data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Andrew Stachulski' _publ_contact_author_email STACHULS@LIV.AC.UK _publ_section_title ; The acyl nitroso Diels Alder (ANDA) reaction of sorbate derivatives: X-ray structural analysis, a new application to amino-acid synthesis and novel 15N NMR distinction between regioisomeric adducts ; loop_ _publ_author_name 'Andrew Stachulski' 'John Bacsa' 'Lee Bollans' 'Jonathan Iggo' 'Gareth Morris' # Attachment 'Cpd10e_ANDA_CIF.doc' #CIF data for compound 10e data_stac205m _database_code_depnum_ccdc_archive 'CCDC 725211' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tert-butyl 3-methyl-6- ({[(4-nitrophenyl)carbonyl]oxy}methyl)-1,2-oxazinane- 2-carboxylate ; _chemical_name_common ; tert-butyl 3-methyl-6-((((4-nitrophenyl)carbonyl)oxy)methyl)- 1,2-oxazinane-2-carboxylate ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 N2 O7' _chemical_formula_sum 'C18 H22 N2 O7' _chemical_formula_weight 378.38 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8725(14) _cell_length_b 10.826(3) _cell_length_c 14.459(3) _cell_angle_alpha 74.694(4) _cell_angle_beta 88.672(4) _cell_angle_gamma 85.198(4) _cell_volume 883.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1072 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 26.09 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9469 _exptl_absorpt_correction_T_max 0.9836 _exptl_absorpt_process_details 'SADABS V2008-1 (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 diffractometer with APEX detector' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5215 _diffrn_reflns_av_R_equivalents 0.0156 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 27.10 _reflns_number_total 3709 _reflns_number_gt 3168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v.5.632 (Bruker, 2005)' _computing_cell_refinement 'SAINT v6.45a (Bruker, 2005)' _computing_data_reduction 'SAINT v6.45a (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0590P)^2^+0.1229P] 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 3709 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.05280(15) 0.75888(8) 0.57661(6) 1.000 0.0160(3) . . O2 O Uani 0.26712(16) 0.75442(8) 0.39251(6) 1.000 0.0180(3) . . O3 O Uani 0.61876(17) 0.65679(8) 0.38129(6) 1.000 0.0216(3) . . O4 O Uani -0.06615(15) 0.61858(8) 0.73560(6) 1.000 0.0171(3) . . O5 O Uani 0.08058(16) 0.74111(8) 0.82260(6) 1.000 0.0210(3) . . O6 O Uani 0.4746(2) 1.23414(10) -0.01057(7) 1.000 0.0332(3) . . O7 O Uani 0.82112(19) 1.15150(10) -0.01509(7) 1.000 0.0334(3) . . N1 N Uani 0.07834(18) 0.80390(9) 0.65928(7) 1.000 0.0153(3) . . N2 N Uani 0.6300(2) 1.15293(10) 0.02099(8) 1.000 0.0223(3) . . C1 C Uani 0.2784(2) 0.87903(11) 0.65061(9) 1.000 0.0166(4) . . C2 C Uani 0.4829(2) 0.80352(12) 0.62296(8) 1.000 0.0184(4) . . C3 C Uani 0.4631(2) 