# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name C.Klein C.Fischer W.Seichter A.Schwarzer E.Weber _publ_contact_author_name 'Prof. Dr. Edwin Weber' _publ_contact_author_email Edwin.Weber@chemie.tu-freiberg.de data_cokl4_0m _database_code_depnum_ccdc_archive 'CCDC 791758' #TrackingRef '1 Z.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-Diphenyl-ethane-1,2-dione monooxime ; _chemical_name_common '1,2-Diphenyl-ethane-1,2-dione monooxime' _chemical_formula_moiety 'C14 H11 N O2' _chemical_formula_sum 'C14 H11 N O2' _chemical_formula_weight 225.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7957(3) _cell_length_b 26.8487(8) _cell_length_c 10.6539(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.745(2) _cell_angle_gamma 90.00 _cell_volume 2421.55(14) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5177 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 23.31 _exptl_crystal_description splitter _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; 1,2-Diphenyl-ethane-1,2-dione monooxime ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20328 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5562 _reflns_number_gt 3343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.2809P] 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 5562 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1757 _refine_ls_wR_factor_gt 0.1509 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.09096(18) 0.79914(5) 0.89926(13) 0.0801(4) Uani 1 1 d . . . O2 O 1.28189(13) 0.71991(5) 0.76516(13) 0.0663(4) Uani 1 1 d . . . H2 H 1.329(3) 0.6909(10) 0.753(2) 0.106(8) Uiso 1 1 d . . . N1 N 1.12136(15) 0.70955(5) 0.70867(13) 0.0545(3) Uani 1 1 d . . . C1 C 1.19067(18) 0.82812(6) 0.72725(15) 0.0507(4) Uani 1 1 d . . . C2 C 1.1965(2) 0.82188(7) 0.59975(16) 0.0610(4) Uani 1 1 d . . . H2AA H 1.1436 0.7954 0.5504 0.073 Uiso 1 1 calc R . . C3 C 1.2810(3) 0.85499(9) 0.5461(2) 0.0822(6) Uani 1 1 d . . . H3 H 1.2840 0.8511 0.4600 0.099 Uiso 1 1 calc R . . C4 C 1.3610(3) 0.89381(9) 0.6196(3) 0.0932(7) Uani 1 1 d . . . H4 H 1.4189 0.9158 0.5833 0.112 Uiso 1 1 calc R . . C5 C 1.3559(3) 0.90019(8) 0.7457(3) 0.0898(7) Uani 1 1 d . . . H5 H 1.4104 0.9264 0.7949 0.108 Uiso 1 1 calc R . . C6 C 1.2704(2) 0.86788(7) 0.79973(19) 0.0695(5) Uani 1 1 d . . . H6 H 1.2658 0.8726 0.8851 0.083 Uiso 1 1 calc R . . C7 C 1.10490(19) 0.79296(6) 0.79001(15) 0.0520(4) Uani 1 1 d . . . C8 C 1.03389(18) 0.74656(6) 0.71703(14) 0.0481(4) Uani 1 1 d . . . C9 C 0.86221(19) 0.74203(7) 0.66034(16) 0.0568(4) Uani 1 1 d . . . C10 C 0.7578(3) 0.77104(10) 0.7026(3) 0.1012(8) Uani 1 1 d . . . H10 H 0.7959 0.7951 0.7660 0.121 Uiso 1 1 calc R . . C11 C 0.5969(3) 0.76506(12) 0.6523(4) 