# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Mal, Dipak' 'Dinda, Bidyut' 'Jana, Amit' _publ_contact_author_name 'Mal, Dipak' _publ_contact_author_email dmal@chem.iitkgp.ernet.in _publ_section_title ; Anionic [4+3] heteroannulation of 2-azidoacrylates: A direct synthesis of 2-benzazepin-1-ones ; # Attachment '- Crystal 4d .cif' data_bkd169 _database_code_depnum_ccdc_archive 'CCDC 862841' #TrackingRef '- Crystal 4d .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N O4' _chemical_formula_weight 309.31 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 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 7.7053(12) _cell_length_b 18.113(3) _cell_length_c 10.6268(17) _cell_angle_alpha 90.00 _cell_angle_beta 95.382(5) _cell_angle_gamma 90.00 _cell_volume 1476.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 17416 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 25.00 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.988 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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-APEX-II CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17416 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2598 _reflns_number_gt 2099 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0869P)^2^+0.8144P] 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 2598 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1636 _refine_ls_wR_factor_gt 0.1531 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.046 _refine_ls_shift/su_mean 0.002 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 0.4043(3) 0.42374(14) 0.1306(2) 0.0405(6) Uani 1 1 d . . . C2 C 0.1718(3) 0.51486(13) 0.1723(2) 0.0376(5) Uani 1 1 d . . . C3 C 0.1873(3) 0.59564(13) 0.1980(2) 0.0386(6) Uani 1 1 d . . . C4 C 0.1760(5) 0.68790(16) 0.3534(3) 0.0663(9) Uani 1 1 d . . . H4A H 0.1711 0.6922 0.4430 0.099 Uiso 1 1 calc R . . H4B H 0.0751 0.7108 0.3102 0.099 Uiso 1 1 calc R . . H4C H 0.2792 0.7119 0.3298 0.099 Uiso 1 1 calc R . . C5 C 0.0368(3) 0.47433(13) 0.2016(2) 0.0366(5) Uani 1 1 d . . . C6 C -0.1090(3) 0.50632(12) 0.2664(2) 0.0352(5) Uani 1 1 d . . . C7 C -0.2045(3) 0.56513(14) 0.2132(2) 0.0456(6) Uani 1 1 d . . . H7 H -0.1796 0.5836 0.1352 0.055 Uiso 1 1 calc R . . C8 C -0.3362(4) 0.59673(16) 0.2744(3) 0.0543(7) Uani 1 1 d . . . H8 H -0.4002 0.6358 0.2373 0.065 Uiso 1 1 calc R . . C9 C -0.3726(4) 0.57037(16) 0.3905(3) 0.0529(7) Uani 1 1 d . . . H9 H -0.4595 0.5923 0.4329 0.063 Uiso 1 1 calc R . . C10 C -0.2801(4) 0.51158(16) 0.4432(3) 0.0513(7) Uani 1 1 d . . . H10 H -0.3052 0.4936 0.5214 0.062 Uiso 1 1 calc R . . C11 C -0.1510(3) 0.47903(14) 0.3821(2) 0.0435(6) Uani 1 1 d . . . H11 H -0.0912 0.4385 0.4181 0.052 Uiso 1 1 calc R . . C12 C 0.0336(3) 0.39296(14) 0.1657(2) 0.0412(6) Uani 1 1 d . . . H12 H 0.0588 0.3892 0.0772 0.049 Uiso 1 1 calc R . . C13 C 0.1797(3) 0.35456(12) 0.2466(2) 0.0377(5) Uani 1 1 d . . . C14 C 0.1456(3) 0.30376(13) 0.3390(3) 0.0460(6) Uani 1 1 d . . . H14 H 0.0309 0.2944 0.3546 0.055 Uiso 1 1 calc R . . C15 C 0.2793(4) 0.26712(15) 0.4080(3) 0.0526(7) Uani 1 1 d . . . H15 H 0.2545 0.2336 0.4701 0.063 Uiso 1 1 calc R . . C16 C 0.4503(4) 0.28008(15) 0.3850(3) 0.0525(7) Uani 1 1 d . . . H16 H 0.5403 0.2544 0.4302 0.063 Uiso 1 1 calc R . . C17 C 