# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address A.R.Cowley ; Chemical Crystallography Department, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; T.J.Hill ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; 'Petr Kocis' ; AstraZeneca R&D Boston, 35 Gatehouse Drive, Waltham, MA 02451, USA. ; M.G.Moloney ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; R.D.Stevenson ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; _publ_contact_author_name 'Dr M Moloney' _publ_contact_author_email mark.moloney@chem.ox.ac.uk _publ_section_title ; Spirocyclic systems derived from pyroglutamic acid ; _publ_section_abstract ; The synthesis of rigid spirocyclic bislactams and lactam-lactones derived from pyroglutamic acid has been established, and an examination of their likely conformational structure made using molecular modelling. ; #============================================================================== data_3a _database_code_depnum_ccdc_archive 'CCDC 814550' #TrackingRef 'CrystallographicData.cif' #============================================================================== #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #============================================================= _cell_length_a 9.7445(2) _cell_angle_alpha 90 _cell_length_b 9.7445(2) _cell_angle_beta 90 _cell_length_c 37.3937(5) _cell_angle_gamma 120 _cell_volume 3075.02(10) _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M 'P 65 ' _symmetry_space_group_name_Hall 'P 65 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z x-y,x,z+5/6 -y,x-y,z+2/3 -x,-y,z+1/2 -x+y,-x,z+1/3 y,-x+y,z+1/6 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C23 H22 N2 O4 ' _chemical_formula_moiety ' C23 H22 N2 O4 ' _chemical_absolute_configuration syn _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 390.44 _cell_measurement_reflns_used 20963 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 6 _exptl_crystal_description ' fragment ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.35 _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 1236. _exptl_absorpt_coefficient_mu 0.087 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.97 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 20963 _reflns_number_total 2399 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_gt 1557 _diffrn_reflns_theta_min 5.30 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _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 -48 _diffrn_reflns_limit_l_max 48 _reflns_limit_h_min -10 _reflns_limit_h_max 0 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 48 _refine_diff_density_min -0.20 _refine_diff_density_max 0.28 _reflns_threshold_expression >2.00\s(I) _refine_ls_number_reflns 1557 _refine_ls_number_parameters 262 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.0555 _refine_ls_goodness_of_fit_ref 1.0490 _refine_ls_shift/su_max 0.006524 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 0.600 0.279 0.329 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type