Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'McAlonan, Helena' 'Murphy, James P.' 'Nieuwenhuyzen, Mark' 'Reynolds, Karen' 'Sarma, Pakala' 'Stevenson, P. J.' 'Thompson, Norris' _publ_contact_author_name 'Dr P J Stevenson' _publ_contact_author_address ; School of Chemistry Queen's University of Belfast Belfast BT9 5AG UK ; _publ_contact_author_email 'P.STEVENSON@QUB.AC.UK' _publ_section_title ; 4-Phenyloxazolidin-2-one and 2,3-Dihydroisoindol-1-ones: Chiral Auxiliaries for Diels-Alder reactions of N-substituted 1,3-dienes. ; data_kr2 #compound 11 _database_code_CSD 171850 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H20 N2 O3' O.5(C4 H8 O2) _chemical_formula_sum 'C23 H24 N2 O4' _chemical_formula_weight 392.44 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 0.0016 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 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 25.491(2) _cell_length_b 7.7950(10) _cell_length_c 9.9820(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1983.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 2 _cell_measurement_theta_max 12.5 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 P4 _diffrn_measurement_method 'Omega Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1% _diffrn_reflns_number 2439 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2355 _reflns_number_gt 1930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1993)' _computing_cell_refinement 'XSCANS (Fait, 1993)' _computing_data_reduction 'XSCANS (Fait, 1993)' _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^)+(0.0471P)^2^+0.2984P] 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 calc _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 0.1(19) _refine_ls_number_reflns 2355 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 0.79545(11) -0.1884(4) 0.8745(3) 0.0234(7) Uani 1 1 d . . . H1 H 0.7629 -0.1374 0.9140 0.028 Uiso 1 1 calc R . . N11 N 0.80697(9) -0.0874(3) 0.7540(2) 0.0227(6) Uani 1 1 d . . . C12 C 0.84811(11) -0.1233(4) 0.6533(3) 0.0227(7) Uani 1 1 d . . . H12 H 0.8833 -0.1201 0.6976 0.027 Uiso 1 1 calc R . . C121 C 0.84174(12) -0.2931(4) 0.5799(3) 0.0268(7) Uani 1 1 d . . . H12A H 0.8663 -0.2976 0.5044 0.032 Uiso 1 1 calc R . . H12B H 0.8057 -0.3031 0.5464 0.032 Uiso 1 1 calc R . . H12C H 0.8491 -0.3880 0.6415 0.032 Uiso 1 1 calc R . . C13 C 0.84272(11) 0.0294(4) 0.5616(3) 0.0229(7) Uani 1 1 d . . . C14 C 0.86876(11) 0.0673(4) 0.4434(3) 0.0258(7) Uani 1 1 d . . . H14 H 0.8949 -0.0078 0.4090 0.031 Uiso 1 1 calc R . . C15 C 0.85588(11) 0.2167(4) 0.3767(3) 0.0286(8) Uani 1 1 d . . . H15 H 0.8735 0.2444 0.2957 0.034 Uiso 1 1 calc R . . C16 C 0.81763(12) 0.3273(4) 0.4254(3) 0.0304(8) Uani 1 1 d . . . H16 H 0.8095 0.4294 0.3777 0.037 Uiso 1 1 calc R . . C17 C 0.79123(11) 0.2896(4) 0.5435(3) 0.0272(7) Uani 1 1 d . . . H17 H 0.7654 0.3650 0.5786 0.033 Uiso 1 1 calc R . . C18 C 0.80391(11) 0.1381(4) 0.6085(3) 0.0226(7) Uani 1 1 d . . . C19 C 0.78085(11) 0.0640(4) 0.7317(3) 0.0243(7) Uani 1 1 d . . . O19 O 0.74483(8) 0.1215(3) 0.7992(2) 0.0293(5) Uani 1 1 d . . . C2 C 