Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Simon Jones' _publ_contact_author_address ; Department of Chemistry University of Sheffield Dainton Building Sheffield S3 7HF UNITED KINGDOM ; _publ_contact_author_email SIMON.JONES@SHEFFIELD.AC.UK _publ_section_title ; N-Alkyl oxazolidines as stereocontrol elements in asymmetric Diels-Alder cycloadditions of 9-substituted anthracene derivatives ; loop_ _publ_author_name 'Simon Jones' 'Harry Adams' 'Ramadan A. Bawa' # Attachment 'Compound_4.CIF' data_osj8m _database_code_depnum_ccdc_archive 'CCDC 614833' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H23 N O' _chemical_formula_weight 353.44 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 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 18.188(3) _cell_length_b 7.0490(10) _cell_length_c 17.257(2) _cell_angle_alpha 90.00 _cell_angle_beta 121.240(2) _cell_angle_gamma 90.00 _cell_volume 1891.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3417 _cell_measurement_theta_min 4.479 _cell_measurement_theta_max 54.701 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9896 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker smart1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10741 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2328 _reflns_number_gt 1903 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.2084P] 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(10) _refine_ls_number_reflns 2328 _refine_ls_number_parameters 246 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.89484(10) 0.3665(2) 0.85808(10) 0.0331(4) Uani 1 1 d . . . N3 N 0.84135(11) 0.6398(3) 0.77812(12) 0.0259(4) Uani 1 1 d . . . C1 C 1.02020(13) 0.4193(3) 0.72813(15) 0.0267(5) Uani 1 1 d . . . H1 H 1.0348 0.5092 0.7749 0.032 Uiso 1 1 calc R . . C2 C 1.07813(14) 0.3786(4) 0.70296(15) 0.0303(5) Uani 1 1 d . . . H2 H 1.1316 0.4438 0.7313 0.036 Uiso 1 1 calc R . . C3 C 1.06062(15) 0.2421(4) 0.63582(16) 0.0330(6) Uani 1 1 d . . . H3 H 1.1030 0.2114 0.6214 0.040 Uiso 1 1 calc R . . C4 C 0.98351(14) 0.1557(4) 0.59233(15) 0.0293(5) Uani 1 1 d . . . H4 H 0.9719 0.0641 0.5470 0.035 Uiso 1 1 calc R . . C5 C 0.68715(14) 0.0959(3) 0.52238(15) 0.0288(5) Uani 1 1 d . . . H5 H 0.6745 0.0200 0.4714 0.035 Uiso 1 1 calc R . . C6 C 0.62437(14) 0.1344(4) 0.53975(16) 0.0322(5) Uani 1 1 d . . . H6 H 0.5680 0.0861 0.5011 0.039 Uiso 1 1 calc R . . C7 C 0.64278(14) 0.2472(3) 0.61581(16) 0.0309(5) Uani 1 1 d . . . H7 H 0.5984 0.2726 0.6280 0.037 Uiso 1 1 calc R . . C8 C 0.72271(14) 0.3195(3) 0.67166(15) 0.0267(5) Uani 1 1 d . . . H8 H 0.7334 0.3934 0.7225 0.032 Uiso 1 1 calc R . . C9 C 0.87455(13) 0.3641(3) 0.70825(13) 0.0211(4) Uani 1 1 d . . . C10 C 0.83658(13) 0.1216(3) 0.56220(14) 0.0229(5) Uani 1 1 d . . . H10 H 0.8244 0.0354 0.5146 0.028 Uiso 1 1 calc R . . C11 C 0.93746(13) 0.3289(3) 0.68535(14) 0.0208(4) Uani 1 1 d . . . C12 C 0.91849(13) 0.1987(3) 0.61297(14) 0.0224(5) Uani 1 1 d . . . C13 C 0.77224(13) 0.1676(3) 0.57942(14) 0.0222(4) Uani 1 1 d . . . C14 C 0.79117(13) 0.2857(3) 0.65500(14) 0.0213(4) Uani 1 1 d . . . C15 C 0.80499(14) 0.8172(3) 0.87876(15) 0.0296(5) Uani 1 1 d . . . H15A H 0.7969 0.9357 0.8444 0.035 Uiso 1 1 calc R . . H15B H 0.7487 0.7522 0.8514 0.035 Uiso 1 1 calc R . . C16 C 0.8480(2) 0.7932(4) 0.72562(18) 0.0436(7) Uani 1 1 d . . . H16A H 0.8292 0.7478 0.6644 0.065 Uiso 1 1 calc R . . H16B H 0.9079 0.8359 0.7551 0.065 Uiso 1 1 calc R . . H16C H 0.8114 0.8991 0.7220 0.065 Uiso 1 1 calc R . . C2A C 0.89777(14) 0.4812(3) 0.79145(14) 0.0245(5) Uani 1 1 d . . . H2A H 0.9576 0.5304 0.8176 0.029 Uiso 1 1 calc R . . C4A C 0.86870(14) 0.6900(3) 0.87168(14) 0.0253(5) Uani 1 1 d . . . H4A H 0.9263 0.7530 0.9013 0.030 Uiso 1 1 calc R . . C5A C 0.87747(15) 0.4928(3) 0.91230(15) 0.0278(5) Uani 1 1 d . . . H5A1 H 0.9252 0.4900 0.9763 0.033 Uiso 1 1 calc R . . H5A2 H 0.8237 0.4559 0.9096 0.033 Uiso 1 1 calc R . . C1B C 0.83595(13) 0.8654(3) 0.97626(14) 0.0255(5) Uani 1 1 d . . . C2B C 0.89784(14) 1.0068(4) 1.01996(16) 0.0320(5) Uani 1 1 d . . . H2B H 0.9181 1.0754 0.9873 0.038 Uiso 1 1 calc R . . C3B C 0.92978(17) 1.0480(4) 1.11000(18) 0.0428(7) Uani 1 1 d . . . H3B H 0.9721 1.1440 1.1392 0.051 Uiso 1 1 calc R . . C4B C 0.90026(17) 0.9497(4) 1.15790(17) 0.0449(7) Uani 1 1 d . . . H4B H 0.9223 0.9777 1.2200 0.054 Uiso 1 1 calc R . . C5B C 0.83858(17) 0.8104(4) 1.11496(17) 0.0384(6) Uani 1 1 d . . . H5B H 0.8181 0.7427 1.1477 0.046 Uiso 1 1 calc R . . C6B C 0.80640(14) 0.7688(4) 1.02461(16) 0.0321(6) Uani 1 1 d . . . H6B H 0.7638 0.6733 0.9956 0.039 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0532(10) 0.0275(8) 0.0224(8) 0.0041(7) 0.0223(8) 0.0117(8) N3 0.0377(10) 0.0187(9) 0.0214(9) -0.0012(8) 0.0154(8) 0.0006(8) C1 0.0289(11) 0.0264(12) 0.0225(11) 0.0040(9) 0.0116(9) 0.0009(9) C2 0.0249(11) 0.0345(13) 0.0292(12) 0.0082(11) 0.0124(9) -0.0004(11) C3 0.0310(12) 0.0406(14) 0.0351(13) 0.0087(11) 0.0225(11) 0.0093(11) C4 0.0372(12) 0.0295(12) 0.0285(12) 0.0050(10) 0.0222(10) 0.0064(11) C5 0.0341(12) 0.0223(11) 0.0276(13) -0.0034(9) 0.0143(10) -0.0047(10) C6 0.0272(11) 0.0281(12) 0.0375(14) -0.0027(11) 0.0141(10) -0.0067(10) C7 0.0326(12) 0.0247(12) 0.0440(14) -0.0016(11) 0.0258(11) -0.0026(10) C8 0.0339(12) 0.0217(11) 0.0304(12) -0.0023(9) 0.0209(10) -0.0027(9) C9 0.0264(10) 0.0185(10) 0.0185(10) 0.0017(8) 0.0117(8) 0.0022(9) C10 0.0327(11) 0.0179(10) 0.0201(11) 0.0005(9) 0.0150(9) 0.0008(9) C11 0.0254(10) 0.0187(10) 0.0185(10) 0.0046(8) 0.0116(8) 0.0019(8) C12 0.0291(11) 0.0196(10) 0.0210(10) 0.0078(9) 0.0148(9) 0.0055(9) C13 0.0280(10) 0.0155(10) 0.0225(11) 0.0020(9) 0.0126(9) -0.0006(9) C14 0.0266(10) 0.0169(10) 0.0213(10) 0.0039(8) 0.0130(9) 0.0020(9) C15 0.0323(12) 0.0276(12) 0.0254(11) -0.0036(10) 0.0125(10) 0.0026(10) C16 0.077(2) 0.0233(13) 0.0390(15) 0.0038(11) 0.0359(15) 0.0008(13) C2A 0.0268(11) 0.0265(12) 0.0202(11) -0.0018(9) 0.0122(9) 0.0003(9) C4A 0.0284(11) 0.0251(11) 0.0206(11) -0.0033(9) 0.0113(9) -0.0018(9) C5A 0.0353(12) 0.0280(12) 0.0220(11) 0.0000(9) 0.0162(9) 0.0054(10) C1B 0.0265(10) 0.0222(10) 0.0266(11) -0.0041(9) 0.0130(9) 0.0067(9) C2B 0.0336(12) 0.0290(12) 0.0369(13) -0.0070(11) 0.0207(11) -0.0008(10) C3B 0.0397(14) 0.0413(15) 0.0403(15) -0.0198(13) 0.0159(12) -0.0061(12) C4B 0.0486(16) 0.0512(18) 0.0284(14) -0.0092(13) 0.0155(12) 0.0136(14) C5B 0.0508(15) 0.0380(14) 0.0361(14) 0.0074(11) 0.0294(12) 0.0151(12) C6B 0.0316(12) 0.0274(12) 0.0386(14) -0.0024(11) 0.0191(11) 0.0014(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2A 1.429(3) . ? O1 C5A 1.440(3) . ? N3 C2A 1.453(3) . ? N3 C16 1.455(3) . ? N3 C4A 1.465(3) . ? C1 C2 1.362(3) . ? C1 C11 1.436(3) . ? C1 H1 0.9500 . ? C2 C3 1.410(3) . ? C2 H2 0.9500 . ? C3 C4 1.345(3) . ? C3 H3 0.9500 . ? C4 C12 1.433(3) . ? C4 H4 0.9500 . ? C5 C6 1.350(3) . ? C5 C13 1.428(3) . ? C5 H5 0.9500 . ? C6 C7 1.418(3) . ? C6 H6 0.9500 . ? C7 C8 1.360(3) . ? C7 H7 0.9500 . ? C8 C14 1.435(3) . ? C8 H8 0.9500 . ? C9 C11 1.413(3) . ? C9 C14 1.416(3) . ? C9 C2A 1.514(3) . ? C10 C13 1.387(3) . ? C10 C12 1.389(3) . ? C10 H10 0.9500 . ? C11 C12 1.440(3) . ? C13 C14 1.431(3) . ? C15 C1B 1.510(3) . ? C15 C4A 1.519(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C2A H2A 1.0000 . ? C4A C5A 1.528(3) . ? C4A H4A 1.0000 . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C1B C6B 1.383(3) . ? C1B C2B 1.396(3) . ? C2B C3B 1.378(3) . ? C2B H2B 0.9500 . ? C3B C4B 1.383(4) . ? C3B H3B 0.9500 . ? C4B C5B 1.382(4) . ? C4B H4B 0.9500 . ? C5B C6B 1.383(3) . ? C5B H5B 0.9500 . ? C6B H6B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A O1 C5A 106.59(17) . . ? C2A N3 C16 112.97(18) . . ? C2A N3 C4A 101.72(16) . . ? C16 N3 C4A 114.60(18) . . ? C2 C1 C11 121.4(2) . . ? C2 C1 H1 119.3 . . ? C11 C1 H1 119.3 . . ? C1 C2 C3 121.6(2) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C4 C3 C2 119.6(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C12 121.4(2) . . ? C3 C4 H4 119.3 . . ? C12 C4 H4 119.3 . . ? C6 C5 C13 121.0(2) . . ? C6 C5 H5 119.5 . . ? C13 C5 H5 119.5 . . ? C5 C6 C7 119.8(2) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 121.2(2) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C14 121.0(2) . . ? C7 C8 H8 119.5 . . ? C14 C8 H8 119.5 . . ? C11 C9 C14 120.03(19) . . ? C11 C9 C2A 119.53(18) . . ? C14 C9 C2A 120.42(18) . . ? C13 C10 C12 121.4(2) . . ? C13 C10 H10 119.3 . . ? C12 C10 H10 119.3 . . ? C9 C11 C1 124.27(19) . . ? C9 C11 C12 119.33(18) . . ? C1 C11 C12 116.37(18) . . ? C10 C12 C4 120.9(2) . . ? C10 C12 C11 119.52(19) . . ? C4 C12 C11 119.5(2) . . ? C10 C13 C5 120.2(2) . . ? C10 C13 C14 120.03(18) . . ? C5 C13 C14 119.78(19) . . ? C9 C14 C13 119.28(18) . . ? C9 C14 C8 123.63(19) . . ? C13 C14 C8 117.09(19) . . ? C1B C15 C4A 111.28(18) . . ? C1B C15 H15A 109.4 . . ? C4A C15 H15A 109.4 . . ? C1B C15 H15B 109.4 . . ? C4A C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N3 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O1 C2A N3 104.17(16) . . ? O1 C2A C9 110.24(18) . . ? N3 C2A C9 116.28(17) . . ? O1 C2A H2A 108.6 . . ? N3 C2A H2A 108.6 . . ? C9 C2A H2A 108.6 . . ? N3 C4A C15 113.20(17) . . ? N3 C4A C5A 100.41(17) . . ? C15 C4A C5A 113.75(18) . . ? N3 C4A H4A 109.7 . . ? C15 C4A H4A 109.7 . . ? C5A C4A H4A 109.7 . . ? O1 C5A C4A 105.67(16) . . ? O1 C5A H5A1 110.6 . . ? C4A C5A H5A1 110.6 . . ? O1 C5A H5A2 110.6 . . ? C4A C5A H5A2 110.6 . . ? H5A1 C5A H5A2 108.7 . . ? C6B C1B C2B 118.8(2) . . ? C6B C1B C15 121.6(2) . . ? C2B C1B C15 119.5(2) . . ? C3B C2B C1B 120.6(2) . . ? C3B C2B H2B 119.7 . . ? C1B C2B H2B 119.7 . . ? C2B C3B C4B 120.1(2) . . ? C2B C3B H3B 120.0 . . ? C4B C3B H3B 120.0 . . ? C3B C4B C5B 119.6(2) . . ? C3B C4B H4B 120.2 . . ? C5B C4B H4B 120.2 . . ? C4B C5B C6B 120.4(2) . . ? C4B C5B H5B 119.8 . . ? C6B C5B H5B 119.8 . . ? C5B C6B C1B 120.4(2) . . ? C5B C6B H6B 119.8 . . ? C1B C6B H6B 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 C3 -1.9(3) . . . . ? C1 C2 C3 C4 3.1(3) . . . . ? C2 C3 C4 C12 -0.2(3) . . . . ? C13 C5 C6 C7 -0.2(4) . . . . ? C5 C6 C7 C8 0.6(4) . . . . ? C6 C7 C8 C14 0.6(3) . . . . ? C14 C9 C11 C1 172.3(2) . . . . ? C2A C9 C11 C1 -9.4(3) . . . . ? C14 C9 C11 C12 -5.9(3) . . . . ? C2A C9 C11 C12 172.43(18) . . . . ? C2 C1 C11 C9 179.8(2) . . . . ? C2 C1 C11 C12 -1.9(3) . . . . ? C13 C10 C12 C4 -177.63(19) . . . . ? C13 C10 C12 C11 0.2(3) . . . . ? C3 C4 C12 C10 174.1(2) . . . . ? C3 C4 C12 C11 -3.7(3) . . . . ? C9 C11 C12 C10 5.1(3) . . . . ? C1 C11 C12 C10 -173.21(19) . . . . ? C9 C11 C12 C4 -177.03(19) . . . . ? C1 C11 C12 C4 4.6(3) . . . . ? C12 C10 C13 C5 175.9(2) . . . . ? C12 C10 C13 C14 -4.7(3) . . . . ? C6 C5 C13 C10 177.9(2) . . . . ? C6 C5 C13 C14 -1.5(3) . . . . ? C11 C9 C14 C13 1.4(3) . . . . ? C2A C9 C14 C13 -176.84(18) . . . . ? C11 C9 C14 C8 -177.84(19) . . . . ? C2A C9 C14 C8 3.9(3) . . . . ? C10 C13 C14 C9 3.9(3) . . . . ? C5 C13 C14 C9 -176.7(2) . . . . ? C10 C13 C14 C8 -176.80(19) . . . . ? C5 C13 C14 C8 2.6(3) . . . . ? C7 C8 C14 C9 177.1(2) . . . . ? C7 C8 C14 C13 -2.2(3) . . . . ? C5A O1 C2A N3 -28.4(2) . . . . ? C5A O1 C2A C9 -153.84(17) . . . . ? C16 N3 C2A O1 168.74(18) . . . . ? C4A N3 C2A O1 45.39(19) . . . . ? C16 N3 C2A C9 -69.8(2) . . . . ? C4A N3 C2A C9 166.90(18) . . . . ? C11 C9 C2A O1 -113.8(2) . . . . ? C14 C9 C2A O1 64.5(2) . . . . ? C11 C9 C2A N3 128.0(2) . . . . ? C14 C9 C2A N3 -53.7(3) . . . . ? C2A N3 C4A C15 -164.40(18) . . . . ? C16 N3 C4A C15 73.4(2) . . . . ? C2A N3 C4A C5A -42.8(2) . . . . ? C16 N3 C4A C5A -165.0(2) . . . . ? C1B C15 C4A N3 -179.89(18) . . . . ? C1B C15 C4A C5A 66.3(2) . . . . ? C2A O1 C5A C4A 1.0(2) . . . . ? N3 C4A C5A O1 26.1(2) . . . . ? C15 C4A C5A O1 147.29(17) . . . . ? C4A C15 C1B C6B -98.6(2) . . . . ? C4A C15 C1B C2B 79.4(3) . . . . ? C6B C1B C2B C3B 0.8(3) . . . . ? C15 C1B C2B C3B -177.3(2) . . . . ? C1B C2B C3B C4B -0.3(4) . . . . ? C2B C3B C4B C5B -0.1(4) . . . . ? C3B C4B C5B C6B 0.1(4) . . . . ? C4B C5B C6B C1B 0.4(4) . . . . ? C2B C1B C6B C5B -0.8(3) . . . . ? C15 C1B C6B C5B 177.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.199 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.038 # Attachment 'Compound_5.CIF' data_osj15m _database_code_depnum_ccdc_archive 'CCDC 614834' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H27 N O' _chemical_formula_sum 'C31 H27 N O' _chemical_formula_weight 429.54 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.284(3) _cell_length_b 9.462(3) _cell_length_c 18.426(6) _cell_angle_alpha 76.240(5) _cell_angle_beta 84.707(6) _cell_angle_gamma 68.069(5) _cell_volume 1144.2(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3918 _cell_measurement_theta_min 4.552 _cell_measurement_theta_max 53.919 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9687 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12849 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.58 _reflns_number_total 5114 _reflns_number_gt 3768 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0842P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 5114 _refine_ls_number_parameters 595 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1422 _refine_ls_wR_factor_gt 0.1255 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 0.999 _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 N3 N 0.5167(4) 0.7976(3) 0.33281(16) 0.0240(7) Uani 1 1 d . . . O1 O 0.7711(4) 0.7796(3) 0.40449(15) 0.0318(6) Uani 1 1 d . . . C1 C 0.6116(6) 1.2099(4) 0.2741(2) 0.0289(8) Uani 1 1 d . . . H1A H 0.5468 1.1912 0.3192 0.035 Uiso 1 1 calc R . . C2 C 0.5912(6) 1.3600(5) 0.2403(2) 0.0359(10) Uani 1 1 d . . . H2A H 0.5145 1.4411 0.2630 0.043 Uiso 1 1 calc R . . C3 C 0.6842(6) 1.3928(5) 0.1720(2) 0.0365(10) Uani 1 1 d . . . H3A H 0.6695 1.4956 0.1498 0.044 Uiso 1 1 calc R . . C4 C 0.7956(6) 1.2763(5) 0.1381(2) 0.0346(9) Uani 1 1 d . . . H4A H 0.8544 1.3000 0.0921 0.041 Uiso 1 1 calc R . . C5 C 1.0884(6) 0.7220(5) 0.1317(2) 0.0308(9) Uani 1 1 d . . . H5A H 1.1425 0.7489 0.0851 0.037 Uiso 1 1 calc R . . C6 C 1.1224(6) 0.5697(5) 0.1626(2) 0.0363(10) Uani 1 1 d . . . H6A H 1.1998 0.4929 0.1376 0.044 Uiso 1 1 calc R . . C7 C 1.0395(6) 0.5281(4) 0.2332(2) 0.0340(9) Uani 1 1 d . . . H7A H 1.0629 0.4233 0.2541 0.041 Uiso 1 1 calc R . . C8 C 0.9267(5) 0.6375(4) 0.2710(2) 0.0289(8) Uani 1 1 d . . . H8A H 0.8758 0.6068 0.3176 0.035 Uiso 1 1 calc R . . C9 C 0.7600(5) 0.9212(4) 0.2757(2) 0.0223(7) Uani 1 1 d . . . C10 C 0.9382(5) 0.9982(4) 0.1365(2) 0.0287(8) Uani 1 1 d . . . H10B H 0.9935 1.0238 0.0900 0.034 Uiso 1 1 calc R . . C11 C 0.7309(5) 1.0797(4) 0.2420(2) 0.0244(8) Uani 1 1 d . . . C12 C 0.8241(5) 1.1164(4) 0.1722(2) 0.0261(8) Uani 1 1 d . . . C13 C 0.9716(5) 0.8414(4) 0.1690(2) 0.0240(8) Uani 1 1 d . . . C14 C 0.8849(5) 0.8009(4) 0.2397(2) 0.0230(8) Uani 1 1 d . . . C15 C 0.4121(6) 0.5876(4) 0.4120(2) 0.0311(9) Uani 1 1 d . . . H15C H 0.2906 0.6249 0.3839 0.037 Uiso 1 1 calc R . . H15D H 0.5122 0.5104 0.3889 0.037 Uiso 1 1 calc R . . C16 C 0.3365(5) 0.9019(4) 0.2904(2) 0.0284(8) Uani 1 1 d . . . H16A H 0.2766 0.9942 0.3111 0.034 Uiso 1 1 calc R . . H16B H 0.2429 0.8491 0.2967 0.034 Uiso 1 1 calc R . . C17 C 0.3735(5) 0.9514(4) 0.2087(2) 0.0242(8) Uani 1 1 d . . . C18 C 0.3095(5) 1.1083(4) 0.1719(2) 0.0265(8) Uani 1 1 d . . . H18A H 0.2453 1.1847 0.1989 0.032 Uiso 1 1 calc R . . C19 C 0.3393(6) 1.1518(5) 0.0971(2) 0.0343(9) Uani 1 1 d . . . H19B H 0.2930 1.2571 0.0735 0.041 Uiso 1 1 calc R . . C20 C 0.4379(6) 1.0404(5) 0.0561(2) 0.0333(9) Uani 1 1 d . . . H20B H 0.4586 1.0701 0.0051 0.040 Uiso 1 1 calc R . . C21 C 0.5059(6) 0.8831(5) 0.0921(2) 0.0339(9) Uani 1 1 d . . . H21B H 0.5734 0.8070 0.0652 0.041 Uiso 1 1 calc R . . C22 C 0.4729(5) 0.8407(4) 0.1672(2) 0.0263(8) Uani 1 1 d . . . H22A H 0.5182 0.7354 0.1907 0.032 Uiso 1 1 calc R . . N3' N 0.4318(4) 0.7904(3) 0.70403(16) 0.0239(6) Uani 1 1 d . . . O1' O 0.6997(4) 0.8148(3) 0.63323(15) 0.0328(6) Uani 1 1 d . . . C1' C 0.9028(6) 0.3853(4) 0.7635(2) 0.0294(9) Uani 1 1 d . . . H1'A H 0.8434 0.4033 0.7179 0.035 Uiso 1 1 calc R . . C2' C 