0.4870(3) 0.33092(15) 0.2954(2) 0.0464(6) Uani 1 1 d . . . H17 H 0.6022 0.3396 0.2804 0.056 Uiso 1 1 calc R . . C18 C 0.3530(3) 0.36983(13) 0.2262(2) 0.0390(6) Uani 1 1 d . . . N1 N 0.3113(3) 0.48706(12) 0.1091(2) 0.0422(5) Uani 1 1 d . . . H1 H 0.354(4) 0.5147(16) 0.062(3) 0.051 Uiso 1 1 d . . . O1 O 0.5325(2) 0.41241(11) 0.07245(19) 0.0547(5) Uani 1 1 d . . . O2 O 0.1800(2) 0.61104(9) 0.31912(16) 0.0464(5) Uani 1 1 d . . . O3 O 0.2070(3) 0.64136(10) 0.11751(19) 0.0607(6) Uani 1 1 d . . . O4 O -0.1257(2) 0.35845(11) 0.1771(2) 0.0554(5) Uani 1 1 d . . . H4 H -0.233(4) 0.3772(17) 0.107(3) 0.067 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 0.0300(12) 0.0429(14) 0.0495(14) -0.0055(11) 0.0087(10) -0.0014(10) C2 0.0330(12) 0.0385(13) 0.0426(13) 0.0003(10) 0.0099(10) 0.0012(10) C3 0.0310(12) 0.0367(13) 0.0487(14) 0.0043(11) 0.0073(10) 0.0004(10) C4 0.091(2) 0.0393(15) 0.0672(19) -0.0110(14) 0.0023(17) 0.0008(15) C5 0.0314(12) 0.0361(13) 0.0429(13) 0.0009(10) 0.0059(9) 0.0019(9) C6 0.0288(12) 0.0337(12) 0.0434(13) 0.0007(10) 0.0053(9) -0.0028(9) C7 0.0398(14) 0.0502(15) 0.0476(14) 0.0114(12) 0.0085(11) 0.0052(11) C8 0.0432(15) 0.0474(16) 0.0737(19) 0.0103(14) 0.0132(13) 0.0138(12) C9 0.0406(14) 0.0552(17) 0.0657(17) -0.0070(14) 0.0197(12) 0.0025(12) C10 0.0489(15) 0.0623(18) 0.0447(14) 0.0056(12) 0.0152(12) -0.0018(13) C11 0.0374(13) 0.0442(14) 0.0497(14) 0.0100(11) 0.0078(11) 0.0021(11) C12 0.0306(12) 0.0391(13) 0.0546(14) -0.0057(11) 0.0077(10) -0.0027(10) C13 0.0346(13) 0.0311(12) 0.0485(13) -0.0077(10) 0.0091(10) -0.0015(9) C14 0.0432(14) 0.0350(13) 0.0613(16) -0.0016(12) 0.0131(12) -0.0033(11) C15 0.0639(18) 0.0398(14) 0.0549(16) 0.0020(12) 0.0093(13) -0.0040(13) C16 0.0528(16) 0.0446(15) 0.0583(16) -0.0003(13) -0.0050(13) 0.0055(12) C17 0.0354(13) 0.0469(15) 0.0565(15) -0.0076(12) 0.0025(11) 0.0028(11) C18 0.0351(12) 0.0360(13) 0.0464(13) -0.0073(10) 0.0075(10) 0.0003(10) N1 0.0373(11) 0.0392(12) 0.0529(12) 0.0024(9) 0.0181(9) -0.0016(9) O1 0.0412(10) 0.0589(12) 0.0681(12) 0.0044(9) 0.0261(9) 0.0082(9) O2 0.0569(11) 0.0350(9) 0.0468(10) 0.0008(7) 0.0012(8) 0.0000(8) O3 0.0800(15) 0.0446(11) 0.0604(12) 0.0098(9) 0.0217(10) -0.0046(10) O4 0.0408(10) 0.0479(11) 0.0775(14) 0.0061(9) 0.0047(9) -0.0066(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.231(3) . ? C1 N1 1.360(3) . ? C1 C18 1.489(3) . ? C2 C5 1.334(3) . ? C2 N1 1.413(3) . ? C2 C3 1.491(3) . ? C3 O3 1.210(3) . ? C3 O2 1.323(3) . ? C4 O2 1.440(3) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.489(3) . ? C5 C12 1.522(3) . ? C6 C7 1.385(3) . ? C6 C11 1.391(3) . ? C7 C8 1.379(4) . ? C7 H7 0.9300 . ? C8 C9 1.376(4) . ? C8 H8 0.9300 . ? C9 C10 1.372(4) . ? C9 H9 0.9300 . ? C10 C11 1.372(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 O4 1.393(3) . ? C12 C13 1.519(3) . ? C12 H12 0.9800 . ? C13 C14 1.389(4) . ? C13 C18 1.400(3) . ? C14 C15 1.377(4) . ? C14 H14 0.9300 . ? C15 C16 1.383(4) . ? C15 H15 0.9300 . ? C16 C17 1.373(4) . ? C16 H16 0.9300 . ? C17 C18 1.400(4) . ? C17 H17 0.9300 . ? N1 H1 0.80(3) . ? O4 H4 1.11(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 O1 C1 N1 119.4(2) . . ? O1 C1 C18 120.7(2) . . ? N1 C1 C18 119.9(2) . . ? C5 C2 N1 124.1(2) . . ? C5 C2 C3 123.2(2) . . ? N1 C2 C3 112.7(2) . . ? O3 C3 O2 