0.70508(12) 0.58625(8) 1.000 0.0182(4) . . C4 C Uani 0.2350(2) 0.66393(11) 0.56820(8) 1.000 0.0168(4) . . C5 C Uani 0.0361(2) 0.71807(11) 0.74764(9) 1.000 0.0161(3) . . C6 C Uani -0.1354(2) 0.51560(12) 0.81937(8) 1.000 0.0176(4) . . C7 C Uani -0.3130(2) 0.57075(13) 0.87798(9) 1.000 0.0235(4) . . C8 C Uani 0.0751(2) 0.45069(13) 0.87666(10) 1.000 0.0242(4) . . C9 C Uani -0.2384(2) 0.42582(12) 0.77053(9) 1.000 0.0227(4) . . C10 C Uani 0.2336(2) 1.00933(12) 0.57872(9) 1.000 0.0200(4) . . C11 C Uani 0.2060(2) 0.64498(12) 0.46893(8) 1.000 0.0184(4) . . C12 C Uani 0.4748(2) 0.74444(11) 0.35274(8) 1.000 0.0166(4) . . C13 C Uani 0.5069(2) 0.85435(11) 0.26671(8) 1.000 0.0163(4) . . C14 C Uani 0.3371(2) 0.95352(12) 0.23341(9) 1.000 0.0181(4) . . C15 C Uani 0.3755(2) 1.05228(12) 0.15216(9) 1.000 0.0193(4) . . C16 C Uani 0.5856(2) 1.04859(12) 0.10704(9) 1.000 0.0186(4) . . C17 C Uani 0.7568(2) 0.95206(12) 0.13838(9) 1.000 0.0206(4) . . C18 C Uani 0.7160(2) 0.85416(12) 0.21926(9) 1.000 0.0201(4) . . H1 H Uiso 0.20960 0.58150 0.61690 1.000 0.0200 calc R H2 H Uiso 0.59760 0.65930 0.57090 1.000 0.0220 calc R H3 H Uiso 0.63130 0.82720 0.63210 1.000 0.0220 calc R H4 H Uiso 0.30840 0.89340 0.71460 1.000 0.0200 calc R H6A H Uiso 0.30240 0.56760 0.46370 1.000 0.0220 calc R H6B H Uiso 0.04480 0.62960 0.46060 1.000 0.0220 calc R H7A H Uiso 0.19450 0.99700 0.51640 1.000 0.0300 calc R H7B H Uiso 0.37090 1.05650 0.57210 1.000 0.0300 calc R H7C H Uiso 0.10640 1.05830 0.60140 1.000 0.0300 calc R H10 H Uiso 0.83130 0.78670 0.24240 1.000 0.0240 calc R H11 H Uiso 0.89880 0.95260 0.10550 1.000 0.0250 calc R H13 H Uiso 0.26110 1.12010 0.12840 1.000 0.0230 calc R H14 H Uiso 0.19510 0.95360 0.26620 1.000 0.0220 calc R H18A H Uiso 0.18810 0.42250 0.83400 1.000 0.0360 calc R H18B H Uiso 0.03240 0.37610 0.92700 1.000 0.0360 calc R H18C H Uiso 0.14080 0.51150 0.90600 1.000 0.0360 calc R H19A H Uiso -0.37200 0.47050 0.73310 1.000 0.0340 calc R H19B H Uiso -0.28520 0.35040 0.81910 1.000 0.0340 calc R H19C H Uiso -0.12470 0.39830 0.72780 1.000 0.0340 calc R H20A H Uiso -0.24240 0.62810 0.90910 1.000 0.0350 calc R H20B H Uiso -0.37520 0.50070 0.92690 1.000 0.0350 calc R H20C H Uiso -0.43660 0.61920 0.83590 1.000 0.0350 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0174(5) 0.0164(4) 0.0141(4) -0.0045(3) -0.0006(3) 0.0006(3) O2 0.0221(5) 0.0158(4) 0.0145(4) -0.0013(3) 0.0031(4) -0.0014(4) O3 0.0252(5) 0.0162(4) 0.0209(5) -0.0016(4) 0.0006(4) 0.0021(4) O4 0.0206(5) 0.0167(4) 0.0131(4) -0.0014(3) 0.0019(3) -0.0047(4) O5 0.0257(5) 0.0220(5) 0.0156(4) -0.0049(4) 0.0017(4) -0.0048(4) O6 0.0379(7) 0.0266(5) 0.0263(5) 0.0054(4) 0.0051(4) 0.0063(5) O7 0.0367(7) 0.0276(5) 0.0311(6) -0.0013(4) 0.0192(5) -0.0020(5) N1 0.0178(6) 0.0155(5) 0.0130(5) -0.0042(4) 0.0005(4) -0.0017(4) N2 0.0310(7) 