1.0121(6) 0.2346(5) 0.7987(2) 0.0352(10) Uani 1 1 d . . . H2'A H 1.0276 0.1527 0.7762 0.042 Uiso 1 1 calc R . . C3' C 1.1001(6) 0.2033(5) 0.8681(3) 0.0403(11) Uani 1 1 d . . . H3'A H 1.1719 0.1008 0.8916 0.048 Uiso 1 1 calc R . . C4' C 1.0812(6) 0.3206(5) 0.9008(3) 0.0383(10) Uani 1 1 d . . . H4'A H 1.1409 0.2981 0.9468 0.046 Uiso 1 1 calc R . . C5' C 0.8279(5) 0.8747(5) 0.9065(2) 0.0302(9) Uani 1 1 d . . . H5'A H 0.8864 0.8486 0.9531 0.036 Uiso 1 1 calc R . . C6' C 0.7256(6) 1.0275(5) 0.8753(2) 0.0333(9) Uani 1 1 d . . . H6'A H 0.7158 1.1052 0.8999 0.040 Uiso 1 1 calc R . . C7' C 0.6348(6) 1.0668(4) 0.8052(2) 0.0328(9) Uani 1 1 d . . . H7'A H 0.5641 1.1711 0.7841 0.039 Uiso 1 1 calc R . . C8' C 0.6483(5) 0.9559(4) 0.7679(2) 0.0281(8) Uani 1 1 d . . . H8'A H 0.5878 0.9860 0.7215 0.034 Uiso 1 1 calc R . . C9' C 0.7669(5) 0.6734(4) 0.76241(19) 0.0226(8) Uani 1 1 d . . . C10' C 0.9512(5) 0.5982(4) 0.9016(2) 0.0297(9) Uani 1 1 d . . . H10A H 1.0091 0.5732 0.9481 0.036 Uiso 1 1 calc R . . C11' C 0.8789(5) 0.5147(4) 0.7955(2) 0.0242(8) Uani 1 1 d . . . C12' C 0.9711(5) 0.4796(4) 0.8664(2) 0.0264(8) Uani 1 1 d . . . C13' C 0.8468(5) 0.7541(4) 0.8691(2) 0.0252(8) Uani 1 1 d . . . C14' C 0.7544(5) 0.7923(4) 0.7984(2) 0.0239(8) Uani 1 1 d . . . C15' C 0.1569(6) 0.9974(5) 0.6255(2) 0.0324(9) Uani 1 1 d . . . H15A H 0.0602 0.9579 0.6536 0.039 Uiso 1 1 calc R . . H15B H 0.1695 1.0747 0.6491 0.039 Uiso 1 1 calc R . . C16' C 0.3375(6) 0.6827(4) 0.7465(2) 0.0284(8) Uani 1 1 d . . . H16C H 0.3862 0.5874 0.7279 0.034 Uiso 1 1 calc R . . H16D H 0.1958 0.7302 0.7382 0.034 Uiso 1 1 calc R . . C17' C 0.3770(5) 0.6427(4) 0.8289(2) 0.0242(8) Uani 1 1 d . . . C18' C 0.4555(5) 0.4884(5) 0.8685(2) 0.0298(9) Uani 1 1 d . . . H18B H 0.4862 0.4074 0.8438 0.036 Uiso 1 1 calc R . . C19' C 0.4879(6) 0.4551(5) 0.9446(2) 0.0369(10) Uani 1 1 d . . . H19A H 0.5397 0.3516 0.9706 0.044 Uiso 1 1 calc R . . C20' C 0.4441(6) 0.5738(5) 0.9821(2) 0.0378(10) Uani 1 1 d . . . H20A H 0.4662 0.5513 1.0332 0.045 Uiso 1 1 calc R . . C21' C 0.3660(6) 0.7286(5) 0.9420(2) 0.0331(9) Uani 1 1 d . . . H21A H 0.3345 0.8101 0.9665 0.040 Uiso 1 1 calc R . . C22' C 0.3361(5) 0.7601(4) 0.8669(2) 0.0247(8) Uani 1 1 d . . . H22B H 0.2867 0.8636 0.8407 0.030 Uiso 1 1 calc R . . C2A C 0.6427(5) 0.8810(4) 0.3439(2) 0.0258(8) Uani 1 1 d . . . H2AA H 0.5592 0.9776 0.3592 0.031 Uiso 1 1 calc R . . C4A C 0.4790(6) 0.7243(4) 0.4091(2) 0.0264(8) Uani 1 1 d . . . H4AA H 0.3785 0.8024 0.4327 0.032 Uiso 1 1 calc R . . C5A C 0.6776(6) 0.6755(4) 0.4457(2) 0.0296(8) Uani 1 1 d . . . H5AA H 0.6600 0.6836 0.4975 0.036 Uiso 1 1 calc R . . H5AB H 0.7577 0.5684 0.4437 0.036 Uiso 1 1 calc R . . C2A' C 0.6450(5) 0.7116(4) 0.6933(2) 0.0240(8) Uani 1 1 d . . . H2AB H 0.6668 0.6144 0.6778 0.029 Uiso 1 1 calc R . . C4A' C 0.3567(5) 0.8631(4) 0.6275(2) 0.0265(8) Uani 1 1 d . . . H4AB H 0.3460 0.7845 0.6035 0.032 Uiso 1 1 calc R . . C5A' C 0.5240(6) 0.9172(4) 0.5914(2) 0.0298(8) Uani 1 1 d . . . H5AC H 0.5406 0.9100 0.5394 0.036 Uiso 1 1 calc R . . H5AD H 0.4953 1.0246 0.5940 0.036 Uiso 1 1 calc R . . C1B C 0.3784(6) 0.5128(4) 0.4912(2) 0.0269(8) Uani 1 1 d . . . C2B C 0.1959(6) 0.5731(4) 0.5261(2) 0.0294(9) Uani 1 1 d . . . H2BA H 0.0928 0.6552 0.4990 0.035 Uiso 1 1 calc R . . C3B C 0.1672(6) 0.5123(5) 0.5998(2) 0.0343(9) Uani 1 1 d . . . H3BA H 0.0454 0.5542 0.6224 0.041 Uiso 1 1 calc R . . C4B C 0.3186(6) 0.3888(5) 0.6408(2) 0.0327(9) Uani 1 1 d . . . H4BB H 0.2984 0.3470 0.6905 0.039 Uiso 1 1 calc R . . C5B C 0.4981(6) 0.3290(5) 0.6073(2) 0.0341(9) Uani 1 1 d . . . H5BB H 0.6004 0.2470 0.6348 0.041 Uiso 1 1 calc R . . C6B C 0.5293(6) 0.3884(4) 0.5334(2) 0.0307(9) Uani 1 1 d . . . H6BA H 0.6516 0.3455 0.5114 0.037 Uiso 1 1 calc R . . C1B' C 0.0854(5) 1.0733(4) 0.5467(2) 0.0276(8) Uani 1 1 d . . . C2B' C 0.1329(6) 1.2004(4) 0.5059(2) 0.0335(9) Uani 1 1 d . . . H2BB H 0.2021 1.2430 0.5286 0.040 Uiso 1 1 calc R . . C3B' C 0.0772(6) 1.2624(5) 0.4320(2) 0.0339(9) Uani 1 1 d . . . H3BB H 0.1111 1.3459 0.4054 0.041 Uiso 1 1 calc R . . C4B' C -0.0275(6) 1.2033(5) 0.3969(2) 0.0333(9) Uani 1 1 d . . . H4BA H -0.0650 1.2466 0.3472 0.040 Uiso 1 1 calc R . . C5B' C -0.0763(6) 1.0768(5) 0.4374(2) 0.0331(9) Uani 1 1 d . . . H5BA H -0.1465 1.0349 0.4146 0.040 Uiso 1 1 calc R . . C6B' C -0.0202(5) 1.0145(4) 0.5110(2) 0.0290(8) Uani 1 1 d . . . H6BB H -0.0540 0.9309 0.5375 0.035 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 N3 0.0230(15) 0.0204(15) 0.0248(17) -0.0015(12) -0.0004(12) -0.0059(12) O1 0.0387(16) 0.0255(14) 0.0311(15) 0.0029(11) -0.0096(12) -0.0149(12) C1 0.035(2) 0.0209(19) 0.029(2) -0.0045(16) -0.0079(16) -0.0071(16) C2 0.045(3) 0.020(2) 0.038(2) -0.0070(17) -0.0136(19) -0.0024(18) C3 0.044(2) 0.0164(19) 0.046(3) 0.0004(18) -0.014(2) -0.0084(18) C4 0.035(2) 0.027(2) 0.038(2) 0.0044(17) -0.0048(18) -0.0119(18) C5 0.0265(19) 0.031(2) 0.037(2) -0.0097(17) 0.0087(16) -0.0127(17) C6 0.033(2) 0.026(2) 0.048(3) -0.0149(19) 0.0082(18) -0.0062(17) C7 0.036(2) 0.0192(19) 0.045(3) -0.0060(17) 0.0027(18) -0.0088(17) C8 0.0276(19) 0.0196(19) 0.037(2) -0.0038(16) 0.0015(16) -0.0081(15) C9 0.0199(17) 0.0179(17) 0.028(2) -0.0035(15) -0.0047(14) -0.0052(14) C10 0.0230(18) 0.026(2) 0.035(2) -0.0008(16) 0.0015(15) -0.0110(16) C11 0.0238(18) 0.0164(18) 0.032(2) -0.0021(15) -0.0078(15) -0.0062(14) C12 0.0247(19) 0.0176(18) 0.034(2) -0.0016(16) -0.0072(15) -0.0067(15) C13 0.0208(17) 0.0204(18) 0.032(2) -0.0052(16) -0.0026(15) -0.0083(15) C14 0.0208(17) 0.0181(18) 0.031(2) -0.0044(15) -0.0050(14) -0.0072(14) C15 0.042(2) 0.023(2) 0.031(2) -0.0050(16) -0.0004(17) -0.0154(17) C16 0.0189(17) 0.029(2) 0.031(2) -0.0046(17) 0.0010(15) -0.0037(15) C17 0.0199(17) 0.0218(18) 0.029(2) -0.0051(15) -0.0035(14) -0.0051(15) C18 0.0214(18) 0.0230(19) 0.033(2) -0.0072(16) -0.0084(15) -0.0031(15) C19 0.041(2) 0.022(2) 0.039(2) 0.0014(17) -0.0120(18) -0.0114(17) C20 0.034(2) 0.042(2) 0.022(2) -0.0017(17) -0.0004(16) -0.0144(19) C21 0.031(2) 0.031(2) 0.038(2) -0.0147(18) -0.0028(17) -0.0056(17) C22 0.0282(19) 0.0200(19) 0.029(2) -0.0051(16) -0.0051(15) -0.0062(15) N3' 0.0293(16) 0.0185(15) 0.0241(16) -0.0020(12) -0.0023(12) -0.0098(13) O1' 0.0283(14) 0.0300(15) 0.0305(15) 0.0021(12) 0.0031(11) -0.0060(12) C1' 0.033(2) 0.0194(19) 0.032(2) -0.0018(16) 0.0032(16) -0.0081(16) C2' 0.041(2) 0.0182(19) 0.041(3) -0.0061(17) 0.0082(18) -0.0066(17) C3' 0.040(2) 0.018(2) 0.053(3) 0.0018(19) -0.007(2) -0.0040(18) C4' 0.033(2) 0.026(2) 0.049(3) 0.0008(19) -0.0117(18) -0.0047(17) C5' 0.026(2) 0.034(2) 0.032(2) -0.0082(17) -0.0029(16) -0.0111(17) C6' 0.034(2) 0.026(2) 0.044(3) -0.0139(18) 0.0030(18) -0.0134(18) C7' 0.035(2) 0.0159(19) 0.044(2) -0.0065(17) -0.0041(18) -0.0047(16) C8' 0.032(2) 0.023(2) 0.028(2) 0.0000(16) -0.0033(16) -0.0103(16) C9' 0.0187(17) 0.0220(18) 0.025(2) -0.0037(15) 0.0022(14) -0.0064(14) C10' 0.026(2) 0.028(2) 0.032(2) -0.0033(17) -0.0093(16) -0.0065(17) C11' 0.0191(17) 0.0189(18) 0.033(2) -0.0044(15) 0.0042(14) -0.0076(14) C12' 0.0196(18) 0.0235(19) 0.033(2) -0.0019(16) -0.0015(15) -0.0071(15) C13' 0.0204(17) 0.024(2) 0.032(2) -0.0064(16) 0.0026(15) -0.0093(15) C14' 0.0208(18) 0.0169(17) 0.032(2) -0.0049(15) 0.0013(14) -0.0056(14) C15' 0.030(2) 0.030(2) 0.031(2) -0.0081(17) -0.0007(16) -0.0033(16) C16' 0.032(2) 0.025(2) 0.034(2) -0.0069(16) 0.0017(16) -0.0173(17) C17' 0.0240(18) 0.0204(18) 0.030(2) -0.0033(15) 0.0040(14) -0.0126(14) C18' 0.027(2) 0.0210(19) 0.039(2) -0.0070(17) 0.0085(16) -0.0080(16) C19' 0.030(2) 0.028(2) 0.039(3) 0.0049(18) 0.0088(17) -0.0044(17) C20' 0.028(2) 0.051(3) 0.026(2) 0.0002(19) -0.0027(16) -0.0101(19) C21' 0.035(2) 0.032(2) 0.033(2) -0.0073(18) 0.0042(17) -0.0143(18) C22' 0.0255(19) 0.0206(19) 0.026(2) -0.0013(15) 0.0043(15) -0.0097(15) C2A 0.0292(19) 0.0175(18) 0.028(2) -0.0047(15) -0.0051(15) -0.0048(15) C4A 0.034(2) 0.0192(18) 0.021(2) -0.0019(15) 0.0033(15) -0.0056(15) C5A 0.036(2) 0.0234(19) 0.028(2) -0.0029(16) 0.0003(16) -0.0113(17) C2A' 0.0294(19) 0.0170(17) 