0.1270(11) Uani 1 1 d . . . H11 H 0.5280 0.7842 0.6848 0.152 Uiso 1 1 calc R . . C12 C 0.5389(3) 0.73214(14) 0.5576(3) 0.1109(9) Uani 1 1 d . . . H12 H 0.4305 0.7300 0.5202 0.133 Uiso 1 1 calc R . . C13 C 0.6392(3) 0.70164(15) 0.5157(3) 0.1263(11) Uani 1 1 d . . . H13 H 0.5990 0.6777 0.4524 0.152 Uiso 1 1 calc R . . C14 C 0.8013(3) 0.70638(11) 0.5676(2) 0.1027(8) Uani 1 1 d . . . H14 H 0.8693 0.6853 0.5394 0.123 Uiso 1 1 calc R . . O1A O 0.33252(19) 0.96589(5) 0.00261(13) 0.0816(4) Uani 1 1 d . . . O2A O 0.16176(16) 0.88814(5) 0.13857(15) 0.0765(4) Uani 1 1 d . . . H2A H 0.108(3) 0.8587(10) 0.152(2) 0.113(8) Uiso 1 1 d . . . N1A N 0.32235(17) 0.87794(5) 0.19528(15) 0.0597(4) Uani 1 1 d . . . C1A C 0.2689(2) 0.99932(6) 0.18712(16) 0.0570(4) Uani 1 1 d . . . C2A C 0.2902(2) 0.99649(7) 0.31904(18) 0.0729(5) Uani 1 1 d . . . H2AB H 0.3476 0.9703 0.3661 0.087 Uiso 1 1 calc R . . C3A C 0.2265(3) 1.03246(10) 0.3825(2) 0.0989(8) Uani 1 1 d . . . H3A H 0.2439 1.0311 0.4725 0.119 Uiso 1 1 calc R . . C4A C 0.1378(3) 1.07009(10) 0.3122(3) 0.1116(9) Uani 1 1 d . . . H4A H 0.0927 1.0938 0.3546 0.134 Uiso 1 1 calc R . . C5A C 0.1149(4) 1.07308(9) 0.1817(3) 0.1129(9) Uani 1 1 d . . . H5A H 0.0546 1.0989 0.1350 0.136 Uiso 1 1 calc R . . C6A C 0.1802(3) 1.03828(8) 0.1184(2) 0.0867(6) Uani 1 1 d . . . H6A H 0.1653 1.0407 0.0287 0.104 Uiso 1 1 calc R . . C7A C 0.3355(2) 0.96183(6) 0.11630(16) 0.0559(4) Uani 1 1 d . . . C8A C 0.4096(2) 0.91510(5) 0.18773(15) 0.0514(4) Uani 1 1 d . . . C9A C 0.5813(2) 0.91141(6) 0.24274(15) 0.0546(4) Uani 1 1 d . . . C10A C 0.6788(2) 0.94772(8) 0.2165(2) 0.0772(6) Uani 1 1 d . . . H10A H 0.6354 0.9750 0.1657 0.093 Uiso 1 1 calc R . . C11A C 0.8407(3) 0.94385(12) 0.2650(2) 0.1042(8) Uani 1 1 d . . . H11A H 0.9055 0.9684 0.2457 0.125 Uiso 1 1 calc R . . C12A C 0.9057(3) 0.90464(13) 0.3404(3) 0.1049(8) Uani 1 1 d . . . H12A H 1.0148 0.9025 0.3733 0.126 Uiso 1 1 calc R . . C13A C 0.8111(3) 0.86820(9) 0.3685(2) 0.0945(7) Uani 1 1 d . . . H13A H 0.8563 0.8412 0.4197 0.113 Uiso 1 1 calc R . . C14A C 0.6501(3) 0.87140(7) 0.3213(2) 0.0767(6) Uani 1 1 d . . . H14A H 0.5865 0.8468 0.3418 0.092 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0966(10) 0.0880(9) 0.0664(8) -0.0208(7) 0.0405(7) -0.0157(7) O2 0.0435(7) 0.0567(7) 0.0932(9) -0.0102(6) 0.0090(6) 0.0073(5) N1 0.0452(7) 0.0536(7) 0.0633(8) -0.0058(6) 0.0125(6) 0.0025(6) C1 0.0489(9) 0.0466(8) 0.0560(9) -0.0002(7) 0.0134(7) 0.0122(7) C2 0.0610(11) 0.0636(10) 0.0582(10) 0.0039(8) 0.0157(8) 0.0108(8) C3 0.0921(16) 0.0893(15) 0.0706(12) 0.0188(11) 0.0316(11) 0.0092(12) C4 0.1018(18) 0.0751(14) 0.1104(19) 0.0216(13) 0.0421(15) -0.0072(12) C5 0.1055(18) 0.0588(12) 0.1075(18) -0.0053(11) 