# Electronic Supplementary Material (ESI) for RSC Advances # 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_global data_ss01 #TrackingRef 'ss01.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 N2 O5' _chemical_formula_weight 365.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0098(8) _cell_length_b 11.0194(11) _cell_length_c 18.008(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.284(10) _cell_angle_gamma 90.00 _cell_volume 1753.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5048 _cell_measurement_theta_min 2.9191 _cell_measurement_theta_max 32.3872 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_min 0.9675 _exptl_absorpt_correction_T_max 0.9791 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Micro-Focus (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15508 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3067 _reflns_number_gt 2681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0936P)^2^+4.1564P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3067 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0962 _refine_ls_wR_factor_ref 0.2504 _refine_ls_wR_factor_gt 0.2440 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.7792(4) 0.5434(3) 0.9185(4) 0.123(2) Uani 1 1 d . . . O2 O 0.9973(4) 0.2993(4) 0.9385(3) 0.0914(13) Uani 1 1 d . . . O3 O 0.9172(4) 0.3238(4) 0.8202(3) 0.0875(12) Uani 1 1 d . . . O4 O 0.3750(5) 0.1433(4) 0.7718(2) 0.0908(12) Uani 1 1 d . . . O5 O 0.2537(4) 0.1312(3) 0.8663(2) 0.0715(10) Uani 1 1 d . . . N1 N 0.8971(4) 0.3146(3) 0.8850(3) 0.0574(10) Uani 1 1 d . . . N2 N 0.2914(4) 0.4014(3) 0.8964(2) 0.0504(9) Uani 1 1 d . . . H2 H 0.2152 0.3534 0.9001 0.060 Uiso 1 1 calc R . . C1 C 0.6897(4) 0.4547(4) 0.8865(3) 0.0526(11) Uani 1 1 d . . . H1 H 0.6885 0.4658 0.8313 0.063 Uiso 1 1 calc R . . C2 C 0.7401(5) 0.3263(4) 0.9005(4) 0.0668(14) Uani 1 1 d . . . H2A H 0.7519 0.3149 0.9565 0.080 Uiso 1 1 calc R . . C3 C 0.6402(5) 0.2282(4) 0.8670(3) 0.0627(13) Uani 1 1 d . . . H3 H 0.6189 0.2442 0.8113 0.075 Uiso 1 1 calc R . . C4 C 0.4848(4) 0.2339(4) 0.8909(3) 0.0484(10) Uani 1 1 d . . . H4 H 0.4944 0.1979 0.9426 0.058 Uiso 1 1 calc R . . C5 C 0.4372(4) 0.3647(4) 0.8934(2) 0.0456(9) Uani 1 1 d . . . C6 C 0.5267(4) 0.4630(3) 0.8911(2) 0.0420(9) Uani 1 1 d . . . C7 C 0.7059(4) 0.1008(3) 0.8762(3) 0.0485(10) Uani 1 1 d . . . C8 C 0.7481(6) 0.0430(5) 0.9443(3) 0.0701(14) Uani 1 1 d . . . H8 H 0.7404 0.0844 0.9897 0.084 Uiso 1 1 calc R . . C9 C 0.8017(7) -0.0748(5) 0.9479(4) 0.0844(17) Uani 1 1 d . . . H9 H 0.8315 -0.1138 0.9955 0.101 Uiso 1 1 calc R . . C10 C 0.8118(6) -0.1349(4) 0.8831(4) 0.0800(18) Uani 1 1 d . . . H10 H 0.8454 -0.2167 0.8852 0.096 Uiso 1 