0.0229(19) -0.0037(14) 0.0039(14) -0.0068(15) C4A' 0.033(2) 0.0233(19) 0.023(2) -0.0082(15) -0.0022(15) -0.0065(15) C5A' 0.037(2) 0.0209(19) 0.028(2) -0.0007(15) -0.0020(16) -0.0092(16) C1B 0.032(2) 0.0205(18) 0.032(2) -0.0079(16) -0.0013(16) -0.0124(16) C2B 0.0282(19) 0.0189(19) 0.040(2) -0.0037(16) -0.0015(16) -0.0085(15) C3B 0.031(2) 0.033(2) 0.040(2) -0.0135(19) 0.0112(17) -0.0131(18) C4B 0.043(2) 0.028(2) 0.031(2) -0.0060(17) 0.0047(18) -0.0189(19) C5B 0.042(2) 0.0175(18) 0.039(2) 0.0026(16) -0.0051(18) -0.0115(17) C6B 0.028(2) 0.0206(19) 0.042(2) -0.0110(17) 0.0080(16) -0.0061(16) C1B' 0.0265(19) 0.0215(19) 0.031(2) -0.0066(16) 0.0009(15) -0.0044(15) C2B' 0.037(2) 0.0198(19) 0.045(3) -0.0051(17) -0.0137(18) -0.0103(17) C3B' 0.032(2) 0.022(2) 0.042(2) 0.0017(17) -0.0026(17) -0.0084(17) C4B' 0.034(2) 0.027(2) 0.031(2) -0.0021(17) -0.0037(17) -0.0037(17) C5B' 0.030(2) 0.028(2) 0.042(2) -0.0135(18) -0.0050(17) -0.0067(17) C6B' 0.0222(19) 0.0224(19) 0.041(2) -0.0060(16) -0.0015(16) -0.0064(15) _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 N3 C4A 1.463(4) . ? N3 C2A 1.470(5) . ? N3 C16 1.470(4) . ? O1 C2A 1.433(4) . ? O1 C5A 1.435(5) . ? C1 C2 1.365(5) . ? C1 C11 1.442(5) . ? C1 H1A 0.9300 . ? C2 C3 1.397(6) . ? C2 H2A 0.9300 . ? C3 C4 1.354(6) . ? C3 H3A 0.9300 . ? C4 C12 1.437(5) . ? C4 H4A 0.9300 . ? C5 C6 1.353(6) . ? C5 C13 1.421(5) . ? C5 H5A 0.9300 . ? C6 C7 1.414(6) . ? C6 H6A 0.9300 . ? C7 C8 1.354(5) . ? C7 H7A 0.9300 . ? C8 C14 1.440(5) . ? C8 H8A 0.9300 . ? C9 C11 1.422(5) . ? C9 C14 1.427(5) . ? C9 C2A 1.508(5) . ? C10 C12 1.389(5) . ? C10 C13 1.397(5) . ? C10 H10B 0.9300 . ? C11 C12 1.427(5) . ? C13 C14 1.425(5) . ? C15 C1B 1.504(5) . ? C15 C4A 1.532(5) . ? C15 H15C 0.9700 . ? C15 H15D 0.9700 . ? C16 C17 1.498(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C22 1.385(5) . ? C17 C18 1.395(5) . ? C18 C19 1.363(5) . ? C18 H18A 0.9300 . ? C19 C20 1.382(6) . ? C19 H19B 0.9300 . ? C20 C21 1.394(6) . ? C20 H20B 0.9300 . ? C21 C22 1.371(5) . ? C21 H21B 0.9300 . ? C22 H22A 0.9300 . ? N3' C2A' 1.468(5) . ? N3' C4A' 1.470(5) . ? N3' C16' 1.471(4) . ? O1' C2A' 1.426(4) . ? O1' C5A' 1.439(5) . ? C1' C2' 1.377(5) . ? C1' C11' 1.430(5) . ? C1' H1'A 0.9300 . ? C2' C3' 1.401(6) . ? C2' H2'A 0.9300 . ? C3' C4' 1.343(6) . ? C3' H3'A 0.9300 . ? C4' C12' 1.430(5) . ? C4' H4'A 0.9300 . ? C5' C6' 1.362(6) . ? C5' C13' 1.426(5) . ? C5' H5'A 0.9300 . ? C6' C7' 1.411(6) . ? C6' H6'A 0.9300 . ? C7' C8' 1.355(5) . ? C7' H7'A 0.9300 . ? C8' C14' 1.443(5) . ? C8' H8'A 0.9300 . ? C9' C14' 1.407(5) . ? C9' C11' 1.426(5) . ? C9' C2A' 1.513(5) . ? C10' C12' 1.381(5) . ? C10' C13' 1.392(5) . ? C10' H10A 0.9300 . ? C11' C12' 1.433(5) . ? C13' C14' 1.429(5) . ? C15' C1B' 1.504(5) . ? C15' C4A' 1.530(5) . ? C15' H15A 0.9700 . ? C15' H15B 0.9700 . ? C16' C17' 1.504(5) . ? C16' H16C 0.9700 . ? C16' H16D 0.9700 . ? C17' C22' 1.378(5) . ? C17' C18' 1.392(5) . ? C18' C19' 1.384(6) . ? C18' H18B 0.9300 . ? C19' C20' 1.380(6) . ? C19' H19A 0.9300 . ? C20' C21' 1.398(6) . ? C20' H20A 0.9300 . ? C21' C22' 1.364(5) . ? C21' H21A 0.9300 . ? C22' H22B 0.9300 . ? C2A H2AA 0.9800 . ? C4A C5A 1.514(5) . ? C4A H4AA 0.9800 . ? C5A H5AA 0.9700 . ? C5A H5AB 0.9700 . ? C2A' H2AB 0.9800 . ? C4A' C5A' 1.531(5) . ? C4A' H4AB 0.9800 . ? C5A' H5AC 0.9700 . ? C5A' H5AD 0.9700 . ? C1B C6B 1.398(5) . ? C1B C2B 1.398(5) . ? C2B C3B 1.373(5) . ? C2B H2BA 0.9300 . ? C3B C4B 1.386(6) . ? C3B H3BA 0.9300 . ? C4B C5B 1.370(6) . ? C4B H4BB 0.9300 . ? C5B C6B 1.376(6) . ? C5B H5BB 0.9300 . ? C6B H6BA 0.9300 . ? C1B' C6B' 1.385(5) . ? C1B' C2B' 1.401(5) . ? C2B' C3B' 1.381(6) . ? C2B' H2BB 0.9300 . ? C3B' C4B' 1.376(6) . ? C3B' H3BB 0.9300 . ? C4B' C5B' 1.400(6) . ? C4B' H4BA 0.9300 . ? C5B' C6B' 1.378(6) . ? C5B' H5BA 0.9300 . ? C6B' H6BB 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 C4A N3 C2A 103.1(3) . . ? C4A N3 C16 114.0(3) . . ? C2A N3 C16 112.4(3) . . ? C2A O1 C5A 107.4(3) . . ? C2 C1 C11 121.9(4) . . ? C2 C1 H1A 119.1 . . ? C11 C1 H1A 119.1 . . ? C1 C2 C3 120.7(4) . . ? C1 C2 H2A 119.6 . . ? C3 C2 H2A 119.6 . . ? C4 C3 C2 120.5(4) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C12 120.8(4) . . ? C3 C4 H4A 119.6 . . ? C12 C4 H4A 119.6 . . ? C6 C5 C13 121.2(4) . . ? C6 C5 H5A 119.4 . . ? C13 C5 H5A 119.4 . . ? C5 C6 C7 119.7(4) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C8 C7 C6 121.5(4) . . ? C8 C7 H7A 119.3 . . ? C6 C7 H7A 119.3 . . ? C7 C8 C14 120.7(4) . . ? C7 C8 H8A 119.7 . . ? C14 C8 H8A 119.7 . . ? C11 C9 C14 119.4(3) . . ? C11 C9 C2A 120.5(3) . . ? C14 C9 C2A 119.8(3) . . ? C12 C10 C13 121.3(4) . . ? C12 C10 H10B 119.4 . . ? C13 C10 H10B 119.4 . . ? C9 C11 C12 119.7(3) . . ? C9 C11 C1 124.0(3) . . ? C12 C11 C1 116.3(3) . . ? C10 C12 C11 120.1(3) . . ? C10 C12 C4 120.1(4) . . ? C11 C12 C4 119.8(3) . . ? C10 C13 C5 120.6(3) . . ? C10 C13 C14 119.8(3) . . ? C5 C13 C14 119.6(3) . . ? C13 C14 C9 119.7(3) . . ? C13 C14 C8 117.4(3) . . ? C9 C14 C8 122.9(3) . . ? C1B C15 C4A 111.3(3) . . ? C1B C15 H15C 109.4 . . ? C4A C15 H15C 109.4 . . ? C1B C15 H15D 109.4 . . ? C4A C15 H15D 109.4 . . ? H15C C15 H15D 108.0 . . ? N3 C16 C17 113.5(3) . . ? N3 C16 H16A 108.9 . . ? C17 C16 H16A 108.9 . . ? N3 C16 H16B 108.9 . . ? C17 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C22 C17 C18 117.9(3) . . ? C22 C17 C16 120.4(3) . . ? C18 C17 C16 121.8(3) . . ? C19 C18 C17 121.3(4) . . ? C19 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? C18 C19 C20 120.4(4) . . ? C18 C19 H19B 119.8 . . ? C20 C19 H19B 119.8 . . ? C19 C20 C21 119.2(4) . . ? C19 C20 H20B 120.4 . . ? C21 C20 H20B 120.4 . . ? C22 C21 C20 119.8(4) . . ? C22 C21 H21B 120.1 . . ? C20 C21 H21B 120.1 . . ? C21 C22 C17 121.4(3) . . ? C21 C22 H22A 119.3 . . ? C17 C22 H22A 119.3 . . ? C2A' N3' C4A' 103.6(3) . . ? C2A' N3' C16' 112.5(3) . . ? C4A' N3' C16' 113.9(3) . . ? C2A' O1' C5A' 108.0(3) . . ? C2' C1' C11' 121.3(4) . . ? C2' C1' H1'A 119.4 . . ? C11' C1' H1'A 119.4 . . ? C1' C2' C3' 120.8(4) . . ? C1' C2' H2'A 119.6 . . ? C3' C2' H2'A 119.6 . . ? C4' C3' C2' 120.3(4) . . ? C4' C3' H3'A 119.9 . . ? C2' C3' H3'A 119.9 . . ? C3' C4' C12' 121.4(4) . . ? C3' C4' H4'A 119.3 . . ? C12' C4' H4'A 119.3 . . ? C6' C5' C13' 121.1(4) . . ? C6' C5' H5'A 119.5 . . ? C13' C5' H5'A 119.5 . . ? C5' C6' C7' 119.4(4) . . ? C5' C6' H6'A 120.3 . . ? C7' C6' H6'A 120.3 . . ? C8' C7' C6' 121.5(4) . . ? C8' C7' H7'A 119.3 . . ? C6' C7' H7'A 119.3 . . ? C7' C8' C14' 121.6(4) . . ? C7' C8' H8'A 119.2 . . ? C14' C8' H8'A 119.2 . . ? C14' C9' C11' 119.7(3) . . ? C14' C9' C2A' 120.1(3) . . ? C11' C9' C2A' 119.9(3) . . ? C12' C10' C13' 121.7(4) . . ? C12' C10' H10A 119.1 . . ? C13' C10' H10A 119.1 . . ? C9' C11' C1' 124.2(3) . . ? C9' C11' C12' 118.9(3) . . ? C1' C11' C12' 116.8(3) . . ? C10' C12' C4' 120.4(4) . . ? C10' C12' C11' 120.2(3) . . ? C4' C12' C11' 119.4(4) . . ? C10' C13' C14' 119.2(3) . . ? C10' C13' C5' 120.8(4) . . ? C14' C13' C5' 120.1(3) . . ? C9' C14' C13' 120.3(3) . . ? C9' C14' C8' 123.3(3) . . ? C13' C14' C8' 116.4(3) . . ? C1B' C15' C4A' 111.3(3) . . ? C1B' C15' H15A 109.4 . . ? C4A' C15' H15A 109.4 . . ? C1B' C15' H15B 109.4 . . ? C4A' C15' H15B 109.4 . . ? H15A C15' H15B 108.0 . . ? N3' C16' C17' 112.6(3) . . ? N3' C16' H16C 109.1 . . ? C17' C16' H16C 109.1 . . ? N3' C16' H16D 109.1 . . ? C17' C16' H16D 109.1 . . ? H16C C16' H16D 107.8 . . ? C22' C17' C18' 118.5(4) . . ? C22' C17' C16' 119.9(3) . . ? C18' C17' C16' 121.5(3) . . ? C19' C18' C17' 120.2(4) . . ? C19' C18' H18B 119.9 . . ? C17' C18' H18B 119.9 . . ? C18' C19' C20' 120.6(4) . . ? C18' C19' H19A 119.7 . . ? C20' C19' H19A 119.7 . . ? C19' C20' C21' 118.8(4) . . ? C19' C20' H20A 120.6 . . ? C21' C20' H20A 120.6 . . ? C22' C21' C20' 120.0(4) . . ? C22' C21' H21A 120.0 . . ? C20' C21' H21A 120.0 . . ? C21' C22' C17' 121.7(3) . . ? C21' C22' H22B 119.2 . . ? C17' C22' H22B 119.2 . . ? O1 C2A N3 105.2(3) . . ? O1 C2A C9 111.0(3) . . ? N3 C2A C9 114.0(3) . . ? O1 C2A H2AA 108.8 . . ? N3 C2A H2AA 108.8 . . ? C9 C2A H2AA 