0.78257(12) -0.3730(4) 0.8454(3) 0.0289(8) Uani 1 1 d . . . H2 H 0.7537 -0.3957 0.7880 0.035 Uiso 1 1 calc R . . C3 C 0.80806(13) -0.5040(4) 0.8932(3) 0.0303(8) Uani 1 1 d . . . H3 H 0.7954 -0.6155 0.8724 0.036 Uiso 1 1 calc R . . C4 C 0.85599(13) -0.4903(4) 0.9788(3) 0.0315(8) Uani 1 1 d . . . H41 H 0.8818 -0.5777 0.9498 0.038 Uiso 1 1 calc R . . H42 H 0.8464 -0.5154 1.0729 0.038 Uiso 1 1 calc R . . C5 C 0.88170(11) -0.3123(4) 0.9719(3) 0.0240(7) Uani 1 1 d . . . H5 H 0.8980 -0.2984 0.8815 0.029 Uiso 1 1 calc R . . C51 C 0.92425(11) -0.2920(4) 1.0770(3) 0.0249(7) Uani 1 1 d . . . C52 C 0.91362(12) -0.3138(5) 1.2130(3) 0.0307(8) Uani 1 1 d . . . H52 H 0.8788 -0.3390 1.2410 0.037 Uiso 1 1 calc R . . C53 C 0.95294(11) -0.2995(5) 1.3078(3) 0.0349(8) Uani 1 1 d . . . H53 H 0.9452 -0.3160 1.4000 0.042 Uiso 1 1 calc R . . C54 C 1.00346(13) -0.2612(5) 1.2679(3) 0.0379(9) Uani 1 1 d . . . H54 H 1.0306 -0.2506 1.3326 0.045 Uiso 1 1 calc R . . C55 C 1.01433(12) -0.2384(5) 1.1339(3) 0.0409(9) Uani 1 1 d . . . H55 H 1.0491 -0.2121 1.1064 0.049 Uiso 1 1 calc R . . C56 C 0.97526(11) -0.2533(5) 1.0397(3) 0.0339(8) Uani 1 1 d . . . H56 H 0.9834 -0.2369 0.9477 0.041 Uiso 1 1 calc R . . C6 C 0.83768(11) -0.1801(4) 0.9860(3) 0.0213(7) Uani 1 1 d . . . H6 H 0.8197 -0.2020 1.0734 0.026 Uiso 1 1 calc R . . N61 N 0.85946(10) -0.0006(4) 0.9907(2) 0.0234(6) Uani 1 1 d . . . O61 O 0.89514(9) 0.0377(3) 0.9133(2) 0.0340(6) Uani 1 1 d . . . O62 O 0.84060(9) 0.0988(3) 1.0711(2) 0.0402(6) Uani 1 1 d . . . C1S C 0.9443(3) -0.6649(11) 0.6817(8) 0.047(2) Uiso 0.50 1 d P . 1 H1SA H 0.9529 -0.7848 0.6851 0.056 Uiso 0.50 1 d PR . 1 H1SB H 0.9247 -0.6341 0.7602 0.056 Uiso 0.50 1 d PR . 1 H1SC H 0.9237 -0.6422 0.6033 0.056 Uiso 0.50 1 d PR . 1 C2S C 0.9948(3) -0.5623(8) 0.6762(7) 0.0281(17) Uiso 0.50 1 d P . 1 O1S O 1.0378(2) -0.6222(9) 0.6771(6) 0.0501(19) Uiso 0.50 1 d P . 1 O2S O 0.9831(3) -0.3917(8) 0.6715(6) 0.0368(15) Uiso 0.50 1 d P . 1 C3S C 1.0297(3) -0.2833(10) 0.6660(8) 0.0401(18) Uiso 0.50 1 d P . 1 H3SA H 1.0508 -0.3112 0.5893 0.048 Uiso 0.50 1 d PR . 1 H3SB H 1.0505 -0.2968 0.7455 0.048 Uiso 0.50 1 d PR . 1 C4S C 1.0094(3) -0.1009(9) 0.6554(7) 0.0406(18) Uiso 0.50 1 d P . 1 H4SA H 1.0379 -0.0209 0.6513 0.049 Uiso 0.50 1 d PR . 1 H4SB H 0.9884 -0.0909 0.5759 0.049 Uiso 0.50 1 d PR . 1 H4SC H 0.9881 -0.0765 0.7325 0.049 Uiso 0.50 1 d PR . 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0198(14) 0.0282(17) 0.0222(15) -0.0019(14) 0.0029(13) -0.0010(14) N11 0.0206(12) 0.0260(15) 0.0215(12) -0.0003(12) 0.0046(11) 0.0006(12) C12 0.0182(14) 0.0262(17) 0.0237(15) -0.0018(14) 0.0028(13) 0.0002(14) C121 0.0291(15) 0.0259(17) 0.0254(15) -0.0021(15) 0.0049(15) 0.0024(15) C13 0.0204(14) 0.0253(17) 0.0229(15) -0.0047(14) -0.0020(14) -0.0049(14) C14 0.0243(15) 0.0299(18) 0.0230(16) -0.0054(15) -0.0019(14) -0.0039(15) C15 0.0301(16) 0.0335(19) 0.0221(15) 0.0011(15) -0.0025(14) -0.0087(16) C16 0.0344(17) 0.0268(17) 0.0301(16) 0.0044(16) -0.0121(15) -0.0049(16) C17 0.0253(15) 0.0240(17) 0.0324(17) -0.0031(14) -0.0071(14) -0.0011(15) C18 0.0227(15) 0.0247(16) 