# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_as1 _database_code_depnum_ccdc_archive 'CCDC 873751' #TrackingRef 'web_deposit_cif_file_1_GuyClarkson_1332948394.as1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N2 O3' _chemical_formula_sum 'C18 H16 N2 O3' _chemical_formula_weight 308.33 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.8161(4) _cell_length_b 9.6613(2) _cell_length_c 11.7717(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.2680(10) _cell_angle_gamma 90.00 _cell_volume 1500.48(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9224 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8558 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cooler (Cosier & Glazer, 1986). The data collection nominally covered over a hemisphere of Reciprocal space, by a combination of three sets of exposures with different \f angles for the crystal; each 10 s exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.0 cm. Coverage of the unique Set is over 97% complete to at least 26\% in \q. Crystal decay was found to be negligible by by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. Hydrogen atoms were added at calculated positions and refined using a riding model. Anisotropic displacement parameters were used for all non-H atoms; H-atoms were given isotropic displacement parameter equal to 1.2 (or 1.5 for methyl H-atoms) times the equivalent isotropic displacement parameter of the atom to which they are attached. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a __diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 20600 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3425 _reflns_number_gt 2745 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _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^)+(0.0582P)^2^+0.4520P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3425 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1120 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.72995(10) 0.34077(15) 1.03881(12) 0.0245(3) Uani 1 1 d . . . H1A H 0.6917 0.3325 1.0935 0.029 Uiso 1 1 calc R . . C2 C 0.79023(11) 0.45695(16) 1.04219(13) 0.0300(4) Uani 1 1 d . . . H2A H 0.7933 0.5271 1.0997 0.036 Uiso 1 1 calc R . . C3 C 0.84579(11) 0.47121(16) 0.96230(14) 0.0309(4) Uani 1 1 d . . . H3A H 0.8872 0.5504 0.9654 0.037 Uiso 1 1 calc R . . C4 C 0.84060(11) 0.36960(16) 0.87818(14) 0.0293(3) Uani 1 1 d . . . H4A H 0.8776 0.3797 0.8223 0.035 Uiso 1 1 calc R . . C5 C 0.78121(10) 0.25236(15) 0.87526(12) 0.0238(3) Uani 1 1 d . . . H5A H 0.7786 0.1823 0.8178 0.029 Uiso 1 1 calc R . . C6 C 0.72550(9) 0.23676(14) 0.95583(11) 0.0186(3) Uani 1 1 d . . . C7 C 0.66279(9) 0.10834(14) 0.95502(12) 0.0209(3) Uani 1 1 d . . . H7A H 0.6992 0.0270 0.9369 0.025 Uiso 1 1 calc R . . H7B H 0.6552 0.0948 1.0353 0.025 Uiso 1 1 calc R . . N8 N 0.56051(8) 0.11557(11) 0.86674(10) 