0.0181(5) 0.0173(5) -0.0044(4) 0.0062(5) -0.0024(5) C1 0.0173(7) 0.0160(6) 0.0161(6) -0.0031(5) -0.0002(5) -0.0033(5) C2 0.0155(7) 0.0201(6) 0.0167(6) 0.0000(5) -0.0006(5) -0.0012(5) C3 0.0177(7) 0.0187(6) 0.0149(6) -0.0003(5) 0.0000(5) 0.0035(5) C4 0.0208(7) 0.0127(6) 0.0147(6) -0.0007(5) 0.0013(5) 0.0017(5) C5 0.0132(6) 0.0165(6) 0.0172(6) -0.0028(5) 0.0009(5) 0.0008(5) C6 0.0213(7) 0.0160(6) 0.0135(6) 0.0005(5) 0.0025(5) -0.0045(5) C7 0.0233(7) 0.0269(7) 0.0191(6) -0.0039(5) 0.0053(5) -0.0042(6) C8 0.0257(8) 0.0207(6) 0.0231(7) -0.0004(5) -0.0041(5) -0.0013(5) C9 0.0285(8) 0.0194(6) 0.0188(6) -0.0012(5) -0.0012(5) -0.0055(5) C10 0.0231(7) 0.0152(6) 0.0206(6) -0.0025(5) 0.0009(5) -0.0020(5) C11 0.0238(7) 0.0142(6) 0.0162(6) -0.0019(5) 0.0035(5) -0.0043(5) C12 0.0204(7) 0.0154(6) 0.0154(6) -0.0064(5) 0.0010(5) -0.0017(5) C13 0.0214(7) 0.0145(6) 0.0139(6) -0.0051(5) 0.0006(5) -0.0021(5) C14 0.0164(7) 0.0201(6) 0.0176(6) -0.0048(5) 0.0029(5) -0.0013(5) C15 0.0215(7) 0.0165(6) 0.0186(6) -0.0029(5) -0.0009(5) 0.0012(5) C16 0.0251(7) 0.0167(6) 0.0142(6) -0.0043(5) 0.0030(5) -0.0037(5) C17 0.0208(7) 0.0209(6) 0.0205(6) -0.0069(5) 0.0064(5) -0.0018(5) C18 0.0210(7) 0.0173(6) 0.0213(6) -0.0054(5) 0.0009(5) 0.0026(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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.4202(14) . . yes O1 C4 1.4464(15) . . yes O2 C11 1.4544(15) . . yes O2 C12 1.3446(15) . . yes O3 C12 1.2086(16) . . yes O4 C5 1.3278(16) . . yes O4 C6 1.4885(15) . . yes O5 C5 1.2132(15) . . yes O6 N2 1.2195(16) . . yes O7 N2 1.2273(16) . . yes N1 C1 1.4686(16) . . yes N1 C5 1.3980(16) . . yes N2 C16 1.4779(17) . . yes C1 C2 1.5021(18) . . no C1 C10 1.5218(18) . . no C2 C3 1.3241(19) . . no C3 C4 1.4961(17) . . no C4 C11 1.5179(17) . . no C6 C7 1.5114(18) . . no C6 C8 1.5175(18) . . no C6 C9 1.5132(18) . . no C12 C13 1.4980(17) . . no C13 C14 1.3960(18) . . no C13 C18 1.3928(17) . . no C14 C15 1.3925(18) . . no C15 C16 1.3848(17) . . no C16 C17 1.3796(18) . . no C17 C18 1.3869(18) . . no C1 H4 1.0000 . . no C2 H3 0.9500 . . no C3 H2 0.9500 . . no C4 H1 1.0000 . . no C7 H20A 0.9800 . . no C7 H20B 0.9800 . . no C7 H20C 0.9800 . . no C8 H18A 0.9800 . . no C8 H18B 0.9800 . . no C8 H18C 0.9800 . . no C9 H19A 0.9800 . . no C9 H19B 0.9800 . . no C9 H19C 0.9800 . . no C10 H7A 0.9800 . . no C10 H7B 0.9800 . . no C10 H7C 0.9800 . . no C11 H6A 0.9900 . . no C11 H6B 0.9900 . . no C14 H14 0.9500 . . no C15 H13 0.9500 . . no C17 H11 0.9500 . . no C18 H10 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 O1 C4 111.89(8) . . . yes C11 O2 C12 116.69(9) . . . yes C5 O4 C6 121.02(9) . . . yes O1 N1 C1 111.18(9) . . . yes O1 N1 C5 116.44(9) . . . yes C1 N1 C5 118.35(10) . . . yes O6 N2 O7 123.96(12) . . . yes O6 N2 C16 118.30(11) . . . yes O7 N2 C16 