0.0204(14) -0.0053(14) -0.0054(13) -0.0073(14) C19 0.0218(15) 0.0240(18) 0.0271(16) -0.0108(14) -0.0010(14) -0.0016(14) O19 0.0267(11) 0.0282(12) 0.0331(12) -0.0074(11) 0.0066(10) 0.0016(11) C2 0.0281(17) 0.037(2) 0.0220(15) -0.0052(16) 0.0033(14) -0.0149(17) C3 0.0408(19) 0.0236(16) 0.0263(16) -0.0022(16) 0.0083(16) -0.0153(16) C4 0.042(2) 0.0194(16) 0.0334(17) -0.0027(16) 0.0064(16) -0.0040(16) C5 0.0243(15) 0.0222(16) 0.0257(16) -0.0030(14) 0.0062(13) 0.0004(14) C51 0.0251(15) 0.0200(16) 0.0297(16) -0.0031(15) 0.0032(14) 0.0035(14) C52 0.0213(15) 0.037(2) 0.0344(17) 0.0002(17) 0.0045(15) 0.0028(16) C53 0.0298(17) 0.049(2) 0.0263(17) 0.0011(18) -0.0006(15) 0.0059(19) C54 0.0318(17) 0.044(2) 0.0380(18) 0.0048(18) -0.0097(16) 0.0053(17) C55 0.0247(16) 0.053(2) 0.045(2) 0.007(2) 0.0021(16) -0.0012(18) C56 0.0287(16) 0.045(2) 0.0274(17) 0.0012(17) 0.0062(14) 0.0007(17) C6 0.0234(15) 0.0186(16) 0.0218(14) -0.0029(14) 0.0027(13) -0.0050(14) N61 0.0223(14) 0.0239(14) 0.0239(13) -0.0012(13) -0.0067(12) -0.0003(12) O61 0.0386(13) 0.0322(14) 0.0312(12) 0.0009(11) 0.0067(11) -0.0120(12) O62 0.0435(13) 0.0305(14) 0.0466(14) -0.0180(13) 0.0092(13) -0.0024(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N11 1.467(4) . ? C1 C2 1.504(4) . ? C1 C6 1.550(4) . ? N11 C19 1.374(4) . ? N11 C12 1.480(3) . ? C12 C13 1.508(4) . ? C12 C121 1.521(4) . ? C13 C18 1.384(4) . ? C13 C14 1.386(4) . ? C14 C15 1.381(4) . ? C15 C16 1.390(4) . ? C16 C17 1.389(4) . ? C17 C18 1.386(4) . ? C18 C19 1.480(4) . ? C19 O19 1.224(3) . ? C2 C3 1.301(5) . ? C3 C4 1.494(5) . ? C4 C5 1.536(5) . ? C5 C51 1.517(4) . ? C5 C6 1.530(4) . ? C51 C56 1.386(4) . ? C51 C52 1.395(4) . ? C52 C53 1.383(4) . ? C53 C54 1.380(5) . ? C54 C55 1.378(5) . ? C55 C56 1.375(4) . ? C6 N61 1.506(4) . ? N61 O62 1.215(3) . ? N61 O61 1.230(3) . ? C1S C3S 0.791(9) 2_745 ? C1S C2S 1.515(10) . ? C1S O2S 1.904(10) 2_745 ? C2S O2S 0.669(8) 2_745 ? C2S C2S 1.008(12) 2_745 ? C2S O1S 1.193(10) . ? C2S C3S 1.359(9) 2_745 ? C2S O2S 1.364(10) . ? C2S O1S 1.661(10) 2_745 ? O1S O2S 0.548(8) 2_745 ? O1S C2S 1.661(10) 2_745 ? O1S C3S 1.875(9) 2_745 ? O2S O1S 0.548(8) 2_745 ? O2S C2S 0.669(8) 2_745 ? O2S C3S 1.458(9) . ? O2S C1S 1.904(10) 2_745 ? C3S C1S 0.791(9) 2_745 ? C3S C2S 1.359(9) 2_745 ? C3S C4S 1.517(10) . ? C3S O1S 1.875(9) 2_745 ? C4S C4S 1.644(14) 2_755 ? 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 N11 C1 C2 113.5(2) . . ? N11 C1 C6 115.3(2) . . ? C2 C1 C6 109.3(3) . . ? C19 N11 C1 119.8(2) . . ? C19 N11 C12 113.3(2) . . ? C1 N11 C12 126.7(2) . . ? N11 C12 C13 101.5(2) . . ? N11 C12 C121 114.6(2) . . ? C13 C12 C121 112.6(2) . . ? C18 C13 C14 120.0(3) . . ? C18 C13 C12 110.0(2) . . ? C14 C13 C12 129.9(3) . . ? C15 C14 C13 118.5(3) . . ? C14 C15 C16 121.4(3) . . ? C17 C16 C15 120.4(3) . . ? C18 C17 C16 117.7(3) . . ? C13 C18 C17 122.0(3) . . ? C13 C18 C19 109.1(3) . . ? C17 C18 C19 128.9(3) . . ? O19 C19 N11 126.1(3) . . ? O19 C19 C18 127.8(3) . . ? N11 C19 C18 106.1(2) . . ? C3 C2 C1 124.8(3) . . ? C2 C3 C4 124.2(3) . . ? C3 C4 C5 112.8(3) . . ? C51 C5 C6 113.0(2) . . ? C51 C5 C4 111.6(3) . . ? C6 