 0.002(4) 0.014(6) -0.002(3) C11 0.036(4) 0.031(6) 0.057(7) -0.004(5) 0.007(5) 0.004(4) C12 0.033(4) 0.026(5) 0.060(7) -0.006(4) -0.006(5) 0.002(3) C13 0.041(5) 0.047(6) 0.069(8) 0.009(5) 0.008(6) 0.002(4) C14 0.050(5) 0.056(7) 0.065(9) -0.006(5) 0.010(7) 0.016(5) C15 0.034(4) 0.064(8) 0.058(8) -0.001(6) 0.007(6) 0.002(5) C16 0.045(5) 0.057(7) 0.067(8) -0.004(6) 0.005(7) -0.008(5) C17 0.030(4) 0.069(8) 0.064(8) 0.005(6) 0.007(6) -0.004(4) C19 0.029(4) 0.064(8) 0.052(8) 0.002(5) -0.002(6) -0.002(4) C20 0.034(4) 0.039(6) 0.043(7) -0.005(4) 0.001(5) -0.006(3) C21 0.033(4) 0.041(6) 0.045(7) -0.008(4) 0.002(6) 0.004(4) C22 0.026(4) 0.062(7) 0.047(7) -0.017(5) 0.008(5) 0.011(4) O23 0.031(3) 0.083(6) 0.042(5) -0.001(4) 0.010(4) 0.002(3) O24 0.046(4) 0.091(6) 0.037(5) -0.018(4) 0.005(4) 0.019(4) O25 0.035(3) 0.058(5) 0.041(5) -0.010(3) 0.006(4) -0.002(3) C26 0.036(4) 0.062(7) 0.034(6) -0.019(5) 0.016(5) -0.015(5) O27 0.031(3) 0.068(5) 0.052(5) -0.013(4) 0.002(4) -0.005(3) C28 0.054(5) 0.085(9) 0.047(8) -0.008(6) 0.021(7) -0.012(5) C29 0.052(5) 0.044(7) 0.078(9) -0.002(5) 0.015(7) -0.003(4) C30 0.032(4) 0.038(6) 0.055(7) -0.008(5) -0.004(6) 0.000(4) C31 0.048(5) 0.057(8) 0.072(10) 0.002(6) 0.022(7) -0.003(5) C32 0.061(6) 0.068(9) 0.075(9) 0.024(8) 0.007(7) -0.010(6) C33 0.076(8) 0.043(8) 0.076(11) 0.000(6) -0.004(9) 0.001(7) C34 0.073(8) 0.045(9) 0.149(18) -0.019(8) -0.010(11) 0.015(6) C35 0.046(5) 0.084(10) 0.056(8) -0.011(7) 0.021(7) 0.001(6) C36 0.030(4) 0.046(7) 0.037(7) -0.005(4) 0.014(5) 0.001(4) C37 0.048(6) 0.088(10) 0.053(8) -0.006(6) 0.003(7) -0.010(6) C38 0.040(5) 0.108(11) 0.046(8) -0.002(7) 0.011(6) -0.007(6) C39 0.052(6) 0.083(10) 0.061(9) -0.011(6) -0.013(7) -0.020(6) C40 0.081(8) 0.089(11) 0.103(13) 0.014(9) -0.025(10) -0.046(8) C41 0.076(7) 0.081(11) 0.067(9) 0.007(7) -0.006(8) -0.025(7) C42 0.037(5) 0.067(8) 0.035(7) 0.005(5) -0.001(6) -0.008(5) C43 0.037(4) 0.088(10) 0.041(7) 0.004(6) 0.009(6) 0.004(5) C44 0.082(8) 0.096(12) 0.038(8) 0.015(7) 0.008(8) -0.034(8) C45 0.097(10) 0.060(9) 0.084(13) -0.009(7) 0.018(11) 0.010(7) C46 0.064(6) 0.055(9) 0.077(10) -0.004(6) 0.015(8) 0.012(5) C47 0.057(6) 0.046(8) 0.074(10) 0.008(6) 0.004(7) -0.007(5) C48 0.029(4) 0.062(7) 0.048(7) -0.011(5) -0.002(6) 0.001(4) C49 0.039(5) 0.056(8) 0.066(9) -0.010(6) -0.002(6) -0.003(5) C50 0.057(6) 0.052(7) 0.072(9) -0.002(6) -0.002(8) -0.013(5) C51 0.043(6) 0.075(10) 0.117(14) -0.040(9) -0.025(9) 0.002(6) C52 0.059(7) 0.107(12) 0.060(9) -0.012(8) -0.024(8) 0.008(8) C53 0.041(5) 0.101(10) 0.045(8) 0.010(6) 0.000(7) 0.006(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se18 O18 0.65(2) . ? Se18 C11 1.732(10) . ? O18 C11 1.22(3) . ? N1 C11 1.351(11) . ? N1 C10B 1.404(12) . ? N1 C2 1.480(10) . ? C2 C3 1.475(17) . ? C2 H2B 0.9700 . ? C2 H2A 0.9700 . ? C3 C4 1.473(16) . ? C3 H3B 0.9700 . ? C3 H3A 0.9700 . ? C4A C5 1.360(17) . ? C4A C10B 1.409(13) . ? C4A C4 1.493(19) . ? C4 H4B 0.9700 . ? C4 H4A 0.9700 . ? C5 C5 1.40(3) 2_656 ? C5 H5 0.9300 . ? C10B C10B 1.40(2) 2_656 ? C11 C12 1.504(11) . ? C12 C17 1.354(15) . ? C12 C13 1.382(15) . ? C13 C14 1.377(12) . ? C13 H13 0.9300 . ? C14 C15 1.345(17) . ? C14 H14 0.9300 . ? C15 C16 1.360(17) . ? C15 H15 0.9300 . ? C16 C17 1.404(12) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C19 O23 1.438(15) . ? C19 C36 1.515(11) . ? C19 C30 1.516(15) . ? C19 C20 1.540(15) . ? C20 O25 1.413(14) . ? C20 C21 1.583(10) . ? C20 H20 0.9800 . ? C21 O27 1.400(14) . ? C21 C22 1.594(16) . ? C21 H21 0.9800 . ? C22 O24 1.424(14) . ? C22 C42 1.492(15) . ? C22 C48 1.569(12) . ? O23 H23 0.8200 . ? O24 H24 0.8200 . ? O25 C26 1.413(12) . ? C26 O27 1.437(11) . ? C26 C29 1.501(15) . ? C26 C28 1.499(17) . ? C28 H28C 0.9600 . ? C28 H28B 0.9600 . ? C28 H28A 0.9600 . ? C29 H29C 0.9600 . ? C29 H29B 0.9600 . ? C29 H29A 0.9600 . ? C30 C35 1.382(17) . ? C30 C31 1.381(17) . ? C31 C32 1.403(18) . ? C31 H31 0.9300 . ? C32 C33 1.38(2) . ? C32 H32 0.9300 . ? C33 C34 1.42(3) . ? C33 H33 0.9300 . ? C34 C35 1.371(19) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 C41 1.361(17) . ? C36 C37 1.370(16) . ? C37 C38 1.378(14) . ? C37 H37 0.9300 . ? C38 C39 1.337(19) . ? C38 H38 0.9300 . ? C39 C40 1.393(19) . ? C39 H39 0.9300 . ? C40 C41 1.387(14) . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? C42 C43 1.380(16) . ? C42 C47 1.415(18) . ? C43 C44 1.409(18) . ? C43 H43 0.9300 . ? C44 C45 1.32(2) . ? C44 H44 0.9300 . ? C45 C46 1.41(2) . ? C45 H45 0.9300 . ? C46 C47 1.363(16) . ? C46 H46 0.9300 . ? C47 H47 0.9300 . ? C48 C49 1.312(19) . ? C48 C53 1.407(17) . ? C49 C50 1.391(14) . ? C49 H49 0.9300 . ? C50 C51 1.31(2) . ? C50 H50 0.9300 . ? C51 C52 1.39(2) . ? C51 H51 0.9300 . ? C52 C53 1.406(17) . ? C52 H52 0.9300 . ? C53 H53 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 Se18 O18 C11 133(3) . . ? C11 N1 C10B 126.2(7) . . ? C11 N1 C2 120.5(8) . . ? C10B N1 C2 112.3(7) . . ? C3 C2 N1 111.7(8) . . ? C3 C2 H2B 109.3 . . ? N1 C2 H2B 109.3 . . ? C3 C2 H2A 109.3 . . ? N1 C2 H2A 109.3 . . ? H2B C2 H2A 107.9 . . ? C2 C3 C4 114.0(10) . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? H3B C3 H3A 107.7 . . ? C5 C4A C10B 120.3(11) . . ? C5 C4A C4 124.8(10) . . ? C10B C4A C4 114.8(11) . . ? C3 C4 C4A 114.6(11) . . ? C3 C4 H4B 108.6 . . ? C4A C4 H4B 108.6 . . ? C3 C4 H4A 108.6 . . ? C4A C4 H4A 108.6 . . ? H4B C4 H4A 107.6 . . ? C4A C5 C5 120.4(7) . 2_656 ? C4A C5 H5 119.8 . . ? C5 C5 H5 119.8 2_656 . ? C10B C10B N1 123.9(6) 2_656 . ? C10B C10B C4A 119.1(7) 2_656 . ? N1 C10B C4A 116.3(9) . . ? O18 C11 N1 125.2(12) . . ? O18 C11 C12 117.4(12) . . ? N1 C11 C12 116.4(8) . . ? N1 C11 Se18 123.9(6) . . ? C12 C11 Se18 119.3(6) . . ? C17 C12 C13 119.6(7) . . ? C17 C12 C11 120.1(9) . . ? C13 C12 C11 120.1(8) . . ? C14 C13 C12 118.7(10) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C15 C14 C13 122.0(11) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 120.1(9) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 118.8(10) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? C12 C17 C16 120.8(10) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? O23 C19 C36 104.1(9) . . ? O23 C19 C30 109.1(9) . . ? C36 C19 C30 111.8(7) . . ? O23 C19 C20 105.8(8) . . ? C36 C19 C20 108.8(8) . . ? C30 C19 C20 116.4(9) . . ? O25 C20 C19 109.8(8) . . ? O25 C20 C21 100.8(9) . . ? C19 C20 C21 117.9(8) . . ? O25 C20 H20 109.3 . . ? C19 C20 H20 109.3 . . ? C21 C20 H20 109.3 . . ? O27 C21 C20 104.2(8) . . ? O27 C21 C22 110.9(7) . . ? C20 C21 C22 115.0(10) . . ? O27 C21 H21 108.9 . . ? C20 C21 H21 108.9 . . ? C22 C21 H21 108.9 . . ? O24 C22 C42 112.8(11) . . ? O24 C22 C48 109.1(8) . . ? C42 C22 C48 112.4(7) . . ? O24 C22 C21 103.0(7) . . ? C42 C22 C21 111.8(9) . . ? C48 C22 C21 107.1(10) . . ? C19 O23 H23 109.5 . . ? C22 O24 H24 109.5 . . ? C20 O25 C26 108.2(6) . . ? O25 C26 O27 104.8(9) . . ? O25 C26 C29 112.4(9) . . ? O27 C26 C29 110.1(8) . . ? O25 C26 C28 110.1(9) . . ? O27 C26 C28 109.3(8) . . ? C29 C26 C28 110.0(11) . . ? C21 O27 C26 110.1(6) . . ? C26 C28 H28C 109.5 . . ? C26 C28 H28B 109.5 . . ? H28C C28 H28B 109.5 . . ? C26 C28 H28A 109.5 . . ? H28C C28 H28A 109.5 . . ? H28B C28 H28A 109.5 . . ? C26 C29 H29C 109.5 . . ? C26 C29 H29B 109.5 . . ? H29C C29 H29B 109.5 . . ? C26 C29 H29A 109.5 . . ? H29C C29 H29A 109.5 . . ? H29B C29 H29A 109.5 . . ? C35 C30 C31 118.4(11) . . ? C35 C30 C19 119.2(12) . . ? C31 C30 C19 122.3(10) . . ? C30 C31 C32 118.8(13) . . ? C30 C31 H31 120.6 . . ? C32 C31 H31 120.6 . . ? C33 C32 C31 122.4(15) . . ? C33 C32 H32 118.8 . . ? C31 C32 H32 118.8 . . ? C32 C33 C34 118.7(13) . . ? C32 C33 H33 120.7 . . ? C34 C33 H33 120.7 . . ? C35 C34 C33 117.4(16) . . ? C35 C34 H34 121.3 . . ? C33 C34 H34 121.3 . . ? C34 C35 C30 124.2(17) . . ? C34 C35 H35 117.9 . . ? C30 C35 H35 117.9 . . ? C41 C36 C37 117.7(9) . . ? C41 C36 C19 119.8(10) . . ? C37 C36 C19 122.4(11) . . ? C36 C37 C38 121.1(13) . . ? C36 C37 H37 119.4 . . ? C38 C37 H37 119.4 . . ? C39 C38 C37 121.0(12) . . ? C39 C38 H38 119.5 . . ? C37 C38 H38 119.5 . . ? C38 C39 C40 119.5(9) . . ? C38 C39 H39 120.3 . . ? C40 C39 H39 120.3 . . ? C41 C40 C39 118.6(14) . . ? C41 C40 H40 120.7 . . ? C39 C40 H40 120.7 . . ? C36 C41 C40 121.9(12) . . ? C36 C41 H41 119.1 . . ? C40 C41 H41 119.1 . . ? C43 C42 C47 117.6(11) . . ? C43 C42 C22 120.3(10) . . ? C47 C42 C22 121.9(10) . . ? C42 C43 C44 119.9(11) . . ? C42 C43 H43 120.0 . . ? C44 C43 H43 120.0 . . ? C45 C44 C43 120.4(12) . . ? C45 C44 H44 119.8 . . ? C43 C44 H44 119.8 . . ? C44 C45 C46 122.1(14) . . ? C44 C45 H45 118.9 . . ? C46 C45 H45 118.9 . . ? C47 C46 C45 117.2(13) . . ? C47 C46 H46 121.4 . . ? C45 C46 H46 121.4 . . ? C46 C47 C42 122.4(12) . . ? C46 C47 H47 118.8 . . ? C42 C47 H47 118.8 . . ? C49 C48 C53 119.4(9) . . ? C49 C48 C22 127.5(10) . . ? C53 C48 C22 113.0(12) . . ? C48 C49 C50 121.2(12) . . ? C48 C49 H49 119.4 . . ? C50 C49 H49 119.4 . . ? C51 C50 C49 121.4(15) . . ? C51 C50 H50 119.3 . . ? C49 C50 H50 119.3 . . ? C50 C51 C52 120.3(10) . . ? C50 C51 H51 119.9 . . ? C52 C51 H51 119.9 . . ? C51 C52 C53 118.8(13) . . ? C51 C52 H52 120.6 . . ? C53 C52 H52 120.6 . . ? C52 C53 C48 118.8(15) . . ? C52 C53 H53 120.6 . . ? C48 C53 H53 120.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C2 C3 110.2(13) . . . . ? C10B N1 C2 C3 -59.0(13) . . . . ? N1 C2 C3 C4 19.9(16) . . . . ? C2 C3 C4 C4A 29.3(17) . . . . ? C5 C4A C4 C3 137.2(11) . . . . ? C10B C4A C4 C3 -44.8(13) . . . . ? C10B C4A C5 C5 0.4(18) . . . 2_656 ? C4 C4A C5 C5 178.3(12) . . . 2_656 ? C11 N1 C10B C10B 65.8(16) . . . 2_656 ? C2 N1 C10B C10B -125.7(10) . . . 2_656 ? C11 N1 C10B C4A -123.5(11) . . . . ? C2 N1 C10B C4A 44.9(11) . . . . ? C5 C4A C10B C10B -4.4(14) . . . 2_656 ? C4 C4A C10B C10B 177.5(9) . . . 2_656 ? C5 C4A C10B N1 -175.6(9) . . . . ? C4 C4A C10B N1 6.3(11) . . . . ? Se18 O18 C11 N1 91(4) . . . . ? Se18 O18 C11 C12 -101(3) . . . . ? C10B N1 C11 O18 172.2(18) . . . . ? C2 N1 C11 O18 5(2) . . . . ? C10B N1 C11 C12 3.8(16) . . . . ? C2 N1 C11 C12 -163.7(10) . . . . ? C10B N1 C11 Se18 -168.4(9) . . . . ? C2 N1 C11 Se18 24.1(15) . . . . ? O18 Se18 C11 N1 -100(4) . . . . ? O18 Se18 C11 C12 88(4) . . . . ? O18 C11 C12 C17 -114.3(18) . . . . ? N1 C11 C12 C17 55.0(16) . . . . ? Se18 C11 C12 C17 -132.4(10) . . . . ? O18 C11 C12 C13 60(2) . . . . ? N1 C11 C12 C13 -130.5(11) . . . . ? Se18 C11 C12 C13 42.1(15) . . . . ? C17 C12 C13 C14 1.5(18) . . . . ? C11 C12 C13 C14 -173.1(12) . . . . ? C12 C13 C14 C15 -2.3(19) . . . . ? C13 C14 C15 C16 1(2) . . . . ? C14 C15 C16 C17 1.5(19) . . . . ? C13 C12 C17 C16 0.8(18) . . . . ? C11 C12 C17 C16 175.3(12) . . . . ? C15 C16 C17 C12 -2.3(19) . . . . ? O23 C19 C20 O25 -168.6(7) . . . . ? C36 C19 C20 O25 -57.3(12) . . . . ? C30 C19 C20 O25 70.1(10) . . . . ? O23 C19 C20 C21 76.9(12) . . . . ? C36 C19 C20 C21 -171.8(10) . . . . ? C30 C19 C20 C21 -44.4(15) . . . . ? O25 C20 C21 O27 23.1(9) . . . . ? C19 C20 C21 O27 142.5(10) . . . . ? O25 C20 C21 C22 144.6(8) . . . . ? C19 C20 C21 C22 -96.0(11) . . . . ? O27 C21 C22 O24 177.2(7) . . . . ? C20 C21 C22 O24 59.4(10) . . . . ? O27 C21 C22 C42 55.8(11) . . . . ? C20 C21 C22 C42 -62.0(12) . . . . ? O27 C21 C22 C48 -67.8(10) . . . . ? C20 C21 C22 C48 174.3(8) . . . . ? C19 C20 O25 C26 -159.4(8) . . . . ? C21 C20 O25 C26 -34.4(9) . . . . ? C20 O25 C26 O27 33.2(11) . . . . ? C20 O25 C26 C29 -86.3(10) . . . . ? C20 O25 C26 C28 150.6(8) . . . . ? C20 C21 O27 C26 -4.2(11) . . . . ? C22 C21 O27 C26 -128.4(9) . . . . ? O25 C26 O27 C21 -16.6(12) . . . . ? C29 C26 O27 C21 104.5(11) . . . . ? C28 C26 O27 C21 -134.5(9) . . . . ? O23 C19 C30 C35 35.6(9) . . . . ? C36 C19 C30 C35 -79.0(13) . . . . ? C20 C19 C30 C35 155.1(9) . . . . ? O23 C19 C30 C31 -148.7(8) . . . . ? C36 C19 C30 C31 96.7(11) . . . . ? C20 C19 C30 C31 -29.2(13) . . . . ? C35 C30 C31 C32 