117.73(11) . . . yes N1 C1 C2 109.17(10) . . . yes N1 C1 C10 110.75(10) . . . yes C2 C1 C10 111.69(10) . . . no C1 C2 C3 122.13(11) . . . no C2 C3 C4 121.87(11) . . . no O1 C4 C3 111.29(10) . . . yes O1 C4 C11 104.79(9) . . . yes C3 C4 C11 114.79(10) . . . no O4 C5 O5 127.74(12) . . . yes O4 C5 N1 110.80(10) . . . yes O5 C5 N1 121.35(11) . . . yes O4 C6 C7 109.91(10) . . . yes O4 C6 C8 109.42(10) . . . yes O4 C6 C9 101.54(9) . . . yes C7 C6 C8 113.27(10) . . . no C7 C6 C9 110.93(10) . . . no C8 C6 C9 111.14(11) . . . no O2 C11 C4 112.99(10) . . . yes O2 C12 O3 124.67(11) . . . yes O2 C12 C13 111.97(10) . . . yes O3 C12 C13 123.35(11) . . . yes C12 C13 C14 122.67(11) . . . no C12 C13 C18 117.13(11) . . . no C14 C13 C18 120.19(11) . . . no C13 C14 C15 120.12(11) . . . no C14 C15 C16 117.92(12) . . . no N2 C16 C15 118.71(11) . . . yes N2 C16 C17 118.02(11) . . . yes C15 C16 C17 123.27(12) . . . no C16 C17 C18 118.19(11) . . . no C13 C18 C17 120.31(11) . . . no N1 C1 H4 108.00 . . . no C2 C1 H4 108.00 . . . no C10 C1 H4 108.00 . . . no C1 C2 H3 119.00 . . . no C3 C2 H3 119.00 . . . no C2 C3 H2 119.00 . . . no C4 C3 H2 119.00 . . . no O1 C4 H1 109.00 . . . no C3 C4 H1 109.00 . . . no C11 C4 H1 109.00 . . . no C6 C7 H20A 109.00 . . . no C6 C7 H20B 109.00 . . . no C6 C7 H20C 109.00 . . . no H20A C7 H20B 110.00 . . . no H20A C7 H20C 109.00 . . . no H20B C7 H20C 109.00 . . . no C6 C8 H18A 109.00 . . . no C6 C8 H18B 109.00 . . . no C6 C8 H18C 109.00 . . . no H18A C8 H18B 109.00 . . . no H18A C8 H18C 109.00 . . . no H18B C8 H18C 109.00 . . . no C6 C9 H19A 110.00 . . . no C6 C9 H19B 109.00 . . . no C6 C9 H19C 109.00 . . . no H19A C9 H19B 109.00 . . . no H19A C9 H19C 109.00 . . . no H19B C9 H19C 109.00 . . . no C1 C10 H7A 109.00 . . . no C1 C10 H7B 109.00 . . . no C1 C10 H7C 109.00 . . . no H7A C10 H7B 109.00 . . . no H7A C10 H7C 109.00 . . . no H7B C10 H7C 109.00 . . . no O2 C11 H6A 109.00 . . . no O2 C11 H6B 109.00 . . . no C4 C11 H6A 109.00 . . . no C4 C11 H6B 109.00 . . . no H6A C11 H6B 108.00 . . . no C13 C14 H14 120.00 . . . no C15 C14 H14 120.00 . . . no C14 C15 H13 121.00 . . . no C16 C15 H13 121.00 . . . no C16 C17 H11 121.00 . . . no C18 C17 H11 121.00 . . . no C13 C18 H10 120.00 . . . no C17 C18 H10 120.00 . . . no 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 C4 O1 N1 C1 67.76(11) . . . . no C4 O1 N1 C5 -71.84(12) . . . . no N1 O1 C4 C3 -45.39(12) . . . . no N1 O1 C4 C11 -170.02(9) . . . . no C12 O2 C11 C4 100.16(12) . . . . no C11 O2 C12 O3 -6.56(17) . . . . no C11 O2 C12 C13 172.34(9) . . . . no C6 O4 C5 O5 -1.98(19) . . . . no C6 O4 C5 N1 -178.15(10) . . . . no C5 O4 C6 C7 63.22(13) . . . . no C5 O4 C6 C8 -61.75(14) . . . . no C5 O4 C6 C9 -179.29(10) . . . . no O1 N1 C1 C2 -50.78(12) . . . . no O1 N1 C1 C10 72.60(12) . . . . no C5 N1 C1 C2 