C5 C4 106.9(2) . . ? C56 C51 C52 118.1(3) . . ? C56 C51 C5 120.5(3) . . ? C52 C51 C5 121.4(3) . . ? C53 C52 C51 121.0(3) . . ? C54 C53 C52 119.8(3) . . ? C55 C54 C53 119.7(3) . . ? C56 C55 C54 120.5(3) . . ? C55 C56 C51 121.0(3) . . ? N61 C6 C5 111.0(2) . . ? N61 C6 C1 108.5(2) . . ? C5 C6 C1 114.5(2) . . ? O62 N61 O61 123.6(3) . . ? O62 N61 C6 117.8(2) . . ? O61 N61 C6 118.6(2) . . ? C3S C1S C2S 63.4(8) 2_745 . ? C3S C1S O2S 45.1(8) 2_745 2_745 ? C2S C1S O2S 18.5(3) . 2_745 ? O2S C2S C2S 107.0(14) 2_745 2_745 ? O2S C2S O1S 10.4(8) 2_745 . ? C2S C2S O1S 97.7(10) 2_745 . ? O2S C2S C3S 84.7(9) 2_745 2_745 ? C2S C2S C3S 167.2(12) 2_745 2_745 ? O1S C2S C3S 94.4(6) . 2_745 ? O2S C2S O2S 134.6(10) 2_745 . ? C2S C2S O2S 28.0(6) 2_745 . ? O1S C2S O2S 125.6(7) . . ? C3S C2S O2S 139.6(8) 2_745 . ? O2S C2S C1S 115.7(10) 2_745 . ? C2S C2S C1S 137.2(12) 2_745 . ? O1S C2S C1S 125.0(7) . . ? C3S C2S C1S 31.4(4) 2_745 . ? O2S C2S C1S 109.4(8) . . ? O2S C2S O1S 152.2(11) 2_745 2_745 ? C2S C2S O1S 45.4(8) 2_745 2_745 ? O1S C2S O1S 143.0(5) . 2_745 ? C3S C2S O1S 122.5(7) 2_745 2_745 ? O2S C2S O1S 17.6(4) . 2_745 ? C1S C2S O1S 91.9(6) . 2_745 ? O2S O1S C2S 12.8(10) 2_745 . ? O2S O1S C2S 48.8(10) 2_745 2_745 ? C2S O1S C2S 37.0(5) . 2_745 ? O2S O1S C3S 34.6(11) 2_745 2_745 ? C2S O1S C3S 46.3(4) . 2_745 ? C2S O1S C3S 83.2(4) 2_745 2_745 ? O1S O2S C2S 156.8(18) 2_745 2_745 ? O1S O2S C2S 113.7(13) 2_745 . ? C2S O2S C2S 45.0(10) 2_745 . ? O1S O2S C3S 133.1(14) 2_745 . ? C2S O2S C3S 68.1(8) 2_745 . ? C2S O2S C3S 112.9(8) . . ? O1S O2S C1S 153.6(14) 2_745 2_745 ? C2S O2S C1S 45.8(8) 2_745 2_745 ? C2S O2S C1S 90.8(7) . 2_745 ? C3S O2S C1S 22.6(4) . 2_745 ? C1S C3S C2S 85.3(10) 2_745 2_745 ? C1S C3S O2S 112.2(11) 2_745 . ? C2S C3S O2S 27.2(4) 2_745 . ? C1S C3S C4S 141.1(11) 2_745 . ? C2S C3S C4S 132.7(7) 2_745 . ? O2S C3S C4S 105.5(6) . . ? C1S C3S O1S 123.8(10) 2_745 2_745 ? C2S C3S O1S 39.4(4) 2_745 2_745 ? O2S C3S O1S 12.3(4) . 2_745 ? C4S C3S O1S 93.4(5) . 2_745 ? C3S C4S C4S 174.9(6) . 2_755 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.180 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.045 #### data_ps4m #Compound 27 _database_code_CSD 171852 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 N2 O4' _chemical_formula_weight 388.41 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.6451(7) _cell_length_b 9.5458(7) _cell_length_c 9.9442(8) _cell_angle_alpha 90.00 _cell_angle_beta 99.358(2) _cell_angle_gamma 90.00 _cell_volume 903.38(12) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6143 _diffrn_reflns_av_R_equivalents 0.0651 _diffrn_reflns_av_sigmaI/netI 0.1112 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.69 _reflns_number_total 3890 _reflns_number_gt 2698 _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^)+(0.0415P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 -0.8(14) _refine_ls_number_reflns 3890 _refine_ls_number_parameters 339 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_restrained_S_all 0.921 _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 0.1905(3) 0.0261(4) -0.5877(3) 0.0284(7) Uani 