1 calc R . . C11 C 0.7735(6) -0.0773(5) 0.8155(4) 0.0793(16) Uani 1 1 d . . . H11 H 0.7834 -0.1183 0.7703 0.095 Uiso 1 1 calc R . . C12 C 0.7210(5) 0.0390(5) 0.8117(3) 0.0641(12) Uani 1 1 d . . . H12 H 0.6944 0.0779 0.7639 0.077 Uiso 1 1 calc R . . C13 C 0.3697(5) 0.1638(4) 0.8370(3) 0.0527(10) Uani 1 1 d . . . C14 C 0.1274(6) 0.0720(5) 0.8184(4) 0.0845(18) Uani 1 1 d . . . H14A H 0.0851 0.1255 0.7761 0.127 Uiso 1 1 calc R . . H14B H 0.0495 0.0538 0.8479 0.127 Uiso 1 1 calc R . . H14C H 0.1618 -0.0037 0.7987 0.127 Uiso 1 1 calc R . . C15 C 0.2867(4) 0.5267(4) 0.8924(2) 0.0448(9) Uani 1 1 d . . . C16 C 0.1639(5) 0.6053(4) 0.8883(3) 0.0541(11) Uani 1 1 d . . . H16 H 0.0652 0.5762 0.8897 0.065 Uiso 1 1 calc R . . C17 C 0.1929(5) 0.7274(4) 0.8820(3) 0.0614(12) Uani 1 1 d . . . H17 H 0.1118 0.7836 0.8781 0.074 Uiso 1 1 calc R . . C18 C 0.3376(6) 0.7702(4) 0.8813(3) 0.0644(12) Uani 1 1 d . . . H18 H 0.3533 0.8551 0.8780 0.077 Uiso 1 1 calc R . . C19 C 0.4585(5) 0.6932(4) 0.8853(3) 0.0534(10) Uani 1 1 d . . . H19 H 0.5567 0.7239 0.8844 0.064 Uiso 1 1 calc R . . C20 C 0.4338(4) 0.5684(3) 0.8906(2) 0.0417(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.051(2) 0.050(2) 0.268(7) -0.008(3) 0.032(3) -0.0094(17) O2 0.053(2) 0.096(3) 0.121(3) 0.024(3) 0.004(2) 0.010(2) O3 0.075(2) 0.091(3) 0.106(3) 0.002(2) 0.040(2) 0.010(2) O4 0.090(3) 0.114(3) 0.070(2) -0.016(2) 0.021(2) -0.007(2) O5 0.0478(18) 0.068(2) 0.102(3) -0.0173(19) 0.0215(17) -0.0194(16) N1 0.0387(19) 0.0421(19) 0.094(3) 0.0044(19) 0.019(2) 0.0007(15) N2 0.0343(17) 0.0428(18) 0.077(2) -0.0032(16) 0.0185(16) -0.0007(14) C1 0.037(2) 0.037(2) 0.087(3) 0.002(2) 0.019(2) -0.0003(16) C2 0.034(2) 0.042(2) 0.129(4) 0.001(3) 0.028(2) 0.0013(18) C3 0.046(2) 0.042(2) 0.106(4) 0.001(2) 0.026(2) 0.0022(19) C4 0.037(2) 0.039(2) 0.071(3) 0.0002(18) 0.0129(18) 0.0001(16) C5 0.0325(18) 0.041(2) 0.065(2) -0.0027(18) 0.0128(17) 0.0030(16) C6 0.0361(19) 0.039(2) 0.052(2) -0.0003(16) 0.0120(15) 0.0015(15) C7 0.0323(19) 0.037(2) 0.075(3) 0.0021(19) 0.0088(18) 0.0016(16) C8 0.075(3) 0.072(3) 0.063(3) -0.002(2) 0.015(2) 0.021(3) C9 0.086(4) 0.076(4) 0.095(4) 0.036(3) 0.028(3) 0.026(3) C10 0.055(3) 0.038(2) 0.153(6) 0.002(3) 0.036(3) 0.004(2) C11 0.068(3) 0.065(3) 0.105(4) -0.035(3) 0.015(3) -0.002(3) C12 0.057(3) 0.066(3) 0.066(3) -0.003(2) 0.006(2) 0.006(2) C13 0.050(2) 0.040(2) 0.069(3) -0.0023(19) 0.014(2) 0.0064(18) C14 0.050(3) 0.068(3) 0.130(5) -0.023(3) 0.004(3) -0.014(2) C15 0.041(2) 0.043(2) 0.052(2) -0.0072(17) 0.0137(17) 0.0028(16) C16 0.038(2) 0.058(3) 0.069(3) -0.007(2) 0.0157(19) 0.0080(18) C17 0.054(3) 0.051(3) 0.080(3) -0.005(2) 0.017(2) 0.016(2) C18 0.062(3) 0.040(2) 