0.1(13) . . . . ? C19 C30 C31 C32 -175.7(8) . . . . ? C30 C31 C32 C33 1.1(15) . . . . ? C31 C32 C33 C34 -0.2(17) . . . . ? C32 C33 C34 C35 -1.8(18) . . . . ? C33 C34 C35 C30 3.1(18) . . . . ? C31 C30 C35 C34 -2.3(15) . . . . ? C19 C30 C35 C34 173.6(10) . . . . ? O23 C19 C36 C41 42.1(14) . . . . ? C30 C19 C36 C41 159.7(12) . . . . ? C20 C19 C36 C41 -70.3(16) . . . . ? O23 C19 C36 C37 -137.5(11) . . . . ? C30 C19 C36 C37 -19.9(16) . . . . ? C20 C19 C36 C37 110.0(12) . . . . ? C41 C36 C37 C38 -2.5(19) . . . . ? C19 C36 C37 C38 177.2(12) . . . . ? C36 C37 C38 C39 4(2) . . . . ? C37 C38 C39 C40 -1(2) . . . . ? C38 C39 C40 C41 -3(2) . . . . ? C37 C36 C41 C40 -1(2) . . . . ? C19 C36 C41 C40 179.0(14) . . . . ? C39 C40 C41 C36 4(3) . . . . ? O24 C22 C42 C43 -26.7(14) . . . . ? C48 C22 C42 C43 -150.6(11) . . . . ? C21 C22 C42 C43 88.9(14) . . . . ? O24 C22 C42 C47 158.2(10) . . . . ? C48 C22 C42 C47 34.2(17) . . . . ? C21 C22 C42 C47 -86.3(11) . . . . ? C47 C42 C43 C44 2.2(17) . . . . ? C22 C42 C43 C44 -173.2(10) . . . . ? C42 C43 C44 C45 -6(2) . . . . ? C43 C44 C45 C46 4(2) . . . . ? C44 C45 C46 C47 1(2) . . . . ? C45 C46 C47 C42 -5(2) . . . . ? C43 C42 C47 C46 3.3(19) . . . . ? C22 C42 C47 C46 178.6(11) . . . . ? O24 C22 C48 C49 116.2(14) . . . . ? C42 C22 C48 C49 -117.9(15) . . . . ? C21 C22 C48 C49 5.4(16) . . . . ? O24 C22 C48 C53 -60.8(12) . . . . ? C42 C22 C48 C53 65.2(14) . . . . ? C21 C22 C48 C53 -171.6(10) . . . . ? C53 C48 C49 C50 0.4(19) . . . . ? C22 C48 C49 C50 -176.4(11) . . . . ? C48 C49 C50 C51 0(2) . . . . ? C49 C50 C51 C52 -2(2) . . . . ? C50 C51 C52 C53 2(2) . . . . ? C51 C52 C53 C48 -1(2) . . . . ? C49 C48 C53 C52 -0.1(19) . . . . ? C22 C48 C53 C52 177.1(11) . . . . ? _diffrn_measured_fraction_theta_max 0.98 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.98 _refine_diff_density_max 0.243 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 927854' ####################################################################### # # 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_4 #TrackingRef 'AS-05-03-2013-5B-6A.CIF' #============================================================= _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _journal_coeditor_?tes ; ? ; _iucr_compatibility_tag ACTA95 loop_ _publ_author_foot?te ; ? ; ; to whom correspondence should be addressed ; ; ? ; ; to whom correspondence should be addressed ; # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H30 O4, 0.5(C26 H24 N2 S2)' _chemical_formula_sum 'C44 H42 N O4 S' _chemical_formula_weight 680.85 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 monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.387(3) _cell_length_b 9.477(2) _cell_length_c 23.828(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.58(3) _cell_angle_gamma 90.00 _cell_volume 3597.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _cell_measurement_reflns_used 34884 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 25.00 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1444 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9418 _exptl_absorpt_correction_T_max 0.9893 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34884 _diffrn_reflns_av_R_equivalents 0.1114 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6146 _reflns_number_gt 5477 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _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^)+(0.0904P)^2^+18.5990P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.11(19) _chemical_absolute_configuration rm _refine_ls_number_reflns 6146 _refine_ls_number_parameters 453 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0974 _refine_ls_wR_factor_ref 0.2313 _refine_ls_wR_factor_gt 0.2276 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4997(3) 0.4427(5) 0.5636(2) 0.0352(10) Uani 1 1 d . . . C2 C 0.5639(4) 0.4339(7) 0.6189(3) 0.0434(14) Uani 1 1 d . . . H2B H 0.5642 0.5210 0.6403 0.052 Uiso 1 1 calc R . . H2A H 0.6190 0.4218 0.6111 0.052 Uiso 1 1 calc R . . C3 C 0.5451(6) 0.3094(9) 0.6552(3) 0.065(2) Uani 1 1 d . . . H3B H 0.5977 0.2671 0.6754 0.078 Uiso 1 1 calc R . . H3A H 0.5170 0.3445 0.6839 0.078 Uiso 1 1 calc R . . C4A C 0.4953(4) 0.1861(6) 0.5581(3) 0.0422(14) Uani 1 1 d . . . C4 C 0.4909(5) 0.1974(9) 0.6192(3) 0.0570(17) Uani 1 1 d . . . H4B H 0.5063 0.1068 0.6375 0.068 Uiso 1 1 calc R . . H4A H 0.4330 0.2155 0.6202 0.068 Uiso 1 1 calc R . . C5 C 0.4984(4) 0.0631(7) 0.5287(3) 0.0522(17) Uani 1 1 d . . . H5 H 0.4982 -0.0225 0.5478 0.063 Uiso 1 1 calc R . . C10B C 0.4973(3) 0.3174(5) 0.5284(3) 0.0321(11) Uani 1 1 d . . . C11 C 0.4466(3) 0.5518(6) 0.5513(2) 0.0351(12) Uani 1 1 d . . . C12 C 0.3684(3) 0.5323(5) 0.5034(2) 0.0317(11) Uani 1 1 d . . . C13 C 0.3418(4) 0.6384(6) 0.4626(3) 0.0403(13) Uani 1 1 d . . . H13 H 0.3730 0.7210 0.4644 0.048 Uiso 1 1 calc R . . C14 C 0.2699(4) 0.6218(8) 0.4196(3) 0.0508(16) Uani 1 1 d . . . H14 H 0.2542 0.6911 0.3915 0.061 Uiso 1 1 calc R . . C15 C 0.2220(4) 0.5053(8) 0.4181(3) 0.0543(18) Uani 1 1 d . . . H15 H 0.1727 0.4968 0.3895 0.065 Uiso 1 1 calc R . . C16 C 0.2453(4) 0.3959(8) 0.4590(3) 0.0548(17) Uani 1 1 d . . . H16 H 0.2122 0.3155 0.4574 0.066 Uiso 1 1 calc R . . C17 C 0.3189(4) 0.4116(7) 0.5017(3) 0.0435(14) Uani 1 1 d . . . H17 H 0.3353 0.3413 0.5293 0.052 Uiso 1 1 calc R . . S18 S 0.45798(10) 0.70219(17) 0.58847(7) 0.0467(4) Uani 1 1 d . . . C19 C 0.5875(4) 0.5534(8) 0.8411(3) 0.0449(15) Uani 1 1 d . . . C20 C 0.5099(4) 0.6465(8) 0.8413(3) 0.0458(14) Uani 1 1 d . . . H20 H 0.5181 0.7406 0.8264 0.055 Uiso 1 1 calc R . . C21 C 0.4225(3) 0.5862(7) 0.8083(3) 0.0419(14) Uani 1 1 d . . . H21 H 0.4250 0.4829 0.8079 0.050 Uiso 1 1 calc R . . C22 C 0.3883(3) 0.6415(7) 0.7453(3) 0.0405(14) Uani 1 1 d . . . O23 O 0.6051(3) 0.5710(6) 0.78540(19) 0.0556(13) Uani 1 1 d . . . H23 H 0.5613 0.5862 0.7613 0.083 Uiso 1 1 calc R . . O24 O 0.4513(3) 0.5924(6) 0.71623(19) 0.0520(12) Uani 1 1 d . . . H24 H 0.4415 0.6251 0.6835 0.078 Uiso 1 1 calc R . . O25 O 0.4991(3) 0.6581(5) 0.89922(18) 0.0499(12) Uani 1 1 d . . . C26 C 0.4142(4) 0.6991(10) 0.8952(3) 0.0540(16) Uani 1 1 d . . . O27 O 0.3668(3) 0.6307(6) 0.84349(19) 0.0519(12) Uani 1 1 d . . . C28 C 0.3865(5) 0.6409(11) 0.9475(3) 0.067(2) Uani 1 1 d . . . H28C H 0.3964 0.5410 0.9502 0.100 Uiso 1 1 calc R . . H28B H 0.3278 0.6591 0.9433 0.100 Uiso 1 1 calc R . . H28A H 0.4180 0.6860 0.9819 0.100 Uiso 1 1 calc R . . C29 C 0.4048(6) 0.8567(8) 0.8909(4) 0.065(2) Uani 1 1 d . . . H29C H 0.4270 0.8905 0.8596 0.098 Uiso 1 1 calc R . . H29B H 0.4349 0.8992 0.9263 0.098 Uiso 1 1 calc R . . H29A H 0.3464 0.8811 0.8841 0.098 Uiso 1 1 calc R . . C30 C 0.5792(4) 0.3976(8) 0.8545(3) 0.0491(16) Uani 1 1 d . . . C31 C 0.5303(4) 0.3416(9) 0.8875(3) 0.0588(18) Uani 1 1 d . . . H31 H 0.4962 0.4019 0.9027 0.071 Uiso 1 1 calc R . . C32 C 0.5288(5) 0.1979(12) 0.8999(4) 0.077(2) Uani 1 1 d . . . H32 H 0.4931 0.1654 0.9222 0.093 Uiso 1 1 calc R . . C33 C 0.5789(5) 0.1033(9) 0.8799(4) 0.076(3) Uani 1 1 d . . . H33 H 0.5782 0.0074 0.8881 0.091 Uiso 1 1 calc R . . C34 C 0.6318(6) 0.1594(11) 0.8460(5) 0.083(3) Uani 1 1 d . . . H34 H 0.6683 0.1004 0.8325 0.100 Uiso 1 1 calc R . . C35 C 0.6290(5) 0.3011(11) 0.8330(4) 0.074(2) Uani 1 1 d . . . H35 H 0.6617 0.3344 0.8088 0.089 Uiso 1 1 calc R . . C36 C 0.6648(4) 0.6165(9) 0.8835(3) 0.0534(18) Uani 1 1 d . . . C37 C 0.7023(5) 0.5534(10) 0.9355(3) 0.061(2) Uani 1 1 d . . . H37 H 0.6791 0.4723 0.9473 0.074 Uiso 1 1 calc R . . C38 C 0.7755(5) 0.6123(11) 0.9704(3) 0.069(2) Uani 1 1 d . . . H38 H 0.8030 0.5662 1.0040 0.083 Uiso 1 1 calc R . . C39 C 0.8072(5) 0.7392(11) 0.9551(4) 0.074(3) Uani 1 1 d . . . H39 H 0.8543 0.7796 0.9793 0.089 Uiso 1 1 calc R . . C40 C 0.7694(7) 0.8045(13) 0.9047(4) 0.100(4) Uani 1 1 d . . . H40 H 0.7909 0.8879 0.8935 0.120 Uiso 1 1 calc R . . C41 C 0.6964(6) 0.7418(9) 0.8700(4) 0.080(3) Uani 1 1 d . . . H41 H 0.6689 0.7880 0.8364 0.096 Uiso 1 1 calc R . . C42 C 0.3762(4) 0.8029(8) 0.7409(3) 0.0458(15) Uani 1 1 d . . . C43 C 0.4436(4) 0.8892(8) 0.7375(3) 0.0510(16) Uani 1 1 d . . . H43 H 0.4940 0.8481 0.7345 0.061 Uiso 1 1 calc R . . C44 C 0.4377(5) 1.0310(10) 0.7385(3) 0.067(2) Uani 1 1 d . . . H44 H 0.4827 1.0873 0.7351 0.080 Uiso 1 1 calc R . . C45 C 0.3639(6) 1.0911(11) 0.7446(4) 0.078(2) Uani 1 1 d . . . H45 H 0.3605 1.1887 0.7474 0.094 Uiso 1 1 calc R . . C46 C 0.2959(6) 1.0107(9) 0.7467(4) 0.074(2) Uani 1 1 d . . . H46 H 0.2458 1.0530 0.7495 0.089 Uiso 1 1 calc R . . C47 C 0.3021(5) 0.8663(9) 0.7446(3) 0.0605(19) Uani 1 1 d . . . H47 H 0.2557 0.8108 0.7456 0.073 Uiso 1 1 calc R . . C48 C 0.3041(4) 0.5651(7) 0.7146(3) 0.0434(15) Uani 1 1 d . . . C49 C 0.2640(5) 0.4712(9) 0.7427(3) 0.0590(19) Uani 1 1 d . . . H49 H 0.2842 0.4541 0.7819 0.071 Uiso 1 1 calc R . . C50 C 0.1924(4) 0.4016(9) 0.7118(4) 0.062(2) Uani 1 1 d . . . H50 H 0.1642 0.3399 0.7310 0.074 Uiso 1 1 calc R . . C51 C 0.1633(5) 0.4227(9) 0.6541(4) 0.065(2) Uani 1 1 d . . . H51 H 0.1163 0.3737 0.6341 0.078 Uiso 1 1 calc R . . C52 C 0.2030(5) 0.5161(11) 0.6254(4) 0.074(2) Uani 1 1 d . . . H52 H 0.1840 0.5316 0.5859 0.088 Uiso 1 1 calc R . . C53 C 0.2729(4) 0.5865(9) 0.6578(3) 0.0548(17) Uani 1 1 d . . . H53 H 0.2995 0.6520 0.6391 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.035(2) 0.022(2) 0.048(3) 0.0012(19) 0.0087(19) 0.0062(19) C2 0.039(3) 0.034(3) 0.055(4) 0.004(3) 0.004(3) -0.008(3) C3 0.089(6) 0.051(4) 0.052(4) 0.006(3) 0.009(4) -0.012(4) C4A 0.035(3) 0.020(3) 0.069(4) 0.012(3) 0.007(3) -0.010(2) C4 0.061(4) 0.049(4) 0.059(4) 0.010(4) 0.009(3) -0.019(4) C5 0.055(4) 0.022(3) 0.071(4) 0.008(3) -0.004(3) -0.004(3) C10B 0.028(2) 0.010(2) 0.056(3) 0.000(2) 0.006(2) 0.003(2) C11 0.035(3) 0.029(3) 0.043(3) 0.000(2) 0.013(2) 0.001(2) C12 0.021(2) 0.018(2) 0.057(3) 0.001(2) 0.012(2) 0.004(2) C13 0.038(3) 0.018(2) 0.065(4) 0.001(3) 0.012(3) 0.003(2) C14 0.048(4) 0.047(4) 0.054(4) 0.009(3) 0.005(3) 0.009(3) C15 0.024(3) 0.065(5) 0.068(4) 0.007(4) 0.000(3) 0.008(3) C16 0.035(3) 0.048(4) 0.080(5) 0.002(3) 0.010(3) -0.014(3) C17 0.030(3) 0.042(3) 0.059(4) 0.010(3) 0.010(3) -0.003(3) S18 0.0417(8) 0.0323(7) 0.0653(10) -0.0073(7) 0.0109(7) -0.0008(7) C19 0.033(3) 0.057(4) 0.042(3) -0.004(3) 0.003(2) 0.000(3) C20 0.041(3) 0.057(4) 0.039(3) 0.002(3) 0.007(2) -0.003(3) C21 0.018(2) 0.053(4) 0.056(4) -0.007(3) 0.011(2) -0.001(2) C22 0.021(2) 0.045(3) 0.057(4) -0.005(3) 0.011(2) -0.002(2) O23 0.035(2) 0.086(4) 0.044(2) 0.000(2) 0.0060(18) -0.005(2) O24 0.037(2) 0.072(3) 0.046(2) -0.013(2) 0.0102(18) 0.004(2) O25 0.043(2) 0.067(3) 0.041(2) -0.007(2) 0.0103(18) 0.001(2) C26 0.046(3) 0.070(4) 0.048(4) -0.005(4) 0.016(3) -0.020(4) O27 0.032(2) 0.075(3) 0.051(3) -0.012(2) 0.0142(18) -0.009(2) C28 0.048(4) 0.101(7) 0.057(4) -0.012(4) 0.023(3) -0.013(4) C29 0.070(5) 0.046(4) 0.085(5) -0.008(4) 0.030(4) -0.004(4) C30 0.033(3) 0.061(4) 0.049(4) -0.003(3) 0.001(3) -0.009(3) C31 0.043(4) 0.063(5) 0.071(5) 0.005(4) 0.015(3) 0.005(3) C32 0.061(5) 0.082(6) 0.085(6) 0.030(5) 0.009(4) -0.002(5) C33 0.058(5) 0.053(5) 0.102(7) 0.003(4) -0.011(4) -0.003(4) C34 0.069(5) 0.072(7) 0.105(7) -0.014(5) 0.013(5) 0.007(4) C35 0.051(4) 0.084(6) 0.089(6) -0.005(5) 0.021(4) 0.026(4) C36 0.033(3) 0.071(5) 0.056(4) -0.002(3) 0.009(3) -0.005(3) C37 0.048(4) 0.083(6) 0.051(4) -0.002(4) 0.008(3) -0.003(4) C38 0.047(4) 0.107(7) 0.048(4) -0.006(4) -0.002(3) -0.005(4) C39 0.045(4) 0.092(7) 0.081(6) -0.028(5) 0.007(4) -0.026(4) C40 0.097(7) 0.100(8) 0.087(7) 0.010(6) -0.010(6) -0.070(7) C41 0.077(6) 0.061(6) 0.090(6) 0.014(4) -0.008(5) -0.032(4) C42 0.048(4) 0.048(4) 0.043(3) 0.000(3) 0.014(3) -0.006(3) C43 0.044(4) 0.062(5) 0.047(4) 0.008(3) 0.009(3) -0.003(3) C44 0.067(5) 0.074(6) 0.056(4) 0.013(4) 0.007(4) -0.026(4) C45 0.088(6) 0.061(5) 0.087(6) 0.006(5) 0.022(5) -0.004(5) C46 0.061(5) 0.056(5) 0.108(7) 