124.2(2) . . ? O3 C3 C2 123.7(2) . . ? O2 C3 C2 112.0(2) . . ? O2 C4 H4A 109.5 . . ? O2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 C6 122.2(2) . . ? C2 C5 C12 118.0(2) . . ? C6 C5 C12 119.8(2) . . ? C7 C6 C11 118.4(2) . . ? C7 C6 C5 120.4(2) . . ? C11 C6 C5 121.2(2) . . ? C8 C7 C6 120.9(2) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C9 C8 C7 120.0(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 119.6(2) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C11 120.8(2) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C6 120.3(2) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? O4 C12 C13 110.9(2) . . ? O4 C12 C5 114.0(2) . . ? C13 C12 C5 107.89(19) . . ? O4 C12 H12 107.9 . . ? C13 C12 H12 107.9 . . ? C5 C12 H12 107.9 . . ? C14 C13 C18 119.1(2) . . ? C14 C13 C12 121.6(2) . . ? C18 C13 C12 119.3(2) . . ? C15 C14 C13 120.9(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 119.9(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.8(2) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C13 C18 C17 119.1(2) . . ? C13 C18 C1 123.6(2) . . ? C17 C18 C1 117.3(2) . . ? C1 N1 C2 129.2(2) . . ? C1 N1 H1 113(2) . . ? C2 N1 H1 117(2) . . ? C3 O2 C4 117.0(2) . . ? C12 O4 H4 114.3(16) . . ? 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 C2 C3 O3 -124.1(3) . . . . ? N1 C2 C3 O3 53.4(3) . . . . ? C5 C2 C3 O2 57.0(3) . . . . ? N1 C2 C3 O2 -125.5(2) . . . . ? N1 C2 C5 C6 -178.9(2) . . . . ? C3 C2 C5 C6 -1.7(4) . . . . ? N1 C2 C5 C12 0.5(4) . . . . ? C3 C2 C5 C12 177.7(2) . . . . ? C2 C5 C6 C7 57.5(3) . . . . ? C12 C5 C6 C7 -121.9(3) . . . . ? C2 C5 C6 C11 -121.4(3) . . . . ? C12 C5 C6 C11 59.2(3) . . . . ? C11 C6 C7 C8 1.1(4) . . . . ? C5 C6 C7 C8 -177.8(2) . . . . ? C6 C7 C8 C9 0.7(4) . . . . ? C7 C8 C9 C10 -1.5(5) . . . . ? C8 C9 C10 C11 0.4(4) . . . . ? C9 C10 C11 C6 1.5(4) . . . . ? C7 C6 C11 C10 -2.2(4) . . . . ? C5 C6 C11 C10 176.8(2) . . . . ? C2 C5 C12 O4 -168.1(2) . . . . ? C6 C5 C12 O4 11.2(3) . . . . ? C2 C5 C12 C13 68.2(3) . . . . ? C6 C5 C12 C13 -112.5(2) . . . . ? O4 C12 C13 C14 -13.6(3) . . . . ? C5 C12 C13 C14 111.9(2) . . . . ? O4 C12 C13 C18 165.4(2) . . . . ? C5 C12 C13 C18 -69.1(3) . . . . ? C18 C13 C14 C15 -1.7(4) . . . . ? C12 C13 C14 C15 177.3(2) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C14 C15 C16 C17 1.6(4) . . . . ? C15 C16 C17 C18 -0.2(4) . . . . ? C14 C13 C18 C17 3.0(3) . . . . ? C12 C13 C18 C17 -176.0(2) . . . . ? C14 C13 C18 C1 -179.4(2) . . . . ? C12 C13 C18 C1 1.6(3) . . . . ? C16 C17 C18 C13 -2.1(4) . . . . ? C16 C17 C18 C1 -179.8(2) . . . . ? O1 C1 C18 C13 -144.6(2) . . . . ? N1 C1 C18 C13 36.9(3) . . . . ? O1 C1 C18 C17 33.0(3) . . . . ? N1 C1 C18 C17 -145.5(2) . . . . ? O1 C1 N1 C2 -173.3(2) . . . . ? C18 C1 N1 C2 5.2(4) . . . . ? C5 C2 N1 C1 -45.8(4) . . . . ? C3 C2 N1 C1 136.8(3) . . . . ? O3 C3 O2 C4 7.2(4) . . . . ? C2 C3 O2 C4 -173.9(2) . . . . ? 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 N1 H1 O1 0.80(3) 2.19(3) 2.986(3) 178(3) 3_665 O4 H4 O1 1.11(3) 1.92(3) 2.929(3) 149(2) 1_455 O4 H4 O3 1.11(3) 2.44(3) 3.135(3) 119(2) 3_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.074 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.051 # Attachment '- Crystal 4g .cif' data_bkd210 _database_code_depnum_ccdc_archive 'CCDC 862842' #TrackingRef '- Crystal 4g .