108.8 . . ? N3 C4A C5A 101.7(3) . . ? N3 C4A C15 112.6(3) . . ? C5A C4A C15 113.4(3) . . ? N3 C4A H4AA 109.6 . . ? C5A C4A H4AA 109.6 . . ? C15 C4A H4AA 109.6 . . ? O1 C5A C4A 106.5(3) . . ? O1 C5A H5AA 110.4 . . ? C4A C5A H5AA 110.4 . . ? O1 C5A H5AB 110.4 . . ? C4A C5A H5AB 110.4 . . ? H5AA C5A H5AB 108.6 . . ? O1' C2A' N3' 105.2(3) . . ? O1' C2A' C9' 111.5(3) . . ? N3' C2A' C9' 113.8(3) . . ? O1' C2A' H2AB 108.7 . . ? N3' C2A' H2AB 108.7 . . ? C9' C2A' H2AB 108.7 . . ? N3' C4A' C5A' 100.9(3) . . ? N3' C4A' C15' 112.1(3) . . ? C5A' C4A' C15' 113.1(3) . . ? N3' C4A' H4AB 110.1 . . ? C5A' C4A' H4AB 110.1 . . ? C15' C4A' H4AB 110.1 . . ? O1' C5A' C4A' 106.1(3) . . ? O1' C5A' H5AC 110.5 . . ? C4A' C5A' H5AC 110.5 . . ? O1' C5A' H5AD 110.5 . . ? C4A' C5A' H5AD 110.5 . . ? H5AC C5A' H5AD 108.7 . . ? C6B C1B C2B 118.0(3) . . ? C6B C1B C15 121.7(3) . . ? C2B C1B C15 120.1(4) . . ? C3B C2B C1B 120.7(4) . . ? C3B C2B H2BA 119.6 . . ? C1B C2B H2BA 119.6 . . ? C2B C3B C4B 120.4(4) . . ? C2B C3B H3BA 119.8 . . ? C4B C3B H3BA 119.8 . . ? C5B C4B C3B 119.4(4) . . ? C5B C4B H4BB 120.3 . . ? C3B C4B H4BB 120.3 . . ? C4B C5B C6B 120.9(4) . . ? C4B C5B H5BB 119.5 . . ? C6B C5B H5BB 119.5 . . ? C5B C6B C1B 120.5(4) . . ? C5B C6B H6BA 119.8 . . ? C1B C6B H6BA 119.8 . . ? C6B' C1B' C2B' 118.1(4) . . ? C6B' C1B' C15' 121.0(4) . . ? C2B' C1B' C15' 120.8(4) . . ? C3B' C2B' C1B' 120.2(4) . . ? C3B' C2B' H2BB 119.9 . . ? C1B' C2B' H2BB 119.9 . . ? C4B' C3B' C2B' 121.4(4) . . ? C4B' C3B' H3BB 119.3 . . ? C2B' C3B' H3BB 119.3 . . ? C3B' C4B' C5B' 118.7(4) . . ? C3B' C4B' H4BA 120.7 . . ? C5B' C4B' H4BA 120.7 . . ? C6B' C5B' C4B' 119.9(4) . . ? C6B' C5B' H5BA 120.1 . . ? C4B' C5B' H5BA 120.1 . . ? C5B' C6B' C1B' 121.7(4) . . ? C5B' C6B' H6BB 119.2 . . ? C1B' C6B' H6BB 119.2 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.339 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.056 # Attachment 'Compound_12.CIF' data_osj11m _database_code_depnum_ccdc_archive 'CCDC 614835' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H30 Cl2 N2 O3' _chemical_formula_weight 549.47 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.6834(10) _cell_length_b 10.5554(14) _cell_length_c 16.299(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.517(2) _cell_angle_gamma 90.00 _cell_volume 1319.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6694 _cell_measurement_theta_min 4.600 _cell_measurement_theta_max 54.909 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.283 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8737 _exptl_absorpt_correction_T_max 0.9300 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11779 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.62 _reflns_number_total 3123 _reflns_number_gt 2922 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.3111P] 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 1(10) _refine_ls_number_reflns 3123 _refine_ls_number_parameters 346 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0766 _refine_ls_wR_factor_gt 0.0745 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.5444(2) 1.02323(19) 0.33387(11) 0.0228(4) Uani 1 1 d . . . N3 N -0.0313(2) 0.80366(18) 0.14898(11) 0.0200(4) Uani 1 1 d . . . O1 O 0.1959(2) 0.91189(16) 0.10167(9) 0.0237(3) Uani 1 1 d . . . O2 O 0.5188(2) 1.19964(17) 0.41408(10) 0.0301(4) Uani 1 1 d . . . O3 O 0.5193(2) 0.87321(17) 0.23274(10) 0.0287(4) Uani 1 1 d . . . C1 C -0.1398(3) 1.0750(2) 0.15607(13) 0.0219(4) Uani 1 1 d . . . H1 H -0.1474 1.0073 0.1176 0.026 Uiso 1 1 calc R . . C1B C -0.2448(3) 0.8020(2) -0.02045(14) 0.0245(5) Uani 1 1 d . . . C2 C -0.2589(3) 1.1751(2) 0.14946(14) 0.0248(5) Uani 1 1 d . . . H2 H -0.3486 1.1739 0.1067 0.030 Uiso 1 1 calc R . . C2A C 0.1353(3) 0.8638(2) 0.17615(12) 0.0189(4) Uani 1 1 d . . . H2A H 0.2179 0.7975 0.1986 0.023 Uiso 1 1 calc R . . C2B C -0.2121(3) 0.8444(3) -0.09908(14) 0.0286(5) Uani 1 1 d . . . H2B H -0.1259 0.8029 -0.1288 0.034 Uiso 1 1 calc R . . C3 C -0.2492(3) 1.2753(2) 0.20347(14) 0.0270(5) Uani 1 1 d . . . H3 H -0.3310 1.3427 0.1978 0.032 Uiso 1 1 calc R . . C3B C -0.3028(3) 0.9458(3) -0.13469(15) 0.0317(5) Uani 1 1 d . . . H3B H -0.2782 0.9735 -0.1882 0.038 Uiso 1 1 calc R . . C4 C -0.1178(3) 1.2773(2) 0.26692(14) 0.0250(5) Uani 1 1 d . . . H4 H -0.1091 1.3464 0.3043 0.030 Uiso 1 1 calc R . . C4A C 0.0165(3) 0.7333(2) 0.07564(13) 0.0228(5) Uani 1 1 d . . . H4A H 0.0809 0.6550 0.0941 0.027 Uiso 1 1 calc R . . C4B C -0.4296(3) 1.0069(3) -0.09228(15) 0.0325(5) Uani 1 1 d . . . H4B H -0.4915 1.0768 -0.1164 0.039 Uiso 1 1 calc R . . C5 C 0.1392(3) 1.0242(2) 0.46625(13) 0.0240(5) Uani 1 1 d . . . H5 H 0.1398 1.0954 0.5020 0.029 Uiso 1 1 calc R . . C5A C 0.1447(3) 0.8234(3) 0.03821(14) 0.0284(5) Uani 1 1 d . . . H5A1 H 0.2473 0.7765 0.0203 0.034 Uiso 1 1 calc R . . H5A2 H 0.0884 0.8678 -0.0099 0.034 Uiso 1 1 calc R . . C5B C -0.4650(3) 0.9652(3) -0.01468(16) 0.0301(5) Uani 1 1 d . . . H5B H -0.5521 1.0064 0.0145 0.036 Uiso 1 1 calc R . . C6 C 0.1435(3) 0.9027(3) 0.49798(14) 0.0289(5) Uani 1 1 d . . . H6 H 0.1427 0.8901 0.5557 0.035 Uiso 1 1 calc R . . C6B C -0.3742(3) 0.8637(3) 0.02080(14) 0.0271(5) Uani 1 1 d . . . H6B H -0.4005 0.8357 0.0740 0.033 Uiso 1 1 calc R . . C7 C 0.1491(3) 0.7999(2) 0.44609(14) 0.0264(5) Uani 1 1 d . . . H7 H 0.1559 0.7168 0.4685 0.032 Uiso 1 1 calc R . . C8 C 0.1447(3) 0.8163(2) 0.36097(14) 0.0216(4) Uani 1 1 d . . . H8 H 0.1508 0.7450 0.3257 0.026 Uiso 1 1 calc R . . C9 C 0.1335(2) 0.9753(2) 0.23721(12) 0.0171(4) Uani 1 1 d . . . C10 C 0.1455(3) 1.1680(2) 0.34044(13) 0.0207(4) Uani 1 1 d . . . H10 H 0.1445 1.2399 0.3804 0.025 Uiso 1 1 calc R . . C11 C -0.0094(3) 1.0755(2) 0.21976(12) 0.0194(4) Uani 1 1 d . . . C12 C -0.0006(3) 1.1776(2) 0.27468(13) 0.0206(4) Uani 1 1 d . . . C13 C 0.1340(2) 1.0413(2) 0.38198(12) 0.0189(4) Uani 1 1 d . . . C14 C 0.1315(2) 0.9379(2) 0.32844(13) 0.0184(4) Uani 1 1 d . . . C16 C 0.3180(3) 1.1637(2) 0.29409(13) 0.0212(4) Uani 1 1 d . . . H16 H 0.3362 1.2452 0.2645 0.025 Uiso 1 1 calc R . . C15 C -0.1408(3) 0.6939(2) 0.01819(14) 0.0261(5) Uani 1 1 d . . . H15A H -0.0982 0.6403 -0.0262 0.031 Uiso 1 1 calc R . . H15B H -0.2196 0.6413 0.0498 0.031 Uiso 1 1 calc R . . C17 C 0.3121(3) 1.0511(2) 0.23363(12) 0.0194(4) Uani 1 1 d . . . H17 H 0.3265 1.0821 0.1765 0.023 Uiso 1 1 calc R . . C18 C 0.4707(3) 1.1362(2) 0.35487(13) 0.0220(4) Uani 1 1 d . . . C19 C 0.4674(3) 0.9696(2) 0.26244(13) 0.0215(5) Uani 1 1 d . . . C20 C 0.6869(3) 0.9620(3) 0.38179(16) 0.0333(6) Uani 1 1 d . . . H20A H 0.7771 0.9363 0.3452 0.050 Uiso 1 1 calc R . . H20B H 0.6427 0.8872 0.4094 0.050 Uiso 1 1 calc R . . H20C H 0.7368 1.0215 0.4230 0.050 Uiso 1 1 calc R . . C21 C -0.1084(3) 0.7213(2) 0.20827(15) 0.0270(5) Uani 1 1 d . . . H21A H -0.2181 0.6864 0.1841 0.041 Uiso 1 1 calc R . . H21B H -0.1314 0.7700 0.2576 0.041 Uiso 1 1 calc R . . H21C H -0.0277 0.6519 0.2231 0.041 Uiso 1 1 calc R . . Cl1 Cl 0.75463(8) -0.00878(6) 0.62602(4) 0.03930(16) Uani 1 1 d . . . Cl2 Cl 0.41100(12) 0.07797(10) 0.66852(5) 0.0594(2) Uani 1 1 d . . . C1S C 0.5334(3) 0.0131(3) 0.59117(16) 0.0362(6) Uani 1 1 d . . . H1S1 H 0.5274 0.0703 0.5429 0.043 Uiso 1 1 calc R . . H1S2 H 0.4826 -0.0695 0.5736 0.043 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 0.0158(8) 0.0301(11) 0.0222(9) -0.0014(8) -0.0006(6) 0.0001(7) N3 0.0202(8) 0.0203(9) 0.0195(8) -0.0029(7) 0.0000(6) -0.0014(7) O1 0.0272(8) 0.0276(8) 0.0165(7) -0.0037(7) 0.0033(6) -0.0059(7) O2 0.0310(8) 0.0305(9) 0.0276(9) -0.0057(7) -0.0068(7) -0.0047(7) O3 0.0227(8) 0.0302(9) 0.0332(9) -0.0067(8) 0.0025(6) 0.0044(7) C1 0.0231(10) 0.0236(11) 0.0189(10) 0.0019(9) 0.0009(8) -0.0013(9) C1B 0.0209(10) 0.0276(12) 0.0245(11) -0.0071(10) -0.0029(8) -0.0069(9) C2 0.0232(10) 0.0299(13) 0.0208(10) 0.0068(9) -0.0016(8) 0.0025(9) C2A 0.0186(9) 0.0207(11) 0.0175(9) -0.0005(8) 0.0016(7) 0.0000(8) C2B 0.0264(11) 0.0356(14) 0.0238(11) -0.0079(10) 0.0017(8) -0.0055(10) C3 0.0267(11) 0.0283(12) 0.0262(11) 0.0056(10) 0.0026(9) 0.0084(9) C3B 