0.007(5) 0.025(5) 0.018(4) C47 0.048(4) 0.074(6) 0.060(4) 0.005(4) 0.013(3) -0.006(4) C48 0.026(3) 0.040(4) 0.063(4) -0.014(3) 0.008(3) -0.004(2) C49 0.046(4) 0.064(5) 0.063(5) -0.006(4) 0.005(3) -0.019(4) C50 0.028(3) 0.054(4) 0.103(6) -0.006(4) 0.012(3) -0.011(3) C51 0.045(4) 0.050(4) 0.094(6) -0.018(4) 0.006(4) -0.013(3) C52 0.048(4) 0.093(7) 0.068(5) -0.015(5) -0.010(4) -0.007(4) C53 0.027(3) 0.065(5) 0.069(5) 0.002(4) 0.005(3) -0.002(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 N1 C11 1.339(7) . ? N1 C10B 1.448(7) . ? N1 C2 1.483(8) . ? C2 C3 1.536(9) . ? C2 H2B 0.9700 . ? C2 H2A 0.9700 . ? C3 C4 1.514(10) . ? C3 H3B 0.9700 . ? C3 H3A 0.9700 . ? C4A C5 1.367(9) . ? C4A C10B 1.436(8) . ? C4A C4 1.478(10) . ? C4 H4B 0.9700 . ? C4 H4A 0.9700 . ? C5 C5 1.382(15) 2_656 ? C5 H5 0.9300 . ? C10B C10B 1.379(12) 2_656 ? C11 C12 1.513(8) . ? C11 S18 1.665(6) . ? C12 C13 1.395(8) . ? C12 C17 1.397(8) . ? C13 C14 1.378(9) . ? C13 H13 0.9300 . ? C14 C15 1.350(10) . ? C14 H14 0.9300 . ? C15 C16 1.411(10) . ? C15 H15 0.9300 . ? C16 C17 1.393(9) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C19 O23 1.434(8) . ? C19 C30 1.523(10) . ? C19 C36 1.543(9) . ? C19 C20 1.548(9) . ? C20 O25 1.436(7) . ? C20 C21 1.571(8) . ? C20 H20 0.9800 . ? C21 O27 1.440(7) . ? C21 C22 1.563(9) . ? C21 H21 0.9800 . ? C22 O24 1.448(7) . ? C22 C42 1.543(10) . ? C22 C48 1.578(8) . ? O23 H23 0.8200 . ? O24 H24 0.8200 . ? O25 C26 1.426(8) . ? C26 O27 1.447(8) . ? C26 C29 1.503(12) . ? C26 C28 1.525(10) . ? C28 H28C 0.9600 . ? C28 H28B 0.9600 . ? C28 H28A 0.9600 . ? C29 H29C 0.9600 . ? C29 H29B 0.9600 . ? C29 H29A 0.9600 . ? C30 C31 1.355(10) . ? C30 C35 1.401(11) . ? C31 C32 1.395(13) . ? C31 H31 0.9300 . ? C32 C33 1.374(14) . ? C32 H32 0.9300 . ? C33 C34 1.420(14) . ? C33 H33 0.9300 . ? C34 C35 1.377(14) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 C41 1.364(11) . ? C36 C37 1.384(11) . ? C37 C38 1.405(11) . ? C37 H37 0.9300 . ? C38 C39 1.393(13) . ? C38 H38 0.9300 . ? C39 C40 1.362(14) . ? C39 H39 0.9300 . ? C40 C41 1.415(11) . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? C42 C47 1.376(10) . ? C42 C43 1.392(9) . ? C43 C44 1.348(12) . ? C43 H43 0.9300 . ? C44 C45 1.374(13) . ? C44 H44 0.9300 . ? C45 C46 1.361(13) . ? C45 H45 0.9300 . ? C46 C47 1.374(12) . ? C46 H46 0.9300 . ? C47 H47 0.9300 . ? C48 C53 1.345(10) . ? C48 C49 1.371(10) . ? C49 C50 1.395(10) . ? C49 H49 0.9300 . ? C50 C51 1.360(12) . ? C50 H50 0.9300 . ? C51 C52 1.373(13) . ? C51 H51 0.9300 . ? C52 C53 1.392(10) . ? C52 H52 0.9300 . ? C53 H53 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 C11 N1 C10B 125.3(5) . . ? C11 N1 C2 121.8(5) . . ? C10B N1 C2 112.6(4) . . ? N1 C2 C3 110.5(5) . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? H2B C2 H2A 108.1 . . ? C4 C3 C2 112.9(6) . . ? C4 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? H3B C3 H3A 107.8 . . ? C5 C4A C10B 118.6(6) . . ? C5 C4A C4 125.7(6) . . ? C10B C4A C4 115.7(6) . . ? C4A C4 C3 116.7(6) . . ? C4A C4 H4B 108.1 . . ? C3 C4 H4B 108.1 . . ? C4A C4 H4A 108.1 . . ? C3 C4 H4A 108.1 . . ? H4B C4 H4A 107.3 . . ? C4A C5 C5 121.5(4) . 2_656 ? C4A C5 H5 119.2 . . ? C5 C5 H5 119.2 2_656 . ? C10B C10B C4A 119.9(4) 2_656 . ? C10B C10B N1 124.7(3) 2_656 . ? C4A C10B N1 115.3(5) . . ? N1 C11 C12 117.5(5) . . ? N1 C11 S18 123.9(5) . . ? C12 C11 S18 118.4(4) . . ? C13 C12 C17 119.1(5) . . ? C13 C12 C11 120.5(5) . . ? C17 C12 C11 120.3(5) . . ? C14 C13 C12 120.6(6) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 120.2(6) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 121.5(6) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C17 C16 C15 118.2(6) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C16 C17 C12 120.4(6) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? O23 C19 C30 110.8(5) . . ? O23 C19 C36 104.3(5) . . ? C30 C19 C36 109.8(5) . . ? O23 C19 C20 106.3(5) . . ? C30 C19 C20 116.0(5) . . ? C36 C19 C20 109.0(5) . . ? O25 C20 C19 109.4(5) . . ? O25 C20 C21 101.9(5) . . ? C19 C20 C21 116.4(6) . . ? O25 C20 H20 109.6 . . ? C19 C20 H20 109.6 . . ? C21 C20 H20 109.6 . . ? O27 C21 C22 109.2(5) . . ? O27 C21 C20 103.2(5) . . ? C22 C21 C20 116.0(5) . . ? O27 C21 H21 109.4 . . ? C22 C21 H21 109.4 . . ? C20 C21 H21 109.4 . . ? O24 C22 C42 112.3(5) . . ? O24 C22 C21 102.5(4) . . ? C42 C22 C21 114.2(5) . . ? O24 C22 C48 105.9(5) . . ? C42 C22 C48 109.8(5) . . ? C21 C22 C48 111.6(5) . . ? C19 O23 H23 109.5 . . ? C22 O24 H24 109.5 . . ? C26 O25 C20 107.2(4) . . ? O25 C26 O27 104.7(5) . . ? O25 C26 C29 111.0(6) . . ? O27 C26 C29 111.1(7) . . ? O25 C26 C28 108.7(6) . . ? O27 C26 C28 109.3(6) . . ? C29 C26 C28 111.7(7) . . ? C21 O27 C26 110.0(4) . . ? C26 C28 H28C 109.5 . . ? C26 C28 H28B 109.5 . . ? H28C C28 H28B 109.5 . . ? C26 C28 H28A 109.5 . . ? H28C C28 H28A 109.5 . . ? H28B C28 H28A 109.5 . . ? C26 C29 H29C 109.5 . . ? C26 C29 H29B 109.5 . . ? H29C C29 H29B 109.5 . . ? C26 C29 H29A 109.5 . . ? H29C C29 H29A 109.5 . . ? H29B C29 H29A 109.5 . . ? C31 C30 C35 115.5(8) . . ? C31 C30 C19 126.6(7) . . ? C35 C30 C19 117.9(7) . . ? C30 C31 C32 123.2(8) . . ? C30 C31 H31 118.4 . . ? C32 C31 H31 118.4 . . ? C33 C32 C31 121.5(8) . . ? C33 C32 H32 119.3 . . ? C31 C32 H32 119.3 . . ? C32 C33 C34 116.6(8) . . ? C32 C33 H33 121.7 . . ? C34 C33 H33 121.7 . . ? C35 C34 C33 120.0(9) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C30 123.1(9) . . ? C34 C35 H35 118.4 . . ? C30 C35 H35 118.4 . . ? C41 C36 C37 118.3(7) . . ? C41 C36 C19 118.8(7) . . ? C37 C36 C19 122.8(7) . . ? C36 C37 C38 119.8(8) . . ? C36 C37 H37 120.1 . . ? C38 C37 H37 120.1 . . ? C39 C38 C37 120.5(8) . . ? C39 C38 H38 119.8 . . ? C37 C38 H38 119.8 . . ? C40 C39 C38 120.2(7) . . ? C40 C39 H39 119.9 . . ? C38 C39 H39 119.9 . . ? C39 C40 C41 118.2(9) . . ? C39 C40 H40 120.9 . . ? C41 C40 H40 120.9 . . ? C36 C41 C40 122.9(9) . . ? C36 C41 H41 118.6 . . ? C40 C41 H41 118.6 . . ? C47 C42 C43 118.1(7) . . ? C47 C42 C22 122.0(6) . . ? C43 C42 C22 119.7(6) . . ? C44 C43 C42 121.5(7) . . ? C44 C43 H43 119.3 . . ? C42 C43 H43 119.3 . . ? C43 C44 C45 119.0(8) . . ? C43 C44 H44 120.5 . . ? C45 C44 H44 120.5 . . ? C46 C45 C44 121.3(9) . . ? C46 C45 H45 119.3 . . ? C44 C45 H45 119.3 . . ? C45 C46 C47 119.2(8) . . ? C45 C46 H46 120.4 . . ? C47 C46 H46 120.4 . . ? C46 C47 C42 120.7(8) . . ? C46 C47 H47 119.6 . . ? C42 C47 H47 119.6 . . ? C53 C48 C49 118.4(6) . . ? C53 C48 C22 118.9(6) . . ? C49 C48 C22 122.6(6) . . ? C48 C49 C50 119.3(7) . . ? C48 C49 H49 120.4 . . ? C50 C49 H49 120.4 . . ? C51 C50 C49 121.1(8) . . ? C51 C50 H50 119.5 . . ? C49 C50 H50 119.5 . . ? C50 C51 C52 120.2(7) . . ? C50 C51 H51 119.9 . . ? C52 C51 H51 119.9 . . ? C51 C52 C53 117.1(8) . . ? C51 C52 H52 121.4 . . ? C53 C52 H52 121.4 . . ? C48 C53 C52 123.8(7) . . ? C48 C53 H53 118.1 . . ? C52 C53 H53 118.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C2 C3 114.2(7) . . . . ? C10B N1 C2 C3 -60.9(7) . . . . ? N1 C2 C3 C4 22.3(9) . . . . ? C5 C4A C4 C3 137.9(8) . . . . ? C10B C4A C4 C3 -41.5(9) . . . . ? C2 C3 C4 C4A 26.6(10) . . . . ? C10B C4A C5 C5 -1.3(11) . . . 2_656 ? C4 C4A C5 C5 179.4(8) . . . 2_656 ? C5 C4A C10B C10B -0.4(9) . . . 2_656 ? C4 C4A C10B C10B 179.0(6) . . . 2_656 ? C5 C4A C10B N1 -175.9(6) . . . . ? C4 C4A C10B N1 3.5(7) . . . . ? C11 N1 C10B C10B 58.0(9) . . . 2_656 ? C2 N1 C10B C10B -127.1(7) . . . 2_656 ? C11 N1 C10B C4A -126.8(6) . . . . ? C2 N1 C10B C4A 48.1(6) . . . . ? C10B N1 C11 C12 12.2(8) . . . . ? C2 N1 C11 C12 -162.2(5) . . . . ? C10B N1 C11 S18 -172.4(4) . . . . ? C2 N1 C11 S18 13.1(8) . . . . ? N1 C11 C12 C13 -136.5(5) . . . . ? S18 C11 C12 C13 47.8(7) . . . . ? N1 C11 C12 C17 47.6(7) . . . . ? S18 C11 C12 C17 -128.0(5) . . . . ? C17 C12 C13 C14 -2.9(9) . . . . ? C11 C12 C13 C14 -178.8(6) . . . . ? C12 C13 C14 C15 3.1(10) . . . . ? C13 C14 C15 C16 -2.0(11) . . . . ? C14 C15 C16 C17 0.7(11) . . . . ? C15 C16 C17 C12 -0.5(10) . . . . ? C13 C12 C17 C16 1.6(9) . . . . ? C11 C12 C17 C16 177.6(6) . . . . ? O23 C19 C20 O25 -167.8(5) . . . . ? C30 C19 C20 O25 68.5(7) . . . . ? C36 C19 C20 O25 -55.9(7) . . . . ? O23 C19 C20 C21 77.4(7) . . . . ? C30 C19 C20 C21 -46.2(7) . . . . ? C36 C19 C20 C21 -170.7(5) . . . . ? O25 C20 C21 O27 24.4(7) . . . . ? C19 C20 C21 O27 143.3(5) . . . . ? O25 C20 C21 C22 143.7(5) . . . . ? C19 C20 C21 C22 -97.4(7) . . . . ? O27 C21 C22 O24 178.5(5) . . . . ? C20 C21 C22 O24 62.4(7) . . . . ? O27 C21 C22 C42 56.7(6) . . . . ? C20 C21 C22 C42 -59.3(7) . . . . ? O27 C21 C22 C48 -68.6(6) . . . . ? C20 C21 C22 C48 175.4(5) . . . . ? C19 C20 O25 C26 -159.8(6) . . . . ? C21 C20 O25 C26 -36.1(7) . . . . ? C20 O25 C26 O27 34.0(7) . . . . ? C20 O25 C26 C29 -86.0(7) . . . . ? C20 O25 C26 C28 150.7(6) . . . . ? C22 C21 O27 C26 -128.7(6) . . . . ? C20 C21 O27 C26 -4.8(7) . . . . ? O25 C26 O27 C21 -17.0(8) . . . . ? C29 C26 O27 C21 103.0(7) . . . . ? C28 C26 O27 C21 -133.3(7) . . . . ? O23 C19 C30 C31 -149.5(6) . . . . ? C36 C19 C30 C31 95.9(8) . . . . ? C20 C19 C30 C31 -28.2(9) . . . . ? O23 C19 C30 C35 33.3(8) . . . . ? C36 C19 C30 C35 -81.4(7) . . . . ? C20 C19 C30 C35 154.5(6) . . . . ? C35 C30 C31 C32 0.1(11) . . . . ? C19 C30 C31 C32 -177.2(7) . . . . ? C30 C31 C32 C33 1.3(13) . . . . ? C31 C32 C33 C34 -0.2(13) . . . . ? C32 C33 C34 C35 -2.3(13) . . . . ? C33 C34 C35 C30 3.9(15) . . . . ? C31 C30 C35 C34 -2.7(12) . . . . ? C19 C30 C35 C34 174.8(8) . . . . ? O23 C19 C36 C41 44.1(9) . . . . ? C30 C19 C36 C41 162.8(8) . . . . ? C20 C19 C36 C41 -69.2(9) . . . . ? O23 C19 C36 C37 -137.7(7) . . . . ? C30 C19 C36 C37 -19.0(9) . . . . ? C20 C19 C36 C37 109.1(8) . . . . ? C41 C36 C37 C38 -5.5(12) . . . . ? C19 C36 C37 C38 176.2(7) . . . . ? C36 C37 C38 C39 4.7(13) . . . . ? C37 C38 C39 C40 -2.8(14) . . . . ? C38 C39 C40 C41 1.8(17) . . . . ? C37 C36 C41 C40 4.7(15) . . . . ? C19 C36 C41 C40 -177.0(10) . . . . ? C39 C40 C41 C36 -2.9(18) . . . . ? O24 C22 C42 C47 154.5(6) . . . . ? C21 C22 C42 C47 -89.3(7) . . . . ? C48 C22 C42 C47 36.9(9) . . . . ? O24 C22 C42 C43 -30.6(8) . . . . ? C21 C22 C42 C43 85.6(7) . . . . ? C48 C22 C42 C43 -148.1(6) . . . . ? C47 C42 C43 C44 0.9(10) . . . . ? C22 C42 C43 C44 -174.3(7) . . . . ? C42 C43 C44 C45 1.8(11) . . . . ? C43 C44 C45 C46 -3.3(13) . . . . ? C44 C45 C46 C47 2.2(14) . . . . ? C45 C46 C47 C42 0.6(13) . . . . ? C43 C42 C47 C46 -2.1(11) . . . . ? C22 C42 C47 C46 173.0(7) . . . . ? O24 C22 C48 C53 -60.1(7) . . . . ? C42 C22 C48 C53 61.4(7) . . . . ? C21 C22 C48 C53 -170.9(6) . . . . ? O24 C22 C48 C49 116.0(7) . . . . ? C42 C22 C48 C49 -122.5(7) . . . . ? C21 C22 C48 C49 5.2(8) . . . . ? C53 C48 C49 C50 -0.2(11) . . . . ? C22 C48 C49 C50 -176.3(6) . . . . ? C48 C49 C50 C51 1.8(12) . . . . ? C49 C50 C51 C52 -1.6(13) . . . . ? C50 C51 C52 C53 -0.2(13) . . . . ? C49 C48 C53 C52 -1.6(12) . . . . ? C22 C48 C53 C52 174.7(7) . . . . ? C51 C52 C53 C48 1.8(13) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.552 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 927855' ####################################################################### # # 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_5 #TrackingRef 'AS-05-03-2013-5c.CIF' #============================================================= _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _journal_coeditor_?tes ; ? ; _iucr_compatibility_tag ACTA95 loop_ _publ_author_foot?te ; ? ; ; to whom correspondence should be addressed ; ; ? ; ; to whom correspondence should be addressed ; # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 N2 Se2' _chemical_formula_sum 'C26 H24 N2 Se2' _chemical_formula_weight 522.39 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.339(2) _cell_length_b 16.111(3) _cell_length_c 15.343(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.10(3) _cell_angle_gamma 90.00 _cell_volume 2239.