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 Cl N O4' _chemical_formula_weight 343.75 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 13.3925(14) _cell_length_b 10.8664(12) _cell_length_c 22.610(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3290.3(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 37126 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 24.99 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.254 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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-APEX-II CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37126 _diffrn_reflns_av_R_equivalents 0.1497 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2899 _reflns_number_gt 1514 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0504P)^2^+4.1419P] 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 2899 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1243 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1425 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.901 _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 0.6218(3) 0.2769(3) 0.73260(15) 0.0454(9) Uani 1 1 d . . . C2 C 0.5013(2) 0.1586(3) 0.66858(15) 0.0393(8) Uani 1 1 d . . . C3 C 0.5156(3) 0.0349(3) 0.64152(17) 0.0492(9) Uani 1 1 d . . . C4 C 0.4749(5) -0.0990(4) 0.5635(2) 0.129(3) Uani 1 1 d . . . H4A H 0.4437 -0.0968 0.5253 0.194 Uiso 1 1 calc R . . H4B H 0.4385 -0.1537 0.5889 0.194 Uiso 1 1 calc R . . H4C H 0.5424 -0.1276 0.5595 0.194 Uiso 1 1 calc R . . C5 C 0.4309(2) 0.2414(3) 0.65490(14) 0.0369(8) Uani 1 1 d . . . C6 C 0.3632(2) 0.2331(3) 0.60294(14) 0.0391(8) Uani 1 1 d . . . C7 C 0.2829(3) 0.1533(4) 0.60241(17) 0.0567(11) Uani 1 1 d . . . H7 H 0.2699 0.1045 0.6353 0.068 Uiso 1 1 calc R . . C8 C 0.2216(3) 0.1454(4) 0.55332(19) 0.0668(12) Uani 1 1 d . . . H8 H 0.1684 0.0904 0.5528 0.080 Uiso 1 1 calc R . . C9 C 0.2400(3) 0.2193(4) 0.50532(17) 0.0587(11) Uani 1 1 d . . . C10 C 0.3168(3) 0.3020(4) 0.50547(17) 0.0568(10) Uani 1 1 d . . . H10 H 0.3275 0.3535 0.4732 0.068 Uiso 1 1 calc R . . C11 C 0.3781(3) 0.3077(3) 0.55434(17) 0.0492(9) Uani 1 1 d . . . H11 H 0.4310 0.3632 0.5546 0.059 Uiso 1 1 calc R . . C12 C 0.4212(2) 0.3533(3) 0.69484(15) 0.0403(8) Uani 1 1 d . . . H12 H 0.4226 0.3256 0.7361 0.048 Uiso 1 1 calc R . . C13 C 0.5100(2) 0.4362(3) 0.68440(13) 0.0379(8) Uani 1 1 d . . . C14 C 0.4999(3) 0.5513(3) 0.65897(15) 0.0490(10) Uani 1 1 d . . . H14 H 0.4373 0.5795 0.6475 0.059 Uiso 1 1 calc R . . C15 C 0.5837(3) 0.6247(4) 0.65070(17) 0.0624(12) Uani 1 1 d . . . H15 H 0.5767 0.7025 0.6340 0.075 Uiso 1 1 calc R . . C16 C 0.6763(3) 0.5839(4) 0.66680(19) 0.0699(12) Uani 1 1 d . . . H16 H 0.7320 0.6333 0.6603 0.084 Uiso 1 1 calc R . . C17 C 0.6876(3) 0.4696(4) 0.69263(16) 0.0581(11) Uani 1 1 d . . . H17 H 0.7506 0.4421 0.7038 0.070 Uiso 1 1 calc R . . C18 C 0.6042(3) 0.3961(3) 0.70183(15) 0.0415(9) Uani 1 1 d . . . N1 N 0.5676(2) 0.1759(3) 0.71655(13) 0.0446(8) Uani 1 1 d . . . H1 H 0.589(2) 0.108(3) 0.7337(15) 0.054 Uiso 1 1 d . . . O1 O 0.6848(2) 0.2659(2) 0.77173(12) 0.0658(8) Uani 1 1 d . . . O2 O 0.33276(18) 0.4206(2) 0.68551(12) 0.0571(8) Uani 1 1 d . . . H2 H 0.286(3) 0.375(4) 0.6994(17) 0.069 Uiso 1 1 d . . . O3 O 