1 1 d . . . H1 H 0.198(3) 0.118(4) -0.642(4) 0.037(10) Uiso 1 1 d . . . C2 C 0.0637(4) -0.0411(4) -0.5860(4) 0.0319(8) Uani 1 1 d . . . H2 H -0.016(3) -0.001(4) -0.639(4) 0.037(10) Uiso 1 1 d . . . C3 C 0.0584(4) -0.1584(4) -0.5057(4) 0.0311(8) Uani 1 1 d . . . H3 H -0.027(4) -0.194(4) -0.500(3) 0.032(9) Uiso 1 1 d . . . C4 C 0.1790(3) -0.2086(4) -0.4265(3) 0.0288(8) Uani 1 1 d . . . H4 H 0.172(3) -0.294(3) -0.364(3) 0.019(8) Uiso 1 1 d . . . C5 C 0.3069(3) -0.1431(3) -0.4296(3) 0.0242(7) Uani 1 1 d . . . H5 H 0.397(3) -0.184(4) -0.367(3) 0.033(9) Uiso 1 1 d . . . C6 C 0.3143(3) -0.0243(3) -0.5107(3) 0.0215(7) Uani 1 1 d . . . C7 C 0.4520(3) 0.0466(3) -0.5233(3) 0.0222(7) Uani 1 1 d . . . H7 H 0.440(3) 0.149(3) -0.545(3) 0.024(9) Uiso 1 1 d . . . C8 C 0.5229(4) -0.0141(4) -0.6377(3) 0.0277(8) Uani 1 1 d . . . H8A H 0.569(3) 0.060(4) -0.690(3) 0.036(10) Uiso 1 1 d . . . H8B H 0.456(3) -0.066(3) -0.703(3) 0.011(8) Uiso 1 1 d . . . O9 O 0.6322(2) -0.1065(3) -0.5707(2) 0.0293(5) Uani 1 1 d . . . C10 C 0.6655(3) -0.0647(3) -0.4373(3) 0.0238(7) Uani 1 1 d . . . O10 O 0.7692(2) -0.1057(2) -0.3629(2) 0.0304(5) Uani 1 1 d . . . N11 N 0.5643(2) 0.0240(3) -0.4071(2) 0.0207(6) Uani 1 1 d . . . C12 C 0.5776(3) 0.1044(3) -0.2812(3) 0.0201(7) Uani 1 1 d . . . H12 H 0.508(3) 0.177(3) -0.301(3) 0.005(7) Uiso 1 1 d . . . C13 C 0.7186(3) 0.1741(3) -0.2464(3) 0.0226(7) Uani 1 1 d . . . H13 H 0.782(3) 0.164(4) -0.305(4) 0.033(10) Uiso 1 1 d . . . C14 C 0.7459(3) 0.2475(3) -0.1311(3) 0.0261(8) Uani 1 1 d . . . H14 H 0.832(3) 0.298(4) -0.105(3) 0.034(10) Uiso 1 1 d . . . C15 C 0.6409(4) 0.2497(4) -0.0354(4) 0.0287(8) Uani 1 1 d . . . H15A H 0.561(3) 0.312(4) -0.075(3) 0.034(9) Uiso 1 1 d . . . H15B H 0.682(3) 0.286(4) 0.059(4) 0.037(10) Uiso 1 1 d . . . C16 C 0.5844(3) 0.1018(3) -0.0229(3) 0.0220(7) Uani 1 1 d . . . H16 H 0.514(3) 0.112(3) 0.025(3) 0.020(8) Uiso 1 1 d . . . C17 C 0.5372(3) 0.0223(3) -0.1576(3) 0.0219(7) Uani 1 1 d . . . H17 H 0.436(3) 0.009(3) -0.178(3) 0.019(8) Uiso 1 1 d . . . C18 C 0.6040(3) -0.1217(4) -0.1335(3) 0.0222(7) Uani 1 1 d . . . O18 O 0.5755(2) -0.2266(2) -0.1988(2) 0.0251(5) Uani 1 1 d . . . N19 N 0.7028(2) -0.1158(3) -0.0137(2) 0.0206(6) Uani 1 1 d . . . C20 C 0.6988(3) 0.0114(3) 0.0555(3) 0.0221(7) Uani 1 1 d . . . O20 O 0.7743(2) 0.0408(2) 0.1607(2) 0.0294(5) Uani 1 1 d . . . C21 C 0.7869(3) -0.2350(3) 0.0382(3) 0.0214(7) Uani 1 1 d . . . C22 C 0.7939(3) -0.2752(3) 0.1729(3) 0.0256(8) Uani 1 1 d . . . H22 H 0.741(4) -0.221(4) 0.233(3) 0.038(10) Uiso 1 1 d . . . C23 C 0.8711(4) -0.3935(4) 0.2185(4) 0.0318(8) Uani 1 1 d . . . H23 H 0.875(4) -0.431(4) 0.317(4) 0.050(11) Uiso 1 1 d . . . C24 C 0.9399(4) -0.4689(4) 0.1302(4) 0.0327(8) Uani 1 1 d . . . H24 H 0.984(3) -0.549(4) 0.159(4) 0.037(10) Uiso 1 1 d . . . C25 C 0.9320(3) -0.4272(3) -0.0042(4) 0.0318(8) Uani 1 1 d . . . H25 H 0.9785 -0.4802 -0.0643 0.033(9) Uiso 1 1 calc R . . C26 C 0.8565(3) -0.3083(3) -0.0515(4) 0.0250(8) Uani 1 1 d . . . H26 H 0.851(3) -0.277(3) -0.144(3) 0.029(9) Uiso 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 0.0308(18) 