N1 0.2223(4) 0.0501(4) 0.30482(8) 0.0360 1.0000 Uani C1 0.1858(4) 0.0833(4) 0.3370(1) 0.0363 1.0000 Uani O1 0.2307(3) 0.0628(4) 0.36624(7) 0.0507 1.0000 Uani C2 0.0722(4) 0.1478(5) 0.3316(1) 0.0391 1.0000 Uani C3 0.0967(5) 0.1980(5) 0.29192(11) 0.0451 1.0000 Uani C4 0.1878(4) 0.1251(5) 0.2752(1) 0.0406 1.0000 Uani C5 0.3539(6) 0.2355(9) 0.26197(18) 0.0988 1.0000 Uani O2 0.4488(3) 0.1732(3) 0.27235(9) 0.0559 1.0000 Uani C6 0.3635(5) 0.0427(5) 0.29629(11) 0.0427 1.0000 Uani C7 -0.0989(5) 0.0150(6) 0.34164(11) 0.0480 1.0000 Uani C8 -0.2086(6) 0.0734(7) 0.33447(15) 0.0696 1.0000 Uani N2 -0.2917(6) 0.1197(8) 0.32828(17) 0.1026 1.0000 Uani C9 -0.1533(4) -0.1450(5) 0.3246(1) 0.0449 1.0000 Uani C10 -0.2167(5) -0.1817(5) 0.29018(12) 0.0498 1.0000 Uani C11 -0.2679(5) -0.3305(6) 0.27581(13) 0.0563 1.0000 Uani C12 -0.2586(5) -0.4461(5) 0.29564(14) 0.0558 1.0000 Uani C13 -0.1982(6) -0.4125(6) 0.32986(14) 0.0621 1.0000 Uani C14 -0.1451(5) -0.2625(6) 0.34399(11) 0.0534 1.0000 Uani C15 0.1210(5) 0.2827(5) 0.35848(11) 0.0474 1.0000 Uani O3 0.0535(4) 0.2701(4) 0.38625(9) 0.0644 1.0000 Uani O4 0.2475(5) 0.4119(4) 0.34773(9) 0.0678 1.0000 Uani C16 0.3012(9) 0.5505(7) 0.37160(17) 0.0923 1.0000 Uani C17 0.427(1) 0.6829(8) 0.35486(18) 0.1061 1.0000 Uani C18 0.3242(4) -0.1131(5) 0.27840(11) 0.0426 1.0000 Uani C19 0.4378(5) -0.1219(6) 0.25838(11) 0.0490 1.0000 Uani C20 0.4046(6) -0.2627(6) 0.24237(13) 0.0567 1.0000 Uani C21 0.2588(7) -0.3953(6) 0.24619(14) 0.0616 1.0000 Uani C22 0.1442(6) -0.3876(5) 0.26661(16) 0.0657 1.0000 Uani C23 0.1762(5) -0.2467(5) 0.28227(15) 0.0579 1.0000 Uani H31 0.1590 0.3161 0.2899 0.0550 1.0000 Uiso H32 -0.0080 0.1574 0.2798 0.0550 1.0000 Uiso H41 0.1204 0.0616 0.2546 0.0459 1.0000 Uiso H51 0.3950 0.3431 0.2727 0.1079 1.0000 Uiso H52 0.3538 0.2436 0.2353 0.1079 1.0000 Uiso H61 0.4253 0.0486 0.3182 0.0512 1.0000 Uiso H71 -0.0976 -0.0071 0.3677 0.0586 1.0000 Uiso H101 -0.2254 -0.1000 0.2758 0.0607 1.0000 Uiso H111 -0.3117 -0.3549 0.2510 0.0636 1.0000 Uiso H121 -0.2956 -0.5533 0.2851 0.0602 1.0000 Uiso H131 -0.1926 -0.4957 0.3444 0.0676 1.0000 Uiso H141 -0.0998 -0.2383 0.3687 0.0575 1.0000 Uiso H161 0.3381 0.5295 0.3948 0.0963 1.0000 Uiso H162 0.2118 0.5710 0.3761 0.0963 1.0000 Uiso H171 0.4646 0.7778 0.3707 0.1070 1.0000 Uiso H172 0.5159 0.6619 0.3504 0.1070 1.0000 Uiso H173 0.3897 0.7034 0.3316 0.1070 1.0000 Uiso H191 0.5449 -0.0259 0.2554 0.0617 1.0000 Uiso H201 0.4879 -0.2680 0.2278 0.0750 1.0000 Uiso H211 0.2351 -0.4968 0.2343 0.0820 1.0000 Uiso H221 0.0381 -0.4845 0.2700 0.0781 1.0000 Uiso H231 0.0924 -0.2409 0.2965 0.0701 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0332(16) 0.0374(16) 0.0366(16) 0.0002(13) -0.0003(12) 0.0170(13) C1 0.0310(17) 0.0350(19) 0.0386(19) 0.0012(15) -0.0010(16) 0.0134(15) O1 0.0455(16) 0.0693(19) 0.0396(15) 0.0118(14) -0.0029(13) 0.0304(15) C2 0.042(2) 0.044(2) 0.0389(19) -0.0096(17) -0.0087(16) 0.0266(18) C3 0.060(3) 0.041(2) 0.0370(18) -0.0101(16) -0.0196(18) 0.0268(19) C4 0.0341(18) 0.051(2) 