87.96(13) . . . . no C5 N1 C1 C10 -148.67(11) . . . . no O1 N1 C5 O4 -12.88(14) . . . . no O1 N1 C5 O5 170.66(11) . . . . no C1 N1 C5 O4 -149.51(10) . . . . no C1 N1 C5 O5 34.04(17) . . . . no O6 N2 C16 C15 -4.53(18) . . . . no O6 N2 C16 C17 175.48(12) . . . . no O7 N2 C16 C15 176.35(12) . . . . no O7 N2 C16 C17 -3.64(18) . . . . no N1 C1 C2 C3 17.67(16) . . . . no C10 C1 C2 C3 -105.15(13) . . . . no C1 C2 C3 C4 1.12(18) . . . . no C2 C3 C4 O1 11.93(15) . . . . no C2 C3 C4 C11 130.73(12) . . . . no O1 C4 C11 O2 71.29(12) . . . . no C3 C4 C11 O2 -51.09(14) . . . . no O2 C12 C13 C14 -0.31(17) . . . . no O2 C12 C13 C18 -179.83(11) . . . . no O3 C12 C13 C14 178.60(12) . . . . no O3 C12 C13 C18 -0.91(18) . . . . no C12 C13 C14 C15 -179.05(11) . . . . no C18 C13 C14 C15 0.45(19) . . . . no C12 C13 C18 C17 179.23(11) . . . . no C14 C13 C18 C17 -0.30(19) . . . . no C13 C14 C15 C16 -0.44(19) . . . . no C14 C15 C16 N2 -179.68(11) . . . . no C14 C15 C16 C17 0.3(2) . . . . no N2 C16 C17 C18 179.83(11) . . . . no C15 C16 C17 C18 -0.2(2) . . . . no C16 C17 C18 C13 0.15(19) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C4 H1 O4 1.0000 2.4200 2.9235(16) 110.00 . yes C1 H4 O5 1.0000 2.4200 2.8212(17) 103.00 . yes C11 H6A O3 0.9900 2.3200 2.7058(17) 102.00 . yes C17 H11 O7 0.9500 2.4600 3.3111(19) 149.00 2_775 yes C8 H18C O5 0.9800 2.4600 3.0357(19) 117.00 . yes C7 H20A O5 0.9800 2.4800 3.0386(18) 116.00 . yes _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.325 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.049 # Attachment 'Cpd7_ANDA_CIF.doc' #Cif data for compound 7 data_bphthlac _database_code_depnum_ccdc_archive 'CCDC 738892' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(6-methyl-2-oxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione ; _chemical_name_common 2-(6-methyl-2-oxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 N2 O3' _chemical_formula_sum 'C14 H14 N2 O3' _chemical_formula_weight 258.27 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 P21/c _symmetry_Int_Tables_number 14 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 5.6187(10) _cell_length_b 17.695(3) _cell_length_c 12.511(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.957(3) _cell_angle_gamma 90.00 _cell_volume 1212.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1590 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 22.6 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9511 _exptl_absorpt_correction_T_max 0.9751 _exptl_absorpt_process_details 'SADABS V2008-1 (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 diffractometer with APEX detector' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6404 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2183 _reflns_number_gt 1708 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v.5.632 (Bruker, 2005)' _computing_cell_refinement 'SAINT v6.45a (Bruker, 2005)' _computing_data_reduction 'SAINT v6.45a (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0500P)^2^+0.4187P] 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 2183 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1088 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.4170(3) 0.51177(8) 0.12700(11) 1.000 0.0250(5) . . O2 O Uani 0.5636(3) 0.67765(8) 0.23045(12) 1.000 0.0275(5) . . O3 O Uani -0.0420(3) 0.53543(9) 0.31897(12) 1.000 0.0302(5) . . N1 N Uani 0.2373(3) 0.56825(10) -0.03231(14) 1.000 0.0215(6) . . N2 N Uani 0.2222(3) 0.61048(10) 0.24914(14) 1.000 0.0219(6) . . C1 C Uani 0.2675(4) 0.55734(11) 0.07538(17) 1.000 0.0214(6) . . C2 C Uani 0.1014(4) 0.60119(12) 0.13426(17) 1.000 0.0220(7) . . C3 C Uani 0.0024(4) 0.67389(12) 0.07628(18) 1.000 0.0236(7) . . C4 C Uani -0.1142(4) 0.65261(13) -0.04166(18) 1.000 0.0248(7) . . C5 C Uani 0.0727(4) 0.62238(12) -0.10167(17) 1.000 0.0237(7) . . C6 C Uani 0.2194(5) 0.68453(14) -0.1402(2) 1.000 0.0298(8) . . C7 C Uani 0.4501(4) 0.64412(11) 0.28701(17) 1.000 0.0224(6) . . C8 C Uani 0.5115(4) 0.63085(11) 0.40718(17) 1.000 0.0221(7) . . C9 C Uani 0.7171(4) 0.65055(12) 0.48607(18) 1.000 0.0266(7) . . C10 C Uani 0.7242(5) 0.62983(13) 0.59334(18) 1.000 0.0300(8) . . C11 C Uani 0.5338(5) 0.59058(13) 0.62130(19) 1.000 0.0307(8) . . C12 C Uani 0.3279(4) 0.57006(13) 0.54184(18) 1.000 0.0264(7) . . C13 C Uani 0.3236(4) 0.59114(12) 0.43523(17) 1.000 0.0228(7) . . C14 C Uani 0.1403(4) 0.57388(12) 0.33225(17) 1.000 0.0226(7) . . H1 H Uiso 0.331(4) 0.5420(13) -0.0644(19) 1.000 0.024(6) . . H2 H Uiso -0.037(4) 0.5685(11) 0.1346(16) 1.000 0.014(5) . . H3A H Uiso -0.123(5) 0.6955(13) 0.1138(19) 1.000 0.032(6) . . H3B H Uiso 0.135(4) 0.7101(13) 0.0809(18) 1.000 0.025(6) . . H4A H Uiso -0.240(4) 0.6136(13) -0.0396(18) 1.000 0.029(6) . . H4B H Uiso -0.190(4) 0.6947(13) -0.0844(18) 1.000 0.024(6) . . H5 H Uiso -0.008(4) 0.5936(11) -0.1671(16) 1.000 0.010(5) . . H6A H Uiso 0.115(4) 0.7206(13) -0.1920(19) 1.000 0.028(6) . . H6B H Uiso 0.335(5) 0.6603(14) -0.183(2) 1.000 0.038(7) . . H6C H Uiso 0.306(4) 0.7151(13) -0.072(2) 1.000 0.035(6) . . H9 H Uiso 0.855(4) 0.6770(13) 0.4654(18) 1.000 0.029(6) . . H10 H Uiso 0.866(5) 0.6419(13) 0.650(2) 1.000 0.029(6) . . H11 H Uiso 0.548(5) 0.5749(14) 0.694(2) 1.000 0.040(7) . . H12 H Uiso 0.200(4) 0.5389(12) 0.5612(18) 1.000 0.025(6) . . 