0.093(3) -0.003(2) 0.020(2) 0.010(2) C19 0.046(2) 0.044(2) 0.072(3) -0.004(2) 0.016(2) 0.0012(18) C20 0.0369(19) 0.042(2) 0.048(2) -0.0064(16) 0.0114(15) 0.0024(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.325(6) . ? O2 N1 1.195(5) . ? O3 N1 1.221(5) . ? O4 C13 1.205(6) . ? O5 C13 1.311(5) . ? O5 C14 1.442(6) . ? N1 C2 1.500(5) . ? N2 C15 1.383(5) . ? N2 C5 1.386(5) . ? N2 H2 0.8800 . ? C1 C6 1.490(5) . ? C1 C2 1.492(6) . ? C1 H1 1.0000 . ? C2 C3 1.459(6) . ? C2 H2A 1.0000 . ? C3 C7 1.520(6) . ? C3 C4 1.545(6) . ? C3 H3 1.0000 . ? C4 C13 1.490(6) . ? C4 C5 1.507(5) . ? C4 H4 1.0000 . ? C5 C6 1.356(5) . ? C6 C20 1.431(5) . ? C7 C8 1.368(7) . ? C7 C12 1.374(6) . ? C8 C9 1.383(7) . ? C8 H8 0.9500 . ? C9 C10 1.359(9) . ? C9 H9 0.9500 . ? C10 C11 1.357(9) . ? C10 H10 0.9500 . ? C11 C12 1.363(7) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.396(5) . ? C15 C20 1.409(5) . ? C16 C17 1.379(6) . ? C16 H16 0.9500 . ? C17 C18 1.389(7) . ? C17 H17 0.9500 . ? C18 C19 1.371(6) . ? C18 H18 0.9500 . ? C19 C20 1.399(6) . ? C19 H19 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 C13 O5 C14 118.8(4) . . ? O2 N1 O3 123.5(4) . . ? O2 N1 C2 117.0(5) . . ? O3 N1 C2 119.5(4) . . ? C15 N2 C5 108.0(3) . . ? C15 N2 H2 126.0 . . ? C5 N2 H2 126.0 . . ? O1 C1 C6 116.9(4) . . ? O1 C1 C2 119.1(4) . . ? C6 C1 C2 108.7(3) . . ? O1 C1 H1 103.2 . . ? C6 C1 H1 103.2 . . ? C2 C1 H1 103.2 . . ? C3 C2 C1 119.3(4) . . ? C3 C2 N1 112.8(4) . . ? C1 C2 N1 108.5(3) . . ? C3 C2 H2A 105.0 . . ? C1 C2 H2A 105.0 . . ? N1 C2 H2A 105.0 . . ? C2 C3 C7 116.3(4) . . ? C2 C3 C4 112.0(4) . . ? C7 C3 C4 111.2(3) . . ? C2 C3 H3 105.4 . . ? C7 C3 H3 105.4 . . ? C4 C3 H3 105.4 . . ? C13 C4 C5 110.4(3) . . ? C13 C4 C3 110.5(4) . . ? C5 C4 C3 109.0(3) . . ? C13 C4 H4 109.0 . . ? C5 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? C6 C5 N2 110.0(3) . . ? C6 C5 C4 126.1(3) . . ? N2 C5 C4 123.9(3) . . ? C5 C6 C20 107.4(3) . . ? C5 C6 C1 123.4(3) . . ? C20 C6 C1 129.2(3) . . ? C8 C7 C12 118.0(4) . . ? C8 C7 C3 124.1(4) . . ? C12 C7 C3 117.9(4) . . ? C7 C8 C9 120.8(5) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 119.9(5) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C11 C10 C9 119.6(5) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.6(5) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 121.0(5) . . ? C11 C12 H12 119.5 . . ? C7 C12 H12 119.5 . . ? O4 C13 O5 121.8(4) . . ? O4 C13 C4 125.3(4) . . ? O5 C13 C4 112.8(4) . . ? O5 C14 H14A 109.5 . . ? O5 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O5 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C16 129.7(4) . . ? N2 C15 C20 108.0(3) . . ? C16 C15 C20 122.4(4) . . ? C17 C16 C15 116.7(4) . . ? C17 C16 H16 121.7 . . ? C15 C16 H16 121.7 . . ? C16 C17 C18 121.7(4) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C19 C18 C17 121.8(4) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C18 C19 C20 118.4(4) . . ? C18 C19 H19 120.8 . . ? C20 C19 H19 120.8 . . ? C19 C20 C15 119.1(3) . . ? C19 C20 C6 134.2(4) . . ? C15 C20 C6 106.6(3) . . ? 