0.0180(3) Uani 1 1 d . . . O9 O 0.62187(7) 0.01308(10) 0.72842(9) 0.0260(2) Uani 1 1 d . . . C9 C 0.54896(10) 0.05920(13) 0.75428(12) 0.0193(3) Uani 1 1 d . . . C10 C 0.44352(10) 0.05379(15) 0.66957(12) 0.0222(3) Uani 1 1 d . . . H10A H 0.4114 -0.0348 0.6805 0.027 Uiso 1 1 calc R . . H10B H 0.4473 0.0564 0.5869 0.027 Uiso 1 1 calc R . . C11 C 0.37786(10) 0.17348(14) 0.68807(11) 0.0194(3) Uani 1 1 d . . . H11A H 0.4040 0.2619 0.6663 0.023 Uiso 1 1 calc R . . H11B H 0.3074 0.1611 0.6364 0.023 Uiso 1 1 calc R . . C12 C 0.37950(9) 0.17755(13) 0.81579(11) 0.0166(3) Uani 1 1 d . . . O13 O 0.49361(7) 0.18309(11) 1.01272(9) 0.0278(3) Uani 1 1 d . . . C13 C 0.47997(10) 0.15967(13) 0.90760(12) 0.0183(3) Uani 1 1 d . . . C14 C 0.30022(9) 0.19093(13) 0.85758(12) 0.0170(3) Uani 1 1 d . . . H14A H 0.3125 0.1830 0.9411 0.020 Uiso 1 1 calc R . . N15 N 0.19892(8) 0.21609(11) 0.78724(9) 0.0163(2) Uani 1 1 d . . . C16 C 0.17717(10) 0.31345(13) 0.69712(12) 0.0185(3) Uani 1 1 d . . . H16A H 0.2311 0.3612 0.6795 0.022 Uiso 1 1 calc R . . C17 C 0.08039(10) 0.34188(14) 0.63363(12) 0.0215(3) Uani 1 1 d . . . H17A H 0.0661 0.4078 0.5709 0.026 Uiso 1 1 calc R . . C18 C 0.00051(10) 0.27166(15) 0.66220(12) 0.0230(3) Uani 1 1 d . . . H18A H -0.0678 0.2908 0.6183 0.028 Uiso 1 1 calc R . . C19 C 0.02064(10) 0.17747(14) 0.75156(13) 0.0228(3) Uani 1 1 d . . . H19A H -0.0343 0.1325 0.7693 0.027 Uiso 1 1 calc R . . O20 O 0.14700(7) 0.05783(10) 0.90172(8) 0.0240(2) Uani 1 1 d . . . C20 C 0.12266(9) 0.14342(13) 0.82044(11) 0.0177(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0216(7) 0.0315(8) 0.0189(7) 0.0016(6) 0.0034(5) 0.0088(5) C2 0.0314(8) 0.0252(8) 0.0261(8) -0.0050(6) -0.0027(6) 0.0068(6) C3 0.0264(8) 0.0225(8) 0.0377(9) 0.0042(6) 0.0000(6) -0.0025(6) C4 0.0274(8) 0.0311(8) 0.0314(8) 0.0047(6) 0.0118(6) -0.0032(6) C5 0.0240(7) 0.0257(7) 0.0225(7) -0.0016(6) 0.0083(6) -0.0009(5) C6 0.0131(6) 0.0233(7) 0.0170(6) 0.0030(5) 0.0008(5) 0.0040(5) C7 0.0137(6) 0.0266(7) 0.0211(7) 0.0074(6) 0.0029(5) 0.0032(5) N8 0.0121(5) 0.0212(6) 0.0201(6) 0.0022(4) 0.0040(4) 0.0006(4) O9 0.0215(5) 0.0250(5) 0.0337(6) -0.0023(4) 0.0118(4) 0.0045(4) C9 0.0197(6) 0.0137(6) 0.0259(7) 0.0013(5) 0.0088(5) 0.0005(5) C10 0.0192(7) 0.0244(7) 0.0234(7) -0.0048(5) 0.0067(5) -0.0006(5) C11 0.0156(6) 0.0250(7) 0.0172(6) -0.0002(5) 0.0045(5) 0.0003(5) C12 0.0153(6) 0.0163(6) 0.0174(6) 0.0009(5) 0.0037(5) -0.0001(5) O13 0.0173(5) 0.0467(7) 0.0187(5) -0.0020(4) 0.0040(4) 0.0026(4) C13 0.0150(6) 0.0205(7) 0.0198(6) 0.0016(5) 0.0059(5) -0.0006(5) C14 0.0150(6) 0.0180(6) 0.0164(6) 0.0005(5) 0.0021(5) -0.0003(5) N15 0.0128(5) 0.0183(5) 0.0176(5) 0.0003(4) 0.0044(4) 0.0006(4) C16 0.0199(6) 0.0176(7) 0.0192(6) 0.0017(5) 0.0074(5) 0.0006(5) C17 0.0219(7) 0.0216(7) 0.0199(7) 0.0026(5) 0.0044(5) 0.0043(5) C18 0.0162(6) 0.0267(7) 0.0231(7) -0.0019(6) 0.0012(5) 