0.0298(17) 0.0012(16) -0.0036(15) 0.0160(17) C5 0.034(2) 0.137(6) 0.098(5) 0.071(4) 0.005(3) 0.023(3) O2 0.0377(15) 0.0402(15) 0.083(2) 0.0042(15) 0.0170(15) 0.0141(13) C6 0.0337(18) 0.044(2) 0.051(2) 0.0018(18) 0.0069(17) 0.0192(17) C7 0.035(2) 0.066(3) 0.045(2) -0.0127(19) -0.0032(17) 0.027(2) C8 0.045(3) 0.091(4) 0.079(3) -0.049(3) -0.022(2) 0.039(3) N2 0.068(3) 0.131(5) 0.140(5) -0.083(4) -0.054(3) 0.074(3) C9 0.0299(19) 0.050(2) 0.048(2) -0.0061(19) 0.0015(17) 0.0150(18) C10 0.044(2) 0.055(2) 0.053(2) -0.010(2) -0.0049(19) 0.027(2) C11 0.044(2) 0.055(3) 0.060(3) -0.015(2) -0.006(2) 0.017(2) C12 0.036(2) 0.041(2) 0.074(3) -0.006(2) -0.001(2) 0.0063(18) C13 0.048(2) 0.053(3) 0.068(3) 0.009(2) 0.004(2) 0.012(2) C14 0.043(2) 0.057(3) 0.045(2) 0.0023(19) 0.0031(18) 0.013(2) C15 0.053(2) 0.054(2) 0.043(2) -0.0143(19) -0.0094(19) 0.032(2) O3 0.066(2) 0.070(2) 0.0563(18) -0.0256(17) 0.0014(17) 0.0337(18) O4 0.078(2) 0.0484(18) 0.0501(17) -0.0189(14) -0.0007(16) 0.0113(17) C16 0.113(5) 0.056(3) 0.072(4) -0.029(3) -0.001(3) 0.015(3) C17 0.125(6) 0.065(4) 0.078(4) -0.016(3) -0.001(4) 0.009(4) C18 0.0365(19) 0.042(2) 0.053(2) 0.0033(17) 0.0051(17) 0.0223(16) C19 0.044(2) 0.060(3) 0.051(2) 0.005(2) 0.0070(18) 0.031(2) C20 0.068(3) 0.065(3) 0.054(3) 0.003(2) 0.009(2) 0.046(3) C21 0.082(4) 0.059(3) 0.064(3) -0.008(2) -0.007(3) 0.050(3) C22 0.056(3) 0.041(2) 0.098(4) -0.007(2) 0.005(3) 0.023(2) C23 0.043(2) 0.045(2) 0.087(3) -0.006(2) 0.010(2) 0.023(2) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.341(5) yes N1 . C4 . 1.456(5) yes N1 . C6 . 1.449(5) yes C1 . O1 . 1.229(5) yes C1 . C2 . 1.535(5) yes C2 . C3 . 1.544(6) yes C2 . C7 . 1.561(6) yes C2 . C15 . 1.529(5) yes C3 . C4 . 1.521(6) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C5 . 1.511(6) yes C4 . H41 . 1.000 no C5 . O2 . 1.391(7) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no O2 . C6 . 1.433(5) yes C6 . C18 . 1.522(6) yes C6 . H61 . 1.000 no C7 . C8 . 1.465(7) yes C7 . C9 . 1.514(6) yes C7 . H71 . 1.000 no C8 . N2 . 1.131(7) yes C9 . C10 . 1.394(6) yes C9 . C14 . 1.391(7) yes C10 . C11 . 1.384(6) yes C10 . H101 . 1.000 no C11 . C12 . 1.389(7) yes C11 . H111 . 1.000 no C12 . C13 . 1.378(7) yes C12 . H121 . 1.000 no C13 . C14 . 1.388(7) yes C13 . H131 . 1.000 no C14 . H141 . 1.000 no C15 . O3 . 1.202(5) yes C15 . O4 . 1.309(6) yes O4 . C16 . 1.479(6) yes C16 . C17 . 1.41(1) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . H171 . 1.000 no C17 . H172 . 1.00 no C17 . H173 . 1.000 no C18 . C19 . 1.374(6) yes C18 . C23 . 1.385(6) yes C19 . C20 . 1.379(7) yes C19 . H191 . 1.000 no C20 . C21 . 1.369(8) yes C20 . H201 . 1.000 no C21 . C22 . 1.385(7) yes C21 . H211 . 1.000 no C22 . C23 . 1.378(7) yes C22 . H221 . 1.000 no C23 . H231 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C4 . 114.0(3) yes C1 . N1 . C6 . 125.7(3) yes C4 . N1 . C6 . 108.7(3) yes N1 . C1 . O1 . 126.9(4) yes N1 . C1 . C2 . 108.3(3) yes O1 . C1 . C2 . 124.9(3) yes C1 . C2 . C3 . 103.2(3) yes C1 . C2 . C7 . 