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 O1 C1 C2 C3 178.4(5) . . . . ? C6 C1 C2 C3 41.0(6) . . . . ? O1 C1 C2 N1 -50.6(7) . . . . ? C6 C1 C2 N1 172.1(4) . . . . ? O2 N1 C2 C3 -116.0(5) . . . . ? O3 N1 C2 C3 65.7(6) . . . . ? O2 N1 C2 C1 109.6(5) . . . . ? O3 N1 C2 C1 -68.7(6) . . . . ? C1 C2 C3 C7 173.2(4) . . . . ? N1 C2 C3 C7 44.1(7) . . . . ? C1 C2 C3 C4 -57.3(7) . . . . ? N1 C2 C3 C4 173.7(4) . . . . ? C2 C3 C4 C13 160.0(4) . . . . ? C7 C3 C4 C13 -67.9(5) . . . . ? C2 C3 C4 C5 38.5(6) . . . . ? C7 C3 C4 C5 170.6(4) . . . . ? C15 N2 C5 C6 2.8(5) . . . . ? C15 N2 C5 C4 -175.7(4) . . . . ? C13 C4 C5 C6 -134.5(4) . . . . ? C3 C4 C5 C6 -12.9(6) . . . . ? C13 C4 C5 N2 43.8(6) . . . . ? C3 C4 C5 N2 165.3(4) . . . . ? N2 C5 C6 C20 -1.5(5) . . . . ? C4 C5 C6 C20 176.9(4) . . . . ? N2 C5 C6 C1 -179.1(4) . . . . ? C4 C5 C6 C1 -0.7(7) . . . . ? O1 C1 C6 C5 -149.6(5) . . . . ? C2 C1 C6 C5 -11.2(6) . . . . ? O1 C1 C6 C20 33.4(7) . . . . ? C2 C1 C6 C20 171.8(4) . . . . ? C2 C3 C7 C8 64.9(6) . . . . ? C4 C3 C7 C8 -65.0(6) . . . . ? C2 C3 C7 C12 -116.5(5) . . . . ? C4 C3 C7 C12 113.6(5) . . . . ? C12 C7 C8 C9 -1.1(7) . . . . ? C3 C7 C8 C9 177.5(5) . . . . ? C7 C8 C9 C10 -0.6(9) . . . . ? C8 C9 C10 C11 2.1(9) . . . . ? C9 C10 C11 C12 -1.9(8) . . . . ? C10 C11 C12 C7 0.2(8) . . . . ? C8 C7 C12 C11 1.3(7) . . . . ? C3 C7 C12 C11 -177.4(4) . . . . ? C14 O5 C13 O4 -1.7(7) . . . . ? C14 O5 C13 C4 174.7(4) . . . . ? C5 C4 C13 O4 95.4(5) . . . . ? C3 C4 C13 O4 -25.2(6) . . . . ? C5 C4 C13 O5 -80.8(5) . . . . ? C3 C4 C13 O5 158.6(4) . . . . ? C5 N2 C15 C16 175.3(4) . . . . ? C5 N2 C15 C20 -2.9(5) . . . . ? N2 C15 C16 C17 -177.7(4) . . . . ? C20 C15 C16 C17 0.3(6) . . . . ? C15 C16 C17 C18 -1.2(7) . . . . ? C16 C17 C18 C19 1.4(8) . . . . ? C17 C18 C19 C20 -0.4(7) . . . . ? C18 C19 C20 C15 -0.5(6) . . . . ? C18 C19 C20 C6 175.5(5) . . . . ? N2 C15 C20 C19 178.9(4) . . . . ? C16 C15 C20 C19 0.6(6) . . . . ? N2 C15 C20 C6 2.0(4) . . . . ? C16 C15 C20 C6 -176.4(4) . . . . ? C5 C6 C20 C19 -176.6(5) . . . . ? C1 C6 C20 C19 0.8(8) . . . . ? C5 C6 C20 C15 -0.3(4) . . . . ? C1 C6 C20 C15 177.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.149 _refine_diff_density_min -0.740 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 928334' # Attachment 'ss007.cif' data_ss007 #TrackingRef 'ss007.