0.0031(5) C19 0.0145(6) 0.0272(7) 0.0272(7) 0.0005(6) 0.0066(5) -0.0014(5) O20 0.0189(5) 0.0290(5) 0.0244(5) 0.0080(4) 0.0069(4) 0.0008(4) C20 0.0164(6) 0.0192(6) 0.0187(6) -0.0009(5) 0.0069(5) 0.0001(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.3901(19) . ? C1 C2 1.391(2) . ? C1 H1A 0.9500 . ? C2 C3 1.386(2) . ? C2 H2A 0.9500 . ? C3 C4 1.381(2) . ? C3 H3A 0.9500 . ? C4 C5 1.393(2) . ? C4 H4A 0.9500 . ? C5 C6 1.3958(19) . ? C5 H5A 0.9500 . ? C6 C7 1.5117(18) . ? C7 N8 1.4865(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N8 C9 1.3962(17) . ? N8 C13 1.4032(16) . ? O9 C9 1.2199(16) . ? C9 C10 1.5023(18) . ? C10 C11 1.5248(18) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.4973(18) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.3336(18) . ? C12 C13 1.4946(18) . ? O13 C13 1.2164(16) . ? C14 N15 1.4198(16) . ? C14 H14A 0.9500 . ? N15 C16 1.3824(17) . ? N15 C20 1.4143(16) . ? C16 C17 1.3523(18) . ? C16 H16A 0.9500 . ? C17 C18 1.4183(19) . ? C17 H17A 0.9500 . ? C18 C19 1.356(2) . ? C18 H18A 0.9500 . ? C19 C20 1.4401(18) . ? C19 H19A 0.9500 . ? O20 C20 1.2334(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.30(14) . . ? C6 C1 H1A 119.8 . . ? C2 C1 H1A 119.8 . . ? C3 C2 C1 120.55(14) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C4 C3 C2 119.63(14) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C3 C4 C5 120.03(14) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C4 C5 C6 120.70(14) . . ? C4 C5 H5A 119.6 . . ? C6 C5 H5A 119.6 . . ? C1 C6 C5 118.76(13) . . ? C1 C6 C7 120.23(12) . . ? C5 C6 C7 121.00(12) . . ? N8 C7 C6 112.95(10) . . ? N8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? N8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 N8 C13 124.35(11) . . ? C9 N8 C7 117.52(10) . . ? C13 N8 C7 117.43(11) . . ? O9 C9 N8 120.57(12) . . ? O9 C9 C10 122.12(12) . . ? N8 C9 C10 117.29(11) . . ? C9 C10 C11 112.31(11) . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 109.33(11) . . ? C12 C11 H11A 109.8 . . ? C10 C11 H11A 109.8 . . ? C12 C11 H11B 109.8 . . ? C10 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? C14 C12 C13 115.63(11) . . ? C14 C12 C11 127.13(12) . . ? C13 C12 C11 117.20(11) . . ? O13 C13 N8 120.39(11) . . ? O13 C13 C12 122.98(12) . . ? N8 C13 C12 116.62(11) . . ? C12 C14 N15 125.23(12) . . ? C12 C14 H14A 117.4 . . ? N15 C14 H14A 117.4 . . ? C16 N15 C20 122.67(10) . . ? C16 N15 C14 121.07(11) . . ? C20 N15 C14 116.11(10) . . ? C17 C16 N15 121.09(12) . . ? C17 C16 H16A 119.5 . . ? N15 C16 H16A 119.5 . . ? C16 C17 C18 118.89(12) . . ? C16 C17 H17A 120.6 . . ? C18 C17 H17A 120.6 . . ? C19 C18 C17 120.68(12) . . ? C19 C18 H18A 119.7 . . ? C17 C18 H18A 119.7 . . ? C18 C19 C20 122.09(12) . . ? C18 C19 H19A 119.0 . . ? C20 C19 H19A 119.0 . . ? O20 C20 N15 119.56(11) . . ? O20 C20 C19 125.86(12) . . ? N15 C20 C19 