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 0.0284(9) 0.0257(8) 0.0198(8) 0.0013(6) 0.0030(6) 0.0055(7) O2 0.0274(9) 0.0301(9) 0.0259(8) 0.0042(7) 0.0082(7) -0.0037(7) O3 0.0250(9) 0.0349(9) 0.0297(9) 0.0059(7) 0.0042(7) -0.0055(7) N1 0.0236(10) 0.0223(10) 0.0184(10) 0.0006(7) 0.0042(8) 0.0057(8) N2 0.0217(10) 0.0236(10) 0.0199(9) -0.0006(7) 0.0036(7) -0.0012(8) C1 0.0214(11) 0.0191(11) 0.0222(11) 0.0000(9) 0.0016(9) -0.0016(9) C2 0.0220(12) 0.0246(12) 0.0187(11) -0.0003(9) 0.0033(9) -0.0009(9) C3 0.0222(12) 0.0248(12) 0.0234(11) -0.0001(9) 0.0041(9) 0.0017(10) C4 0.0251(13) 0.0222(12) 0.0246(12) 0.0036(9) 0.0001(10) 0.0028(10) C5 0.0238(12) 0.0262(12) 0.0183(11) 0.0019(9) -0.0012(9) 0.0009(9) C6 0.0306(14) 0.0305(13) 0.0272(13) 0.0060(11) 0.0041(11) -0.0018(11) C7 0.0255(12) 0.0181(10) 0.0242(11) 0.0000(9) 0.0067(10) 0.0027(9) C8 0.0265(12) 0.0184(11) 0.0215(11) -0.0003(8) 0.0058(9) 0.0026(9) C9 0.0275(13) 0.0235(11) 0.0264(12) -0.0019(9) 0.0011(10) -0.0010(10) C10 0.0342(14) 0.0287(13) 0.0227(12) -0.0031(9) -0.0030(11) 0.0016(10) C11 0.0413(15) 0.0299(12) 0.0200(12) 0.0029(10) 0.0050(11) 0.0082(11) C12 0.0302(13) 0.0257(12) 0.0238(12) 0.0038(9) 0.0073(10) 0.0040(10) C13 0.0255(12) 0.0196(11) 0.0232(11) 0.0011(9) 0.0051(9) 0.0049(9) C14 0.0241(12) 0.0204(11) 0.0239(11) 0.0017(9) 0.0064(9) 0.0030(9) _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.237(3) . . yes O2 C7 1.209(3) . . yes O3 C14 1.210(3) . . yes N1 C1 1.334(3) . . yes N1 C5 1.472(3) . . yes N2 C2 1.455(3) . . yes N2 C7 1.395(3) . . yes N2 C14 1.388(3) . . yes N1 H1 0.87(2) . . no C1 C2 1.525(3) . . no C2 C3 1.520(3) . . no C3 C4 1.521(3) . . no C4 C5 1.519(3) . . no C5 C6 1.516(3) . . no C7 C8 1.484(3) . . no C8 C13 1.378(3) . . no C8 C9 1.385(3) . . no C9 C10 1.383(3) . . no C10 C11 1.385(4) . . no C11 C12 1.394(3) . . no C12 C13 1.380(3) . . no C13 C14 1.490(3) . . no C2 H2 0.97(2) . . no C3 H3A 1.01(3) . . no C3 H3B 0.98(2) . . no C4 H4A 0.99(2) . . no C4 H4B 0.96(2) . . no C5 H5 0.98(2) . . no C6 H6A 1.00(2) . . no C6 H6B 1.02(3) . . no C6 H6C 1.04(2) . . no C9 H9 0.99(2) . . no C10 H10 0.96(3) . . no C11 H11 0.94(2) . . no C12 H12 0.98(2) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 127.64(18) . . . yes C2 N2 C7 124.97(17) . . . yes C2 N2 C14 121.86(18) . . . yes C7 N2 C14 112.20(17) . . . yes C5 N1 H1 116.3(16) . . . no C1 N1 H1 116.0(16) . . . no O1 C1 C2 119.82(18) . . . yes O1 C1 N1 122.7(2) . . . yes N1 C1 C2 117.48(18) . . . yes N2 C2 C3 114.56(17) . . . yes N2 C2 C1 109.54(18) . . . yes C1 C2 C3 113.48(18) . . . no C2 C3 C4 106.58(17) . . . no C3 C4 C5 111.81(19) . . . no N1 C5 C4 110.52(17) . . . yes N1 C5 C6 110.18(19) . . . yes C4 C5 C6 112.78(19) . . . no O2 C7 N2 125.10(19) . . . yes N2 C7 C8 105.29(18) . . . yes O2 C7 C8 129.6(2) . . . yes C7 C8 C13 108.75(19) . . . no C9 C8 C13 120.7(2) . . . no C7 C8 C9 130.5(2) . . . no C8 C9 C10 117.6(2) . . . no C9 C10 C11 121.5(2) . . . no C10 C11 C12 121.0(2) . . . no C11 C12 C13 116.8(2) . . . no C8 C13 C14 107.76(18) . . . no C12 C13 C14 129.8(2) . . . no C8 C13 C12 122.4(2) . . . no N2 C14 C13 105.74(18) . . . yes O3 C14 N2 124.91(19) . . . yes O3 C14 C13 129.4(2) . . . yes