0.0330(14) -0.0150(11) C6 0.0840(14) 0.0542(10) 0.0723(11) -0.0083(8) 0.0246(10) -0.0005(9) C7 0.0491(9) 0.0565(9) 0.0514(9) -0.0058(7) 0.0154(7) 0.0104(7) C8 0.0453(9) 0.0517(9) 0.0480(8) 0.0006(6) 0.0141(6) 0.0061(7) C9 0.0446(9) 0.0710(11) 0.0535(9) 0.0050(8) 0.0109(7) 0.0038(7) C10 0.0567(13) 0.0991(17) 0.139(2) -0.0310(15) 0.0122(13) 0.0200(11) C11 0.0513(14) 0.146(2) 0.176(3) -0.026(2) 0.0165(16) 0.0264(15) C12 0.0449(12) 0.187(3) 0.0930(17) 0.0137(18) 0.0057(12) 0.0021(16) C13 0.0654(16) 0.219(4) 0.0887(17) -0.0412(19) 0.0115(13) -0.0318(18) C14 0.0542(12) 0.167(2) 0.0846(15) -0.0452(16) 0.0144(10) -0.0099(13) O1A 0.1205(12) 0.0676(8) 0.0616(8) 0.0114(6) 0.0334(8) 0.0050(7) O2A 0.0578(8) 0.0550(7) 0.1120(11) 0.0163(7) 0.0152(7) -0.0026(6) N1A 0.0573(9) 0.0447(7) 0.0786(9) 0.0064(6) 0.0207(7) -0.0015(6) C1A 0.0618(10) 0.0438(8) 0.0632(10) 0.0003(7) 0.0130(8) -0.0017(7) C2A 0.0836(13) 0.0674(11) 0.0647(11) -0.0018(9) 0.0151(10) 0.0145(10) C3A 0.115(2) 0.1049(17) 0.0748(13) -0.0179(12) 0.0228(13) 0.0273(15) C4A 0.126(2) 0.0960(18) 0.109(2) -0.0178(15) 0.0245(17) 0.0473(16) C5A 0.134(2) 0.0853(16) 0.113(2) 0.0068(14) 0.0225(17) 0.0495(16) C6A 0.1054(17) 0.0697(13) 0.0808(13) 0.0105(10) 0.0181(12) 0.0226(12) C7A 0.0657(11) 0.0449(9) 0.0573(10) 0.0042(7) 0.0169(8) -0.0079(7) C8A 0.0641(10) 0.0411(8) 0.0528(9) 0.0007(6) 0.0223(7) -0.0018(7) C9A 0.0615(10) 0.0507(9) 0.0545(9) -0.0041(7) 0.0206(7) -0.0012(7) C10A 0.0715(13) 0.0870(14) 0.0757(12) 0.0150(10) 0.0248(10) -0.0128(10) C11A 0.0703(15) 0.148(2) 0.0982(17) 0.0164(17) 0.0297(13) -0.0265(15) C12A 0.0624(14) 0.153(3) 0.0973(18) -0.0058(18) 0.0188(12) 0.0094(16) C13A 0.0809(16) 0.0903(16) 0.1001(17) -0.0012(13) 0.0039(13) 0.0194(13) C14A 0.0761(14) 0.0591(11) 0.0880(14) 0.0055(9) 0.0108(11) 0.0017(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_2 _geom_bond_publ_flag O1 C7 1.2144(19) . ? O2 N1 1.4043(17) . ? O2 H2 0.91(3) . ? N1 C8 1.2744(19) . ? C2 C3 1.378(3) . ? C1 C2 1.383(2) . ? C2 H2AA 0.9300 . ? C3 C4 1.377(3) . ? C3 H3 0.9300 . ? C4 C5 1.367(3) . ? C4 H4 0.9300 . ? C5 C6 1.373(3) . ? C5 H5 0.9300 . ? C1 C6 1.391(2) . ? C6 H6 0.9300 . ? C1 C7 1.477(2) . ? C7 C8 1.511(2) . ? C8 C9 1.471(2) . ? C9 C10 1.370(3) . ? C9 C14 1.376(3) . ? C10 C11 1.380(3) . ? C10 H10 0.9300 . ? C11 C12 1.334(4) . ? C11 H11 0.9300 . ? C12 C13 1.365(4) . ? C12 H12 0.9300 . ? C13 C14 1.388(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? O1A C7A 1.2093(19) . ? O2A N1A 1.4043(19) . ? O2A H2A 0.95(3) . ? N1A C8A 1.274(2) . ? C1A C2A 1.369(2) . ? C2A C3A 1.381(3) . ? C2A H2AB 0.9300 . ? C3A C4A 1.369(3) . ? C3A H3A 0.9300 . ? C4A C5A 1.352(4) . ? C4A H4A 0.9300 . ? C5A C6A 1.367(3) . ? C5A H5A 0.9300 . ? C1A C6A 