0.5598(2) -0.0463(2) 0.66639(13) 0.0716(9) Uani 1 1 d . . . O4 O 0.4750(2) 0.0237(2) 0.58883(13) 0.0789(10) Uani 1 1 d . . . Cl1 Cl 0.16265(10) 0.20791(16) 0.44347(6) 0.1055(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.046(2) 0.050(2) 0.040(2) 0.0016(18) -0.0028(18) -0.0028(18) C2 0.045(2) 0.0372(19) 0.0359(18) 0.0036(16) -0.0004(17) -0.0021(17) C3 0.056(2) 0.041(2) 0.051(2) 0.0008(19) -0.006(2) 0.0001(19) C4 0.224(7) 0.054(3) 0.110(4) -0.042(3) -0.073(5) 0.033(4) C5 0.0377(19) 0.0315(18) 0.041(2) 0.0028(15) 0.0055(15) -0.0035(16) C6 0.0364(19) 0.042(2) 0.039(2) 0.0005(17) 0.0019(15) 0.0015(16) C7 0.052(2) 0.063(3) 0.055(3) 0.008(2) 0.000(2) -0.015(2) C8 0.048(2) 0.086(3) 0.066(3) -0.009(3) -0.003(2) -0.021(2) C9 0.047(2) 0.080(3) 0.048(2) -0.014(2) -0.0101(19) 0.001(2) C10 0.066(3) 0.062(3) 0.042(2) 0.008(2) -0.004(2) 0.003(2) C11 0.050(2) 0.046(2) 0.052(2) 0.0040(19) -0.0026(19) -0.0067(18) C12 0.038(2) 0.0406(19) 0.042(2) -0.0004(16) 0.0049(16) 0.0028(17) C13 0.045(2) 0.037(2) 0.0316(19) -0.0069(15) 0.0038(16) -0.0012(16) C14 0.058(3) 0.044(2) 0.045(2) 0.0021(18) -0.0023(18) -0.001(2) C15 0.088(3) 0.041(2) 0.059(3) 0.0102(19) -0.004(2) -0.009(2) C16 0.075(3) 0.063(3) 0.072(3) 0.017(2) -0.009(3) -0.030(3) C17 0.053(2) 0.067(3) 0.054(2) 0.012(2) -0.010(2) -0.016(2) C18 0.046(2) 0.043(2) 0.036(2) 0.0010(16) -0.0024(16) -0.0067(18) N1 0.0523(19) 0.0390(18) 0.0424(18) 0.0060(14) -0.0087(15) 0.0025(15) O1 0.0720(18) 0.0593(17) 0.0661(18) 0.0095(14) -0.0334(16) -0.0092(15) O2 0.0454(16) 0.0536(17) 0.072(2) 0.0062(14) 0.0139(14) 0.0090(13) O3 0.093(2) 0.0436(16) 0.078(2) 0.0011(15) -0.0280(17) 0.0152(15) O4 0.123(3) 0.0499(17) 0.0637(19) -0.0189(15) -0.0355(19) 0.0274(17) Cl1 0.0858(9) 0.1644(14) 0.0664(8) -0.0114(8) -0.0320(7) -0.0150(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.228(4) . ? C1 N1 1.366(4) . ? C1 C18 1.489(5) . ? C2 C5 1.339(4) . ? C2 N1 1.414(4) . ? C2 C3 1.489(5) . ? C3 O3 1.203(4) . ? C3 O4 1.315(4) . ? C4 O4 1.451(5) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.487(4) . ? C5 C12 1.521(4) . ? C6 C11 1.380(5) . ? C6 C7 1.381(5) . ? C7 C8 1.383(5) . ? C7 H7 0.9300 . ? C8 C9 1.373(6) . ? C8 H8 0.9300 . ? C9 C10 1.366(5) . ? C9 Cl1 1.745(4) . ? C10 C11 1.378(5) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 O2 1.408(4) . ? C12 C13 1.510(4) . ? C12 H12 0.9800 . ? C13 C14 1.383(5) . ? C13 C18 1.392(5) . ? C14 C15 1.390(5) . ? C14 H14 0.9300 . ? C15 C16 1.366(5) . ? C15 H15 0.9300 . ? C16 C17 1.381(5) . ? C16 H16 0.9300 . ? C17 C18 1.388(5) . ? C17 H17 0.9300 . ? N1 H1 0.88(3) . ? O2 H2 0.86(4) . ? 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 O1 C1 N1 118.5(3) . . ? O1 C1 C18 122.0(3) . . ? N1 C1 C18 119.4(3) . . ? C5 C2 N1 122.0(3) . . ? C5 C2 C3 127.0(3) . . ? N1 C2 C3 110.8(3) . . ? O3 C3 O4 124.0(4) . . ? O3 C3 C2 122.2(4) . . ? O4 C3 C2 113.8(3) . . ? O4 C4 H4A 109.5 . . ? O4 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O4 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 C6 124.8(3) . . ? C2 C5 C12 117.4(3) . . ? C6 C5 C12 117.7(3) . . ? C11 C6 C7 118.4(3) . . ? C11 C6 C5 120.3(3) . . ? C7 C6 C5 121.3(3) . . ? C8 C7 C6 120.5(4) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C9 C8 C7 119.4(4) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 