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 3.318 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.550 _exptl_absorpt_correction_T_max 0.711 _exptl_absorpt_process_details difabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4' _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.09 _diffrn_reflns_number 4061 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.1111 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3908 _reflns_number_gt 1653 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _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^)+(0.0998P)^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 3908 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1798 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1640 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.1153(5) 0.4730(3) 0.2047(3) 0.0457(13) Uani 1 1 d . . . C2 C -0.0057(8) 0.4195(5) 0.2119(6) 0.076(2) Uani 1 1 d . . . H2A H 0.0037 0.4036 0.2740 0.092 Uiso 1 1 calc R . . H2B H -0.0060 0.3696 0.1765 0.092 Uiso 1 1 calc R . . C3 C -0.1487(10) 0.4687(8) 0.1765(8) 0.120(4) Uani 1 1 d . . . H3A H -0.1679 0.4723 0.1116 0.144 Uiso 1 1 calc R . . H3B H -0.2299 0.4384 0.1908 0.144 Uiso 1 1 calc R . . C4A C -0.0032(9) 0.5856(5) 0.2594(5) 0.070(2) Uani 1 1 d . . . C4 C -0.1459(10) 0.5524(7) 0.2129(8) 0.110(3) Uani 1 1 d . . . H4A H -0.1887 0.5897 0.1638 0.132 Uiso 1 1 calc R . . H4B H -0.2097 0.5534 0.2543 0.132 Uiso 1 1 calc R . . C5 C 0.0017(12) 0.6610(6) 0.3081(6) 0.095(3) Uani 1 1 d . . . H5A H -0.0848 0.6874 0.3124 0.114 Uiso 1 1 calc R . . C6A C 0.2636(11) 0.6550(5) 0.3511(5) 0.071(2) Uani 1 1 d . . . C6 C 0.1349(14) 0.6934(6) 0.3479(6) 0.100(3) Uani 1 1 d . . . H6A H 0.1377 0.7453 0.3747 0.120 Uiso 1 1 calc R . . C7 C 0.4158(12) 0.6903(5) 0.3905(6) 0.099(3) Uani 1 1 d . . . H7A H 0.4096 0.7493 0.4016 0.118 Uiso 1 1 calc R . . H7B H 0.4608 0.6631 0.4470 0.118 Uiso 1 1 calc R . . C8 C 0.5053(12) 0.6751(5) 0.3236(6) 0.097(3) Uani 1 1 d . . . H8A H 0.4562 0.6996 0.2664 0.117 Uiso 1 1 calc R . . H8B H 0.6013 0.7012 0.3440 0.117 Uiso 1 1 calc R . . C9 C 0.5243(8) 0.5845(5) 0.3122(5) 0.072(2) Uani 1 1 d . . . H9A H 0.5429 0.5747 0.2536 0.086 Uiso 1 1 calc R . . H9B H 0.6102 0.5658 0.3571 0.086 Uiso 1 1 calc R . . N10 N 0.3964(5) 0.5353(3) 0.3202(3) 0.0429(12) Uani 1 1 d . . . C10A C 0.2607(8) 0.5770(4) 0.3093(4) 0.0470(16) Uani 1 1 d . . . C10B C 0.1267(7) 0.5467(4) 0.2579(4) 0.0447(16) Uani 1 1 d . . . C11 C 0.1880(6) 0.4606(3) 0.1392(4) 0.0403(15) Uani 1 1 d . . . C12 C 0.2706(7) 0.5320(4) 0.1135(4) 0.0431(15) Uani 1 1 d . . . C13 C 0.4105(7) 0.5186(5) 0.1003(4) 0.0588(19) Uani 1 1 d . . . H13A H 0.4538 0.4663 0.1087 0.071 Uiso 1 1 calc R . . C14 C 0.4840(9) 0.5850(7) 0.0742(5) 0.088(3) Uani 1 1 d . . . H14A H 0.5780 0.5766 0.0654 0.105 Uiso 1 1 calc R . . C15 C 0.4244(13) 0.6617(7) 0.0609(5) 0.097(3) Uani 1 1 d . . . H15A H 0.4770 0.7055 0.0444 0.117 Uiso 1 1 calc R . . C16 C 0.2816(12) 0.6740(5) 0.0727(5) 0.082(3) Uani 1 1 d . . . H16A H 0.2372 0.7259 0.0631 0.098 Uiso 1 1 calc R . . C17 C 0.2094(8) 0.6089(5) 0.0983(4) 0.0612(19) Uani 1 1 d . . . H17A H 0.1145 0.6171 0.1057 0.073 Uiso 1 1 calc R . . Se18 Se 0.18448(11) 0.36411(5) 0.07975(6) 0.0790(3) Uani 1 1 d . . . C19 C 0.4150(7) 0.4562(4) 0.3447(4) 0.0452(16) Uani 1 1 d . . . C20 C 0.3028(7) 0.4136(4) 0.3815(4) 0.0455(16) Uani 1 1 d . . . C21 C 0.2651(8) 0.3309(4) 0.3606(4) 0.0583(18) Uani 1 1 d . . . H21A H 0.3059 0.3033 0.3192 0.070 Uiso 1 1 calc R . . C22 C 0.1697(10) 0.2901(5) 0.3998(6) 0.083(2) Uani 1 1 d . . . H22A H 0.1443 0.2352 0.3850 0.099 Uiso 1 1 calc R . . C23 C 0.1103(9) 0.3324(6) 0.4631(5) 0.075(2) Uani 1 1 d . . . H23A H 0.0439 0.3052 0.4896 0.090 Uiso 1 1 calc R . . C24 C 0.1470(9) 0.4103(5) 0.4856(5) 0.070(2) Uani 1 1 d . . . H24A H 0.1075 0.4367 0.5284 0.084 Uiso 1 1 calc R . . C25 C 0.2441(7) 0.4529(4) 0.4458(4) 0.0517(17) Uani 1 1 d . . . H25A H 0.2697 0.5075 0.4622 0.062 Uiso 1 1 calc R . . Se26 Se 0.58150(9) 0.40014(6) 0.34155(6) 0.0798(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.033(3) 0.053(3) 0.054(3) 0.002(3) 0.016(3) -0.008(2) C2 0.048(5) 0.098(6) 0.080(6) 0.021(4) 0.010(4) -0.023(4) C3 0.052(6) 0.193(13) 0.112(8) 0.014(8) 0.015(5) -0.034(7) C4A 0.062(5) 0.098(6) 0.055(5) 0.035(4) 0.025(4) 0.025(5) C4 0.073(7) 0.124(9) 0.138(10) 0.019(7) 0.038(7) 0.020(7) C5 0.122(8) 0.107(8) 0.074(6) 0.025(6) 0.056(6) 0.084(7) C6A 0.120(7) 0.057(5) 0.040(4) 0.009(3) 0.024(5) 0.021(5) C6 0.163(11) 0.082(7) 0.065(6) 0.005(5) 0.048(7) 0.055(8) C7 0.167(10) 0.047(5) 0.066(6) -0.010(4) -0.002(6) -0.019(5) C8 0.127(8) 0.078(6) 0.072(6) -0.002(5) -0.002(6) -0.040(6) C9 0.073(5) 0.095(6) 0.044(4) -0.004(4) 0.008(4) -0.037(5) N10 0.045(3) 0.046(3) 0.037(3) -0.001(2) 0.009(2) -0.003(3) C10A 0.077(5) 0.035(4) 0.030(3) 0.005(3) 0.015(3) 0.006(3) C10B 0.057(4) 0.048(4) 0.039(4) 0.015(3) 0.030(3) 0.027(3) C11 0.035(3) 0.047(4) 0.035(4) -0.002(3) 0.002(3) 0.005(3) C12 0.042(4) 0.062(4) 0.027(3) -0.001(3) 0.012(3) 0.000(3) C13 0.047(4) 0.092(5) 0.038(4) -0.003(4) 0.011(3) -0.008(4) C14 0.065(5) 0.161(10) 0.041(5) -0.001(5) 0.022(4) -0.045(6) C15 0.110(8) 0.118(8) 0.056(5) 0.030(5) 0.004(5) -0.061(7) C16 0.117(8) 0.067(5) 0.052(5) 0.018(4) 0.002(5) -0.020(5) C17 0.069(5) 0.066(5) 0.051(4) 0.019(4) 0.017(4) -0.006(4) Se18 0.1043(7) 0.0635(5) 0.0710(6) -0.0231(4) 0.0245(5) -0.0123(5) C19 0.051(4) 0.057(4) 0.026(3) -0.004(3) 0.007(3) 0.006(3) C20 0.047(4) 0.056(4) 0.029(3) 0.010(3) -0.001(3) 0.010(3) C21 0.080(5) 0.041(4) 0.055(4) 0.005(3) 0.018(4) -0.004(4) C22 0.113(7) 0.058(5) 0.075(6) 0.012(5) 0.018(5) -0.018(5) C23 0.077(5) 0.084(6) 0.064(5) 0.023(5) 0.018(4) -0.016(5) C24 0.090(6) 0.078(6) 0.049(5) 0.019(4) 0.031(4) 0.011(5) C25 0.072(5) 0.051(4) 0.032(4) 0.013(3) 0.013(4) 0.011(4) Se26 0.0626(5) 0.0929(7) 0.0877(6) 0.0098(5) 0.0253(5) 0.0265(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C11 1.358(7) . ? N1 C10B 1.430(8) . ? N1 C2 1.447(8) . ? C2 C3 1.534(13) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.458(14) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4A C10B 1.371(9) . ? C4A C5 1.420(13) . ? C4A C4 1.452(13) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.351(13) . ? C5 H5A 0.9300 . ? C6A C6 1.342(12) . ? C6A C10A 1.409(9) . ? C6A C7 1.514(12) . ? C6 H6A 0.9300 . ? C7 C8 1.493(13) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.486(11) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N10 1.463(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? N10 C19 1.328(7) . ? N10 C10A 1.407(8) . ? C10A C10B 1.395(9) . ? C11 C12 1.491(8) . ? C11 Se18 1.799(6) . ? C12 C17 1.360(9) . ? C12 C13 1.387(9) . ? C13 C14 1.381(11) . ? C13 H13A 0.9300 . ? C14 C15 1.350(13) . ? C14 H14A 0.9300 . ? C15 C16 1.402(13) . ? C15 H15A 0.9300 . ? C16 C17 1.356(10) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C19 C20 1.476(9) . ? C19 Se26 1.809(6) . ? C20 C25 1.391(8) . ? C20 C21 1.395(9) . ? C21 C22 1.360(10) . ? C21 H21A 0.9300 . ? C22 C23 1.407(11) . ? C22 H22A 0.9300 . ? C23 C24 1.324(11) . ? C23 H23A 0.9300 . ? C24 C25 1.391(9) . ? C24 H24A 0.9300 . ? C25 H25A 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 C11 N1 C10B 124.3(5) . . ? C11 N1 C2 120.6(6) . . ? C10B N1 C2 113.7(5) . . ? N1 C2 C3 107.1(7) . . ? N1 C2 H2A 110.3 . . ? C3 C2 H2A 110.3 . . ? N1 C2 H2B 110.3 . . ? C3 C2 H2B 110.3 . . ? H2A C2 H2B 108.5 . . ? C4 C3 C2 114.2(8) . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3B 108.7 . . ? C2 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C10B C4A C5 119.0(8) . . ? C10B C4A C4 122.2(8) . . ? C5 C4A C4 118.8(9) . . ? C4A C4 C3 117.3(8) . . ? C4A C4 H4A 108.0 . . ? C3 C4 H4A 108.0 . . ? C4A C4 H4B 108.0 . . ? C3 C4 H4B 108.0 . . ? H4A C4 H4B 107.2 . . ? C6 C5 C4A 118.5(8) . . ? C6 C5 H5A 120.8 . . ? C4A C5 H5A 120.8 . . ? C6 C6A C10A 118.5(8) . . ? C6 C6A C7 126.0(8) . . ? C10A C6A C7 115.4(8) . . ? C6A C6 C5 123.8(9) . . ? C6A C6 H6A 118.1 . . ? C5 C6 H6A 118.1 . . ? C8 C7 C6A 107.0(7) . . ? C8 C7 H7A 110.3 . . ? C6A C7 H7A 110.3 . . ? C8 C7 H7B 110.3 . . ? C6A C7 H7B 110.3 . . ? H7A C7 H7B 108.6 . . ? C9 C8 C7 110.1(7) . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N10 C9 C8 113.5(7) . . ? N10 C9 H9A 108.9 . . ? C8 C9 H9A 108.9 . . ? N10 C9 H9B 108.9 . . ? C8 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C19 N10 C10A 122.9(5) . . ? C19 N10 C9 119.4(6) . . ? C10A N10 C9 117.5(5) . . ? C10B C10A N10 123.9(5) . . ? C10B C10A C6A 119.0(6) . . ? N10 C10A C6A 117.1(7) . . ? C4A C10B C10A 120.4(6) . . ? C4A C10B N1 116.5(6) . . ? C10A C10B N1 123.0(5) . . ? N1 C11 C12 117.8(5) . . ? N1 C11 Se18 123.5(4) . . ? C12 C11 Se18 118.7(4) . . ? C17 C12 C13 119.2(6) . . ? C17 C12 C11 121.6(6) . . ? C13 C12 C11 119.0(6) . . ? C14 C13 C12 118.3(8) . . ? C14 C13 H13A 120.9 . . ? C12 C13 H13A 120.9 . . ? C15 C14 C13 122.4(8) . . ? C15 C14 H14A 118.8 . . ? C13 C14 H14A 118.8 . . ? C14 C15 C16 118.7(8) . . ? C14 C15 H15A 120.7 . . ? C16 C15 H15A 120.7 . . ? C17 C16 C15 118.9(8) . . ? C17 C16 H16A 120.5 . . ? C15 C16 H16A 120.5 . . ? C16 C17 C12 122.4(7) . . ? C16 C17 H17A 118.8 . . ? C12 C17 H17A 118.8 . . ? N10 C19 C20 119.9(5) . . ? N10 C19 Se26 121.7(5) . . ? C20 C19 Se26 118.3(5) . . ? C25 C20 C21 118.4(6) . . ? C25 C20 C19 120.0(6) . . ? C21 C20 C19 121.2(6) . . ? C22 C21 C20 121.1(7) . . ? C22 C21 H21A 119.5 . . ? C20 C21 H21A 119.5 . . ? C21 C22 C23 118.8(7) . . ? C21 C22 H22A 120.6 . . ? C23 C22 H22A 120.6 . . ? C24 C23 C22 121.2(7) . . ? C24 C23 H23A 119.4 . . ? C22 C23 H23A 119.4 . . ? C23 C24 C25 120.5(7) . . ? C23 C24 H24A 119.7 . . ? C25 C24 H24A 119.7 . . ? C24 C25 C20 119.9(6) . . ? C24 C25 H25A 120.1 . . ? C20 C25 H25A 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C2 C3 -105.0(8) . . . . ? C10B N1 C2 C3 62.2(8) . . . . ? N1 C2 C3 C4 -47.9(11) . . . . ? C10B C4A C4 C3 10.0(14) . . . . ? C5 C4A C4 C3 -170.0(9) . . . . ? C2 C3 C4 C4A 14.0(14) . . . . ? C10B C4A C5 C6 2.8(12) . . . . ? C4 C4A C5 C6 -177.2(9) . . . . ? C10A C6A C6 C5 1.1(13) . . . . ? C7 C6A C6 C5 176.6(9) . . . . ? C4A C5 C6 C6A -6.1(14) . . . . ? C6 C6A C7 C8 -132.7(8) . . . . ? C10A C6A C7 C8 43.0(9) . . . . ? C6A C7 C8 C9 -64.3(9) . . . . ? C7 C8 C9 N10 34.3(9) . . . . ? C8 C9 N10 C19 -155.1(6) . . . . ? C8 C9 N10 C10A 19.1(8) . . . . ? C19 N10 C10A C10B -50.8(8) . . . . ? C9 N10 C10A C10B 135.3(6) . . . . ? C19 N10 C10A C6A 131.3(6) . . . . ? C9 N10 C10A C6A -42.7(7) . . . . ? C6 C6A C10A C10B 7.1(10) . . . . ? C7 C6A C10A C10B -168.9(6) . . . . ? C6 C6A C10A N10 -174.9(7) . . . . ? C7 C6A C10A N10 9.1(8) . . . . ? C5 C4A C10B C10A 5.3(9) . . . . ? C4 C4A C10B C10A -174.8(7) . . . . ? C5 C4A C10B N1 -177.4(6) . . . . ? C4 C4A C10B N1 2.6(10) . . . . ? N10 C10A C10B C4A 171.9(5) . . . . ? C6A C10A C10B C4A -10.2(9) . . . . ? N10 C10A C10B N1 -5.3(9) . . . . ? C6A C10A C10B N1 172.6(5) . . . . ? C11 N1 C10B C4A 125.8(6) . . . . ? C2 N1 C10B C4A -40.9(7) . . . . ? C11 N1 C10B C10A -56.9(8) . . . . ? C2 N1 C10B C10A 136.4(6) . . . . ? C10B N1 C11 C12 -7.6(8) . . . . ? C2 N1 C11 C12 158.2(5) . . . . ? C10B N1 C11 Se18 174.5(4) . . . . ? C2 N1 C11 Se18 -19.7(8) . . . . ? N1 C11 C12 C17 -46.7(8) . . . . ? Se18 C11 C12 C17 131.3(5) . . . . ? N1 C11 C12 C13 136.8(6) . . . . ? Se18 C11 C12 C13 -45.2(7) . . . . ? C17 C12 C13 C14 1.7(9) . . . . ? C11 C12 C13 C14 178.3(5) . . . . ? C12 C13 C14 C15 -0.3(11) . . . . ? C13 C14 C15 C16 -1.1(13) . . . . ? C14 C15 C16 C17 1.1(12) . . . . ? C15 C16 C17 C12 0.4(11) . . . . ? C13 C12 C17 C16 -1.8(10) . . . . ? C11 C12 C17 C16 -178.3(6) . . . . ? C10A N10 C19 C20 -13.9(8) . . . . ? C9 N10 C19 C20 160.0(5) . . . . ? C10A N10 C19 Se26 170.4(4) . . . . ? C9 N10 C19 Se26 -15.7(7) . . . . ? N10 C19 C20 C25 -45.0(8) . . . . ? Se26 C19 C20 C25 130.8(5) . . . . ? N10 C19 C20 C21 142.0(6) . . . . ? Se26 C19 C20 C21 -42.1(7) . . . . ? C25 C20 C21 C22 2.1(10) . . . . ? C19 C20 C21 C22 175.1(6) . . . . ? C20 C21 C22 C23 -0.7(11) . . . . ? C21 C22 C23 C24 -0.9(12) . . . . ? C22 C23 C24 C25 1.1(12) . . . . ? C23 C24 C25 C20 0.3(10) . . . . ? C21 C20 C25 C24 -1.8(9) . . . . ? C19 C20 C25 C24 -175.