108.6(3) yes C3 . C2 . C7 . 115.2(3) yes C1 . C2 . C15 . 106.7(3) yes C3 . C2 . C15 . 115.2(3) yes C7 . C2 . C15 . 107.4(3) yes C2 . C3 . C4 . 106.3(3) yes C2 . C3 . H31 . 110.3 no C4 . C3 . H31 . 110.3 no C2 . C3 . H32 . 110.3 no C4 . C3 . H32 . 110.3 no H31 . C3 . H32 . 109.5 no N1 . C4 . C3 . 104.9(3) yes N1 . C4 . C5 . 99.9(3) yes C3 . C4 . C5 . 118.0(5) yes N1 . C4 . H41 . 121.3 no C3 . C4 . H41 . 104.4 no C5 . C4 . H41 . 109.1 no C4 . C5 . O2 . 107.9(4) yes C4 . C5 . H51 . 109.9 no O2 . C5 . H51 . 109.9 no C4 . C5 . H52 . 109.9 no O2 . C5 . H52 . 109.9 no H51 . C5 . H52 . 109.5 no C5 . O2 . C6 . 110.2(3) yes N1 . C6 . O2 . 103.7(3) yes N1 . C6 . C18 . 112.0(3) yes O2 . C6 . C18 . 110.9(3) yes N1 . C6 . H61 . 112.1 no O2 . C6 . H61 . 113.2 no C18 . C6 . H61 . 105.1 no C2 . C7 . C8 . 108.6(4) yes C2 . C7 . C9 . 115.5(3) yes C8 . C7 . C9 . 112.0(3) yes C2 . C7 . H71 . 106.8 no C8 . C7 . H71 . 110.7 no C9 . C7 . H71 . 102.9 no C7 . C8 . N2 . 178.6(7) yes C7 . C9 . C10 . 122.4(4) yes C7 . C9 . C14 . 119.6(4) yes C10 . C9 . C14 . 118.1(4) yes C9 . C10 . C11 . 120.6(4) yes C9 . C10 . H101 . 119.7 no C11 . C10 . H101 . 119.7 no C10 . C11 . C12 . 120.4(4) yes C10 . C11 . H111 . 119.8 no C12 . C11 . H111 . 119.8 no C11 . C12 . C13 . 119.8(4) yes C11 . C12 . H121 . 120.1 no C13 . C12 . H121 . 120.1 no C12 . C13 . C14 . 119.6(5) yes C12 . C13 . H131 . 120.2 no C14 . C13 . H131 . 120.2 no C9 . C14 . C13 . 121.6(4) yes C9 . C14 . H141 . 119.2 no C13 . C14 . H141 . 119.2 no C2 . C15 . O3 . 124.1(4) yes C2 . C15 . O4 . 111.3(4) yes O3 . C15 . O4 . 124.6(4) yes C15 . O4 . C16 . 115.2(4) yes O4 . C16 . C17 . 108.5(5) yes O4 . C16 . H161 . 109.7 no C17 . C16 . H161 . 109.7 no O4 . C16 . H162 . 109.7 no C17 . C16 . H162 . 109.7 no H161 . C16 . H162 . 109.5 no C16 . C17 . H171 . 109.5 no C16 . C17 . H172 . 109.5 no H171 . C17 . H172 . 109.5 no C16 . C17 . H173 . 109.5 no H171 . C17 . H173 . 109.5 no H172 . C17 . H173 . 109.5 no C6 . C18 . C19 . 119.5(4) yes C6 . C18 . C23 . 121.1(4) yes C19 . C18 . C23 . 119.4(4) yes C18 . C19 . C20 . 120.2(4) yes C18 . C19 . H191 . 119.9 no C20 . C19 . H191 . 119.9 no C19 . C20 . C21 . 120.7(4) yes C19 . C20 . H201 . 119.7 no C21 . C20 . H201 . 119.7 no C20 . C21 . C22 . 119.4(4) yes C20 . C21 . H211 . 120.3 no C22 . C21 . H211 . 120.3 no C21 . C22 . C23 . 120.1(4) yes C21 . C22 . H221 . 120.0 no C23 . C22 . H221 . 120.0 no C18 . C23 . C22 . 120.2(4) yes C18 . C23 . H231 . 119.9 no C22 . C23 . H231 . 119.9 no #============================================================================== data_4b _database_code_depnum_ccdc_archive 'CCDC 814551' #TrackingRef 'CrystallographicData.cif' #============================================================================== #============================================================== # Diffractometer details #============================================================== _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================== # General computing #============================================================== _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; . ; _chemical_melting_point 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #============================================================= _cell_length_a 10.5991(4) _cell_angle_alpha 90 _cell_length_b 6.3352(2) _cell_angle_beta 93.8504(16) _cell_length_c 11.6093(5) _cell_angle_gamma 90 _cell_volume 777.8 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C17 H18 N2 O4 ' _chemical_formula_moiety ' C17 H18 N2 O4 ' _chemical_absolute_configuration syn _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 314.34 _cell_measurement_reflns_used 8397 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 2 _exptl_crystal_description ' fragment ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.24 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 0.32 _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_meas ? _exptl_crystal_F_000 332.093 _exptl_absorpt_coefficient_mu 0.097 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.98 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 8397 _reflns_number_total 1926 #1929 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.031 # Number of reflections with Friedels Law is 1929 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1783 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 26.928 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_gt 1583 _diffrn_reflns_theta_min 5.08 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _refine_diff_density_min -0.16 _refine_diff_density_max 0.18 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 1583 _refine_ls_number_parameters 208 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0350 _refine_ls_goodness_of_fit_ref 1.0537 _refine_ls_shift/su_max 0.004892 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 0.558 0.135 0.247 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type N1 0.74575(15) 0.3955(3) 0.17673(13) 0.0197 1.0000 Uani C1 0.73699(18) 0.5376(3) 0.26305(17) 0.0218 1.0000 Uani C2 0.71690(17) 0.4211(3) 0.37632(16) 0.0208 1.0000 Uani C3 0.71647(18) 0.1842(3) 0.34275(16) 0.0218 1.0000 Uani C4 0.71697(18) 0.1786(3) 0.20950(16) 0.0209 1.0000 Uani C5 0.59538(19) 0.1400(4) 0.13554(17) 0.0260 1.0000 Uani O1 0.61626(13) 0.2549(3) 0.03130(12) 0.0287 1.0000 Uani C6 0.69284(18) 0.4370(4) 0.05845(16) 0.0233 1.0000 Uani O2 0.74136(15) 0.7292(2) 0.25295(14) 0.0315 1.0000 Uani C7 0.58775(19) 0.4965(3) 0.41116(17) 0.0249 1.0000 Uani O3 0.56946(14) 0.5945(3) 0.49692(13) 0.0371 1.0000 Uani O4 0.49972(12) 0.4419(3) 0.32955(12) 0.0293 1.0000 Uani C8 0.3719(2) 0.5202(5) 0.3412(2) 0.0451 1.0000 Uani C9 0.3584(3) 0.7285(7) 0.2812(2) 0.0690 1.0000 Uani C10 0.81528(18) 0.4860(4) 0.47302(17) 0.0265 1.0000 Uani C11 0.94621(19) 0.4649(4) 0.44163(17) 0.0273 1.0000 Uani N2 1.04930(18) 0.4543(4) 0.41862(17) 0.0376 1.0000 Uani C12 0.78981(18) 0.4597(4) -0.02993(16) 0.0264 1.0000 Uani C13 0.8729(2) 0.2963(5) -0.05029(19) 0.0385 1.0000 Uani C14 0.9578(2) 