114.58(11) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.275 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.048 data_as2 _database_code_depnum_ccdc_archive 'CCDC 873752' #TrackingRef '10402_web_deposit_cif_file_2_GuyClarkson_1332948394.as2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N2 O3' _chemical_formula_sum 'C18 H16 N2 O3' _chemical_formula_weight 308.33 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.0338(5) _cell_length_b 8.3474(3) _cell_length_c 13.1017(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.381(2) _cell_angle_gamma 90.00 _cell_volume 1525.30(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 13564 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour 'pale blue' _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8912 _exptl_absorpt_correction_T_max 0.9772 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; The crystal was mounted on a glass fibre using silicon grease and the data recorded at room temperature. The data collection nominally covered over a hemisphere of Reciprocal space, by a combination of three sets of exposures with different \f angles for the crystal; each 10 s exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.0 cm. Coverage of the unique Set is over 97% complete to at least 26\% in \q. Crystal decay was found to be negligible by by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. Hydrogen atoms were added at calculated positions and refined using a riding model. Anisotropic displacement parameters were used for all non-H atoms; H-atoms were given isotropic displacement parameter equal to 1.2 times the equivalent isotropic displacement parameter of the atom to which they are attached. The central glutarimide ring was modelled as disordered over two positions with nearly 50:50 occupancy (52:48) and the disorder was modelled over the whole glutaramide ring. Several SIMU and ISOR restraints were used to give the thermal parameters of some of the disordered components similar values to other atoms in the disordered part. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 27338 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3487 _reflns_number_gt 2290 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0687P)^2^+0.1319P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3487 _refine_ls_number_parameters 281 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.05649(12) 0.12722(19) 0.83276(13) 0.0577(4) Uani 1 1 d . . . H1A H 0.0696 0.0814 0.7711 0.069 Uiso 1 1 calc R . . C2 C -0.01926(13) 0.2328(2) 0.83354(15) 0.0691(5) Uani 1 1 d . . . H2A H -0.0564 0.2577 0.7724 0.083 Uiso 1 1 calc R . . C3 C -0.04005(13) 0.3007(2) 0.92268(17) 0.0679(5) Uani 1 1 d . . . H3A H -0.0913 0.3714 0.9226 0.081 Uiso 1 1 calc R . . C4 C 0.01465(14) 0.2644(2) 1.01228(15) 0.0674(5) Uani 1 1 d . . . H4A H 0.0005 0.3104 1.0735 0.081 Uiso 1 1 calc