0.0263(18) 0.0257(18) -0.0003(16) -0.0026(14) 0.0022(16) C2 0.0263(19) 0.036(2) 0.032(2) -0.0037(17) -0.0017(16) 0.0001(16) C3 0.0223(18) 0.036(2) 0.036(2) -0.0095(16) 0.0085(16) -0.0046(15) C4 0.0310(19) 0.031(2) 0.0264(19) -0.0011(16) 0.0099(15) -0.0067(15) C5 0.0248(17) 0.0256(19) 0.0216(17) 0.0000(15) 0.0017(14) 0.0001(14) C6 0.0236(16) 0.0228(17) 0.0171(16) -0.0031(13) 0.0009(13) 0.0022(13) C7 0.0276(17) 0.0201(17) 0.0178(17) 0.0028(14) 0.0001(13) -0.0002(14) C8 0.0310(18) 0.0290(19) 0.0218(18) -0.0001(16) 0.0010(15) -0.0001(16) O9 0.0357(13) 0.0295(12) 0.0241(12) -0.0006(11) 0.0091(10) 0.0041(11) C10 0.0264(17) 0.0205(17) 0.0263(18) 0.0009(14) 0.0100(15) -0.0044(13) O10 0.0253(12) 0.0292(12) 0.0364(14) 0.0034(12) 0.0042(10) 0.0053(11) N11 0.0197(13) 0.0221(14) 0.0202(14) -0.0002(12) 0.0028(10) 0.0016(12) C12 0.0192(16) 0.0195(17) 0.0208(17) -0.0008(14) 0.0011(13) 0.0043(13) C13 0.0224(17) 0.0239(17) 0.0211(18) 0.0019(14) 0.0027(15) -0.0019(14) C14 0.0242(17) 0.0230(18) 0.0297(19) 0.0010(15) 0.0003(15) -0.0009(14) C15 0.036(2) 0.0234(18) 0.025(2) -0.0032(15) 0.0003(16) 0.0047(16) C16 0.0219(16) 0.0238(17) 0.0206(17) 0.0000(14) 0.0043(14) 0.0031(14) C17 0.0238(16) 0.0206(17) 0.0214(17) 0.0004(14) 0.0045(13) 0.0006(14) C18 0.0223(15) 0.0263(17) 0.0190(16) 0.0027(15) 0.0060(12) -0.0011(14) O18 0.0272(12) 0.0220(12) 0.0244(12) -0.0008(10) -0.0005(10) -0.0029(10) N19 0.0231(13) 0.0201(14) 0.0178(13) -0.0007(12) 0.0013(11) 0.0008(12) C20 0.0219(15) 0.0228(18) 0.0226(17) 0.0016(14) 0.0065(14) 0.0001(14) O20 0.0343(13) 0.0317(13) 0.0206(13) -0.0039(11) -0.0007(10) 0.0007(11) C21 0.0197(15) 0.0201(16) 0.0221(17) -0.0009(14) -0.0033(13) -0.0001(13) C22 0.0254(17) 0.0266(19) 0.0242(19) 0.0002(15) 0.0017(15) -0.0008(14) C23 0.0325(19) 0.0302(19) 0.030(2) 0.0069(17) -0.0017(16) -0.0029(16) C24 0.0319(19) 0.0232(19) 0.040(2) 0.0092(18) -0.0031(16) 0.0047(16) C25 0.0258(18) 0.0248(19) 0.044(2) -0.0051(16) 0.0033(16) 0.0001(14) C26 0.0248(17) 0.0257(19) 0.024(2) -0.0007(15) 0.0038(15) -0.0022(14) _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 1.383(5) . ? C1 C6 1.395(4) . ? C2 C3 1.382(5) . ? C3 C4 1.380(5) . ? C4 C5 1.387(4) . ? C5 C6 1.400(4) . ? C6 C7 1.514(4) . ? C7 N11 1.466(4) . ? C7 C8 1.533(5) . ? C8 O9 1.450(4) . ? O9 C10 1.372(4) . ? C10 O10 1.209(3) . ? C10 N11 1.362(4) . ? N11 C12 1.456(4) . ? C12 C13 1.503(4) . ? C12 C17 1.560(4) . ? C13 C14 1.333(5) . ? C14 C15 1.499(5) . ? C15 C16 1.525(5) . ? C16 C20 1.514(4) . ? C16 C17 1.542(4) . ? C17 C18 1.520(5) . ? C18 O18 1.201(4) . ? C18 N19 1.400(4) . ? N19 C20 1.399(4) . ? N19 C21 1.443(4) . ? C20 O20 1.207(3) . ? C21 C22 1.384(4) . ? C21 C26 1.389(5) . ? C22 C23 1.387(5) . ? C23 C24 1.386(5) . ? C24 C25 1.385(5) . ? C25 C26 1.389(5) . ? 