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.729 _refine_diff_density_min -0.914 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 927856' ####################################################################### # # 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_6 #TrackingRef 'AS-05-03-2013-5a.CIF' #============================================================= _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _journal_coeditor_?tes ; ? ; _iucr_compatibility_tag ACTA95 loop_ _publ_author_foot?te ; ? ; ; to whom correspondence should be addressed ; ; ? ; ; to whom correspondence should be addressed ; # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 N2 O2, C H2 Cl2' _chemical_formula_sum 'C27 H26 Cl2 N2 O2' _chemical_formula_weight 481.40 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' _symmetry_space_group_name_Hall '-P 2yn' 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 10.8405(7) _cell_length_b 9.3369(4) _cell_length_c 23.9357(16) _cell_angle_alpha 90.00 _cell_angle_beta 98.990(7) _cell_angle_gamma 90.00 _cell_volume 2392.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4188 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.869 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18981 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4188 _reflns_number_gt 2400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _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^)+(0.0822P)^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 4188 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1264 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.927 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.39928(19) 0.28634(18) 0.18466(8) 0.0409(5) Uani 1 1 d . . . C2 C 0.4563(3) 0.3350(3) 0.24162(10) 0.0560(7) Uani 1 1 d . . . H2A H 0.5197 0.4061 0.2379 0.067 Uiso 1 1 calc R . . H2B H 0.4973 0.2543 0.2623 0.067 Uiso 1 1 calc R . . C3 C 0.3643(4) 0.3974(4) 0.27462(13) 0.0850(11) Uani 1 1 d . . . H3A H 0.3786 0.4998 0.2782 0.102 Uiso 1 1 calc R . . H3B H 0.3783 0.3569 0.3124 0.102 Uiso 1 1 calc R . . C4A C 0.2111(3) 0.4175(3) 0.18807(11) 0.0525(7) Uani 1 1 d . . . C4 C 0.2306(3) 0.3721(4) 0.24887(13) 0.0758(10) Uani 1 1 d . . . H4A H 0.2105 0.2713 0.2515 0.091 Uiso 1 1 calc R . . H4B H 0.1758 0.4264 0.2693 0.091 Uiso 1 1 calc R . . C5 C 0.1139(3) 0.5027(3) 0.16240(15) 0.0652(8) Uani 1 1 d . . . H5A H 0.0542 0.5351 0.1835 0.078 Uiso 1 1 calc R . . C6A C 0.1946(2) 0.5005(2) 0.07440(11) 0.0476(6) Uani 1 1 d . . . C6 C 0.1040(3) 0.5405(3) 0.10606(15) 0.0648(8) Uani 1 1 d . . . H6A H 0.0355 0.5935 0.0892 0.078 Uiso 1 1 calc R . . C7 C 0.1894(3) 0.5290(3) 0.01254(12) 0.0596(8) Uani 1 1 d . . . H7A H 0.2522 0.5990 0.0067 0.072 Uiso 1 1 calc R . . H7B H 0.1080 0.5664 -0.0034 0.072 Uiso 1 1 calc R . . C8 C 0.2136(3) 0.3876(3) -0.01589(11) 0.0592(8) Uani 1 1 d . . . H8A H 0.1500 0.3186 -0.0099 0.071 Uiso 1 1 calc R . . H8B H 0.2084 0.4025 -0.0563 0.071 Uiso 1 1 calc R . . C9 C 0.3417(3) 0.3291(2) 0.00800(10) 0.0497(7) Uani 1 1 d . . . H9A H 0.3377 0.2253 0.0092 0.060 Uiso 1 1 calc R . . H9B H 0.4006 0.3554 -0.0169 0.060 Uiso 1 1 calc R . . N10 N 0.38701(19) 0.38398(18) 0.06553(8) 0.0378(5) Uani 1 1 d . . . C10A C 0.2962(2) 0.4193(2) 0.10019(10) 0.0391(6) Uani 1 1 d . . . C10B C 0.3016(2) 0.3735(2) 0.15585(10) 0.0397(6) Uani 1 1 d . . . C11 C 0.4390(3) 0.1587(2) 0.16540(10) 0.0423(6) Uani 1 1 d . . . C12 C 0.3623(2) 0.0834(2) 0.11712(9) 0.0391(6) Uani 1 1 d . . . C13 C 0.4244(3) 0.0003(2) 0.08202(10) 0.0491(7) Uani 1 1 d . . . H13A H 0.5113 -0.0007 0.0874 0.059 Uiso 1 1 calc R . . C14 C 0.3580(3) -0.0804(2) 0.03944(11) 0.0586(8) Uani 1 1 d . . . H14A H 0.4002 -0.1352 0.0161 0.070 Uiso 1 1 calc R . . C15 C 0.2299(3) -0.0805(2) 0.03133(12) 0.0617(8) Uani 1 1 d . . . H15A H 0.1855 -0.1349 0.0024 0.074 Uiso 1 1 calc R . . C16 C 0.1671(3) -0.0001(3) 0.06599(12) 0.0573(7) Uani 1 1 d . . . H16A H 0.0802 -0.0007 0.0607 0.069 Uiso 1 1 calc R . . C17 C 0.2333(3) 0.0819(2) 0.10884(10) 0.0471(7) Uani 1 1 d . . . H17A H 0.1905 0.1362 0.1322 0.056 Uiso 1 1 calc R . . O18 O 0.53603(19) 0.10393(19) 0.18911(8) 0.0629(5) Uani 1 1 d . . . C19 C 0.5123(2) 0.3968(2) 0.08123(10) 0.0398(6) Uani 1 1 d . . . C20 C 0.5636(2) 0.4963(2) 0.12826(10) 0.0399(6) Uani 1 1 d . . . C21 C 0.5076(2) 0.6267(2) 0.13793(11) 0.0474(6) Uani 1 1 d . . . H21A H 0.4310 0.6514 0.1169 0.057 Uiso 1 1 calc R . . C22 C 0.5657(3) 0.7183(3) 0.17855(12) 0.0592(8) Uani 1 1 d . . . H22A H 0.5283 0.8053 0.1847 0.071 Uiso 1 1 calc R . . C23 C 0.6782(3) 0.6835(3) 0.21020(12) 0.0616(8) Uani 1 1 d . . . H23A H 0.7162 0.7465 0.2377 0.074 Uiso 1 1 calc R . . C24 C 0.7349(3) 0.5559(3) 0.20126(12) 0.0612(8) Uani 1 1 d . . . H24A H 0.8108 0.5314 0.2229 0.073 Uiso 1 1 calc R . . C25 C 0.6780(3) 0.4643(3) 0.15982(11) 0.0513(7) Uani 1 1 d . . . H25A H 0.7176 0.3791 0.1530 0.062 Uiso 1 1 calc R . . O26 O 0.58486(17) 0.33284(18) 0.05528(8) 0.0599(5) Uani 1 1 d . . . C27 C 0.7953(4) 0.0773(4) 0.13304(18) 0.1011(12) Uani 1 1 d . . . H27A H 0.7693 0.0714 0.1700 0.121 Uiso 1 1 calc R . . H27B H 0.7261 0.1166 0.1069 0.121 Uiso 1 1 calc R . . Cl31 Cl 0.82696(11) -0.09294(9) 0.11116(4) 0.1065(4) Uani 1 1 d . . . Cl32 Cl 0.92085(9) 0.19266(9) 0.13706(5) 0.1058(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 N1 0.0494(14) 0.0376(10) 0.0359(11) -0.0036(8) 0.0074(10) 0.0038(9) C2 0.070(2) 0.0604(15) 0.0377(15) -0.0062(12) 0.0087(14) -0.0108(14) C3 0.095(3) 0.108(2) 0.054(2) -0.0177(17) 0.017(2) 0.016(2) C4A 0.0484(18) 0.0524(15) 0.0592(18) -0.0188(13) 0.0162(15) -0.0039(13) C4 0.083(3) 0.085(2) 0.069(2) -0.0236(16) 0.041(2) -0.0150(18) C5 0.0432(19) 0.0683(18) 0.086(2) -0.0348(17) 0.0174(17) 0.0005(15) C6A 0.0413(17) 0.0326(12) 0.0651(18) -0.0062(11) -0.0037(14) 0.0022(11) C6 0.0398(19) 0.0558(16) 0.094(3) -0.0195(16) -0.0034(17) 0.0122(13) C7 0.0516(19) 0.0436(14) 0.076(2) 0.0076(13) -0.0127(15) 0.0064(12) C8 0.069(2) 0.0541(15) 0.0489(16) 0.0000(12) -0.0079(15) -0.0039(14) C9 0.065(2) 0.0407(13) 0.0409(15) -0.0014(11) -0.0001(14) 0.0025(12) N10 0.0393(14) 0.0350(10) 0.0385(12) -0.0008(8) 0.0043(10) 0.0031(9) C10A 0.0377(15) 0.0294(11) 0.0494(16) -0.0055(10) 0.0049(12) 0.0008(10) C10B 0.0366(15) 0.0348(11) 0.0481(16) -0.0094(11) 0.0082(12) -0.0035(11) C11 0.0452(17) 0.0415(13) 0.0403(15) 0.0039(11) 0.0070(13) 0.0030(12) C12 0.0498(18) 0.0281(11) 0.0397(14) 0.0032(10) 0.0075(12) 0.0036(11) C13 0.0511(18) 0.0414(13) 0.0562(17) -0.0021(12) 0.0127(14) 0.0068(12) C14 0.084(3) 0.0389(14) 0.0536(17) -0.0088(12) 0.0145(17) 0.0103(14) C15 0.086(3) 0.0396(14) 0.0558(18) -0.0074(12) -0.0003(17) -0.0086(15) C16 0.0567(19) 0.0485(14) 0.0660(18) -0.0074(14) 0.0076(16) -0.0108(14) C17 0.0560(19) 0.0367(12) 0.0508(16) -0.0042(11) 0.0154(14) -0.0032(12) O18 0.0624(14) 0.0571(11) 0.0630(12) -0.0033(9) -0.0099(11) 0.0172(10) C19 0.0431(17) 0.0321(11) 0.0448(14) 0.0007(10) 0.0088(13) 0.0026(11) C20 0.0388(16) 0.0371(12) 0.0451(15) 0.0010(10) 0.0105(13) -0.0019(11) C21 0.0454(17) 0.0374(12) 0.0588(16) -0.0021(12) 0.0064(13) 0.0009(11) C22 0.070(2) 0.0377(14) 0.0705(19) -0.0122(13) 0.0127(18) -0.0034(14) C23 0.068(2) 0.0546(17) 0.0604(19) -0.0102(14) 0.0057(17) -0.0209(16) C24 0.0519(19) 0.0653(18) 0.0629(19) 0.0022(14) -0.0021(15) -0.0108(15) C25 0.0458(18) 0.0451(14) 0.0617(18) -0.0025(12) 0.0049(15) 0.0041(12) O26 0.0517(12) 0.0604(10) 0.0705(12) -0.0186(9) 0.0186(10) 0.0032(9) C27 0.077(3) 0.106(3) 0.126(3) -0.032(2) 0.036(2) -0.015(2) Cl31 0.1305(10) 0.0786(6) 0.1132(8) -0.0072(5) 0.0276(7) -0.0150(5) Cl32 0.0594(6) 0.0840(6) 0.1755(10) -0.0309(6) 0.0227(6) 0.0012(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C11 1.371(3) . ? N1 C10B 1.425(3) . ? N1 C2 1.478(3) . ? C2 C3 1.485(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.502(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4A C5 1.386(4) . ? C4A C10B 1.401(3) . ? C4A C4 1.499(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.382(4) . ? C5 H5A 0.9300 . ? C6A C6 1.382(4) . ? C6A C10A 1.399(3) . ? C6A C7 1.497(4) . ? C6 H6A 0.9300 . ? C7 C8 1.526(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.519(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N10 1.480(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? N10 C19 1.356(3) . ? N10 C10A 1.421(3) . ? C10A C10B 1.392(3) . ? C11 O18 1.226(3) . ? C11 C12 1.490(3) . ? C12 C17 1.382(3) . ? C12 C13 1.392(3) . ? C13 C14 1.377(4) . ? C13 H13A 0.9300 . ? C14 C15 1.373(4) . ? C14 H14A 0.9300 . ? C15 C16 1.375(4) . ? C15 H15A 0.9300 . ? C16 C17 1.387(4) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C19 O26 1.231(3) . ? C19 C20 1.498(3) . ? C20 C25 1.380(3) . ? C20 C21 1.396(3) . ? C21 C22 1.372(4) . ? C21 H21A 0.9300 . ? C22 C23 1.370(4) . ? C22 H22A 0.9300 . ? C23 C24 1.372(4) . ? C23 H23A 0.9300 . ? C24 C25 1.381(4) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C27 Cl31 1.725(3) . ? C27 Cl32 1.727(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? 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 C11 N1 C10B 125.6(2) . . ? C11 N1 C2 118.0(2) . . ? C10B N1 C2 116.31(18) . . ? N1 C2 C3 113.1(3) . . ? N1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? N1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 113.9(3) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C5 C4A C10B 118.3(3) . . ? C5 C4A C4 125.1(3) . . ? C10B C4A C4 116.5(3) . . ? C4A C4 C3 109.5(2) . . ? C4A C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? C4A C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? C6 C5 C4A 121.1(3) . . ? C6 C5 H5A 119.4 . . ? C4A C5 H5A 119.4 . . ? C6 C6A C10A 118.9(3) . . ? C6 C6A C7 125.0(3) . . ? C10A C6A C7 116.0(2) . . ? C5 C6 C6A 120.8(3) . . ? C5 C6 H6A 119.6 . . ? C6A C6 H6A 119.6 . . ? C6A C7 C8 107.7(2) . . ? C6A C7 H7A 110.2 . . ? C8 C7 H7A 110.2 . . ? C6A C7 H7B 110.2 . . ? C8 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? C9 C8 C7 110.8(2) . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? N10 C9 C8 112.1(2) . . ? N10 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? N10 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C19 N10 C10A 124.9(2) . . ? C19 N10 C9 117.44(19) . . ? C10A N10 C9 117.7(2) . . ? C10B C10A C6A 120.1(2) . . ? C10B C10A N10 123.9(2) . . ? C6A C10A N10 116.0(2) . . ? C10A C10B C4A 120.6(2) . . ? C10A C10B N1 123.8(2) . . ? C4A C10B N1 115.6(2) . . ? O18 C11 N1 119.9(2) . . ? O18 C11 C12 119.8(2) . . ? N1 C11 C12 120.3(2) . . ? C17 C12 C13 118.8(2) . . ? C17 C12 C11 123.1(2) . . ? C13 C12 C11 117.9(2) . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? C14 C15 C16 120.0(3) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C15 C16 C17 120.0(3) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C12 C17 C16 120.5(2) . . ? C12 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? O26 C19 N10 120.6(2) . . ? O26 C19 C20 119.2(2) . . ? N10 C19 C20 120.1(2) . . ? C25 C20 C21 118.4(2) . . ? C25 C20 C19 118.3(2) . . ? C21 C20 C19 123.0(2) . . ? C22 C21 C20 119.8(3) . . ? C22 C21 H21A 120.1 . . ? C20 C21 H21A 120.1 . . ? C23 C22 C21 121.0(2) . . ? C23 C22 H22A 119.5 . . ? C21 C22 H22A 119.5 . . ? C22 C23 C24 120.0(3) . . ? C22 C23 H23A 120.0 . . ? C24 C23 H23A 120.0 . . ? C23 C24 C25 119.3(3) . . ? C23 C24 H24A 120.3 . . ? C25 C24 H24A 120.3 . . ? C20 C25 C24 121.4(2) . . ? C20 C25 H25A 119.3 . . ? C24 C25 H25A 119.3 . . ? Cl31 C27 Cl32 113.5(2) . . ? Cl31 C27 H27A 108.9 . . ? Cl32 C27 H27A 108.9 . . ? Cl31 C27 H27B 108.9 . . ? Cl32 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C2 C3 -138.5(3) . . . . ? C10B N1 C2 C3 37.9(3) . . . . ? N1 C2 C3 C4 11.7(4) . . . . ? C5 C4A C4 C3 -132.2(3) . . . . ? C10B C4A C4 C3 45.5(3) . . . . ? C2 C3 C4 C4A -51.5(4) . . . . ? C10B C4A C5 C6 1.7(4) . . . . ? C4 C4A C5 C6 179.4(3) . . . . ? C4A C5 C6 C6A -3.4(4) . . . . ? C10A C6A C6 C5 0.8(4) . . . . ? C7 C6A C6 C5 176.6(2) . . . . ? C6 C6A C7 C8 -128.9(3) . . . . ? C10A C6A C7 C8 47.1(3) . . . . ? C6A C7 C8 C9 -60.8(3) . . . . ? C7 C8 C9 N10 23.8(3) . . . . ? C8 C9 N10 C19 -150.5(2) . . . . ? C8 C9 N10 C10A 29.5(3) . . . . ? C6 C6A C10A C10B 3.5(3) . . . . ? C7 C6A C10A C10B -172.7(2) . . . . ? C6 C6A C10A N10 -178.9(2) . . . . ? C7 C6A C10A N10 4.9(3) . . . . ? C19 N10 C10A C10B -48.9(3) . . . . ? C9 N10 C10A C10B 131.1(2) . . . . ? C19 N10 C10A C6A 133.7(2) . . . . ? C9 N10 C10A C6A -46.3(3) . . . . ? C6A C10A C10B C4A -5.3(3) . . . . ? N10 C10A C10B C4A 177.4(2) . . . . ? C6A C10A C10B N1 177.7(2) . . . . ? N10 C10A C10B N1 0.4(3) . . . . ? C5 C4A C10B C10A 2.6(4) . . . . ? C4 C4A C10B C10A -175.3(2) . . . . ? C5 C4A C10B N1 179.9(2) . . . . ? C4 C4A C10B N1 2.0(3) . . . . ? C11 N1 C10B C10A -52.7(3) . . . . ? C2 N1 C10B C10A 131.2(2) . . . . ? C11 N1 C10B C4A 130.1(2) . . . . ? C2 N1 C10B C4A -46.0(3) . . . . ? C10B N1 C11 O18 168.5(2) . . . . ? C2 N1 C11 O18 -15.5(3) . . . . ? C10B N1 C11 C12 -13.8(3) . . . . ? C2 N1 C11 C12 162.2(2) . . . . ? O18 C11 C12 C17 141.3(2) . . . . ? N1 C11 C12 C17 -36.5(3) . . . . ? O18 C11 C12 C13 -32.7(3) . . . . ? N1 C11 C12 C13 149.6(2) . . . . ? C17 C12 C13 C14 0.8(3) . . . . ? C11 C12 C13 C14 175.0(2) . . . . ? C12 C13 C14 C15 -0.4(4) . . . . ? C13 C14 C15 C16 -0.3(4) . . . . ? C14 C15 C16 C17 0.5(4) . . . . ? C13 C12 C17 C16 -0.5(3) . . . . ? C11 C12 C17 C16 -174.4(2) . . . . ? C15 C16 C17 C12 -0.1(4) . . . . ? C10A N10 C19 O26 162.0(2) . . . . ? C9 N10 C19 O26 -18.0(3) . . . . ? C10A N10 C19 C20 -21.7(3) . . . . ? C9 N10 C19 C20 158.33(19) . . . . ? O26 C19 C20 C25 -32.1(3) . . . . ? N10 C19 C20 C25 151.5(2) . . . . ? O26 C19 C20 C21 141.2(2) . . . . ? N10 C19 C20 C21 -35.2(3) . . . . ? C25 C20 C21 C22 -0.8(3) . . . . ? C19 C20 C21 C22 -174.1(2) . . . . ? C20 C21 C22 C23 -0.4(4) . . . . ? C21 C22 C23 C24 0.4(4) . . . . ? C22 C23 C24 C25 0.7(4) . . . . ? C21 C20 C25 C24 1.9(4) . . . . ? C19 C20 C25 C24 175.6(2) . . . . ? C23 C24 C25 C20 -1.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.262 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 927857' ####################################################################### # # 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_7 #TrackingRef 'AS-05-03-2013-5C-6A.CIF' #============================================================= _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _journal_coeditor_?tes ; ? ; _iucr_compatibility_tag ACTA95 loop_ _publ_author_foot?te ; ? ; ; to whom correspondence should be addressed ; ; ? ; ; to whom correspondence should be addressed ; # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H30 O4, 0.5(C26 H24 N2 Se2)' _chemical_formula_sum 'C44 H42 N O4 Se' _chemical_formula_weight 727.75 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.458(3) _cell_length_b 9.484(2) _cell_length_c 23.761(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.26(3) _cell_angle_gamma 90.00 _cell_volume 3609.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 12792 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 25.00 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1516 _exptl_absorpt_coefficient_mu 1.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9418 _exptl_absorpt_correction_T_max 0.9893 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12792 _diffrn_reflns_av_R_equivalents 0.0714 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 24.99 _reflns_number_total 6036 _reflns_number_gt 5331 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _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^)+(0.0758P)^2^+9.6520P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.09(17) _chemical_absolute_configuration rm _refine_ls_number_reflns 6036 _refine_ls_number_parameters 453 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1518 _refine_ls_wR_factor_gt 0.1469 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4996(3) 0.4390(5) 0.56315(19) 0.0270(10) Uani 1 1 d . . . C2 C 0.5644(4) 0.4258(7) 0.6178(2) 0.0412(14) Uani 1 1 d . . . H2B H 0.6182 0.4092 0.6089 0.049 Uiso 1 1 calc R . . H2A H 0.5677 0.5133 0.6394 0.049 Uiso 1 1 calc R . . C3 C 0.5450(6) 0.3088(9) 0.6537(3) 0.063(2) Uani 1 1 d . . . H3B H 0.5156 0.3467 0.6813 0.076 Uiso 1 1 calc R . . H3A H 0.5970 0.2686 0.6753 0.076 Uiso 1 1 calc R . . C4A C 0.4971(4) 0.1853(7) 0.5575(3) 0.0391(16) Uani 1 1 d . . . C4 C 0.4930(5) 0.1928(10) 0.6199(3) 0.0583(19) Uani 1 1 d . . . H4B H 0.5113 0.1032 0.6382 0.070 Uiso 1 1 calc R . . H4A H 0.4353 0.2063 0.6219 0.070 Uiso 1 1 calc R . . C5 C 0.4980(5) 0.0623(8) 0.5287(4) 0.056(2) Uani 1 1 d . . . H5 H 0.4959 -0.0228 0.5478 0.067 Uiso 1 1 calc R . . C10B C 0.4978(4) 0.3145(6) 0.5284(3) 0.0286(13) Uani 1 1 d . . . C11 C 0.4457(3) 0.5443(5) 0.5504(2) 0.0265(11) Uani 1 1 d . . . C12 C 0.3689(3) 0.5243(6) 0.5034(2) 0.0298(12) Uani 1 1 d . . . C13 C 0.3424(4) 0.6329(6) 0.4619(3) 0.0355(13) Uani 1 1 d . . . H13 H 0.3736 0.7151 0.4631 0.043 Uiso 1 1 calc R . . C14 C 0.2709(4) 0.6149(8) 0.4206(3) 0.0472(16) Uani 1 1 d . . . H14 H 0.2538 0.6849 0.3931 0.057 Uiso 1 1 calc R . . C15 C 0.2236(4) 0.4950(8) 0.4188(3) 0.0521(17) Uani 1 1 d . . . H15 H 0.1747 0.4846 0.3903 0.063 Uiso 1 1 calc R . . C16 C 0.2483(4) 0.3902(9) 0.4592(3) 0.0539(18) Uani 1 1 d . . . H16 H 0.2164 0.3089 0.4583 0.065 Uiso 1 1 calc R . . C17 C 0.3212(4) 0.4075(7) 0.5010(3) 0.0399(14) Uani 1 1 d . . . H17 H 0.3380 0.3367 0.5282 0.048 Uiso 1 1 calc R . . Se18 Se 0.45884(3) 0.70914(7) 0.59110(2) 0.03831(17) Uani 1 1 d . . . C19 C 0.5862(4) 0.5550(7) 0.8430(3) 0.0402(14) Uani 1 1 d . . . C20 C 0.5078(3) 0.6438(7) 0.8432(2) 0.0371(13) Uani 1 1 d . . . H20 H 0.5153 0.7378 0.8279 0.044 Uiso 1 1 calc R . . C21 C 0.4220(3) 0.5859(6) 0.8111(3) 0.0352(13) Uani 1 1 d . . . H21 H 0.4244 0.4827 0.8115 0.042 Uiso 1 1 calc R . . C22 C 0.3879(4) 0.6365(8) 0.7479(3) 0.0347(15) Uani 1 1 d . . . O23 O 0.6044(3) 0.5711(5) 0.78766(18) 0.0484(11) Uani 1 1 d . . . H23 H 0.5611 0.5863 0.7634 0.073 Uiso 1 1 calc R . . O24 O 0.4511(3) 0.5848(5) 0.7207(2) 0.0423(11) Uani 1 1 d . . . H24 H 0.4429 0.6159 0.6877 0.063 Uiso 1 1 calc R . . O25 O 0.4987(2) 0.6582(5) 0.90108(17) 0.0422(11) Uani 1 1 d . . . C26 C 0.4142(3) 0.6956(10) 0.8981(3) 0.0432(15) Uani 1 1 d . . . O27 O 0.3665(2) 0.6307(5) 0.84561(18) 0.0427(10) Uani 1 1 d . . . C28 C 0.3870(5) 0.6393(10) 0.9486(3) 0.061(2) Uani 1 1 d . . . H28C H 0.3909 0.5383 0.9488 0.092 Uiso 1 1 calc R . . H28B H 0.3302 0.6667 0.9464 0.092 Uiso 1 1 calc R . . H28A H 0.4221 0.6763 0.9834 0.092 Uiso 1 1 calc R . . C29 C 0.4042(5) 0.8557(9) 0.8932(4) 0.063(2) Uani 1 1 d . . . H29C H 0.4363 0.8914 0.8673 0.094 Uiso 1 1 calc R . . H29B H 0.4235 0.8976 0.9307 0.094 Uiso 1 1 calc R . . H29A H 0.3464 0.8786 0.8785 0.094 Uiso 1 1 calc R . . C30 C 0.5797(4) 0.3979(7) 0.8555(3) 0.0419(14) Uani 1 1 d . . . C31 C 0.5321(5) 0.3435(9) 0.8906(4) 0.0585(19) Uani 1 1 d . . . H31 H 0.4998 0.4043 0.9071 0.070 Uiso 1 1 calc R . . C32 C 0.5306(5) 0.2008(15) 0.9022(4) 0.069(2) Uani 1 1 d . . . H32 H 0.4963 0.1666 0.9252 0.082 Uiso 1 1 calc R . . C33 C 0.5786(6) 0.1111(10) 0.8802(5) 0.075(3) Uani 1 1 d . . . H33 H 0.5773 0.0152 0.8880 0.089 Uiso 1 1 calc R . . C34 C 0.6296(7) 0.1612(9) 0.8460(5) 0.074(3) Uani 1 1 d . . . H34 H 0.6647 0.1007 0.8319 0.088 Uiso 1 1 calc R . . C35 C 0.6271(5) 0.3054(9) 0.8332(4) 0.062(2) Uani 1 1 d . . . H35 H 0.6591 0.3391 0.8085 0.074 Uiso 1 1 calc R . . C36 C 0.6619(4) 0.6204(8) 0.8855(3) 0.0425(16) Uani 1 1 d . . . C37 C 0.7051(4) 0.5542(8) 0.9349(3) 0.0502(17) Uani 1 1 d . . . H37 H 0.6865 0.4670 0.9448 0.060 Uiso 1 1 calc R . . C38 C 0.7753(5) 0.6130(10) 0.9703(3) 0.061(2) Uani 1 1 d . . . H38 H 0.8029 0.5655 1.0034 0.073 Uiso 1 1 calc R . . C39 C 0.8041(5) 0.7398(9) 0.9570(4) 0.066(3) Uani 1 1 d . . . H39 H 0.8525 0.7777 0.9801 0.079 Uiso 1 1 calc R . . C40 C 0.7609(6) 0.8127(12) 0.9085(5) 0.095(4) Uani 1 1 d . . . H40 H 0.7777 0.9025 0.9002 0.114 Uiso 1 1 calc R . . C41 C 0.6911(5) 0.7477(10) 0.8722(4) 0.081(3) Uani 1 1 d . . . H41 H 0.6643 0.7929 0.8383 0.097 Uiso 1 1 calc R . . C42 C 0.3770(4) 0.7960(8) 0.7436(3) 0.0398(17) Uani 1 1 d . . . C43 C 0.4423(5) 0.8825(9) 0.7377(3) 0.0474(18) Uani 1 1 d . . . H43 H 0.4916 0.8421 0.7327 0.057 Uiso 1 1 calc R . . C44 C 0.4360(6) 1.0244(9) 0.7393(3) 0.062(2) Uani 1 1 d . . . H44 H 0.4813 1.0808 0.7369 0.075 Uiso 1 1 calc R . . C45 C 0.3612(7) 1.0858(10) 0.7444(4) 0.077(3) Uani 1 1 d . . . H45 H 0.3562 1.1834 0.7457 0.093 Uiso 1 1 calc R . . C46 C 0.2956(6) 1.0018(9) 0.7475(4) 0.066(2) Uani 1 1 d . . . H46 H 0.2449 1.0421 0.7497 0.080 Uiso 1 1 calc R . . C47 C 0.3038(4) 0.8578(8) 0.7474(4) 0.0521(19) Uani 1 1 d . . . H47 H 0.2585 0.8014 0.7499 0.063 Uiso 1 1 calc R . . C48 C 0.3056(4) 0.5598(8) 0.7189(3) 0.0448(17) Uani 1 1 d . . . C49 C 0.2669(4) 0.4651(8) 0.7473(3) 0.0503(19) Uani 1 1 d . . . H49 H 0.2873 0.4474 0.7865 0.060 Uiso 1 1 calc R . . C50 C 0.1948(5) 0.3944(9) 0.7157(4) 0.070(2) Uani 1 1 d . . . H50 H 0.1671 0.3308 0.7346 0.084 Uiso 1 1 calc R . . C51 C 0.1654(5) 0.4186(10) 0.6579(4) 0.071(2) Uani 1 1 d . . . H51 H 0.1189 0.3697 0.6375 0.085 Uiso 1 1 calc R . . C52 C 0.2039(5) 0.5135(10) 0.6301(4) 0.068(2) Uani 1 1 d . . . H52 H 0.1833 0.5319 0.5910 0.081 Uiso 1 1 calc R . . C53 C 0.2748(4) 0.5833(9) 0.6612(3) 0.0569(19) Uani 1 1 d . . . H53 H 0.3018 0.6474 0.6421 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.025(2) 0.030(2) 0.026(2) 0.0033(19) 0.0049(18) 0.0057(19) C2 0.037(3) 0.056(4) 0.027(3) 0.004(3) 0.000(2) 0.001(3) C3 0.091(6) 0.062(5) 0.033(4) 0.012(3) 0.005(4) -0.001(4) C4A 0.038(3) 0.031(5) 0.046(3) 0.015(3) 0.006(2) -0.004(3) C4 0.072(4) 0.053(5) 0.051(4) 0.019(4) 0.016(3) -0.009(4) C5 0.063(5) 0.030(4) 0.062(5) 0.017(3) -0.009(4) 0.001(3) C10B 0.027(3) 0.016(3) 0.041(3) 0.002(2) 0.006(3) 0.001(2) C11 0.033(3) 0.021(3) 0.029(3) 0.002(2) 0.014(2) -0.007(2) C12 0.025(3) 0.031(3) 0.032(3) 0.002(2) 0.006(2) 0.003(2) C13 0.036(3) 0.033(3) 0.039(3) 0.003(3) 0.013(3) 0.003(3) C14 0.044(4) 0.052(4) 0.042(4) 0.010(3) 0.002(3) 0.015(3) C15 0.032(3) 0.067(5) 0.051(4) 0.001(4) -0.003(3) -0.004(3) C16 0.036(3) 0.070(5) 0.053(4) -0.002(4) 0.006(3) -0.015(3) C17 0.033(3) 0.045(4) 0.042(4) 0.008(3) 0.008(3) -0.005(3) Se18 0.0379(3) 0.0330(3) 0.0431(3) -0.0095(3) 0.0075(2) 0.0001(3) C19 0.033(3) 0.053(4) 0.036(3) -0.004(3) 0.010(3) -0.003(3) C20 0.032(3) 0.051(3) 0.028(3) 0.000(3) 0.005(2) -0.001(3) C21 0.034(3) 0.037(3) 0.035(3) -0.001(3) 0.010(2) 0.002(2) C22 0.024(3) 0.039(4) 0.040(4) -0.006(3) 0.007(3) -0.003(3) O23 0.032(2) 0.079(3) 0.034(2) 0.003(2) 0.0071(18) 0.000(2) O24 0.031(2) 0.063(3) 0.035(3) -0.005(2) 0.0112(19) 0.008(2) O25 0.037(2) 0.059(3) 0.030(2) -0.0052(18) 0.0074(17) -0.0047(18) C26 0.039(3) 0.051(4) 0.041(3) -0.015(4) 0.014(2) -0.009(4) O27 0.034(2) 0.065(3) 0.033(2) -0.012(2) 0.0150(18) -0.011(2) C28 0.052(4) 0.094(6) 0.045(4) -0.006(4) 0.025(3) -0.017(4) C29 0.062(5) 0.059(5) 0.072(5) -0.024(4) 0.025(4) -0.010(4) C30 0.041(3) 0.048(4) 0.035(3) -0.004(3) 0.003(3) -0.004(3) C31 0.048(4) 0.058(5) 0.070(5) 0.003(4) 0.016(4) 0.007(4) C32 0.062(4) 0.065(5) 0.077(5) 0.000(5) 0.014(4) -0.026(6) C33 0.060(5) 0.064(6) 0.089(7) 0.011(5) -0.005(5) -0.013(5) C34 0.082(6) 0.046(5) 0.091(7) -0.016(4) 0.018(5) 0.008(4) C35 0.053(5) 0.061(5) 0.073(6) 0.000(4) 0.016(4) 0.010(4) C36 0.028(3) 0.062(5) 