R . . C5 C 0.09108(12) 0.1598(2) 1.01269(12) 0.0554(4) Uani 1 1 d . . . H5A H 0.1282 0.1368 1.0742 0.066 Uiso 1 1 calc R . . C6 C 0.11311(10) 0.08885(17) 0.92280(11) 0.0429(4) Uani 1 1 d . B . C7 C 0.19480(10) -0.02812(18) 0.92319(12) 0.0470(4) Uani 1 1 d . . . H7A H 0.1760 -0.1147 0.8758 0.056 Uiso 1 1 calc R A 1 H7B H 0.2083 -0.0738 0.9913 0.056 Uiso 1 1 calc R A 1 N8 N 0.2892(13) 0.054(2) 0.8913(18) 0.036(2) Uani 0.525(8) 1 d PU B 1 O9 O 0.2379(14) -0.0426(16) 0.7291(15) 0.068(3) Uani 0.525(8) 1 d P B 1 C9 C 0.2988(11) 0.034(3) 0.7795(16) 0.062(4) Uani 0.525(8) 1 d P B 1 C10 C 0.3971(9) 0.0765(15) 0.7601(11) 0.060(2) Uani 0.525(8) 1 d P B 1 H10A H 0.3974 0.0981 0.6874 0.072 Uiso 0.525(8) 1 calc PR B 1 H10B H 0.4385 -0.0149 0.7771 0.072 Uiso 0.525(8) 1 calc PR B 1 C11 C 0.4380(3) 0.2191(8) 0.8197(2) 0.0515(13) Uani 0.525(8) 1 d P B 1 H11A H 0.5047 0.2322 0.8087 0.062 Uiso 0.525(8) 1 calc PR B 1 H11B H 0.4036 0.3148 0.7949 0.062 Uiso 0.525(8) 1 calc PR B 1 C12 C 0.4309(13) 0.2007(17) 0.9289(15) 0.0342(19) Uani 0.525(8) 1 d P B 1 C13 C 0.3521(9) 0.1160(18) 0.9649(9) 0.047(4) Uani 0.525(8) 1 d P B 1 O13 O 0.3262(13) 0.124(2) 1.0509(10) 0.056(2) Uani 0.525(8) 1 d P B 1 N8A N 0.2757(15) 0.030(3) 0.8895(19) 0.034(2) Uani 0.475(8) 1 d PU B 2 O9A O 0.2301(14) -0.0010(19) 0.7214(16) 0.067(3) Uani 0.475(8) 1 d PU B 2 C9A C 0.2935(9) 0.034(2) 0.7936(15) 0.042(2) Uani 0.475(8) 1 d P B 2 C10A C 0.3773(10) 0.1189(17) 0.7505(12) 0.053(2) Uani 0.475(8) 1 d PU B 2 H10C H 0.3592 0.2281 0.7319 0.064 Uiso 0.475(8) 1 calc PR B 2 H10D H 0.3925 0.0639 0.6891 0.064 Uiso 0.475(8) 1 calc PR B 2 C11A C 0.4662(3) 0.1199(9) 0.8311(3) 0.0520(14) Uani 0.475(8) 1 d P B 2 H11C H 0.4957 0.0147 0.8337 0.062 Uiso 0.475(8) 1 calc PR B 2 H11D H 0.5125 0.1961 0.8104 0.062 Uiso 0.475(8) 1 calc PR B 2 C12A C 0.4414(15) 0.1636(19) 0.9366(15) 0.033(2) Uani 0.475(8) 1 d P B 2 C13A C 0.3451(10) 0.1097(19) 0.9660(12) 0.038(4) Uani 0.475(8) 1 d P B 2 O13A O 0.3353(16) 0.100(3) 1.0581(13) 0.072(4) Uani 0.475(8) 1 d P B 2 C14 C 0.49608(10) 0.24954(19) 1.00362(11) 0.0455(4) Uani 1 1 d . . . H14A H 0.4850 0.2370 1.0719 0.055 Uiso 1 1 calc R B 1 O15 O 0.57892(7) 0.31787(14) 0.98058(7) 0.0537(3) Uani 1 1 d . B . C16 C 0.64436(10) 0.37379(17) 1.05920(11) 0.0422(3) Uani 1 1 d . . . N17 N 0.62872(10) 0.34527(18) 1.15420(10) 0.0595(4) Uani 1 1 d . B . C18 C 0.69522(14) 0.4017(3) 1.22715(13) 0.0758(6) Uani 1 1 d . . . H18A H 0.6867 0.3833 1.2955 0.091 Uiso 1 1 calc R B . C19 C 0.77463(14) 0.4845(2) 1.20615(15) 0.0712(5) Uani 1 1 d . B . H19A H 0.8184 0.5226 1.2591 0.085 Uiso 1 1 calc R . . C20 C 0.78861(12) 0.5104(2) 1.10562(13) 0.0580(4) Uani 1 1 d . . . H20A H 0.8424 0.5660 1.0894 0.070 Uiso 1 1 calc R B . C21 C 0.72259(11) 0.45376(19) 1.02937(12) 0.0500(4) Uani 1 1 d . B . H21A H 0.7302 0.4686 0.9604 0.060 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0563(10) 