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 120.9(3) . . ? C3 C2 C1 120.0(3) . . ? C4 C3 C2 120.2(3) . . ? C3 C4 C5 120.1(3) . . ? C4 C5 C6 120.4(3) . . ? C1 C6 C5 118.4(3) . . ? C1 C6 C7 119.0(3) . . ? C5 C6 C7 122.5(3) . . ? N11 C7 C6 114.5(3) . . ? N11 C7 C8 99.7(2) . . ? C6 C7 C8 113.3(3) . . ? O9 C8 C7 105.5(3) . . ? C10 O9 C8 107.8(2) . . ? O10 C10 N11 128.2(3) . . ? O10 C10 O9 122.6(3) . . ? N11 C10 O9 109.3(3) . . ? C10 N11 C12 123.4(2) . . ? C10 N11 C7 112.4(2) . . ? C12 N11 C7 123.4(2) . . ? N11 C12 C13 112.4(3) . . ? N11 C12 C17 114.5(2) . . ? C13 C12 C17 111.9(2) . . ? C14 C13 C12 118.4(3) . . ? C13 C14 C15 119.6(3) . . ? C14 C15 C16 109.0(3) . . ? C20 C16 C15 109.2(3) . . ? C20 C16 C17 104.7(3) . . ? C15 C16 C17 116.3(3) . . ? C18 C17 C16 104.5(2) . . ? C18 C17 C12 115.1(3) . . ? C16 C17 C12 111.2(2) . . ? O18 C18 N19 123.9(3) . . ? O18 C18 C17 127.9(3) . . ? N19 C18 C17 108.1(3) . . ? C20 N19 C18 112.6(2) . . ? C20 N19 C21 124.5(2) . . ? C18 N19 C21 122.5(2) . . ? O20 C20 N19 124.6(3) . . ? O20 C20 C16 126.9(3) . . ? N19 C20 C16 108.5(3) . . ? C22 C21 C26 121.9(3) . . ? C22 C21 N19 120.1(3) . . ? C26 C21 N19 118.0(3) . . ? C21 C22 C23 118.8(3) . . ? C24 C23 C22 120.2(3) . . ? C25 C24 C23 120.3(3) . . ? C24 C25 C26 120.4(3) . . ? C25 C26 C21 118.4(3) . . ? _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 28.69 _diffrn_measured_fraction_theta_full 0.886 _refine_diff_density_max 0.216 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.050 #### data_ps5m #compound 15 _database_code_CSD 171853 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 N O2' _chemical_formula_weight 215.24 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.0693(6) _cell_length_b 8.7995(9) _cell_length_c 21.691(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1158.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5654 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.55 _reflns_number_total 2405 _reflns_number_gt 2159 _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^)+(0.0858P)^2^+0.0444P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 -1.2(15) _refine_ls_number_reflns 2405 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1306 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.002 _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 -0.2945(4) 0.5260(3) -0.17498(9) 0.0452(5) Uani 1 1 d . . . H1A H -0.272(4) 0.640(3) -0.1888(12) 0.052(7) Uiso 1 1 d . . . H1B H -0.163(4) 0.474(3) -0.1593(11) 0.047(6) Uiso 1 1 d . . . C2 C -0.4822(3) 0.4566(2) -0.18615(8) 0.0353(4) Uani 1 1 d . . . H2 H -0.596(4) 0.511(3) -0.2066(10) 0.043(6) Uiso 1 1 d . . . C3 C -0.5279(3) 0.2985(2) -0.17195(8) 0.0316(4) Uani 1 1 d . . . H3 H -0.415(4) 0.246(3) -0.1565(9) 0.033(5) Uiso 1 1 d . . . C4 C -0.7199(3) 0.2343(2) -0.18453(8) 0.0308(4) Uani 1 1 d . . . H4 H -0.840(3) 0.284(2) -0.2020(9) 0.026(5) Uiso 1 1 d . . . N5 N -0.7714(3) 0.08209(18) -0.17344(7) 0.0322(3) Uani 1 1 d . . . C6 C -0.9671(3) 0.0221(2) -0.19159(8) 0.0347(4) Uani 1 1 d . . . O6 O -1.1233(2) 0.08834(18) -0.21230(7) 0.0469(4) Uani 1 1 d . . . O7 O -0.9660(2) -0.12883(16) -0.18236(7) 0.0428(4) Uani 1 1 d . . . C8 C -0.7466(4) -0.1770(3) -0.16542(11) 0.0479(6) Uani 1 1 d . . . H8A H -0.675(6) -0.229(4) -0.2031(16) 0.088(11) Uiso 1 1 d . . . H8B H -0.769(4) -0.228(3) -0.1292(12) 0.045(6) Uiso 1 1 d . . . C9 C -0.6156(3) -0.0315(2) -0.15183(8) 0.0322(4) Uani 1 1 d . . . H9A H -0.473(4) -0.028(3) -0.1773(10) 0.040(5) Uiso 1 1 d . . . C10 C -0.5478(3) -0.0127(2) -0.08502(7) 0.0339(4) Uani 1 1 d . . . C11 C -0.6720(4) 0.0688(3) -0.04339(9) 0.0487(6) Uani 1 1 d . . . H11 H -0.805(4) 0.110(3) -0.0567(11) 0.045(6) Uiso 1 1 d . . . C12 C -0.6000(6) 0.0838(4) 0.01748(10) 0.0696(8) Uani 1 1 d . . . H12 H -0.690(5) 0.149(4) 0.0445(14) 0.065(8) Uiso 1 1 d . . . C13 C -0.4102(5) 0.0145(3) 0.03647(10) 0.0646(7) Uani 1 1 d . . . H13 H -0.358(5) 0.024(4) 0.0812(15) 0.076(9) Uiso 1 1 d . . . C14 C -0.2855(5) -0.0671(4) -0.00461(10) 0.0604(7) Uani 1 1 d . . . H14 H -0.155(5) -0.113(4) 0.0035(13) 0.065(9) Uiso 1 1 d . . . C15 C -0.3553(3) -0.0809(3) -0.06553(9) 0.0469(5) Uani 1 1 d . . . H15 H -0.276(5) -0.148(4) -0.0923(14) 0.078(10) Uiso 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 0.0554(13) 0.0427(12) 0.0374(9) 0.0044(8) -0.0025(9) -0.0101(10) C2 0.0458(11) 0.0310(10) 0.0290(7) -0.0006(6) -0.0031(7) 0.0023(8) C3 0.0363(9) 0.0305(9) 0.0279(7) -0.0014(6) -0.0010(7) 0.0036(7) C4 0.0355(9) 0.0297(9) 0.0271(7) 0.0003(6) -0.0012(7) 0.0054(7) N5 0.0333(8) 0.0318(8) 0.0315(7) -0.0001(6) -0.0022(6) -0.0001(6) C6 0.0317(9) 0.0373(10) 0.0350(8) -0.0040(7) 0.0056(7) -0.0017(7) O6 0.0301(7) 0.0503(9) 0.0604(9) -0.0033(7) -0.0031(6) -0.0005(6) O7 0.0407(8) 0.0366(8) 0.0510(7) -0.0053(6) 0.0047(6) -0.0081(6) C8 0.0585(15) 0.0323(11) 0.0528(12) 0.0021(9) -0.0099(10) -0.0060(10) C9 0.0363(9) 0.0280(9) 0.0323(8) 0.0009(6) -0.0020(7) 0.0026(7) C10 0.0373(10) 0.0337(9) 0.0307(7) 0.0052(7) 0.0018(7) -0.0046(8) C11 0.0581(14) 0.0544(13) 0.0336(9) 0.0027(9) 0.0014(8) 0.0134(11) C12 0.103(2) 0.0755(18) 0.0299(10) -0.0037(11) 0.0046(12) 0.0217(18) C13 0.0840(19) 0.0785(18) 0.0314(10) 0.0057(10) -0.0095(11) -0.0034(15) C14 0.0471(13) 0.091(2) 0.0430(11) 0.0171(12) -0.0080(9) 0.0010(14) C15 0.0403(12) 0.0617(14) 0.0386(10) 0.0077(10) -0.0002(8) 0.0044(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.315(3) . ? C2 C3 1.451(3) . ? C3 C4 1.324(3) . ? C4 N5 1.396(3) . ? N5 C6 1.358(3) . ? N5 C9 1.454(2) . ? C6 O6 1.200(2) . ? C6 O7 1.343(3) . ? O7 C8 1.445(3) . ? C8 C9 1.535(3) . ? C9 C10 1.516(2) . ? C10 C11 1.378(3) . ? C10 C15 1.380(3) . ? C11 C12 1.397(3) . ? C12 C13 1.367(4) . ? C13 C14 1.372(4) . ? C14 C15 1.393(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C3 124.86(19) . . ? C4 C3 C2 122.26(19) . . ? C3 C4 N5 124.84(18) . . ? C6 N5 C4 121.24(16) . . ? C6 N5 C9 113.27(16) . . ? C4 N5 C9 124.73(16) . . ? O6 C6 O7 122.66(18) . . ? O6 C6 N5 127.66(19) . . ? O7 C6 N5 109.67(17) . . ? C6 O7 C8 109.43(15) . . ? O7 C8 C9 106.32(17) . . ? N5 C9 C10 114.19(15) . . ? N5 C9 C8 100.08(15) . . ? C10 C9 C8 114.54(16) . . ? C11 C10 C15 119.27(18) . . ? C11 C10 C9 122.35(17) . . ? C15 C10 C9 118.38(17) . . ? C10 C11 C12 119.8(2) . . ? C13 C12 C11 120.4(2) . . ? C12 C13 C14 120.2(2) . . ? C13 C14 C15 119.6(3) . . ? C10 C15 C14 120.7(2) . . ? _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 28.55 _diffrn_measured_fraction_theta_full 0.871 _refine_diff_density_max 0.204 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.056 #end