0.038(4) -0.007(3) 0.009(3) 0.001(3) C37 0.051(4) 0.062(5) 0.035(4) 0.006(3) 0.007(3) -0.003(3) C38 0.045(4) 0.088(7) 0.044(4) -0.009(4) -0.001(3) 0.002(4) C39 0.047(4) 0.073(7) 0.072(5) -0.018(4) -0.001(4) -0.015(4) C40 0.085(7) 0.088(7) 0.095(8) 0.006(6) -0.018(6) -0.056(6) C41 0.059(5) 0.084(8) 0.085(6) 0.014(5) -0.013(5) -0.028(5) C42 0.041(4) 0.054(5) 0.024(3) 0.003(3) 0.007(3) -0.005(3) C43 0.043(4) 0.066(5) 0.036(4) 0.007(3) 0.015(3) 0.002(3) C44 0.081(6) 0.054(5) 0.047(4) 0.009(3) 0.005(4) -0.022(4) C45 0.113(8) 0.050(5) 0.064(6) 0.006(4) 0.009(5) 0.017(5) C46 0.059(5) 0.044(5) 0.097(7) 0.004(4) 0.019(5) 0.007(4) C47 0.040(4) 0.048(4) 0.070(5) 0.005(4) 0.016(4) 0.007(3) C48 0.029(3) 0.053(4) 0.049(4) -0.017(3) 0.000(3) 0.001(3) C49 0.033(3) 0.058(5) 0.059(5) -0.010(4) 0.009(3) -0.007(3) C50 0.050(4) 0.068(5) 0.091(7) -0.019(5) 0.016(4) -0.017(4) C51 0.045(4) 0.074(6) 0.084(6) -0.025(5) -0.006(4) -0.012(4) C52 0.048(4) 0.087(6) 0.059(5) -0.009(4) -0.006(4) -0.009(4) C53 0.042(4) 0.076(5) 0.048(4) 0.011(4) -0.001(3) -0.009(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 N1 C11 1.324(7) . ? N1 C10B 1.436(8) . ? N1 C2 1.485(7) . ? C2 C3 1.478(10) . ? C2 H2B 0.9700 . ? C2 H2A 0.9700 . ? C3 C4 1.507(11) . ? C3 H3B 0.9700 . ? C3 H3A 0.9700 . ? C4A C5 1.354(11) . ? C4A C10B 1.409(9) . ? C4A C4 1.502(9) . ? C4 H4B 0.9700 . ? C4 H4A 0.9700 . ? C5 C5 1.382(17) 2_656 ? C5 H5 0.9300 . ? C10B C10B 1.369(13) 2_656 ? C11 C12 1.494(8) . ? C11 Se18 1.825(5) . ? C12 C17 1.351(8) . ? C12 C13 1.423(8) . ? C13 C14 1.359(9) . ? C13 H13 0.9300 . ? C14 C15 1.374(10) . ? C14 H14 0.9300 . ? C15 C16 1.376(11) . ? C15 H15 0.9300 . ? C16 C17 1.381(9) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C19 O23 1.422(7) . ? C19 C30 1.528(10) . ? C19 C20 1.542(9) . ? C19 C36 1.543(9) . ? C20 O25 1.424(7) . ? C20 C21 1.543(8) . ? C20 H20 0.9800 . ? C21 O27 1.425(7) . ? C21 C22 1.554(9) . ? C21 H21 0.9800 . ? C22 O24 1.430(8) . ? C22 C42 1.523(8) . ? C22 C48 1.553(9) . ? O23 H23 0.8200 . ? O24 H24 0.8200 . ? O25 C26 1.421(7) . ? C26 O27 1.450(7) . ? C26 C28 1.473(10) . ? C26 C29 1.529(13) . ? C28 H28C 0.9600 . ? C28 H28B 0.9600 . ? C28 H28A 0.9600 . ? C29 H29C 0.9600 . ? C29 H29B 0.9600 . ? C29 H29A 0.9600 . ? C30 C35 1.360(11) . ? C30 C31 1.370(10) . ? C31 C32 1.383(16) . ? C31 H31 0.9300 . ? C32 C33 1.345(15) . ? C32 H32 0.9300 . ? C33 C34 1.379(14) . ? C33 H33 0.9300 . ? C34 C35 1.400(13) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 C41 1.362(11) . ? C36 C37 1.377(10) . ? C37 C38 1.381(10) . ? C37 H37 0.9300 . ? C38 C39 1.356(12) . ? C38 H38 0.9300 . ? C39 C40 1.391(14) . ? C39 H39 0.9300 . ? C40 C41 1.410(12) . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? C42 C47 1.362(10) . ? C42 C43 1.383(10) . ? C43 C44 1.351(11) . ? C43 H43 0.9300 . ? C44 C45 1.393(13) . ? C44 H44 0.9300 . ? C45 C46 1.356(13) . ? C45 H45 0.9300 . ? C46 C47 1.373(11) . ? C46 H46 0.9300 . ? C47 H47 0.9300 . ? C48 C49 1.365(10) . ? C48 C53 1.367(10) . ? C49 C50 1.419(10) . ? C49 H49 0.9300 . ? C50 C51 1.368(13) . ? C50 H50 0.9300 . ? C51 C52 1.356(13) . ? C51 H51 0.9300 . ? C52 C53 1.396(10) . ? C52 H52 0.9300 . ? C53 H53 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 C11 N1 C10B 124.3(5) . . ? C11 N1 C2 124.9(5) . . ? C10B N1 C2 110.4(5) . . ? C3 C2 N1 111.1(6) . . ? C3 C2 H2B 109.4 . . ? N1 C2 H2B 109.4 . . ? C3 C2 H2A 109.4 . . ? N1 C2 H2A 109.4 . . ? H2B C2 H2A 108.0 . . ? C2 C3 C4 114.4(6) . . ? C2 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? H3B C3 H3A 107.6 . . ? C5 C4A C10B 119.9(6) . . ? C5 C4A C4 123.2(6) . . ? C10B C4A C4 116.8(6) . . ? C4A C4 C3 114.2(6) . . ? C4A C4 H4B 108.7 . . ? C3 C4 H4B 108.7 . . ? C4A C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? H4B C4 H4A 107.6 . . ? C4A C5 C5 120.5(4) . 2_656 ? C4A C5 H5 119.7 . . ? C5 C5 H5 119.7 2_656 . ? C10B C10B C4A 119.5(4) 2_656 . ? C10B C10B N1 124.6(3) 2_656 . ? C4A C10B N1 115.7(5) . . ? N1 C11 C12 118.9(5) . . ? N1 C11 Se18 122.2(4) . . ? C12 C11 Se18 118.8(4) . . ? C17 C12 C13 118.8(5) . . ? C17 C12 C11 121.3(5) . . ? C13 C12 C11 119.9(5) . . ? C14 C13 C12 119.1(6) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 121.1(6) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C14 C15 C16 120.1(6) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C17 118.9(7) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C12 C17 C16 122.0(6) . . ? C12 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? O23 C19 C30 108.9(5) . . ? O23 C19 C20 107.4(5) . . ? C30 C19 C20 115.9(5) . . ? O23 C19 C36 104.6(5) . . ? C30 C19 C36 110.2(6) . . ? C20 C19 C36 109.2(5) . . ? O25 C20 C19 109.2(5) . . ? O25 C20 C21 103.0(4) . . ? C19 C20 C21 118.4(5) . . ? O25 C20 H20 108.6 . . ? C19 C20 H20 108.6 . . ? C21 C20 H20 108.6 . . ? O27 C21 C20 104.2(5) . . ? O27 C21 C22 109.1(5) . . ? C20 C21 C22 117.0(5) . . ? O27 C21 H21 108.8 . . ? C20 C21 H21 108.8 . . ? C22 C21 H21 108.8 . . ? O24 C22 C42 113.3(6) . . ? O24 C22 C48 106.8(5) . . ? C42 C22 C48 111.0(6) . . ? O24 C22 C21 101.1(5) . . ? C42 C22 C21 112.5(6) . . ? C48 C22 C21 111.7(6) . . ? C19 O23 H23 109.5 . . ? C22 O24 H24 109.5 . . ? C26 O25 C20 107.1(4) . . ? O25 C26 O27 105.5(5) . . ? O25 C26 C28 110.3(6) . . ? O27 C26 C28 109.9(6) . . ? O25 C26 C29 109.8(6) . . ? O27 C26 C29 109.1(6) . . ? C28 C26 C29 112.0(6) . . ? C21 O27 C26 109.2(4) . . ? C26 C28 H28C 109.5 . . ? C26 C28 H28B 109.5 . . ? H28C C28 H28B 109.5 . . ? C26 C28 H28A 109.5 . . ? H28C C28 H28A 109.5 . . ? H28B C28 H28A 109.5 . . ? C26 C29 H29C 109.5 . . ? C26 C29 H29B 109.5 . . ? H29C C29 H29B 109.5 . . ? C26 C29 H29A 109.5 . . ? H29C C29 H29A 109.5 . . ? H29B C29 H29A 109.5 . . ? C35 C30 C31 117.0(8) . . ? C35 C30 C19 118.8(7) . . ? C31 C30 C19 124.1(6) . . ? C30 C31 C32 121.9(8) . . ? C30 C31 H31 119.0 . . ? C32 C31 H31 119.0 . . ? C33 C32 C31 120.1(8) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C34 120.2(9) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C33 C34 C35 118.3(9) . . ? C33 C34 H34 120.8 . . ? C35 C34 H34 120.8 . . ? C30 C35 C34 122.3(9) . . ? C30 C35 H35 118.8 . . ? C34 C35 H35 118.8 . . ? C41 C36 C37 117.4(7) . . ? C41 C36 C19 118.7(7) . . ? C37 C36 C19 123.8(7) . . ? C36 C37 C38 122.1(8) . . ? C36 C37 H37 119.0 . . ? C38 C37 H37 119.0 . . ? C39 C38 C37 120.3(8) . . ? C39 C38 H38 119.9 . . ? C37 C38 H38 119.9 . . ? C38 C39 C40 119.6(8) . . ? C38 C39 H39 120.2 . . ? C40 C39 H39 120.2 . . ? C39 C40 C41 118.6(9) . . ? C39 C40 H40 120.7 . . ? C41 C40 H40 120.7 . . ? C36 C41 C40 121.8(9) . . ? C36 C41 H41 119.1 . . ? C40 C41 H41 119.1 . . ? C47 C42 C43 118.1(7) . . ? C47 C42 C22 121.0(7) . . ? C43 C42 C22 120.9(7) . . ? C44 C43 C42 121.5(7) . . ? C44 C43 H43 119.3 . . ? C42 C43 H43 119.3 . . ? C43 C44 C45 119.6(8) . . ? C43 C44 H44 120.2 . . ? C45 C44 H44 120.2 . . ? C46 C45 C44 119.3(8) . . ? C46 C45 H45 120.3 . . ? C44 C45 H45 120.3 . . ? C45 C46 C47 120.4(8) . . ? C45 C46 H46 119.8 . . ? C47 C46 H46 119.8 . . ? C42 C47 C46 121.1(7) . . ? C42 C47 H47 119.5 . . ? C46 C47 H47 119.5 . . ? C49 C48 C53 119.7(6) . . ? C49 C48 C22 123.2(7) . . ? C53 C48 C22 117.0(7) . . ? C48 C49 C50 118.6(8) . . ? C48 C49 H49 120.7 . . ? C50 C49 H49 120.7 . . ? C51 C50 C49 120.8(8) . . ? C51 C50 H50 119.6 . . ? C49 C50 H50 119.6 . . ? C52 C51 C50 120.3(7) . . ? C52 C51 H51 119.9 . . ? C50 C51 H51 119.9 . . ? C51 C52 C53 118.9(8) . . ? C51 C52 H52 120.6 . . ? C53 C52 H52 120.6 . . ? C48 C53 C52 121.8(7) . . ? C48 C53 H53 119.1 . . ? C52 C53 H53 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C2 C3 110.7(7) . . . . ? C10B N1 C2 C3 -63.5(7) . . . . ? N1 C2 C3 C4 26.6(9) . . . . ? C5 C4A C4 C3 142.1(8) . . . . ? C10B C4A C4 C3 -39.6(9) . . . . ? C2 C3 C4 C4A 22.3(10) . . . . ? C10B C4A C5 C5 1.9(13) . . . 2_656 ? C4 C4A C5 C5 -179.9(9) . . . 2_656 ? C5 C4A C10B C10B -2.2(10) . . . 2_656 ? C4 C4A C10B C10B 179.5(7) . . . 2_656 ? C5 C4A C10B N1 -178.0(7) . . . . ? C4 C4A C10B N1 3.7(8) . . . . ? C11 N1 C10B C10B 57.8(10) . . . 2_656 ? C2 N1 C10B C10B -128.0(8) . . . 2_656 ? C11 N1 C10B C4A -126.6(6) . . . . ? C2 N1 C10B C4A 47.6(6) . . . . ? C10B N1 C11 C12 11.8(7) . . . . ? C2 N1 C11 C12 -161.6(5) . . . . ? C10B N1 C11 Se18 -172.0(4) . . . . ? C2 N1 C11 Se18 14.6(7) . . . . ? N1 C11 C12 C17 47.2(7) . . . . ? Se18 C11 C12 C17 -129.1(5) . . . . ? N1 C11 C12 C13 -136.0(5) . . . . ? Se18 C11 C12 C13 47.6(6) . . . . ? C17 C12 C13 C14 -1.1(9) . . . . ? C11 C12 C13 C14 -177.9(5) . . . . ? C12 C13 C14 C15 0.9(10) . . . . ? C13 C14 C15 C16 -0.2(11) . . . . ? C14 C15 C16 C17 -0.3(11) . . . . ? C13 C12 C17 C16 0.6(9) . . . . ? C11 C12 C17 C16 177.4(6) . . . . ? C15 C16 C17 C12 0.1(10) . . . . ? O23 C19 C20 O25 -166.3(5) . . . . ? C30 C19 C20 O25 71.8(6) . . . . ? C36 C19 C20 O25 -53.4(7) . . . . ? O23 C19 C20 C21 76.5(7) . . . . ? C30 C19 C20 C21 -45.5(7) . . . . ? C36 C19 C20 C21 -170.7(5) . . . . ? O25 C20 C21 O27 24.2(6) . . . . ? C19 C20 C21 O27 144.7(5) . . . . ? O25 C20 C21 C22 144.6(5) . . . . ? C19 C20 C21 C22 -94.9(7) . . . . ? O27 C21 C22 O24 179.2(5) . . . . ? C20 C21 C22 O24 61.3(7) . . . . ? O27 C21 C22 C42 58.0(7) . . . . ? C20 C21 C22 C42 -59.8(7) . . . . ? O27 C21 C22 C48 -67.6(7) . . . . ? C20 C21 C22 C48 174.6(5) . . . . ? C19 C20 O25 C26 -160.2(6) . . . . ? C21 C20 O25 C26 -33.6(7) . . . . ? C20 O25 C26 O27 30.4(7) . . . . ? C20 O25 C26 C28 149.0(6) . . . . ? C20 O25 C26 C29 -87.1(6) . . . . ? C20 C21 O27 C26 -6.4(7) . . . . ? C22 C21 O27 C26 -132.0(6) . . . . ? O25 C26 O27 C21 -13.9(7) . . . . ? C28 C26 O27 C21 -132.8(6) . . . . ? C29 C26 O27 C21 104.0(6) . . . . ? O23 C19 C30 C35 31.2(8) . . . . ? C20 C19 C30 C35 152.4(6) . . . . ? C36 C19 C30 C35 -82.9(8) . . . . ? O23 C19 C30 C31 -152.3(6) . . . . ? C20 C19 C30 C31 -31.1(9) . . . . ? C36 C19 C30 C31 93.6(8) . . . . ? C35 C30 C31 C32 -1.2(11) . . . . ? C19 C30 C31 C32 -177.8(7) . . . . ? C30 C31 C32 C33 2.0(12) . . . . ? C31 C32 C33 C34 0.1(13) . . . . ? C32 C33 C34 C35 -2.7(15) . . . . ? C31 C30 C35 C34 -1.5(13) . . . . ? C19 C30 C35 C34 175.2(9) . . . . ? C33 C34 C35 C30 3.4(16) . . . . ? O23 C19 C36 C41 46.1(9) . . . . ? C30 C19 C36 C41 162.9(7) . . . . ? C20 C19 C36 C41 -68.6(8) . . . . ? O23 C19 C36 C37 -130.3(7) . . . . ? C30 C19 C36 C37 -13.4(9) . . . . ? C20 C19 C36 C37 115.0(7) . . . . ? C41 C36 C37 C38 0.2(12) . . . . ? C19 C36 C37 C38 176.6(7) . . . . ? C36 C37 C38 C39 -0.2(12) . . . . ? C37 C38 C39 C40 2.3(13) . . . . ? C38 C39 C40 C41 -4.3(16) . . . . ? C37 C36 C41 C40 -2.4(14) . . . . ? C19 C36 C41 C40 -178.9(9) . . . . ? C39 C40 C41 C36 4.4(17) . . . . ? O24 C22 C42 C47 156.1(6) . . . . ? C48 C22 C42 C47 35.9(10) . . . . ? C21 C22 C42 C47 -90.1(8) . . . . ? O24 C22 C42 C43 -26.3(10) . . . . ? C48 C22 C42 C43 -146.5(6) . . . . ? C21 C22 C42 C43 87.6(8) . . . . ? C47 C42 C43 C44 4.0(11) . . . . ? C22 C42 C43 C44 -173.7(8) . . . . ? C42 C43 C44 C45 -2.7(12) . . . . ? C43 C44 C45 C46 -0.3(13) . . . . ? C44 C45 C46 C47 2.0(14) . . . . ? C43 C42 C47 C46 -2.3(12) . . . . ? C22 C42 C47 C46 175.4(9) . . . . ? C45 C46 C47 C42 -0.7(14) . . . . ? O24 C22 C48 C49 112.7(7) . . . . ? C42 C22 C48 C49 -123.3(8) . . . . ? C21 C22 C48 C49 3.1(9) . . . . ? O24 C22 C48 C53 -63.0(8) . . . . ? C42 C22 C48 C53 61.0(9) . . . . ? C21 C22 C48 C53 -172.6(6) . . . . ? C53 C48 C49 C50 -0.5(11) . . . . ? C22 C48 C49 C50 -176.1(7) . . . . ? C48 C49 C50 C51 1.1(12) . . . . ? C49 C50 C51 C52 -1.6(13) . . . . ? C50 C51 C52 C53 1.5(13) . . . . ? C49 C48 C53 C52 0.5(12) . . . . ? C22 C48 C53 C52 176.3(7) . . . . ? C51 C52 C53 C48 -1.0(13) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.930 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.096 _database_code_depnum_ccdc_archive 'CCDC 927858' ####################################################################### # # 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_8 #TrackingRef 'AS-05-03-2013-7.CIF' #============================================================= _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _journal_coeditor_?tes ; ? ; _iucr_compatibility_tag ACTA95 loop_ _publ_author_foot?te ; ? ; ; to whom correspondence should be addressed ; ; ? ; ; to whom correspondence should be addressed ; # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H42 N4 O4, C H Cl3' _chemical_formula_sum 'C47 H43 Cl3 N4 O4' _chemical_formula_weight 834.20 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' N N 0.0061 0.0033 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.7348(10) _cell_length_b 9.8890(5) _cell_length_c 24.2605(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.045(6) _cell_angle_gamma 90.00 _cell_volume 3953.