0.0596(11) 0.0536(9) -0.0042(7) -0.0101(7) 0.0000(8) C2 0.0571(11) 0.0658(12) 0.0781(12) 0.0023(10) -0.0201(9) 0.0056(9) C3 0.0466(10) 0.0598(11) 0.0977(15) 0.0056(10) 0.0096(10) 0.0033(8) C4 0.0685(12) 0.0681(12) 0.0708(11) 0.0002(9) 0.0300(10) 0.0004(10) C5 0.0536(10) 0.0645(11) 0.0485(9) 0.0097(7) 0.0081(7) -0.0035(8) C6 0.0372(8) 0.0432(8) 0.0473(8) 0.0055(6) 0.0013(6) -0.0106(6) C7 0.0415(9) 0.0454(9) 0.0537(9) 0.0049(7) 0.0033(7) -0.0062(7) N8 0.025(4) 0.039(5) 0.045(3) -0.001(3) 0.005(3) -0.016(3) O9 0.074(4) 0.074(5) 0.053(4) -0.016(4) -0.008(3) -0.017(4) C9 0.081(7) 0.075(6) 0.032(4) -0.005(3) 0.015(3) 0.004(5) C10 0.054(6) 0.086(7) 0.042(4) -0.009(4) 0.011(4) -0.009(4) C11 0.046(2) 0.066(3) 0.0427(17) 0.0033(16) 0.0068(13) -0.010(2) C12 0.030(3) 0.034(6) 0.038(3) 0.008(3) 0.001(2) 0.011(3) C13 0.052(7) 0.056(6) 0.027(5) -0.009(4) -0.013(4) 0.003(4) O13 0.047(3) 0.088(4) 0.033(3) -0.009(4) 0.009(3) -0.015(3) N8A 0.031(5) 0.034(5) 0.036(3) -0.003(3) -0.005(3) -0.015(3) O9A 0.058(3) 0.094(8) 0.048(3) -0.010(5) -0.003(2) -0.017(5) C9A 0.032(3) 0.059(5) 0.034(6) -0.009(4) -0.002(3) -0.014(3) C10A 0.048(5) 0.076(5) 0.035(3) 0.002(4) 0.002(3) -0.002(3) C11A 0.042(2) 0.071(4) 0.0429(19) -0.006(2) 0.0066(15) -0.002(2) C12A 0.032(5) 0.034(6) 0.032(3) 0.008(4) -0.001(3) 0.008(4) C13A 0.022(4) 0.044(6) 0.051(7) 0.012(4) 0.013(4) -0.003(3) O13A 0.061(6) 0.111(8) 0.044(3) 0.021(3) 0.001(3) -0.023(5) C14 0.0377(8) 0.0591(10) 0.0403(7) 0.0010(7) 0.0067(6) -0.0029(7) O15 0.0387(6) 0.0814(8) 0.0405(6) -0.0023(5) 0.0024(4) -0.0146(5) C16 0.0358(8) 0.0481(9) 0.0421(8) -0.0044(6) 0.0013(6) 0.0004(6) N17 0.0533(8) 0.0829(10) 0.0424(7) -0.0095(6) 0.0062(6) -0.0171(7) C18 0.0719(13) 0.1107(16) 0.0443(9) -0.0159(9) 0.0041(8) -0.0240(12) C19 0.0601(12) 0.0845(14) 0.0658(12) -0.0215(10) -0.0068(9) -0.0172(10) C20 0.0433(9) 0.0551(10) 0.0743(11) 0.0003(8) 0.0014(8) -0.0077(7) C21 0.0403(9) 0.0561(10) 0.0533(9) 0.0068(7) 0.0036(7) -0.0025(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.382(2) . ? C1 C6 1.385(2) . ? C1 H1A 0.9300 . ? C2 C3 1.358(3) . ? C2 H2A 0.9300 . ? C3 C4 1.363(3) . ? C3 H3A 0.9300 . ? C4 C5 1.383(2) . ? C4 H4A 0.9300 . ? C5 C6 1.384(2) . ? C5 H5A 0.9300 . ? C6 C7 1.506(2) . ? C7 N8A 1.35(2) . ? C7 N8 1.589(18) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? N8 C13 1.34(2) . ? N8 C9 1.49(3) . ? O9 C9 1.21(2) . ? C9 C10 1.47(2) . ? C10 C11 1.502(16) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.453(19) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C14 1.33(2) . ? C12 C13 1.44(2) . ? C13 O13 1.223(17) . ? N8A C9A 1.31(3) . ? N8A C13A 1.47(2) . ? O9A C9A 1.26(3) . ? C9A C10A 1.53(2) . ? C10A C11A 1.542(15) . ? C10A H10C 0.9700 . ? C10A H10D 0.9700 . ? C11A C12A 1.51(2) . ? C11A H11C 0.9700 . ? C11A H11D 0.9700 . ? C12A C14 1.31(2) . ? C12A C13A 