1.389(3) . ? C6A H6A 0.9300 . ? C1A C7A 1.472(2) . ? C7A C8A 1.519(2) . ? C8A C9A 1.468(2) . ? C9A C10A 1.376(2) . ? C9A C14A 1.395(3) . ? C10A C11A 1.380(3) . ? C10A H10A 0.9300 . ? C11A C12A 1.354(4) . ? C11A H11A 0.9300 . ? C12A C13A 1.368(4) . ? C12A H12A 0.9300 . ? C13A C14A 1.371(3) . ? C13A H13A 0.9300 . ? C14A H14A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 O2 H2 102.4(16) . . ? C8 N1 O2 111.81(13) . . ? C1 C2 C3 119.81(18) . . ? C3 C2 H2AA 120.1 . . ? C1 C2 H2AA 120.1 . . ? C2 C3 C4 120.1(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.4(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.1(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.21(19) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? C2 C1 C6 119.38(17) . . ? C2 C1 C7 121.80(15) . . ? C6 C1 C7 118.81(15) . . ? O1 C7 C1 122.93(15) . . ? O1 C7 C8 118.07(15) . . ? C1 C7 C8 118.98(13) . . ? N1 C8 C9 118.60(14) . . ? N1 C8 C7 120.38(14) . . ? C9 C8 C7 120.94(13) . . ? C10 C9 C14 117.81(19) . . ? C10 C9 C8 121.54(17) . . ? C14 C9 C8 120.56(16) . . ? C9 C10 C11 121.0(2) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C12 C11 C10 120.8(3) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 119.7(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C9 C14 C13 120.5(2) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? N1A O2A H2A 104.8(15) . . ? C8A N1A O2A 111.88(13) . . ? C1A C2A C3A 120.19(19) . . ? C1A C2A H2AB 119.9 . . ? C3A C2A H2AB 119.9 . . ? C2A C3A C4A 119.7(2) . . ? C4A C3A H3A 120.2 . . ? C2A C3A H3A 120.2 . . ? C3A C4A C5A 120.7(2) . . ? C5A C4A H4A 119.7 . . ? C3A C4A H4A 119.7 . . ? C4A C5A C6A 120.1(2) . . ? C4A C5A H5A 119.9 . . ? C6A C5A H5A 119.9 . . ? C1A C6A C5A 120.3(2) . . ? C5A C6A H6A 119.8 . . ? C1A C6A H6A 119.8 . . ? C2A C1A C6A 118.98(18) . . ? C2A C1A C7A 121.72(15) . . ? C6A C1A C7A 119.30(16) . . ? O1A C7A C1A 123.25(15) . . ? O1A C7A C8A 117.77(15) . . ? C1A C7A C8A 118.97(14) . . ? N1A C8A C9A 119.61(14) . . ? N1A C8A C7A 119.63(15) . . ? C9A C8A C7A 120.70(13) . . ? C10A C9A C14A 118.32(18) . . ? C8A C9A C10A 120.11(16) . . ? C14A C9A C8A 121.56(16) . . ? C9A C10A C11A 120.5(2) . . ? C9A C10A H10A 119.8 . . ? C11A C10A H10A 119.8 . . ? C10A C11A C12A 120.5(2) . . ? C12A C11A H11A 119.7 . . ? C10A C11A H11A 119.7 . . ? C11A C12A C13A 120.1(2) . . ? C11A C12A H12A 120.0 . . ? C13A C12A H12A 120.0 . . ? C12A C13A C14A 120.3(2) . . ? C12A C13A H13A 119.9 . . ? C14A C13A H13A 119.9 . . ? C13A C14A C9A 120.3(2) . . ? C13A C14A H14A 119.8 . . ? C9A C14A H14A 119.8 . . ? 