0.0326(12) 0.0382(15) 0.0241(12) 0.0006(10) -0.0009(9) -0.0087(11) C4 0.0294(11) 0.0247(12) 0.0211(11) 0.0027(9) 0.0037(9) 0.0048(9) C4A 0.0221(10) 0.0234(11) 0.0228(11) -0.0042(9) 0.0007(8) 0.0012(9) C4B 0.0268(11) 0.0348(14) 0.0345(13) -0.0003(11) -0.0088(9) -0.0020(11) C5 0.0247(10) 0.0286(12) 0.0188(10) -0.0020(9) 0.0009(8) 0.0002(9) C5A 0.0258(11) 0.0380(14) 0.0215(11) -0.0107(10) 0.0018(8) -0.0055(10) C5B 0.0199(10) 0.0378(15) 0.0323(13) -0.0062(11) -0.0010(9) -0.0011(10) C6 0.0285(11) 0.0403(14) 0.0176(10) 0.0066(10) 0.0008(8) -0.0012(10) C6B 0.0224(10) 0.0363(13) 0.0226(11) -0.0044(10) 0.0011(8) -0.0054(9) C7 0.0287(11) 0.0255(12) 0.0250(11) 0.0101(10) 0.0005(8) 0.0012(9) C8 0.0195(10) 0.0226(11) 0.0224(10) 0.0008(9) -0.0001(8) -0.0009(9) C9 0.0156(8) 0.0187(10) 0.0168(9) 0.0012(8) -0.0001(7) 0.0002(8) C10 0.0244(10) 0.0200(11) 0.0175(10) -0.0021(8) 0.0002(8) 0.0017(8) C11 0.0193(9) 0.0207(10) 0.0184(10) 0.0043(8) 0.0023(7) 0.0021(8) C12 0.0227(10) 0.0217(11) 0.0175(10) 0.0026(8) 0.0021(7) 0.0009(8) C13 0.0143(9) 0.0228(11) 0.0195(10) 0.0024(8) 0.0004(7) 0.0001(8) C14 0.0135(9) 0.0235(11) 0.0182(10) 0.0019(8) 0.0008(7) 0.0006(8) C16 0.0233(10) 0.0209(11) 0.0189(10) 0.0006(8) -0.0009(8) -0.0029(8) C15 0.0264(11) 0.0250(12) 0.0266(12) -0.0082(10) -0.0004(8) -0.0044(9) C17 0.0191(9) 0.0215(11) 0.0176(10) -0.0012(8) 0.0018(7) -0.0029(8) C18 0.0201(10) 0.0257(12) 0.0202(10) 0.0018(9) 0.0009(8) -0.0064(9) C19 0.0169(9) 0.0264(12) 0.0214(10) -0.0001(9) 0.0040(7) -0.0040(8) C20 0.0218(10) 0.0453(16) 0.0318(12) -0.0059(11) -0.0055(9) 0.0080(10) C21 0.0262(11) 0.0277(12) 0.0272(12) -0.0013(10) 0.0019(9) -0.0060(9) Cl1 0.0418(3) 0.0252(3) 0.0502(4) 0.0024(3) -0.0035(3) 0.0012(3) Cl2 0.0647(5) 0.0738(6) 0.0405(4) -0.0111(4) 0.0101(3) 0.0213(4) C1S 0.0395(13) 0.0382(16) 0.0309(13) -0.0026(11) 0.0021(10) 0.0044(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C18 1.372(3) . ? N1 C19 1.394(3) . ? N1 C20 1.456(3) . ? N3 C21 1.453(3) . ? N3 C2A 1.472(3) . ? N3 C4A 1.473(3) . ? O1 C2A 1.420(2) . ? O1 C5A 1.431(3) . ? O2 C18 1.214(3) . ? O3 C19 1.205(3) . ? C1 C2 1.397(3) . ? C1 C11 1.398(3) . ? C1 H1 0.9500 . ? C1B C2B 1.395(3) . ? C1B C6B 1.396(3) . ? C1B C15 1.509(3) . ? C2 C3 1.375(3) . ? C2 H2 0.9500 . ? C2A C9 1.542(3) . ? C2A H2A 1.0000 . ? C2B C3B 1.385(4) . ? C2B H2B 0.9500 . ? C3 C4 1.400(3) . ? C3 H3 0.9500 . ? C3B C4B 1.387(4) . ? C3B H3B 0.9500 . ? C4 C12 1.386(3) . ? C4 H4 0.9500 . ? C4A C5A 1.524(3) . ? C4A C15 1.540(3) . ? C4A H4A 1.0000 . ? C4B C5B 1.382(4) . ? C4B H4B 0.9500 . ? C5 C6 1.383(4) . ? C5 C13 1.383(3) . ? C5 H5 0.9500 . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C5B C6B 1.385(4) . ? C5B H5B 0.9500 . ? C6 C7 1.378(4) . ? C6 H6 0.9500 . ? C6B H6B 0.9500 . ? C7 C8 1.396(3) . ? C7 H7 0.9500 . ? C8 C14 1.390(3) . ? C8 H8 0.9500 . ? C9 C11 1.538(3) . ? C9 C14 1.540(3) . ? C9 C17 1.593(3) . ? C10 C13 1.504(3) . ? C10 C12 1.507(3) . ? C10 C16 1.566(3) . ? C10 H10 1.0000 . ? C11 C12 1.400(3) . ? C13 C14 1.397(3) . ? C16 C18 1.517(3) . ? C16 C17 1.542(3) . ? C16 H16 1.0000 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C17 C19 1.522(3) . ? C17 H17 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? Cl1 C1S 1.774(3) . ? Cl2 C1S 1.758(3) . ? C1S H1S1 0.9900 . ? C1S H1S2 0.9900 . ? 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 C18 N1 C19 113.63(18) . . ? C18 N1 C20 124.04(19) . . ? C19 N1 C20 122.3(2) . . ? C21 N3 C2A 116.14(17) . . ? C21 N3 C4A 111.71(18) . . ? C2A N3 C4A 101.92(15) . . ? C2A O1 C5A 107.15(17) . . ? C2 C1 C11 119.4(2) . . ? C2 C1 H1 120.3 . . ? C11 C1 H1 120.3 . . ? C2B C1B C6B 117.8(2) . . ? C2B C1B C15 120.4(2) . . ? C6B C1B C15 121.8(2) . . ? C3 C2 C1 121.5(2) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? O1 C2A N3 102.81(16) . . ? O1 C2A C9 107.19(17) . . ? N3 C2A C9 118.78(16) . . ? O1 C2A H2A 109.2 . . ? N3 C2A H2A 109.2 . . ? C9 C2A H2A 109.2 . . ? C3B C2B C1B 121.2(2) . . ? C3B C2B H2B 119.4 . . ? C1B C2B H2B 119.4 . . ? C2 C3 C4 119.5(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C2B C3B C4B 120.1(2) . . ? C2B C3B H3B 120.0 . . ? C4B C3B H3B 120.0 . . ? C12 C4 C3 119.4(2) . . ? C12 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N3 C4A C5A 102.09(18) . . ? N3 C4A C15 113.86(17) . . ? C5A C4A C15 115.31(19) . . ? N3 C4A H4A 108.4 . . ? C5A C4A H4A 108.4 . . ? C15 C4A H4A 108.4 . . ? C5B C4B C3B 119.4(2) . . ? C5B C4B H4B 120.3 . . ? C3B C4B H4B 120.3 . . ? C6 C5 C13 119.4(2) . . ? C6 C5 H5 120.3 . . ? C13 C5 H5 120.3 . . ? O1 C5A C4A 105.90(17) . . ? O1 C5A H5A1 110.6 . . ? C4A C5A H5A1 110.6 . . ? O1 C5A H5A2 110.6 . . ? C4A C5A H5A2 110.6 . . ? H5A1 C5A H5A2 108.7 . . ? C4B C5B C6B 120.4(2) . . ? C4B C5B H5B 119.8 . . ? C6B C5B H5B 119.8 . . ? C7 C6 C5 120.1(2) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C5B C6B C1B 121.0(2) . . ? C5B C6B H6B 119.5 . . ? C1B C6B H6B 119.5 . . ? C6 C7 C8 120.8(2) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C14 C8 C7 119.3(2) . . ? C14 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C11 C9 C14 107.80(16) . . ? C11 C9 C2A 116.10(16) . . ? C14 C9 C2A 115.38(17) . . ? C11 C9 C17 104.76(16) . . ? C14 C9 C17 102.94(15) . . ? C2A C9 C17 108.54(15) . . ? C13 C10 C12 108.51(18) . . ? C13 C10 C16 105.42(17) . . ? C12 C10 C16 105.93(17) . . ? C13 C10 H10 112.2 . . ? C12 C10 H10 112.2 . . ? C16 C10 H10 112.2 . . ? C1 C11 C12 118.8(2) . . ? C1 C11 C9 127.27(19) . . ? C12 C11 C9 113.88(17) . . ? C4 C12 C11 121.36(19) . . ? C4 C12 C10 124.5(2) . . ? C11 C12 C10 114.09(19) . . ? C5 C13 C14 121.1(2) . . ? C5 C13 C10 124.3(2) . . ? C14 C13 C10 114.37(17) . . ? C8 C14 C13 119.04(19) . . ? C8 C14 C9 126.90(19) . . ? C13 C14 C9 113.72(18) . . ? C18 C16 C17 105.15(18) . . ? C18 C16 C10 109.53(17) . . ? C17 C16 C10 109.76(17) . . ? C18 C16 H16 110.8 . . ? C17 C16 H16 110.8 . . ? C10 C16 H16 110.8 . . ? C1B C15 C4A 115.2(2) . . ? C1B C15 H15A 108.5 . . ? C4A C15 H15A 108.5 . . ? C1B C15 H15B 108.5 . . ? C4A C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C19 C17 C16 104.27(16) . . ? C19 C17 C9 111.44(17) . . ? C16 C17 C9 110.82(16) . . ? C19 C17 H17 110.1 . . ? C16 C17 H17 110.1 . . ? C9 C17 H17 110.1 . . ? O2 C18 N1 124.6(2) . . ? O2 C18 C16 126.8(2) . . ? N1 C18 C16 108.54(18) . . ? O3 C19 N1 123.0(2) . . ? O3 C19 C17 128.8(2) . . ? N1 C19 C17 108.23(18) . . ? N1 C20 H20A 109.5 . . ? N1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? Cl2 C1S Cl1 111.44(14) . . ? Cl2 C1S H1S1 109.3 . . ? Cl1 C1S H1S1 109.3 . . ? Cl2 C1S H1S2 109.3 . . ? Cl1 C1S H1S2 109.3 . . ? H1S1 C1S H1S2 108.0 . . ? 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 C1 C2 C3 1.1(3) . . . . ? C5A O1 C2A N3 -35.4(2) . . . . ? C5A O1 C2A C9 -161.32(16) . . . . ? C21 N3 C2A O1 167.00(18) . . . . ? C4A N3 C2A O1 45.4(2) . . . . ? C21 N3 C2A C9 -74.9(2) . . . . ? C4A N3 C2A C9 163.43(18) . . . . ? C6B C1B C2B C3B 1.1(3) . . . . ? C15 C1B C2B C3B -178.2(2) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C1B C2B C3B C4B -0.3(4) . . . . ? C2 C3 C4 C12 -0.6(3) . . . . ? C21 N3 C4A C5A -161.71(18) . . . . ? C2A N3 C4A C5A -37.0(2) . . . . ? C21 N3 C4A C15 73.3(2) . . . . ? C2A N3 C4A C15 -161.99(19) . . . . ? C2B C3B C4B C5B -0.4(4) . . . . ? C2A O1 C5A C4A 11.7(2) . . . . ? N3 C4A C5A O1 16.4(2) . . . . ? C15 C4A C5A O1 140.36(19) . . . . ? C3B C4B C5B C6B 0.4(4) . . . . ? C13 C5 C6 C7 2.4(3) . . . . ? C4B C5B C6B C1B 0.4(4) . . . . ? C2B C1B C6B C5B -1.1(3) . . . . ? C15 C1B C6B C5B 178.1(2) . . . . ? C5 C6 C7 C8 -2.1(3) . . . . ? C6 C7 C8 C14 -1.2(3) . . . . ? O1 C2A C9 C11 72.0(2) . . . . ? N3 C2A C9 C11 -43.8(3) . . . . ? O1 C2A C9 C14 -160.50(16) . . . . ? N3 C2A C9 C14 83.7(2) . . . . ? O1 C2A C9 C17 -45.6(2) . . . . ? N3 C2A C9 C17 -161.40(17) . . . . ? C2 C1 C11 C12 -0.8(3) . . . . ? C2 C1 C11 C9 -179.7(2) . . . . ? C14 C9 C11 C1 -129.5(2) . . . . ? C2A C9 C11 C1 1.7(3) . . . . ? C17 C9 C11 C1 121.3(2) . . . . ? C14 C9 C11 C12 51.6(2) . . . . ? C2A C9 C11 C12 -177.23(18) . . . . ? C17 C9 C11 