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3489 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 25.05 _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.886 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14613 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0625 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3489 _reflns_number_gt 2256 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _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^)+(0.0687P)^2^+5.0927P] 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 3489 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1146 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1521 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.49644(14) 0.6896(2) 0.62576(10) 0.0414(6) Uani 1 1 d . . . C2 C 0.41149(18) 0.6582(3) 0.60043(15) 0.0536(8) Uani 1 1 d . . . H2A H 0.3819 0.6320 0.6298 0.064 Uiso 1 1 calc R . . H2B H 0.4110 0.5820 0.5752 0.064 Uiso 1 1 calc R . . C3 C 0.3692(2) 0.7763(4) 0.56871(17) 0.0698(11) Uani 1 1 d . . . H3A H 0.3758 0.7708 0.5298 0.084 Uiso 1 1 calc R . . H3B H 0.3117 0.7721 0.5699 0.084 Uiso 1 1 calc R . . C4A C 0.4907(2) 0.9149(3) 0.58994(13) 0.0528(8) Uani 1 1 d . . . C4 C 0.4029(2) 0.9085(4) 0.59296(18) 0.0718(11) Uani 1 1 d . . . H4A H 0.3745 0.9830 0.5721 0.086 Uiso 1 1 calc R . . H4B H 0.3953 0.9159 0.6316 0.086 Uiso 1 1 calc R . . C5 C 0.5287(3) 1.0269(3) 0.57195(16) 0.0686(11) Uani 1 1 d . . . H5A H 0.4989 1.1052 0.5621 0.082 Uiso 1 1 calc R . . C6A C 0.6538(2) 0.9070(3) 0.57814(13) 0.0527(9) Uani 1 1 d . B . C6 C 0.6093(3) 1.0241(3) 0.56842(15) 0.0666(11) Uani 1 1 d . . . H6A H 0.6345 1.1028 0.5593 0.080 Uiso 1 1 calc R . . C7 C 0.7423(2) 0.9046(4) 0.57288(17) 0.0772(12) Uani 1 1 d . . . H7A H 0.7458 0.9153 0.5336 0.093 Uiso 1 1 calc R A 1 H7B H 0.7683 0.9827 0.5925 0.093 Uiso 1 1 calc R A 1 C8 C 0.7883(3) 0.7854(6) 0.5936(2) 0.1068(17) Uani 1 1 d . B 1 H8A H 0.8404 0.8140 0.6143 0.128 Uiso 1 1 calc R B 1 H8B H 0.7984 0.7326 0.5619 0.128 Uiso 1 1 calc R B 1 C9 C 0.74829(19) 0.6958(4) 0.63080(14) 0.0590(9) Uani 1 1 d . . . H9A H 0.7772 0.6106 0.6371 0.071 Uiso 1 1 calc R B 1 H9B H 0.7489 0.7390 0.6667 0.071 Uiso 1 1 calc R B 1 N10 N 0.66464(14) 0.6718(2) 0.60308(10) 0.0424(6) Uani 1 1 d . B . C10A C 0.61611(18) 0.7910(3) 0.59407(11) 0.0396(7) Uani 1 1 d . . . C10B C 0.53674(18) 0.7979(3) 0.60387(12) 0.0401(7) Uani 1 1 d . B . C11 C 0.52943(19) 0.6111(3) 0.67064(12) 0.0433(7) Uani 1 1 d . . . C12 C 0.59929(19) 0.6630(3) 0.71163(12) 0.0433(7) Uani 1 1 d . . . C13 C 0.6554(2) 0.5702(3) 0.73753(13) 0.0551(8) Uani 1 1 d . . . H13A H 0.6508 0.4795 0.7272 0.066 Uiso 1 1 calc R . . C14 C 0.7188(2) 0.6124(4) 0.77909(15) 0.0677(10) Uani 1 1 d . . . H14A H 0.7573 0.5503 0.7957 0.081 Uiso 1 1 calc R . . C15 C 0.7246(2) 0.7446(5) 0.79547(15) 0.0695(11) Uani 1 1 d . . . H15A H 0.7666 0.7726 0.8235 0.083 Uiso 1 1 calc R . . C16 C 0.6680(3) 0.8358(4) 0.77032(15) 0.0682(10) Uani 1 1 d . . . H16A H 0.6719 0.9258 0.7816 0.082 Uiso 1 1 calc R . . C17 C 0.6056(2) 0.7964(3) 0.72873(13) 0.0521(8) Uani 1 1 d . . . H17A H 0.5677 0.8595 0.7121 0.063 Uiso 1 1 calc R . . O18 O 0.49798(15) 0.5027(2) 0.67817(10) 0.0622(7) Uani 1 1 d . . . C19 C 0.64417(19) 0.5469(3) 0.58197(12) 0.0446(7) Uani 1 1 d . . . C20 C 0.56796(18) 0.5280(3) 0.54049(12) 0.0398(7) Uani 1 1 d . . . C21 C 0.52257(19) 0.4127(3) 0.54435(12) 0.0432(7) Uani 1 1 d . . . H21A H 0.5377 0.3533 0.5741 0.052 Uiso 1 1 calc R B . C22 C 0.45529(19) 0.3848(3) 0.50481(12) 0.0428(7) Uani 1 1 d . . . H22A H 0.4250 0.3074 0.5082 0.051 Uiso 1 1 calc R . . O26 O 0.68801(15) 0.4502(2) 0.59523(11) 0.0731(8) Uani 1 1 d . B . Cl27 Cl 0.4801(3) 0.1718(3) 0.81385(12) 0.1414(15) Uani 0.50 1 d P . 1 Cl28 Cl 0.59270(19) 0.1968(3) 0.7411(2) 0.1421(15) Uani 0.50 1 d P . 1 Cl29 Cl 0.4268(3) 0.1949(4) 0.70074(18) 0.164(2) Uani 0.50 1 d P . 1 C30 C 0.5000 0.2430(5) 0.7500 0.0575(13) Uani 1 2 d S . 1 H30A H 0.5000 0.3374 0.7500 0.086 Uiso 1 2 d SR . 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 N1 0.0427(14) 0.0365(13) 0.0465(14) 0.0015(11) 0.0117(11) -0.0031(11) C2 0.0415(19) 0.053(2) 0.068(2) -0.0061(16) 0.0148(16) -0.0014(15) C3 0.054(2) 0.070(3) 0.084(3) 0.009(2) 0.0091(19) 0.0102(19) C4A 0.067(2) 0.0382(18) 0.0538(19) -0.0002(15) 0.0131(16) 0.0042(16) C4 0.076(3) 0.053(2) 0.090(3) 0.008(2) 0.023(2) 0.0259(19) C5 0.097(3) 0.0349(19) 0.072(2) 0.0085(17) 0.009(2) 0.0041(19) C6A 0.065(2) 0.050(2) 0.0437(18) -0.0014(15) 0.0111(15) -0.0221(17) C6 0.092(3) 0.039(2) 0.068(2) 0.0115(16) 0.012(2) -0.0207(19) C7 0.076(3) 0.090(3) 0.069(2) 0.002(2) 0.021(2) -0.035(2) C8 0.054(3) 0.136(4) 0.133(4) 0.044(4) 0.026(3) -0.017(3) C9 0.0386(18) 0.079(2) 0.058(2) 0.0006(18) 0.0058(15) -0.0092(17) N10 0.0357(14) 0.0440(14) 0.0475(14) -0.0041(12) 0.0072(11) -0.0041(11) C10A 0.0470(18) 0.0366(16) 0.0352(15) -0.0034(12) 0.0067(13) -0.0084(14) C10B 0.0513(19) 0.0305(15) 0.0390(16) -0.0003(12) 0.0095(13) -0.0038(13) C11 0.0546(19) 0.0371(17) 0.0414(17) -0.0015(13) 0.0167(14) -0.0050(14) C12 0.0526(19) 0.0423(17) 0.0377(16) 0.0025(13) 0.0154(14) -0.0028(14) C13 0.064(2) 0.0507(19) 0.0521(19) 0.0024(16) 0.0147(17) 0.0010(17) C14 0.065(2) 0.089(3) 0.050(2) 0.007(2) 0.0092(18) 0.007(2) C15 0.068(3) 0.090(3) 0.050(2) -0.013(2) 0.0110(18) -0.019(2) C16 0.089(3) 0.062(2) 0.056(2) -0.0190(19) 0.023(2) -0.018(2) C17 0.067(2) 0.0444(19) 0.0478(18) -0.0031(15) 0.0167(16) -0.0027(16) O18 0.0778(17) 0.0447(13) 0.0634(15) 0.0120(11) 0.0106(12) -0.0205(12) C19 0.0453(18) 0.0434(18) 0.0456(17) -0.0003(14) 0.0092(14) 0.0072(15) C20 0.0455(17) 0.0334(15) 0.0412(16) -0.0058(13) 0.0094(13) 0.0047(13) C21 0.061(2) 0.0278(15) 0.0394(16) 0.0001(12) 0.0049(14) 0.0031(14) C22 0.0577(19) 0.0283(15) 0.0441(17) -0.0013(13) 0.0139(15) -0.0035(13) O26 0.0653(16) 0.0526(15) 0.0936(19) -0.0041(13) -0.0076(14) 0.0201(13) Cl27 0.264(5) 0.0778(17) 0.0903(18) 0.0064(14) 0.054(3) -0.050(2) Cl28 0.0850(19) 0.099(2) 0.252(5) 0.034(3) 0.056(3) 0.0303(16) Cl29 0.156(3) 0.160(3) 0.139(3) 0.040(3) -0.078(3) -0.090(3) C30 0.059(3) 0.039(2) 0.071(3) 0.000 0.001(2) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C11 1.372(4) . ? N1 C10B 1.417(4) . ? N1 C2 1.480(4) . ? C2 C3 1.505(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.502(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4A C5 1.385(5) . ? C4A C10B 1.399(4) . ? C4A C4 1.486(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.367(5) . ? C5 H5A 0.9300 . ? C6A C6 1.375(5) . ? C6A C10A 1.395(4) . ? C6A C7 1.508(5) . ? C6 H6A 0.9300 . ? C7 C8 1.450(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.502(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N10 1.463(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? N10 C19 1.358(4) . ? N10 C10A 1.426(4) . ? C10A C10B 1.391(4) . ? C11 O18 1.222(3) . ? C11 C12 1.488(4) . ? C12 C17 1.381(4) . ? C12 C13 1.383(4) . ? C13 C14 1.395(5) . ? C13 H13A 0.9300 . ? C14 C15 1.364(5) . ? C14 H14A 0.9300 . ? C15 C16 1.372(5) . ? C15 H15A 0.9300 . ? C16 C17 1.376(5) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C19 O26 1.214(4) . ? C19 C20 1.492(4) . ? C20 C21 1.382(4) . ? C20 C22 1.398(4) 5_666 ? C21 C22 1.374(4) . ? C21 H21A 0.9300 . ? C22 C20 1.398(4) 5_666 ? C22 H22A 0.9300 . ? Cl27 Cl28 1.661(6) 2_656 ? Cl27 Cl29 1.673(6) 2_656 ? Cl27 C30 1.785(3) . ? Cl28 Cl29 1.502(6) 2_656 ? Cl28 Cl27 1.661(6) 2_656 ? Cl28 C30 1.667(3) . ? Cl29 Cl28 1.502(6) 2_656 ? Cl29 C30 1.627(3) . ? Cl29 Cl27 1.673(6) 2_656 ? C30 Cl29 1.627(3) 2_656 ? C30 Cl28 1.667(3) 2_656 ? C30 Cl27 1.785(3) 2_656 ? C30 H30A 0.9329 . ? 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 C11 N1 C10B 124.9(2) . . ? C11 N1 C2 115.8(2) . . ? C10B N1 C2 119.2(2) . . ? N1 C2 C3 112.4(3) . . ? N1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 111.4(3) . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C5 C4A C10B 118.3(3) . . ? C5 C4A C4 124.2(3) . . ? C10B C4A C4 117.5(3) . . ? C4A C4 C3 108.9(3) . . ? C4A C4 H4A 109.9 . . ? C3 C4 H4A 109.9 . . ? C4A C4 H4B 109.9 . . ? C3 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? C6 C5 C4A 121.1(3) . . ? C6 C5 H5A 119.5 . . ? C4A C5 H5A 119.5 . . ? C6 C6A C10A 118.8(3) . . ? C6 C6A C7 120.6(3) . . ? C10A C6A C7 120.6(3) . . ? C5 C6 C6A 121.1(3) . . ? C5 C6 H6A 119.4 . . ? C6A C6 H6A 119.4 . . ? C8 C7 C6A 116.9(3) . . ? C8 C7 H7A 108.1 . . ? C6A C7 H7A 108.1 . . ? C8 C7 H7B 108.1 . . ? C6A C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? C7 C8 C9 115.0(4) . . ? C7 C8 H8A 108.5 . . ? C9 C8 H8A 108.5 . . ? C7 C8 H8B 108.5 . . ? C9 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? N10 C9 C8 108.1(3) . . ? N10 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? N10 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? C19 N10 C10A 126.5(2) . . ? C19 N10 C9 118.6(3) . . ? C10A N10 C9 114.2(2) . . ? C10B C10A C6A 119.9(3) . . ? C10B C10A N10 123.3(2) . . ? C6A C10A N10 116.7(3) . . ? C10A C10B C4A 120.1(3) . . ? C10A C10B N1 123.9(3) . . ? C4A C10B N1 116.0(3) . . ? O18 C11 N1 119.4(3) . . ? O18 C11 C12 120.8(3) . . ? N1 C11 C12 119.7(3) . . ? C17 C12 C13 119.1(3) . . ? C17 C12 C11 122.7(3) . . ? C13 C12 C11 117.8(3) . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C15 C14 C13 120.3(4) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C14 C15 C16 119.5(3) . . ? C14 C15 H15A 120.3 . . ? C16 C15 H15A 120.3 . . ? C15 C16 C17 121.1(3) . . ? C15 C16 H16A 119.5 . . ? C17 C16 H16A 119.5 . . ? C16 C17 C12 120.0(3) . . ? C16 C17 H17A 120.0 . . ? C12 C17 H17A 120.0 . . ? O26 C19 N10 121.0(3) . . ? O26 C19 C20 119.1(3) . . ? N10 C19 C20 119.9(3) . . ? C21 C20 C22 118.8(3) . 5_666 ? C21 C20 C19 118.2(3) . . ? C22 C20 C19 122.7(3) 5_666 . ? C22 C21 C20 120.8(3) . . ? C22 C21 H21A 119.6 . . ? C20 C21 H21A 119.6 . . ? C21 C22 C20 120.5(3) . 5_666 ? C21 C22 H22A 119.8 . . ? C20 C22 H22A 119.8 5_666 . ? Cl28 Cl27 Cl29 113.0(2) 2_656 2_656 ? Cl28 Cl27 C30 57.73(15) 2_656 . ? Cl29 Cl27 C30 56.01(15) 2_656 . ? Cl29 Cl28 Cl27 120.2(3) 2_656 2_656 ? Cl29 Cl28 C30 61.51(17) 2_656 . ? Cl27 Cl28 C30 64.88(17) 2_656 . ? Cl28 Cl29 C30 64.24(18) 2_656 . ? Cl28 Cl29 Cl27 124.3(3) 2_656 2_656 ? C30 Cl29 Cl27 65.48(18) . 2_656 ? Cl29 C30 Cl29 146.0(4) 2_656 . ? Cl29 C30 Cl28 54.3(2) 2_656 . ? Cl29 C30 Cl28 115.1(3) . . ? Cl29 C30 Cl28 115.1(3) 2_656 2_656 ? Cl29 C30 Cl28 54.3(2) . 2_656 ? Cl28 C30 Cl28 148.2(4) . 2_656 ? Cl29 C30 Cl27 107.0(2) 2_656 2_656 ? Cl29 C30 Cl27 58.5(2) . 2_656 ? Cl28 C30 Cl27 57.4(2) . 2_656 ? Cl28 C30 Cl27 108.8(3) 2_656 2_656 ? Cl29 C30 Cl27 58.5(2) 2_656 . ? Cl29 C30 Cl27 107.0(2) . . ? Cl28 C30 Cl27 108.8(3) . . ? Cl28 C30 Cl27 57.4(2) 2_656 . ? Cl27 C30 Cl27 133.5(3) 2_656 . ? Cl29 C30 H30A 107.0 2_656 . ? Cl29 C30 H30A 107.0 . . ? Cl28 C30 H30A 105.9 . . ? Cl28 C30 H30A 105.9 2_656 . ? Cl27 C30 H30A 113.2 2_656 . ? Cl27 C30 H30A 113.2 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.331 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 927859'