N2 C2 H2 105.1(12) . . . no C1 C2 H2 106.1(12) . . . no C3 C2 H2 107.4(12) . . . no C2 C3 H3A 108.6(13) . . . no C2 C3 H3B 109.6(13) . . . no C4 C3 H3A 110.6(14) . . . no C4 C3 H3B 112.2(13) . . . no H3A C3 H3B 109.2(19) . . . no C3 C4 H4A 107.5(13) . . . no C3 C4 H4B 112.9(14) . . . no C5 C4 H4A 110.1(13) . . . no C5 C4 H4B 105.5(14) . . . no H4A C4 H4B 109.0(19) . . . no N1 C5 H5 105.4(12) . . . no C4 C5 H5 110.7(13) . . . no C6 C5 H5 107.0(12) . . . no C5 C6 H6A 112.8(13) . . . no C5 C6 H6B 108.4(14) . . . no C5 C6 H6C 107.8(13) . . . no H6A C6 H6B 106(2) . . . no H6A C6 H6C 107.4(18) . . . no H6B C6 H6C 115(2) . . . no C8 C9 H9 120.7(13) . . . no C10 C9 H9 121.7(13) . . . no C9 C10 H10 119.6(15) . . . no C11 C10 H10 118.9(15) . . . no C10 C11 H11 119.4(17) . . . no C12 C11 H11 119.4(17) . . . no C11 C12 H12 120.6(13) . . . no C13 C12 H12 122.5(13) . . . no 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 C5 N1 C1 O1 -177.7(2) . . . . no C5 N1 C1 C2 4.9(3) . . . . no C1 N1 C5 C4 -14.8(3) . . . . no C1 N1 C5 C6 110.5(2) . . . . no C7 N2 C2 C1 56.6(3) . . . . no C7 N2 C2 C3 -72.2(3) . . . . no C14 N2 C2 C1 -111.2(2) . . . . no C14 N2 C2 C3 120.0(2) . . . . no C2 N2 C7 O2 9.1(3) . . . . no C2 N2 C7 C8 -172.14(18) . . . . no C14 N2 C7 O2 178.0(2) . . . . no C14 N2 C7 C8 -3.3(2) . . . . no C2 N2 C14 O3 -4.5(3) . . . . no C2 N2 C14 C13 174.35(18) . . . . no C7 N2 C14 O3 -173.8(2) . . . . no C7 N2 C14 C13 5.1(2) . . . . no O1 C1 C2 N2 28.2(3) . . . . no O1 C1 C2 C3 157.7(2) . . . . no N1 C1 C2 N2 -154.23(18) . . . . no N1 C1 C2 C3 -24.8(3) . . . . no N2 C2 C3 C4 179.65(18) . . . . no C1 C2 C3 C4 52.8(2) . . . . no C2 C3 C4 C5 -64.2(2) . . . . no C3 C4 C5 N1 44.7(2) . . . . no C3 C4 C5 C6 -79.1(2) . . . . no O2 C7 C8 C9 -2.7(4) . . . . no O2 C7 C8 C13 178.6(2) . . . . no N2 C7 C8 C9 178.7(2) . . . . no N2 C7 C8 C13 0.0(2) . . . . no C7 C8 C9 C10 -179.5(2) . . . . no C13 C8 C9 C10 -0.9(3) . . . . no C7 C8 C13 C12 179.8(2) . . . . no C7 C8 C13 C14 3.1(2) . . . . no C9 C8 C13 C12 0.9(3) . . . . no C9 C8 C13 C14 -175.83(19) . . . . no C8 C9 C10 C11 0.2(3) . . . . no C9 C10 C11 C12 0.4(4) . . . . no C10 C11 C12 C13 -0.4(3) . . . . no C11 C12 C13 C8 -0.3(3) . . . . no C11 C12 C13 C14 175.7(2) . . . . no C8 C13 C14 O3 173.9(2) . . . . no C8 C13 C14 N2 -5.0(2) . . . . no C12 C13 C14 O3 -2.6(4) . . . . no C12 C13 C14 N2 178.6(2) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1 O1 0.87(2) 2.01(2) 2.866(2) 173(2) 3_665 yes C2 H2 O3 0.97(2) 2.39(2) 2.860(3) 109.5(14) . yes C3 H3A O2 1.01(3) 2.55(3) 3.455(3) 150.2(18) 1_455 yes C4 H4A O1 0.99(2) 2.57(2) 3.418(3) 143.0(17) 3_565 yes C12 H12 O3 0.98(2) 2.32(2) 3.217(3) 152.9(18) 3_566 yes _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.199 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.041