C12 -57.5(2) . . . . ? C3 C4 C12 C11 0.8(3) . . . . ? C3 C4 C12 C10 -179.6(2) . . . . ? C1 C11 C12 C4 -0.1(3) . . . . ? C9 C11 C12 C4 178.90(19) . . . . ? C1 C11 C12 C10 -179.74(19) . . . . ? C9 C11 C12 C10 -0.7(3) . . . . ? C13 C10 C12 C4 128.0(2) . . . . ? C16 C10 C12 C4 -119.3(2) . . . . ? C13 C10 C12 C11 -52.4(2) . . . . ? C16 C10 C12 C11 60.4(2) . . . . ? C6 C5 C13 C14 0.6(3) . . . . ? C6 C5 C13 C10 -174.1(2) . . . . ? C12 C10 C13 C5 -130.7(2) . . . . ? C16 C10 C13 C5 116.2(2) . . . . ? C12 C10 C13 C14 54.3(2) . . . . ? C16 C10 C13 C14 -58.8(2) . . . . ? C7 C8 C14 C13 4.0(3) . . . . ? C7 C8 C14 C9 176.93(19) . . . . ? C5 C13 C14 C8 -3.7(3) . . . . ? C10 C13 C14 C8 171.42(18) . . . . ? C5 C13 C14 C9 -177.57(18) . . . . ? C10 C13 C14 C9 -2.4(2) . . . . ? C11 C9 C14 C8 136.9(2) . . . . ? C2A C9 C14 C8 5.4(3) . . . . ? C17 C9 C14 C8 -112.7(2) . . . . ? C11 C9 C14 C13 -49.8(2) . . . . ? C2A C9 C14 C13 178.61(16) . . . . ? C17 C9 C14 C13 60.6(2) . . . . ? C13 C10 C16 C18 -57.5(2) . . . . ? C12 C10 C16 C18 -172.38(18) . . . . ? C13 C10 C16 C17 57.5(2) . . . . ? C12 C10 C16 C17 -57.4(2) . . . . ? C2B C1B C15 C4A 95.8(2) . . . . ? C6B C1B C15 C4A -83.5(3) . . . . ? N3 C4A C15 C1B 63.7(3) . . . . ? C5A C4A C15 C1B -53.8(3) . . . . ? C18 C16 C17 C19 -2.2(2) . . . . ? C10 C16 C17 C19 -119.94(18) . . . . ? C18 C16 C17 C9 117.80(18) . . . . ? C10 C16 C17 C9 0.1(2) . . . . ? C11 C9 C17 C19 171.36(16) . . . . ? C14 C9 C17 C19 58.7(2) . . . . ? C2A C9 C17 C19 -64.0(2) . . . . ? C11 C9 C17 C16 55.7(2) . . . . ? C14 C9 C17 C16 -56.9(2) . . . . ? C2A C9 C17 C16 -179.65(17) . . . . ? C19 N1 C18 O2 -179.1(2) . . . . ? C20 N1 C18 O2 2.3(3) . . . . ? C19 N1 C18 C16 3.0(2) . . . . ? C20 N1 C18 C16 -175.6(2) . . . . ? C17 C16 C18 O2 -178.1(2) . . . . ? C10 C16 C18 O2 -60.2(3) . . . . ? C17 C16 C18 N1 -0.3(2) . . . . ? C10 C16 C18 N1 117.61(19) . . . . ? C18 N1 C19 O3 176.9(2) . . . . ? C20 N1 C19 O3 -4.5(3) . . . . ? C18 N1 C19 C17 -4.5(2) . . . . ? C20 N1 C19 C17 174.10(19) . . . . ? C16 C17 C19 O3 -177.5(2) . . . . ? C9 C17 C19 O3 62.9(3) . . . . ? C16 C17 C19 N1 4.0(2) . . . . ? C9 C17 C19 N1 -115.61(18) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.264 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.040 # Attachment 'Compound_17.CIF' data_osj17m _database_code_depnum_ccdc_archive 'CCDC 614836' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H32 N2 O3' _chemical_formula_weight 540.64 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.3383(14) _cell_length_b 9.6773(13) _cell_length_c 14.613(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.054(2) _cell_angle_gamma 90.00 _cell_volume 1390.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4364 _cell_measurement_theta_min 5.130 _cell_measurement_theta_max 53.169 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9640 _exptl_absorpt_correction_T_max 0.9830 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker smart1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15882 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3373 _reflns_number_gt 2690 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0493P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 3373 _refine_ls_number_parameters 370 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 1.2683(2) 0.7440(2) 0.54102(15) 0.0227(5) Uani 1 1 d . . . N3 N 0.9191(2) 0.6517(2) 0.77341(15) 0.0204(4) Uani 1 1 d . . . O1 O 0.85892(16) 0.69758(19) 0.61501(12) 0.0260(4) Uani 1 1 d . . . O2 O 1.39751(19) 0.5709(2) 0.50682(15) 0.0332(5) Uani 1 1 d . . . O3 O 1.10344(19) 0.87142(18) 0.57615(14) 0.0293(4) Uani 1 1 d . . . C1 C 0.9323(3) 0.3746(3) 0.68976(18) 0.0219(5) Uani 1 1 d . . . H1A H 0.8621 0.4311 0.6989 0.026 Uiso 1 1 calc R . . C2 C 0.9190(3) 0.2313(3) 0.68704(18) 0.0260(6) Uani 1 1 d . . . H2A H 0.8403 0.1907 0.6962 0.031 Uiso 1 1 calc R . . C3 C 1.0183(3) 0.1468(3) 0.67117(19) 0.0264(6) Uani 1 1 d . . . H3A H 1.0076 0.0492 0.6696 0.032 Uiso 1 1 calc R . . C4 C 1.1332(3) 0.2056(3) 0.65767(18) 0.0235(6) Uani 1 1 d . . . H4A H 1.2010 0.1487 0.6455 0.028 Uiso 1 1 calc R . . C5 C 1.4601(2) 0.5379(3) 0.77537(18) 0.0232(6) Uani 1 1 d . . . H5A H 1.5243 0.4769 0.7626 0.028 Uiso 1 1 calc R . . C6 C 1.5034(2) 0.6413(3) 0.84421(19) 0.0256(6) Uani 1 1 d . . . H6A H 1.5972 0.6495 0.8797 0.031 Uiso 1 1 calc R . . C7 C 1.4102(2) 0.7324(3) 0.86108(18) 0.0247(5) Uani 1 1 d . . . H7A H 1.4403 0.8042 0.9071 0.030 Uiso 1 1 calc R . . C8 C 1.2724(2) 0.7191(3) 0.81101(18) 0.0216(5) Uani 1 1 d . . . H8A H 1.2089 0.7825 0.8224 0.026 Uiso 1 1 calc R . . C9 C 1.0809(2) 0.5890(2) 0.67802(17) 0.0186(5) Uani 1 1 d . . . C10 C 1.2636(2) 0.4257(2) 0.64308(18) 0.0211(5) Uani 1 1 d . . . H10A H 1.3338 0.3620 0.6324 0.025 Uiso 1 1 calc R . . C11 C 1.0490(2) 0.4343(2) 0.67902(17) 0.0192(5) Uani 1 1 d . . . C12 C 1.1486(2) 0.3483(2) 0.66198(18) 0.0206(5) Uani 1 1 d . . . C13 C 1.3235(2) 0.5243(2) 0.72572(18) 0.0203(5) Uani 1 1 d . . . C14 C 1.2275(2) 0.6130(2) 0.74418(17) 0.0182(5) Uani 1 1 d . . . C15 C 0.8398(3) 0.8956(3) 0.7921(2) 0.0274(6) Uani 1 1 d . . . H15A H 0.9158 0.8931 0.8533 0.033 Uiso 1 1 calc R . . H15B H 0.8722 0.9451 0.7441 0.033 Uiso 1 1 calc R . . C16 C 1.1958(2) 0.5165(3) 0.55322(18) 0.0213(5) Uani 1 1 d . . . H16A H 1.1495 0.4567 0.4968 0.026 Uiso 1 1 calc R . . C17 C 1.0926(2) 0.6167(2) 0.57419(17) 0.0191(5) Uani 1 1 d . . . H17A H 1.0015 0.6050 0.5247 0.023 Uiso 1 1 calc R . . C18 C 1.2999(3) 0.6078(3) 0.52989(18) 0.0230(6) Uani 1 1 d . . . C19 C 1.1492(2) 0.7603(2) 0.56519(17) 0.0205(5) Uani 1 1 d . . . C20 C 1.3484(3) 0.8614(3) 0.5263(2) 0.0336(7) Uani 1 1 d . . . H20A H 1.4278 0.8276 0.5098 0.050 Uiso 1 1 calc R . . H20B H 1.3788 0.9164 0.5854 0.050 Uiso 1 1 calc R . . H20C H 1.2924 0.9189 0.4737 0.050 Uiso 1 1 calc R . . C21 C 1.0070(2) 0.6334(3) 0.87210(18) 0.0238(6) Uani 1 1 d . . . H21A H 1.0551 0.7210 0.8959 0.029 Uiso 1 1 calc R . . H21B H 1.0761 0.5618 0.8738 0.029 Uiso 1 1 calc R . . C22 C 0.9246(2) 0.5906(3) 0.93685(18) 0.0235(5) Uani 1 1 d . . . C23 C 0.9260(3) 0.6718(3) 1.01522(19) 0.0296(6) Uani 1 1 d . . . H23A H 0.9806 0.7528 1.0287 0.036 Uiso 1 1 calc R . . C24 C 0.8483(3) 0.6364(3) 1.0747(2) 0.0323(6) Uani 1 1 d . . . H24A H 0.8493 0.6933 1.1278 0.039 Uiso 1 1 calc R . . C25 C 0.7705(3) 0.5184(3) 1.0556(2) 0.0321(7) Uani 1 1 d . . . H25A H 0.7173 0.4939 1.0957 0.039 Uiso 1 1 calc R . . C26 C 0.7692(3) 0.4348(3) 0.9780(2) 0.0320(7) Uani 1 1 d . . . H26A H 0.7162 0.3527 0.9656 0.038 Uiso 1 1 calc R . . C27 C 0.8453(3) 0.4717(3) 0.9189(2) 0.0275(6) Uani 1 1 d . . . H27A H 0.8433 0.4151 0.8654 0.033 Uiso 1 1 calc R . . C2A C 0.9773(2) 0.6890(2) 0.69785(18) 0.0189(5) Uani 1 1 d . . . H2AA H 1.0195 0.7828 0.7119 0.023 Uiso 1 1 calc R . . C4A C 0.8023(2) 0.7450(3) 0.75687(18) 0.0215(5) Uani 1 1 d . . . H4AA H 0.7361 0.7062 0.7875 0.026 Uiso 1 1 calc R . . C5A C 0.7447(2) 0.7316(3) 0.64730(19) 0.0269(6) Uani 1 1 d . . . H5AA H 0.6751 0.6578 0.6295 0.032 Uiso 1 1 calc R . . H5AB H 0.7027 0.8196 0.6183 0.032 Uiso 1 1 calc R . . C1B C 0.7232(2) 0.9753(3) 0.8079(2) 0.0263(6) Uani 1 1 d . . . C2B C 0.7115(3) 0.9858(3) 0.9002(2) 0.0381(7) Uani 1 1 d . . . H2BA H 0.7764 0.9419 0.9528 0.046 Uiso 1 1 calc R . . C3B C 0.6046(4) 1.0609(4) 0.9156(3) 0.0562(11) Uani 1 1 d . . . H3BA H 0.5962 1.0670 0.9784 0.067 Uiso 1 1 calc R . . C4B C 0.5112(4) 1.1261(3) 0.8391(4) 0.0596(12) Uani 1 1 d . . . H4BA H 0.4389 1.1778 0.8496 0.072 Uiso 1 1 calc R . . C5B C 0.5225(3) 1.1166(3) 0.7490(3) 0.0495(9) Uani 1 1 d . . . H5BA H 0.4582 1.1620 0.6967 0.059 Uiso 1 1 calc R . . C6B C 0.6272(3) 1.0413(3) 0.7333(2) 0.0336(7) Uani 1 1 d . . . H6BA H 0.6333 1.0347 0.6699 0.040 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 0.0204(10) 0.0220(10) 0.0265(12) 0.0006(10) 0.0087(9) -0.0017(9) N3 0.0197(10) 0.0213(10) 0.0229(11) 0.0012(9) 0.0106(9) 0.0033(8) O1 0.0172(8) 0.0370(10) 0.0232(10) 0.0021(8) 0.0053(7) 0.0069(7) O2 0.0280(10) 0.0350(11) 0.0445(12) 0.0002(9) 0.0227(9) 0.0040(8) O3 0.0352(10) 0.0201(9) 