1.51(3) . ? C13A O13A 1.23(2) . ? C14 O15 1.3586(17) . ? C14 H14A 0.9300 . ? O15 C16 1.3828(17) . ? C16 N17 1.3095(18) . ? C16 C21 1.378(2) . ? N17 C18 1.344(2) . ? C18 C19 1.365(3) . ? C18 H18A 0.9300 . ? C19 C20 1.370(2) . ? C19 H19A 0.9300 . ? C20 C21 1.369(2) . ? C20 H20A 0.9300 . ? C21 H21A 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 C2 C1 C6 120.68(16) . . ? C2 C1 H1A 119.7 . . ? C6 C1 H1A 119.7 . . ? C3 C2 C1 120.75(17) . . ? C3 C2 H2A 119.6 . . ? C1 C2 H2A 119.6 . . ? C2 C3 C4 119.57(17) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C3 C4 C5 120.38(17) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C4 C5 C6 120.91(16) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C5 C6 C1 117.70(15) . . ? C5 C6 C7 121.12(13) . . ? C1 C6 C7 121.17(14) . . ? N8A C7 C6 115.6(10) . . ? C6 C7 N8 112.1(8) . . ? N8A C7 H7A 103.7 . . ? C6 C7 H7A 109.2 . . ? N8 C7 H7A 109.2 . . ? N8A C7 H7B 110.9 . . ? C6 C7 H7B 109.2 . . ? N8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C13 N8 C9 128.7(16) . . ? C13 N8 C7 118.7(17) . . ? C9 N8 C7 112.2(13) . . ? O9 C9 C10 130.8(19) . . ? O9 C9 N8 117.4(17) . . ? C10 C9 N8 109.3(13) . . ? C9 C10 C11 114.3(12) . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 111.4(10) . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C14 C12 C13 113.7(14) . . ? C14 C12 C11 125.2(15) . . ? C13 C12 C11 121.0(15) . . ? O13 C13 N8 116.4(15) . . ? O13 C13 C12 126.6(15) . . ? N8 C13 C12 115.1(15) . . ? C9A N8A C7 125.4(16) . . ? C9A N8A C13A 117.3(15) . . ? C7 N8A C13A 117.0(19) . . ? O9A C9A N8A 121.4(16) . . ? O9A C9A C10A 109.7(17) . . ? N8A C9A C10A 127.0(13) . . ? C9A C10A C11A 110.2(11) . . ? C9A C10A H10C 109.6 . . ? C11A C10A H10C 109.6 . . ? C9A C10A H10D 109.6 . . ? C11A C10A H10D 109.6 . . ? H10C C10A H10D 108.1 . . ? C12A C11A C10A 112.2(10) . . ? C12A C11A H11C 109.2 . . ? C10A C11A H11C 109.2 . . ? C12A C11A H11D 109.2 . . ? C10A C11A H11D 109.2 . . ? H11C C11A H11D 107.9 . . ? C14 C12A C11A 124.7(16) . . ? C14 C12A C13A 117.6(16) . . ? C11A C12A C13A 117.7(16) . . ? O13A C13A N8A 120.0(15) . . ? O13A C13A C12A 117.9(18) . . ? N8A C13A C12A 120.1(16) . . ? C12A C14 O15 122.1(10) . . ? C12 C14 O15 120.1(9) . . ? C12A C14 H14A 115.7 . . ? C12 C14 H14A 119.9 . . ? O15 C14 H14A 119.9 . . ? C14 O15 C16 119.35(11) . . ? N17 C16 C21 125.50(14) . . ? N17 C16 O15 118.62(13) . . ? C21 C16 O15 115.87(13) . . ? C16 N17 C18 115.82(15) . . ? N17 C18 C19 123.48(17) . . ? N17 C18 H18A 118.3 . . ? C19 C18 H18A 118.3 . . ? C18 C19 C20 118.75(16) . . ? C18 C19 H19A 120.6 . . ? C20 C19 H19A 120.6 . . ? C21 C20 C19 119.29(16) . . ? C21 C20 H20A 120.4 . . ? C19 C20 H20A 120.4 . . ? C20 C21 C16 117.14(15) . . ? C20 C21 H21A 121.4 . . ? C16 C21 H21A 121.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.199 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.039