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 C1 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C4 C5 C6 C1 1.0(3) . . . . ? C3 C2 C1 C6 0.0(2) . . . . ? C3 C2 C1 C7 -178.52(16) . . . . ? C5 C6 C1 C2 -0.9(3) . . . . ? C5 C6 C1 C7 177.67(18) . . . . ? C2 C1 C7 O1 -175.89(16) . . . . ? C6 C1 C7 O1 5.5(2) . . . . ? C2 C1 C7 C8 5.5(2) . . . . ? C6 C1 C7 C8 -173.08(14) . . . . ? O2 N1 C8 C9 178.99(13) . . . . ? O2 N1 C8 C7 -4.2(2) . . . . ? O1 C7 C8 N1 -101.77(19) . . . . ? C1 C7 C8 N1 76.92(19) . . . . ? O1 C7 C8 C9 75.0(2) . . . . ? C1 C7 C8 C9 -106.36(17) . . . . ? N1 C8 C9 C10 156.7(2) . . . . ? C7 C8 C9 C10 -20.1(3) . . . . ? N1 C8 C9 C14 -19.8(3) . . . . ? C7 C8 C9 C14 163.4(2) . . . . ? C14 C9 C10 C11 -0.8(4) . . . . ? C8 C9 C10 C11 -177.4(2) . . . . ? C9 C10 C11 C12 -2.6(5) . . . . ? C10 C11 C12 C13 4.4(5) . . . . ? C11 C12 C13 C14 -2.8(5) . . . . ? C10 C9 C14 C13 2.4(4) . . . . ? C8 C9 C14 C13 179.0(2) . . . . ? C12 C13 C14 C9 -0.6(5) . . . . ? C1A C2A C3A C4A 2.1(4) . . . . ? C2A C3A C4A C5A -1.6(5) . . . . ? C3A C4A C5A C6A 0.2(5) . . . . ? C1A C6A C5A C4A 0.8(4) . . . . ? C3A C2A C1A C6A -1.2(3) . . . . ? C3A C2A C1A C7A 179.7(2) . . . . ? C5A C6A C1A C2A -0.3(4) . . . . ? C5A C6A C1A C7A 178.9(2) . . . . ? C2A C1A C7A O1A -172.32(18) . . . . ? C6A C1A C7A O1A 8.6(3) . . . . ? C2A C1A C7A C8A 8.8(3) . . . . ? C6A C1A C7A C8A -170.35(17) . . . . ? O2A N1A C8A C9A 179.62(13) . . . . ? O2A N1A C8A C7A -3.3(2) . . . . ? O1A C7A C8A N1A -94.0(2) . . . . ? C1A C7A C8A N1A 85.0(2) . . . . ? O1A C7A C8A C9A 83.1(2) . . . . ? C1A C7A C8A C9A -97.95(18) . . . . ? N1A C8A C9A C10A 169.10(17) . . . . ? C7A C8A C9A C10A -8.0(2) . . . . ? N1A C8A C9A C14A -10.4(2) . . . . ? C7A C8A C9A C14A 172.53(16) . . . . ? C14A C9A C10A C11A 1.2(3) . . . . ? C8A C9A C10A C11A -178.27(19) . . . . ? C9A C10A C11A C12A -0.9(4) . . . . ? C10A C11A C12A C13A 0.5(4) . . . . ? C11A C12A C13A C14A -0.6(4) . . . . ? C12A C13A C14A C9A 1.0(4) . . . . ? C10A C9A C14A C13A -1.3(3) . . . . ? C8A C9A C14A C13A 178.21(18) . . . . ? 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 N1A 0.91(3) 1.94(3) 2.7798(18) 152(2) 4_676 O2A H2A N1 0.95(3) 1.92(3) 2.7763(18) 148(2) 4_475 C10A H10A O1A 0.93 2.47 3.273(2) 145.1 3_675 C5 H5 O1A 0.93 2.70 3.310(3) 123.5 1_656 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.195 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.042 # Attachment '2 E.cif' data_cokl_1a_0m _database_code_depnum_ccdc_archive 'CCDC 791759' #TrackingRef '2 E.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 N O2' _chemical_formula_sum 'C14 H11 N O2' _chemical_formula_weight 225.