0.0357(11) 0.0043(8) 0.0156(9) 0.0059(8) C1 0.0210(13) 0.0234(12) 0.0216(14) -0.0016(11) 0.0070(11) -0.0005(10) C2 0.0266(13) 0.0263(13) 0.0268(14) -0.0038(12) 0.0108(11) -0.0086(11) C3 0.0350(15) 0.0185(12) 0.0248(14) -0.0015(11) 0.0081(12) -0.0015(11) C4 0.0250(13) 0.0216(13) 0.0230(14) -0.0007(11) 0.0062(11) 0.0037(10) C5 0.0193(12) 0.0240(13) 0.0276(14) 0.0065(11) 0.0093(11) 0.0046(10) C6 0.0185(12) 0.0318(14) 0.0245(14) 0.0036(12) 0.0040(10) -0.0020(11) C7 0.0236(13) 0.0268(13) 0.0229(13) -0.0021(11) 0.0062(11) -0.0047(11) C8 0.0213(12) 0.0221(12) 0.0242(14) 0.0008(10) 0.0110(10) -0.0020(10) C9 0.0180(12) 0.0179(11) 0.0200(13) 0.0014(10) 0.0061(10) 0.0016(9) C10 0.0182(12) 0.0196(12) 0.0267(14) -0.0013(11) 0.0087(10) 0.0035(10) C11 0.0219(13) 0.0165(11) 0.0187(13) 0.0014(10) 0.0057(10) 0.0011(10) C12 0.0221(13) 0.0206(12) 0.0184(13) 0.0012(10) 0.0052(10) 0.0023(10) C13 0.0180(12) 0.0215(12) 0.0222(13) 0.0037(11) 0.0074(10) -0.0004(10) C14 0.0175(11) 0.0199(12) 0.0182(12) 0.0042(10) 0.0071(10) -0.0002(9) C15 0.0222(13) 0.0215(13) 0.0417(17) -0.0049(12) 0.0148(12) -0.0016(10) C16 0.0199(12) 0.0226(12) 0.0216(13) -0.0036(11) 0.0066(10) 0.0007(10) C17 0.0185(12) 0.0228(12) 0.0174(13) 0.0005(10) 0.0077(10) 0.0010(10) C18 0.0248(13) 0.0264(13) 0.0187(13) 0.0014(11) 0.0080(11) -0.0009(11) C19 0.0203(12) 0.0235(13) 0.0164(12) 0.0017(10) 0.0039(10) 0.0026(10) C20 0.0315(15) 0.0278(14) 0.0435(18) 0.0017(13) 0.0147(14) -0.0084(12) C21 0.0208(12) 0.0271(13) 0.0236(14) 0.0036(11) 0.0070(11) 0.0025(11) C22 0.0181(12) 0.0284(13) 0.0222(14) 0.0033(11) 0.0039(10) 0.0042(10) C23 0.0297(14) 0.0332(15) 0.0252(15) 0.0004(12) 0.0074(12) -0.0041(12) C24 0.0343(15) 0.0387(16) 0.0251(15) 0.0017(13) 0.0111(12) 0.0025(13) C25 0.0291(15) 0.0387(16) 0.0325(16) 0.0174(14) 0.0152(13) 0.0092(12) C26 0.0279(15) 0.0269(14) 0.0412(18) 0.0116(13) 0.0107(13) 0.0030(12) C27 0.0296(14) 0.0219(12) 0.0314(16) 0.0033(11) 0.0101(12) 0.0034(11) C2A 0.0155(11) 0.0181(11) 0.0236(13) 0.0007(10) 0.0067(10) 0.0020(9) C4A 0.0174(11) 0.0182(11) 0.0305(14) 0.0022(11) 0.0099(10) 0.0008(10) C5A 0.0173(12) 0.0335(14) 0.0316(15) -0.0021(13) 0.0100(11) 0.0036(11) C1B 0.0212(13) 0.0202(12) 0.0401(16) -0.0057(12) 0.0136(12) -0.0022(10) C2B 0.0444(18) 0.0332(16) 0.0433(19) -0.0090(14) 0.0232(15) -0.0075(14) C3B 0.075(3) 0.043(2) 0.075(3) -0.029(2) 0.057(2) -0.0195(19) C4B 0.045(2) 0.0279(17) 0.124(4) -0.016(2) 0.053(2) -0.0003(15) C5B 0.0308(16) 0.0298(16) 0.089(3) 0.0028(18) 0.0201(18) 0.0065(13) C6B 0.0282(14) 0.0272(14) 0.0458(18) -0.0014(13) 0.0122(13) 0.0005(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C18 1.380(3) . ? N1 C19 1.391(3) . ? N1 C20 1.461(3) . ? N3 C2A 1.458(3) . ? N3 C21 1.458(3) . ? N3 C4A 1.466(3) . ? O1 C2A 1.433(3) . ? O1 C5A 1.439(3) . ? O2 C18 1.212(3) . ? O3 C19 1.205(3) . ? C1 C11 1.390(3) . ? C1 C2 1.392(4) . ? C1 H1A 0.9500 . ? C2 C3 1.388(4) . ? C2 H2A 0.9500 . ? C3 C4 1.385(4) . ? C3 H3A 0.9500 . ? C4 C12 1.390(3) . ? C4 H4A 0.9500 . ? C5 C13 1.379(3) . ? C5 C6 1.391(4) . ? C5 H5A 0.9500 . ? C6 C7 1.384(3) . ? C6 H6A 0.9500 . ? C7 C8 1.391(3) . ? C7 H7A 0.9500 . ? C8 C14 1.394(3) . ? C8 H8A 0.9500 . ? C9 C2A 1.536(3) . ? C9 C11 1.534(3) . ? C9 C14 1.542(3) . ? C9 C17 1.582(3) . ? C10 C12 1.501(3) . ? C10 C13 1.513(3) . ? C10 C16 1.555(4) . ? C10 H10A 1.0000 . ? C11 C12 1.404(3) . ? C13 C14 1.401(3) . ? C15 C1B 1.508(3) . ? C15 C4A 1.555(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C18 1.511(3) . ? C16 C17 1.541(3) . ? C16 H16A 1.0000 . ? C17 C19 1.530(3) . ? C17 H17A 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.514(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.385(4) . ? C22 C27 1.390(4) . ? C23 C24 1.396(4) . ? C23 H23A 0.9500 . ? C24 C25 1.375(4) . ? C24 H24A 0.9500 . ? C25 C26 1.389(4) . ? C25 H25A 0.9500 . ? C26 C27 1.384(4) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C2A H2AA 1.0000 . ? C4A C5A 1.531(4) . ? C4A H4AA 1.0000 . ? C5A H5AA 0.9900 . ? C5A H5AB 0.9900 . ? C1B C6B 1.383(4) . ? C1B C2B 1.395(4) . ? C2B C3B 1.397(4) . ? C2B H2BA 0.9500 . ? C3B C4B 1.382(6) . ? C3B H3BA 0.9500 . ? C4B C5B 1.361(6) . ? C4B H4BA 0.9500 . ? C5B C6B 1.382(4) . ? C5B H5BA 0.9500 . ? C6B H6BA 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 N1 C19 113.6(2) . . ? C18 N1 C20 124.0(2) . . ? C19 N1 C20 122.4(2) . . ? C2A N3 C21 120.14(18) . . ? C2A N3 C4A 103.60(19) . . ? C21 N3 C4A 117.86(19) . . ? C2A O1 C5A 108.02(17) . . ? C11 C1 C2 119.5(2) . . ? C11 C1 H1A 120.3 . . ? C2 C1 H1A 120.3 . . ? C3 C2 C1 121.4(2) . . ? C3 C2 H2A 119.3 . . ? C1 C2 H2A 119.3 . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C3 C4 C12 119.6(2) . . ? C3 C4 H4A 120.2 . . ? C12 C4 H4A 120.2 . . ? C13 C5 C6 119.8(2) . . ? C13 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? C7 C6 C5 120.0(2) . . ? C7 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? C6 C7 C8 120.3(2) . . ? C6 C7 H7A 119.9 . . ? C8 C7 H7A 119.9 . . ? C7 C8 C14 120.1(2) . . ? C7 C8 H8A 120.0 . . ? C14 C8 H8A 120.0 . . ? C2A C9 C11 116.7(2) . . ? C2A C9 C14 113.19(19) . . ? C11 C9 C14 108.26(19) . . ? C2A C9 C17 109.83(18) . . ? C11 C9 C17 104.77(19) . . ? C14 C9 C17 102.91(18) . . ? C12 C10 C13 108.6(2) . . ? C12 C10 C16 105.14(19) . . ? C13 C10 C16 106.45(19) . . ? C12 C10 H10A 112.1 . . ? C13 C10 H10A 112.1 . . ? C16 C10 H10A 112.1 . . ? C1 C11 C12 118.9(2) . . ? C1 C11 C9 127.1(2) . . ? C12 C11 C9 113.9(2) . . ? C4 C12 C11 121.1(2) . . ? C4 C12 C10 125.0(2) . . ? C11 C12 C10 113.8(2) . . ? C5 C13 C14 120.7(2) . . ? C5 C13 C10 125.4(2) . . ? C14 C13 C10 113.7(2) . . ? C8 C14 C13 119.0(2) . . ? C8 C14 C9 126.9(2) . . ? C13 C14 C9 113.9(2) . . ? C1B C15 C4A 113.7(2) . . ? C1B C15 H15A 108.8 . . ? C4A C15 H15A 108.8 . . ? C1B C15 H15B 108.8 . . ? C4A C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C18 C16 C17 105.2(2) . . ? C18 C16 C10 110.8(2) . . ? C17 C16 C10 110.3(2) . . ? C18 C16 H16A 110.2 . . ? C17 C16 H16A 110.2 . . ? C10 C16 H16A 110.2 . . ? C19 C17 C16 104.34(19) . . ? C19 C17 C9 112.4(2) . . ? C16 C17 C9 110.35(19) . . ? C19 C17 H17A 109.9 . . ? C16 C17 H17A 109.9 . . ? C9 C17 H17A 109.9 . . ? O2 C18 N1 124.2(2) . . ? O2 C18 C16 127.1(2) . . ? N1 C18 C16 108.7(2) . . ? O3 C19 N1 123.4(2) . . ? O3 C19 C17 128.5(2) . . ? N1 C19 C17 108.10(19) . . ? N1 C20 H20A 109.5 . . ? N1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C21 C22 110.63(19) . . ? N3 C21 H21A 109.5 . . ? C22 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 108.1 . . ? C23 C22 C27 118.7(2) . . ? C23 C22 C21 119.8(2) . . ? C27 C22 C21 121.5(2) . . ? C22 C23 C24 120.9(3) . . ? C22 C23 H23A 119.5 . . ? C24 C23 H23A 119.5 . . ? C25 C24 C23 119.4(3) . . ? C25 C24 H24A 120.3 . . ? C23 C24 H24A 120.3 . . ? C24 C25 C26 120.4(2) . . ? C24 C25 H25A 119.8 . . ? C26 C25 H25A 119.8 . . ? C27 C26 C25 119.7(3) . . ? C27 C26 H26A 120.1 . . ? C25 C26 H26A 120.1 . . ? C26 C27 C22 120.8(3) . . ? C26 C27 H27A 119.6 . . ? C22 C27 H27A 119.6 . . ? O1 C2A N3 102.05(17) . . ? O1 C2A C9 109.88(19) . . ? N3 C2A C9 117.57(19) . . ? O1 C2A H2AA 109.0 . . ? N3 C2A H2AA 109.0 . . ? C9 C2A H2AA 109.0 . . ? N3 C4A C5A 98.86(19) . . ? N3 C4A C15 114.49(19) . . ? C5A C4A C15 113.7(2) . . ? N3 C4A H4AA 109.8 . . ? C5A C4A H4AA 109.8 . . ? C15 C4A H4AA 109.8 . . ? O1 C5A C4A 105.63(18) . . ? O1 C5A H5AA 110.6 . . ? C4A C5A H5AA 110.6 . . ? O1 C5A H5AB 110.6 . . ? C4A C5A H5AB 110.6 . . ? H5AA C5A H5AB 108.7 . . ? C6B C1B C2B 118.2(3) . . ? C6B C1B C15 121.9(3) . . ? C2B C1B C15 119.9(3) . . ? C1B C2B C3B 120.2(3) . . ? C1B C2B H2BA 119.9 . . ? C3B C2B H2BA 119.9 . . ? C4B C3B C2B 119.8(3) . . ? C4B C3B H3BA 120.1 . . ? C2B C3B H3BA 120.1 . . ? C5B C4B C3B 120.2(3) . . ? C5B C4B H4BA 119.9 . . ? C3B C4B H4BA 119.9 . . ? C4B C5B C6B 120.2(3) . . ? C4B C5B H5BA 119.9 . . ? C6B C5B H5BA 119.9 . . ? C5B C6B C1B 121.3(3) . . ? C5B C6B H6BA 119.3 . . ? C1B C6B H6BA 119.3 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.194 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.043