121.2(4) . . ? C8 C9 Cl1 119.0(3) . . ? C10 C9 Cl1 119.7(3) . . ? C9 C10 C11 118.7(4) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C10 C11 C6 121.7(3) . . ? C10 C11 H11 119.2 . . ? C6 C11 H11 119.2 . . ? O2 C12 C13 109.2(3) . . ? O2 C12 C5 113.5(3) . . ? C13 C12 C5 108.5(3) . . ? O2 C12 H12 108.5 . . ? C13 C12 H12 108.5 . . ? C5 C12 H12 108.5 . . ? C14 C13 C18 119.3(3) . . ? C14 C13 C12 121.8(3) . . ? C18 C13 C12 118.9(3) . . ? C15 C14 C13 119.7(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 120.7(4) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 120.2(4) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 119.6(4) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C17 C18 C13 120.4(3) . . ? C17 C18 C1 116.3(3) . . ? C13 C18 C1 123.2(3) . . ? C1 N1 C2 130.1(3) . . ? C1 N1 H1 112(2) . . ? C2 N1 H1 116(2) . . ? C12 O2 H2 105(3) . . ? C3 O4 C4 116.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C2 C3 O3 -158.1(4) . . . . ? N1 C2 C3 O3 16.1(5) . . . . ? C5 C2 C3 O4 21.5(5) . . . . ? N1 C2 C3 O4 -164.2(3) . . . . ? N1 C2 C5 C6 175.9(3) . . . . ? C3 C2 C5 C6 -10.4(5) . . . . ? N1 C2 C5 C12 -2.8(5) . . . . ? C3 C2 C5 C12 170.9(3) . . . . ? C2 C5 C6 C11 -105.4(4) . . . . ? C12 C5 C6 C11 73.3(4) . . . . ? C2 C5 C6 C7 76.1(4) . . . . ? C12 C5 C6 C7 -105.3(4) . . . . ? C11 C6 C7 C8 2.5(6) . . . . ? C5 C6 C7 C8 -178.9(3) . . . . ? C6 C7 C8 C9 -1.3(6) . . . . ? C7 C8 C9 C10 -1.0(6) . . . . ? C7 C8 C9 Cl1 179.6(3) . . . . ? C8 C9 C10 C11 1.9(6) . . . . ? Cl1 C9 C10 C11 -178.7(3) . . . . ? C9 C10 C11 C6 -0.6(6) . . . . ? C7 C6 C11 C10 -1.6(5) . . . . ? C5 C6 C11 C10 179.9(3) . . . . ? C2 C5 C12 O2 -166.6(3) . . . . ? C6 C5 C12 O2 14.6(4) . . . . ? C2 C5 C12 C13 71.8(4) . . . . ? C6 C5 C12 C13 -107.0(3) . . . . ? O2 C12 C13 C14 -10.9(4) . . . . ? C5 C12 C13 C14 113.2(3) . . . . ? O2 C12 C13 C18 168.0(3) . . . . ? C5 C12 C13 C18 -67.9(4) . . . . ? C18 C13 C14 C15 0.6(5) . . . . ? C12 C13 C14 C15 179.5(3) . . . . ? C13 C14 C15 C16 0.8(6) . . . . ? C14 C15 C16 C17 -1.2(6) . . . . ? C15 C16 C17 C18 0.4(6) . . . . ? C16 C17 C18 C13 0.9(6) . . . . ? C16 C17 C18 C1 -177.1(4) . . . . ? C14 C13 C18 C17 -1.4(5) . . . . ? C12 C13 C18 C17 179.7(3) . . . . ? C14 C13 C18 C1 176.4(3) . . . . ? C12 C13 C18 C1 -2.5(5) . . . . ? O1 C1 C18 C17 34.9(5) . . . . ? N1 C1 C18 C17 -144.1(3) . . . . ? O1 C1 C18 C13 -143.0(4) . . . . ? N1 C1 C18 C13 37.9(5) . . . . ? O1 C1 N1 C2 -170.5(3) . . . . ? C18 C1 N1 C2 8.6(5) . . . . ? C5 C2 N1 C1 -46.6(5) . . . . ? C3 C2 N1 C1 138.8(4) . . . . ? O3 C3 O4 C4 7.4(7) . . . . ? C2 C3 O4 C4 -172.2(4) . . . . ? 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 O2 H2 O1 0.86(4) 1.91(4) 2.773(4) 177(4) 6_557 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.251 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.045 # Attachment '- Crystal 13 .cif' data_bkd213 _database_code_depnum_ccdc_archive 'CCDC 862843' #TrackingRef '- Crystal 13 .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N O4' _chemical_formula_weight 245.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2752(12) _cell_length_b 7.8865(10) _cell_length_c 15.6249(19) _cell_angle_alpha 90.00 _cell_angle_beta 92.965(4) _cell_angle_gamma 90.00 _cell_volume 1141.