0.3158(6) -0.1363(2) 0.0497 1.0000 Uani C15 0.9588(2) 0.4952(6) -0.2018(2) 0.0537 1.0000 Uani C16 0.8791(3) 0.6608(6) -0.1805(2) 0.0527 1.0000 Uani C17 0.7937(2) 0.6442(4) -0.0939(2) 0.0394 1.0000 Uani H31 0.7934 0.1123 0.3786 0.0261 1.0000 Uiso H32 0.6390 0.1133 0.3686 0.0261 1.0000 Uiso H41 0.7748 0.0581 0.1952 0.0252 1.0000 Uiso H51 0.5828 -0.0139 0.1194 0.0313 1.0000 Uiso H52 0.5206 0.1967 0.1736 0.0313 1.0000 Uiso H61 0.6468 0.5748 0.0557 0.0277 1.0000 Uiso H81 0.3569 0.5378 0.4247 0.0542 1.0000 Uiso H82 0.3091 0.4180 0.3051 0.0542 1.0000 Uiso H91 0.2710 0.7843 0.2884 0.0827 1.0000 Uiso H92 0.4215 0.8302 0.3173 0.0827 1.0000 Uiso H93 0.3737 0.7103 0.1977 0.0827 1.0000 Uiso H101 0.8001 0.6369 0.4933 0.0318 1.0000 Uiso H102 0.8037 0.3949 0.5419 0.0318 1.0000 Uiso H131 0.8718 0.1643 -0.0031 0.0463 1.0000 Uiso H141 1.0180 0.1985 -0.1501 0.0597 1.0000 Uiso H151 1.0176 0.5064 -0.2654 0.0644 1.0000 Uiso H161 0.8822 0.7932 -0.2271 0.0629 1.0000 Uiso H171 0.7361 0.7643 -0.0783 0.0471 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0254(8) 0.0158(9) 0.0178(7) 0.0012(7) 0.0007(6) -0.0014(7) C1 0.0213(9) 0.0216(11) 0.0226(9) -0.0000(8) 0.0026(7) 0.0000(8) C2 0.0240(9) 0.020(1) 0.0187(8) -0.0006(8) 0.0027(7) -0.0004(8) C3 0.0265(9) 0.018(1) 0.0212(9) 0.0020(8) 0.0011(7) 0.0022(8) C4 0.0252(8) 0.016(1) 0.0218(9) 0.0010(8) 0.0027(7) 0.0003(8) C5 0.0295(9) 0.024(1) 0.0249(9) -0.0003(9) 0.0035(7) -0.0044(9) O1 0.0310(7) 0.0327(9) 0.0219(7) 0.0024(7) -0.0027(5) -0.0090(7) C6 0.0253(9) 0.023(1) 0.0213(9) 0.0032(8) -0.0035(7) 0.0005(9) O2 0.0447(9) 0.0148(7) 0.0353(8) 0.0003(6) 0.0052(7) -0.0021(7) C7 0.0272(9) 0.0239(11) 0.0238(9) 0.0003(9) 0.0031(7) 0.0004(8) O3 0.0337(8) 0.0460(11) 0.0320(8) -0.0157(8) 0.0053(6) 0.0068(8) O4 0.0213(6) 0.0388(9) 0.0278(7) -0.0065(7) 0.0016(5) 0.0031(7) C8 0.021(1) 0.076(2) 0.0379(12) -0.0154(14) 0.0017(9) 0.0113(12) C9 0.0644(18) 0.107(3) 0.0354(13) 0.0066(18) 0.0010(12) 0.058(2) C10 0.0252(9) 0.0319(12) 0.0225(9) -0.0041(9) 0.0020(7) -0.0016(9) C11 0.028(1) 0.0277(11) 0.0253(9) -0.0033(9) -0.0018(7) -0.0003(9) N2 0.0314(9) 0.0449(13) 0.036(1) -0.004(1) 0.0021(8) 0.002(1) C12 0.0260(9) 0.0331(12) 0.0195(9) 0.0047(9) -0.0027(7) -0.0028(9) C13 0.0365(12) 0.0532(16) 0.0260(11) 0.0063(11) 0.0032(9) 0.0055(12) C14 0.0303(11) 0.087(2) 0.0319(12) -0.0018(14) 0.0034(9) 0.0077(14) C15 0.024(1) 0.110(3) 0.0269(11) 0.0119(15) 0.0005(8) -0.0155(15) C16 0.0424(13) 0.078(2) 0.0374(13) 0.0231(15) -0.002(1) -0.0254(16) C17 0.0395(12) 0.0440(15) 0.0344(11) 0.0134(12) -0.0010(9) -0.0109(12) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.355(3) yes N1 . C4 . 1.463(2) yes N1 . C6 . 1.472(2) yes C1 . C2 . 1.535(3) yes C1 . O2 . 1.221(3) yes C2 . C3 . 1.550(3) yes C2 . C7 . 1.530(3) yes C2 . C10 . 1.536(3) yes C3 . C4 . 1.548(3) yes C3 . H31 . 1.0000 no C3 . H32 . 1.0000 no C4 . C5 . 1.520(3) yes C4 . H41 . 1.0000 no C5 . O1 . 1.442(2) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no O1 . C6 . 1.433(3) yes C6 . C12 . 1.507(3) yes C6 . H61 . 