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N2 O5' _chemical_formula_weight 366.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8760(2) _cell_length_b 11.1516(2) _cell_length_c 17.9923(6) _cell_angle_alpha 90.00 _cell_angle_beta 104.062(3) _cell_angle_gamma 90.00 _cell_volume 1727.54(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6986 _cell_measurement_theta_min 2.9829 _cell_measurement_theta_max 32.5887 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_T_min 0.9660 _exptl_absorpt_correction_T_max 0.9788 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Micro-Focus (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15096 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3034 _reflns_number_gt 2730 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.1353P)^2^+2.5639P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3034 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0832 _refine_ls_wR_factor_ref 0.2516 _refine_ls_wR_factor_gt 0.2457 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 -0.1140(4) -0.1745(3) 0.77988(16) 0.0627(8) Uani 1 1 d . . . O2 O 0.1051(3) -0.1335(3) 0.86797(16) 0.0515(7) Uani 1 1 d . . . O3 O -0.3962(3) -0.5491(3) 0.8580(2) 0.0681(9) Uani 1 1 d . . . H3 H -0.3430 -0.5989 0.8403 0.102 Uiso 1 1 calc R . . O4 O -0.6177(4) -0.3322(3) 0.8105(2) 0.0721(10) Uani 1 1 d . . . O5 O -0.5491(4) -0.3081(3) 0.9319(2) 0.0749(10) Uani 1 1 d . . . N1 N 0.1110(3) -0.4109(3) 0.90372(17) 0.0388(7) Uani 1 1 d . . . H1 H 0.1927 -0.3641 0.9090 0.047 Uiso 1 1 calc R . . N2 N -0.5191(4) -0.3210(3) 0.8702(2) 0.0500(9) Uani 1 1 d . . . C1 C -0.3014(4) -0.4594(3) 0.8953(2) 0.0420(8) Uani 1 1 d . . . H1A H -0.3083 -0.4621 0.9500 0.050 Uiso 1 1 calc R . . C2 C -0.1332(4) -0.4701(3) 0.8964(2) 0.0359(8) Uani 1 1 d . . . C3 C -0.0364(4) -0.3740(3) 0.90432(19) 0.0347(7) Uani 1 1 d . . . C4 C -0.0812(4) -0.2442(3) 0.9092(2) 0.0375(8) Uani 1 1 d . . . H4 H -0.0162 -0.2113 0.9583 0.045 Uiso 1 1 calc R . . C5 C -0.2545(4) -0.2347(3) 0.9129(2) 0.0439(9) Uani 1 1 d . . . H5 H -0.2558 -0.2510 0.9674 0.053 Uiso 1 1 calc R . . C6 C -0.3524(4) -0.3324(3) 0.8657(2) 0.0448(9) Uani 1 1 d . . . H6 H -0.3464 -0.3252 0.8111 0.054 Uiso 1 1 calc R . . C7 C -0.3178(4) -0.1088(3) 0.8956(2) 0.0397(8) Uani 1 1 d . . . C8 C -0.3931(5) -0.0662(4) 0.8246(2) 0.0511(10) Uani 1 1 d . . . H8 H -0.4098 -0.1183 0.7816 0.061 Uiso 1 1 calc R . . C9 C -0.4449(5) 0.0506(4) 0.8145(3) 0.0610(12) Uani 1 1 d . . . H9 H -0.4962 0.0782 0.7649 0.073 Uiso 1 1 calc R . . C10 C -0.4227(5) 0.1269(4) 0.8756(3) 0.0615(12) Uani 1 1 d . . . H10 H -0.4577 0.2075 0.8685 0.074 Uiso 1 1 calc R . . C11 C -0.3496(6) 0.0861(4) 