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13062 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 25.00 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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-APEX-II CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13062 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2010 _reflns_number_gt 1534 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0563P)^2^+0.4350P] 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 2010 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.7980(2) 0.5930(2) 0.17313(12) 0.0379(5) Uani 1 1 d . . . C2 C 1.07013(19) 0.6123(2) 0.17305(12) 0.0369(5) Uani 1 1 d . . . C3 C 1.1560(2) 0.6586(3) 0.09768(13) 0.0401(5) Uani 1 1 d . . . C4 C 1.3703(3) 0.7680(4) 0.04604(17) 0.0792(9) Uani 1 1 d . . . H4A H 1.4605 0.8159 0.0670 0.119 Uiso 1 1 calc R . . H4B H 1.3195 0.8487 0.0097 0.119 Uiso 1 1 calc R . . H4C H 1.3882 0.6671 0.0139 0.119 Uiso 1 1 calc R . . C5 C 1.1197(2) 0.6085(3) 0.25559(12) 0.0387(5) Uani 1 1 d . . . C6 C 1.2687(2) 0.6558(3) 0.29001(14) 0.0577(6) Uani 1 1 d . . . H6A H 1.2750 0.6413 0.3511 0.087 Uiso 1 1 calc R . . H6B H 1.2878 0.7720 0.2763 0.087 Uiso 1 1 calc R . . H6C H 1.3385 0.5842 0.2646 0.087 Uiso 1 1 calc R . . C7 C 1.0262(2) 0.5467(3) 0.32375(12) 0.0417(5) Uani 1 1 d . . . C8 C 0.8809(2) 0.6226(3) 0.33127(12) 0.0384(5) Uani 1 1 d . . . C9 C 0.8459(2) 0.6706(3) 0.41354(13) 0.0501(6) Uani 1 1 d . . . H9 H 0.9093 0.6462 0.4600 0.060 Uiso 1 1 calc R . . C10 C 0.7187(2) 0.7538(3) 0.42675(15) 0.0589(7) Uani 1 1 d . . . H10 H 0.6980 0.7882 0.4817 0.071 Uiso 1 1 calc R . . C11 C 0.6218(2) 0.7864(3) 0.35902(15) 0.0588(7) Uani 1 1 d . . . H11 H 0.5364 0.8439 0.3680 0.071 Uiso 1 1 calc R . . C12 C 0.6524(2) 0.7332(3) 0.27776(14) 0.0491(6) Uani 1 1 d . . . H12 H 0.5848 0.7509 0.2326 0.059 Uiso 1 1 calc R . . C13 C 0.7824(2) 0.6536(3) 0.26227(12) 0.0381(5) Uani 1 1 d . . . N1 N 0.93104(17) 0.5600(2) 0.14342(10) 0.0411(4) Uani 1 1 d . . . O1 O 0.69098(14) 0.5667(2) 0.12587(8) 0.0504(4) Uani 1 1 d . . . O2 O 1.11105(16) 0.6365(2) 0.02500(9) 0.0536(4) Uani 1 1 d . . . O3 O 1.28338(15) 0.7261(2) 0.11807(9) 0.0611(5) Uani 1 1 d . . . O4 O 1.07662(18) 0.4509(2) 0.37858(9) 0.0602(5) Uani 1 1 d . . . H1 H 0.931(3) 0.528(3) 0.0883(16) 0.072 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 0.0382(10) 0.0452(12) 0.0302(10) 0.0013(8) 0.0014(8) -0.0050(8) C2 0.0343(10) 0.0437(11) 0.0325(10) -0.0032(8) 0.0013(8) 0.0019(8) C3 0.0372(10) 0.0473(12) 0.0360(11) -0.0022(9) 0.0034(8) 0.0045(9) C4 0.0564(15) 0.125(3) 0.0576(16) 0.0120(16) 0.0192(12) -0.0179(15) C5 0.0399(11) 0.0429(11) 0.0330(11) -0.0033(9) -0.0002(8) 0.0027(8) C6 0.0479(12) 0.0791(17) 0.0450(13) -0.0048(12) -0.0085(10) -0.0051(12) C7 0.0513(12) 0.0444(11) 0.0286(10) -0.0033(9) -0.0053(9) -0.0028(9) C8 0.0433(11) 0.0442(11) 0.0280(10) 0.0000(8) 0.0041(8) -0.0114(9) C9 0.0532(13) 0.0670(15) 0.0302(11) -0.0032(10) 0.0034(9) -0.0157(11) C10 0.0551(13) 0.0834(18) 0.0396(12) -0.0206(12) 0.0167(10) -0.0180(12) C11 0.0427(12) 0.0802(17) 0.0550(15) -0.0185(12) 0.0157(10) -0.0072(11) C12 0.0382(11) 0.0672(15) 0.0421(12) -0.0044(10) 0.0048(9) -0.0058(10) C13 0.0369(10) 0.0464(12) 0.0315(10) -0.0012(8) 0.0047(8) -0.0076(8) N1 0.0380(9) 0.0578(11) 0.0273(9) -0.0081(8) 0.0002(7) -0.0026(8) O1 