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.9211(3) _cell_length_b 7.0512(2) _cell_length_c 22.9837(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.948(2) _cell_angle_gamma 90.00 _cell_volume 1118.99(7) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4590 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 30.53 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.9537 _exptl_absorpt_correction_T_max 0.9734 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1% _diffrn_reflns_number 9103 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.09 _reflns_number_total 2458 _reflns_number_gt 2046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+1.7057P] 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 2458 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1663 _refine_ls_wR_factor_gt 0.1561 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.135 _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 O1 O 0.2795(3) 0.9752(2) 0.99634(7) 0.0271(4) Uani 1 1 d . . . O2 O 0.2553(3) 0.3408(2) 1.03123(7) 0.0259(4) Uani 1 1 d . . . H2 H 0.2681 0.2371 1.0139 0.039 Uiso 1 1 calc R . . N1 N 0.2634(3) 0.4880(3) 0.99186(8) 0.0191(4) Uani 1 1 d . . . C1 C 0.2622(3) 0.7876(3) 0.91120(9) 0.0180(5) Uani 1 1 d . . . C2 C 0.1323(3) 0.6662(3) 0.88065(10) 0.0214(5) Uani 1 1 d . . . H2A H 0.0416 0.5947 0.9008 0.026 Uiso 1 1 calc R . . C3 C 0.1367(4) 0.6509(4) 0.82040(10) 0.0248(5) Uani 1 1 d . . . H3 H 0.0468 0.5707 0.7992 0.030 Uiso 1 1 calc R . . C4 C 0.2713(4) 0.7519(4) 0.79144(10) 0.0252(5) Uani 1 1 d . . . H4 H 0.2753 0.7391 0.7504 0.030 Uiso 1 1 calc R . . C5 C 0.4007(4) 0.8719(4) 0.82184(10) 0.0252(5) Uani 1 1 d . . . H5 H 0.4936 0.9404 0.8016 0.030 Uiso 1 1 calc R . . C6 C 0.3948(3) 0.8921(3) 0.88154(10) 0.0219(5) Uani 1 1 d . . . H6 H 0.4810 0.9771 0.9022 0.026 Uiso 1 1 calc R . . C7 C 0.2630(3) 0.8161(3) 0.97555(9) 0.0184(5) Uani 1 1 d . . . C8 C 0.2517(3) 0.6519(3) 1.01609(9) 0.0178(5) Uani 1 1 d . . . C9 C 0.2402(3) 0.6905(3) 1.07965(9) 0.0174(4) Uani 1 1 d . . . C10 C 0.0982(3) 0.8104(3) 1.09864(10) 0.0231(5) Uani 1 1 d . . . H10 H 0.0079 0.8682 1.0711 0.028 Uiso 1 1 calc R . . C11 C 0.0878(4) 0.8460(4) 1.15796(10) 0.0272(5) Uani 1 1 d . . . H11 H -0.0098 0.9275 1.1709 0.033 Uiso 1 1 calc R . . C12 C 0.2206(4) 0.7622(4) 1.19806(10) 0.0268(5) Uani 1 1 d . . . H12 H 0.2136 0.7862 1.2385 0.032 Uiso 1 1 calc R . . C13 C 0.3627(4) 0.6442(4) 1.17929(10) 0.0250(5) Uani 1 1 d . . . H13 H 0.4535 0.5874 1.2069 0.030 Uiso 1 1 calc R . . C14 C 0.3736(3) 0.6080(3) 1.12008(9) 0.0201(5) Uani 1 1 d . . . H14 H 0.4719 0.5271 1.1073 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0481(11) 0.0144(8) 0.0181(8) -0.0025(6) -0.0022(7) -0.0006(7) O2 0.0418(10) 0.0136(8) 0.0223(8) 0.0004(6) 0.0013(7) 0.0012(7) N1 0.0248(10) 0.0145(9) 0.0177(9) 0.0001(7) -0.0006(7) 0.0006(8) C1 0.0231(11) 0.0158(10) 0.0145(10) -0.0009(8) -0.0017(8) 0.0024(9) C2 0.0242(11) 0.0215(11) 0.0186(10) 