0.9472(3) 0.0673(13) Uani 1 1 d . . . H11 H -0.3351 0.1387 0.9899 0.081 Uiso 1 1 calc R . . C12 C -0.2971(5) -0.0305(4) 0.9577(3) 0.0551(10) Uani 1 1 d . . . H12 H -0.2464 -0.0577 1.0076 0.066 Uiso 1 1 calc R . . C13 C -0.0364(4) -0.1786(3) 0.8443(2) 0.0371(8) Uani 1 1 d . . . C14 C 0.1735(6) -0.0821(4) 0.8111(3) 0.0683(13) Uani 1 1 d . . . H14A H 0.1747 -0.1418 0.7712 0.102 Uiso 1 1 calc R . . H14B H 0.2802 -0.0571 0.8349 0.102 Uiso 1 1 calc R . . H14C H 0.1127 -0.0123 0.7881 0.102 Uiso 1 1 calc R . . C15 C 0.1095(4) -0.5335(3) 0.89354(19) 0.0365(8) Uani 1 1 d . . . C16 C 0.2278(4) -0.6113(3) 0.8857(2) 0.0447(9) Uani 1 1 d . . . H16 H 0.3298 -0.5831 0.8879 0.054 Uiso 1 1 calc R . . C17 C 0.1898(5) -0.7306(4) 0.8748(2) 0.0514(10) Uani 1 1 d . . . H17 H 0.2675 -0.7858 0.8688 0.062 Uiso 1 1 calc R . . C18 C 0.0412(5) -0.7730(3) 0.8722(2) 0.0488(9) Uani 1 1 d . . . H18 H 0.0203 -0.8563 0.8650 0.059 Uiso 1 1 calc R . . C19 C -0.0762(4) -0.6968(3) 0.8798(2) 0.0435(8) Uani 1 1 d . . . H19 H -0.1773 -0.7265 0.8780 0.052 Uiso 1 1 calc R . . C20 C -0.0428(4) -0.5739(3) 0.89013(18) 0.0351(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0541(17) 0.086(2) 0.0469(17) 0.0072(14) 0.0108(14) -0.0037(15) O2 0.0403(14) 0.0537(16) 0.0627(17) 0.0064(13) 0.0166(12) -0.0130(12) O3 0.0478(16) 0.0536(18) 0.104(3) -0.0125(16) 0.0203(16) -0.0040(13) O4 0.0382(16) 0.083(2) 0.091(2) 0.0037(18) 0.0074(16) 0.0057(15) O5 0.0514(18) 0.084(2) 0.096(3) -0.0289(19) 0.0321(18) -0.0049(16) N1 0.0249(13) 0.0390(15) 0.0533(17) 0.0021(13) 0.0109(12) -0.0018(11) N2 0.0352(17) 0.0355(16) 0.084(3) -0.0050(15) 0.0228(18) 0.0011(13) C1 0.0311(17) 0.0323(17) 0.064(2) -0.0039(15) 0.0135(16) -0.0019(13) C2 0.0318(16) 0.0334(17) 0.0443(18) -0.0001(13) 0.0126(13) 0.0006(13) C3 0.0288(15) 0.0350(17) 0.0414(17) -0.0007(13) 0.0110(13) 0.0015(13) C4 0.0322(17) 0.0321(17) 0.0494(19) -0.0029(14) 0.0120(14) -0.0029(13) C5 0.0376(19) 0.0368(19) 0.061(2) -0.0019(16) 0.0182(16) -0.0030(14) C6 0.0296(17) 0.0393(19) 0.068(2) -0.0050(16) 0.0171(16) 0.0000(14) C7 0.0334(17) 0.0335(17) 0.056(2) -0.0007(15) 0.0184(15) -0.0022(13) C8 0.051(2) 0.048(2) 0.056(2) -0.0034(18) 0.0171(18) 0.0001(17) C9 0.051(2) 0.050(2) 0.080(3) 0.019(2) 0.013(2) 0.0021(19) C10 0.043(2) 0.035(2) 0.108(4) 0.005(2) 0.021(2) 0.0032(16) C11 0.070(3) 0.048(2) 0.087(3) -0.025(2) 0.025(3) -0.001(2) C12 0.061(3) 0.052(2) 0.053(2) -0.0043(18) 0.0149(19) 0.0039(19) C13 0.0338(17) 0.0332(17) 0.045(2) -0.0014(14) 0.0105(15) 0.0043(13) C14 0.062(3) 0.061(3) 0.094(4) 0.019(2) 0.043(3) -0.002(2) C15 0.0318(16) 0.0422(18) 0.0369(17) 0.0053(14) 0.0109(13) 0.0047(14) C16 0.0337(18) 0.052(2) 0.050(2) 0.0068(17) 0.0139(15) 