1.000 no C7 . O3 . 1.200(3) yes C7 . O4 . 1.330(2) yes O4 . C8 . 1.458(3) yes C8 . C9 . 1.494(5) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C9 . H91 . 1.000 no C9 . H92 . 1.000 no C9 . H93 . 1.000 no C10 . C11 . 1.464(3) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C11 . N2 . 1.144(3) yes C12 . C13 . 1.390(4) yes C12 . C17 . 1.387(3) yes C13 . C14 . 1.393(3) yes C13 . H131 . 1.000 no C14 . C15 . 1.368(5) yes C14 . H141 . 1.000 no C15 . C16 . 1.379(5) yes C15 . H151 . 1.000 no C16 . C17 . 1.401(3) yes C16 . H161 . 1.000 no C17 . H171 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C4 . 113.94(16) yes C1 . N1 . C6 . 122.04(17) yes C4 . N1 . C6 . 109.72(16) yes N1 . C1 . C2 . 109.53(17) yes N1 . C1 . O2 . 125.8(2) yes C2 . C1 . O2 . 124.7(2) yes C1 . C2 . C3 . 104.38(15) yes C1 . C2 . C7 . 104.73(16) yes C3 . C2 . C7 . 112.42(17) yes C1 . C2 . C10 . 111.77(16) yes C3 . C2 . C10 . 115.67(17) yes C7 . C2 . C10 . 107.37(15) yes C2 . C3 . C4 . 105.86(15) yes C2 . C3 . H31 . 110.37 no C4 . C3 . H31 . 110.37 no C2 . C3 . H32 . 110.37 no C4 . C3 . H32 . 110.37 no H31 . C3 . H32 . 109.47 no N1 . C4 . C3 . 104.66(16) yes N1 . C4 . C5 . 100.82(16) yes C3 . C4 . C5 . 120.58(16) yes N1 . C4 . H41 . 122.20 no C3 . C4 . H41 . 103.12 no C5 . C4 . H41 . 106.81 no C4 . C5 . O1 . 102.76(15) yes C4 . C5 . H51 . 111.12 no O1 . C5 . H51 . 111.12 no C4 . C5 . H52 . 111.12 no O1 . C5 . H52 . 111.12 no H51 . C5 . H52 . 109.47 no C5 . O1 . C6 . 109.77(14) yes N1 . C6 . O1 . 103.65(16) yes N1 . C6 . C12 . 114.69(15) yes O1 . C6 . C12 . 109.21(17) yes N1 . C6 . H61 . 109.91 no O1 . C6 . H61 . 115.32 no C12 . C6 . H61 . 104.42 no C2 . C7 . O3 . 125.33(19) yes C2 . C7 . O4 . 109.12(16) yes O3 . C7 . O4 . 125.52(19) yes C7 . O4 . C8 . 117.22(17) yes O4 . C8 . C9 . 108.5(2) yes O4 . C8 . H81 . 109.7 no C9 . C8 . H81 . 109.7 no O4 . C8 . H82 . 109.7 no C9 . C8 . H82 . 109.7 no H81 . C8 . H82 . 109.5 no C8 . C9 . H91 . 109.5 no C8 . C9 . H92 . 109.5 no H91 . C9 . H92 . 109.5 no C8 . C9 . H93 . 109.5 no H91 . C9 . H93 . 109.5 no H92 . C9 . H93 . 109.5 no C2 . C10 . C11 . 113.69(16) yes C2 . C10 . H101 . 108.41 no C11 . C10 . H101 . 108.41 no C2 . C10 . H102 . 108.41 no C11 . C10 . H102 . 108.41 no H101 . C10 . H102 . 109.47 no C10 . C11 . N2 . 177.9(2) yes C6 . C12 . C13 . 120.9(2) yes C6 . C12 . C17 . 119.4(2) yes C13 . C12 . C17 . 119.7(2) yes C12 . C13 . C14 . 120.2(3) yes C12 . C13 . H131 . 119.9 no C14 . C13 . H131 . 119.9 no C13 . C14 . C15 . 120.1(3) yes C13 . C14 . H141 . 119.9 no C15 . C14 . H141 . 119.9 no C14 . C15 . C16 . 120.3(2) yes C14 . C15 . H151 . 119.9 no C16 . C15 . H151 . 119.9 no C15 . C16 . C17 . 120.3(3) yes C15 . C16 . H161 . 119.8 no C17 . C16 . H161 . 119.8 no C12 . C17 . C16 . 119.4(3) yes C12 . C17 . H171 . 120.3 no C16 . C17 . H171 . 120.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H41 . O2 1_545 124 1.00 2.22 2.900 yes C5 . H52 . O4 . 133 1.00 2.41 3.173 yes C16 . H161 . N2 2_755 145 1.00 2.59 3.458 yes _chemical_name_common .