0.0400(8) 0.0758(11) 0.0348(8) -0.0043(7) -0.0040(6) -0.0058(7) O2 0.0562(9) 0.0747(11) 0.0304(8) -0.0068(7) 0.0056(6) -0.0031(8) O3 0.0450(8) 0.0981(13) 0.0405(9) 0.0037(8) 0.0053(7) -0.0154(8) O4 0.0754(11) 0.0627(11) 0.0417(9) 0.0131(8) -0.0045(8) 0.0094(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.224(2) . ? C1 N1 1.366(2) . ? C1 C13 1.487(3) . ? C2 C5 1.347(3) . ? C2 N1 1.409(2) . ? C2 C3 1.501(3) . ? C3 O2 1.202(2) . ? C3 O3 1.319(2) . ? C4 O3 1.456(3) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C7 1.490(3) . ? C5 C6 1.504(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 O4 1.217(2) . ? C7 C8 1.485(3) . ? C8 C9 1.394(3) . ? C8 C13 1.398(3) . ? C9 C10 1.375(3) . ? C9 H9 0.9300 . ? C10 C11 1.377(3) . ? C10 H10 0.9300 . ? C11 C12 1.380(3) . ? C11 H11 0.9300 . ? C12 C13 1.392(3) . ? C12 H12 0.9300 . ? N1 H1 0.90(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 O1 C1 N1 118.79(17) . . ? O1 C1 C13 120.31(17) . . ? N1 C1 C13 120.87(16) . . ? C5 C2 N1 124.69(18) . . ? C5 C2 C3 126.03(17) . . ? N1 C2 C3 109.11(15) . . ? O2 C3 O3 123.31(18) . . ? O2 C3 C2 122.25(18) . . ? O3 C3 C2 114.44(16) . . ? O3 C4 H4A 109.5 . . ? O3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 C7 120.65(17) . . ? C2 C5 C6 126.76(19) . . ? C7 C5 C6 112.55(16) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 C8 120.78(19) . . ? O4 C7 C5 119.31(19) . . ? C8 C7 C5 119.27(17) . . ? C9 C8 C13 119.30(19) . . ? C9 C8 C7 115.96(18) . . ? C13 C8 C7 124.68(17) . . ? C10 C9 C8 120.7(2) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.3(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C12 119.6(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 121.2(2) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C8 118.84(18) . . ? C12 C13 C1 115.79(17) . . ? C8 C13 C1 125.08(18) . . ? C1 N1 C2 131.34(17) . . ? C1 N1 H1 115.1(16) . . ? C2 N1 H1 110.6(16) . . ? C3 O3 C4 115.44(17) . . ? 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 C2 C3 O2 169.3(2) . . . . ? N1 C2 C3 O2 -6.2(3) . . . . ? C5 C2 C3 O3 -11.2(3) . . . . ? N1 C2 C3 O3 173.39(17) . . . . ? N1 C2 C5 C7 -0.2(3) . . . . ? C3 C2 C5 C7 -175.03(19) . . . . ? N1 C2 C5 C6 177.3(2) . . . . ? C3 C2 C5 C6 2.5(3) . . . . ? C2 C5 C7 O4 135.8(2) . . . . ? C6 C5 C7 O4 -42.0(3) . . . . ? C2 C5 C7 C8 -53.3(3) . . . . ? C6 C5 C7 C8 128.86(19) . . . . ? O4 C7 C8 C9 38.5(3) . . . . ? C5 C7 C8 C9 -132.3(2) . . . . ? O4 C7 C8 C13 -144.1(2) . . . . ? C5 C7 C8 C13 45.2(3) . . . . ? C13 C8 C9 C10 -2.6(3) . . . . ? C7 C8 C9 C10 175.0(2) . . . . ? C8 C9 C10 C11 1.9(3) . . . . ? C9 C10 C11 C12 0.8(4) . . . . ? C10 C11 C12 C13 -2.9(4) . . . . ? C11 C12 C13 C8 2.2(3) . . . . ? C11 C12 C13 C1 176.3(2) . . . . ? C9 C8 C13 C12 0.5(3) . . . . ? C7 C8 C13 C12 -176.87(19) . . . . ? C9 C8 C13 C1 -172.98(19) . . . . ? C7 C8 C13 C1 9.6(3) . . . . ? O1 C1 C13 C12 -21.9(3) . . . . ? N1 C1 C13 C12 160.39(19) . . . . ? O1 C1 C13 C8 151.8(2) . . . . ? N1 C1 C13 C8 -25.9(3) . . . . ? O1 C1 N1 C2 163.13(19) . . . . ? C13 C1 N1 C2 -19.1(3) . . . . ? C5 C2 N1 C1 46.1(3) . . . . ? C3 C2 N1 C1 -138.3(2) . . . . ? O2 C3 O3 C4 -2.0(3) . . . . ? C2 C3 O3 C4 178.5(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.230 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.041