0.0082(15) C17 0.049(2) 0.050(2) 0.059(2) 0.0037(18) 0.0197(18) 0.0184(18) C18 0.051(2) 0.0348(18) 0.062(2) 0.0031(16) 0.0167(18) 0.0092(16) C19 0.0402(19) 0.0362(18) 0.055(2) 0.0034(15) 0.0140(16) 0.0011(15) C20 0.0318(16) 0.0373(17) 0.0366(17) 0.0045(13) 0.0090(13) 0.0032(13) _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 C13 1.197(4) . ? O2 C13 1.324(4) . ? O2 C14 1.431(5) . ? O3 C1 1.373(5) . ? O3 H3 0.8400 . ? O4 N2 1.215(5) . ? O5 N2 1.213(5) . ? N1 C3 1.374(4) . ? N1 C15 1.379(5) . ? N1 H1 0.8800 . ? N2 C6 1.507(4) . ? C1 C2 1.493(5) . ? C1 C6 1.542(5) . ? C1 H1A 1.0000 . ? C2 C3 1.359(5) . ? C2 C20 1.429(5) . ? C3 C4 1.509(5) . ? C4 C13 1.510(5) . ? C4 C5 1.559(5) . ? C4 H4 1.0000 . ? C5 C7 1.517(5) . ? C5 C6 1.518(5) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 C8 1.375(6) . ? C7 C12 1.394(6) . ? C8 C9 1.379(6) . ? C8 H8 0.9500 . ? C9 C10 1.365(7) . ? C9 H9 0.9500 . ? C10 C11 1.372(7) . ? C10 H10 0.9500 . ? C11 C12 1.379(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.395(5) . ? C15 C20 1.412(5) . ? C16 C17 1.375(6) . ? C16 H16 0.9500 . ? C17 C18 1.391(6) . ? C17 H17 0.9500 . ? C18 C19 1.378(5) . ? C18 H18 0.9500 . ? C19 C20 1.405(5) . ? C19 H19 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 C13 O2 C14 117.2(3) . . ? C1 O3 H3 109.5 . . ? C3 N1 C15 108.6(3) . . ? C3 N1 H1 125.7 . . ? C15 N1 H1 125.7 . . ? O5 N2 O4 123.4(3) . . ? O5 N2 C6 119.7(4) . . ? O4 N2 C6 116.8(3) . . ? O3 C1 C2 116.1(3) . . ? O3 C1 C6 114.0(3) . . ? C2 C1 C6 106.6(3) . . ? O3 C1 H1A 106.5 . . ? C2 C1 H1A 106.5 . . ? C6 C1 H1A 106.5 . . ? C3 C2 C20 107.1(3) . . ? C3 C2 C1 122.9(3) . . ? C20 C2 C1 130.0(3) . . ? C2 C3 N1 110.0(3) . . ? C2 C3 C4 126.4(3) . . ? N1 C3 C4 123.5(3) . . ? C3 C4 C13 107.3(3) . . ? C3 C4 C5 110.1(3) . . ? C13 C4 C5 116.6(3) . . ? C3 C4 H4 107.5 . . ? C13 C4 H4 107.5 . . ? C5 C4 H4 107.5 . . ? C7 C5 C6 114.6(3) . . ? C7 C5 C4 112.0(3) . . ? C6 C5 C4 111.3(3) . . ? C7 C5 H5 106.1 . . ? C6 C5 H5 106.1 . . ? C4 C5 H5 106.1 . . ? N2 C6 C5 110.2(3) . . ? N2 C6 C1 105.5(3) . . ? C5 C6 C1 112.7(3) . . ? N2 C6 H6 109.4 . . ? C5 C6 H6 109.4 . . ? C1 C6 H6 109.4 . . ? C8 C7 C12 117.9(4) . . ? C8 C7 C5 125.6(3) . . ? C12 C7 C5 116.4(3) . . ? C7 C8 C9 121.3(4) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 120.3(4) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 119.5(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 120.6(4) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 120.4(4) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? O1 C13 O2 125.1(3) . . ? O1 C13 C4 124.7(3) . . ? O2 C13 C4 110.1(3) . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 C16 130.3(3) . . ? N1 C15 C20 107.5(3) . . ? C16 C15 C20 122.2(3) . . ? C17 C16 C15 116.9(3) . . ? C17 C16 H16 121.6 . . ? C15 C16 H16 121.6 . . ? C16 C17 C18 122.1(3) . . ? C16 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C19 C18 C17 121.4(4) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 118.3(3) . . ? C18 C19 H19 120.8 . . ? C20 C19 H19 120.8 . . ? C19 C20 C15 119.1(3) . . ? C19 C20 C2 134.1(3) . . ? C15 C20 C2 106.7(3) . . ? 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 O3 C1 C2 C3 155.0(4) . . . . ? C6 C1 C2 C3 26.7(5) . . . . ? O3 C1 C2 C20 -25.1(6) . . . . ? C6 C1 C2 C20 -153.4(4) . . . . ? C20 C2 C3 N1 -0.3(4) . . . . ? C1 C2 C3 N1 179.7(3) . . . . ? C20 C2 C3 C4 176.9(3) . . . . ? C1 C2 C3 C4 -3.1(6) . . . . ? C15 N1 C3 C2 1.3(4) . . . . ? C15 N1 C3 C4 -175.9(3) . . . . ? C2 C3 C4 C13 -121.7(4) . . . . ? N1 C3 C4 C13 55.1(4) . . . . ? C2 C3 C4 C5 6.2(5) . . . . ? N1 C3 C4 C5 -177.0(3) . . . . ? C3 C4 C5 C7 -164.0(3) . . . . ? C13 C4 C5 C7 -41.5(4) . . . . ? C3 C4 C5 C6 -34.3(4) . . . . ? C13 C4 C5 C6 88.3(4) . . . . ? O5 N2 C6 C5 -47.8(5) . . . . ? O4 N2 C6 C5 136.1(4) . . . . ? O5 N2 C6 C1 74.1(4) . . . . ? O4 N2 C6 C1 -101.9(4) . . . . ? C7 C5 C6 N2 -51.5(4) . . . . ? C4 C5 C6 N2 -179.9(3) . . . . ? C7 C5 C6 C1 -169.2(3) . . . . ? C4 C5 C6 C1 62.5(4) . . . . ? O3 C1 C6 N2 54.2(4) . . . . ? C2 C1 C6 N2 -176.3(3) . . . . ? O3 C1 C6 C5 174.6(3) . . . . ? C2 C1 C6 C5 -55.9(4) . . . . ? C6 C5 C7 C8 -36.0(5) . . . . ? C4 C5 C7 C8 92.1(4) . . . . ? C6 C5 C7 C12 144.0(4) . . . . ? C4 C5 C7 C12 -88.0(4) . . . . ? C12 C7 C8 C9 0.9(6) . . . . ? C5 C7 C8 C9 -179.2(4) . . . . ? C7 C8 C9 C10 -0.3(6) . . . . ? C8 C9 C10 C11 -0.5(7) . . . . ? C9 C10 C11 C12 0.7(7) . . . . ? C10 C11 C12 C7 -0.1(7) . . . . ? C8 C7 C12 C11 -0.7(6) . . . . ? C5 C7 C12 C11 179.4(4) . . . . ? C14 O2 C13 O1 -3.8(6) . . . . ? C14 O2 C13 C4 171.9(3) . . . . ? C3 C4 C13 O1 83.3(4) . . . . ? C5 C4 C13 O1 -40.7(5) . . . . ? C3 C4 C13 O2 -92.4(3) . . . . ? C5 C4 C13 O2 143.5(3) . . . . ? C3 N1 C15 C16 176.9(4) . . . . ? C3 N1 C15 C20 -1.8(4) . . . . ? N1 C15 C16 C17 -178.8(4) . . . . ? C20 C15 C16 C17 -0.3(5) . . . . ? C15 C16 C17 C18 -0.5(6) . . . . ? C16 C17 C18 C19 0.6(6) . . . . ? C17 C18 C19 C20 0.2(6) . . . . ? C18 C19 C20 C15 -0.9(5) . . . . ? C18 C19 C20 C2 176.7(4) . . . . ? N1 C15 C20 C19 179.9(3) . . . . ? C16 C15 C20 C19 1.0(5) . . . . ? N1 C15 C20 C2 1.7(4) . . . . ? C16 C15 C20 C2 -177.2(3) . . . . ? C3 C2 C20 C19 -178.7(4) . . . . ? C1 C2 C20 C19 1.3(7) . . . . ? C3 C2 C20 C15 -0.9(4) . . . . ? C1 C2 C20 C15 179.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.484 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 928335'