0.0003(9) 0.0017(8) -0.0035(9) C3 0.0306(13) 0.0244(12) 0.0189(11) -0.0047(9) -0.0021(9) -0.0029(10) C4 0.0341(13) 0.0284(13) 0.0131(10) -0.0002(9) 0.0015(9) 0.0051(11) C5 0.0281(12) 0.0264(12) 0.0213(11) 0.0053(9) 0.0040(9) -0.0003(10) C6 0.0253(12) 0.0202(11) 0.0196(11) 0.0003(9) -0.0042(9) -0.0017(9) C7 0.0224(11) 0.0161(11) 0.0163(10) 0.0003(8) -0.0017(8) 0.0012(9) C8 0.0208(11) 0.0169(11) 0.0155(10) -0.0003(8) -0.0006(8) 0.0005(8) C9 0.0211(11) 0.0164(10) 0.0147(10) -0.0013(8) 0.0005(8) -0.0022(8) C10 0.0267(12) 0.0219(11) 0.0208(11) 0.0018(9) 0.0015(9) 0.0043(10) C11 0.0321(13) 0.0262(12) 0.0245(12) -0.0033(10) 0.0102(10) 0.0043(11) C12 0.0378(14) 0.0276(13) 0.0155(10) -0.0035(9) 0.0061(9) -0.0079(11) C13 0.0317(13) 0.0252(12) 0.0174(11) 0.0009(9) -0.0038(9) -0.0024(10) C14 0.0235(11) 0.0190(11) 0.0176(10) -0.0025(8) 0.0001(8) 0.0024(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_2 _geom_bond_publ_flag O1 C7 1.222(3) . ? O2 N1 1.381(2) . ? O2 H2 0.8400 . ? N1 C8 1.288(3) . ? C1 C6 1.391(3) . ? C1 C2 1.395(3) . ? C1 C7 1.492(3) . ? C2 C3 1.391(3) . ? C2 H2A 0.9500 . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(4) . ? C4 H4 0.9500 . ? C5 C6 1.383(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.491(3) . ? C8 C9 1.494(3) . ? C9 C10 1.389(3) . ? C9 C14 1.391(3) . ? C14 C13 1.392(3) . ? C14 H14 0.9500 . ? C13 C12 1.380(4) . ? C13 H13 0.9500 . ? C12 C11 1.388(4) . ? C12 H12 0.9500 . ? C11 C10 1.393(3) . ? C11 H11 0.9500 . ? C10 H10 0.9500 . ? 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 N1 O2 H2 109.5 . . ? C8 N1 O2 112.63(17) . . ? C6 C1 C2 120.1(2) . . ? C6 C1 C7 117.2(2) . . ? C2 C1 C7 122.7(2) . . ? C3 C2 C1 119.4(2) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.4(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.1(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 119.8(2) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O1 C7 C8 118.42(19) . . ? O1 C7 C1 120.3(2) . . ? C8 C7 C1 121.19(19) . . ? N1 C8 C7 114.77(19) . . ? N1 C8 C9 126.5(2) . . ? C7 C8 C9 118.59(19) . . ? C10 C9 C14 119.7(2) . . ? C10 C9 C8 120.3(2) . . ? C14 C9 C8 120.0(2) . . ? C9 C14 C13 119.9(2) . . ? C9 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C12 C13 C14 120.2(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C12 C11 120.2(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C11 C10 119.8(2) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C9 C10 C11 120.2(2) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? 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 C6 C1 C2 C3 0.0(3) . . . . ? C7 C1 C2 C3 178.2(2) . . . . ? C1 C2 C3 C4 1.4(4) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? C4 C5 C6 C1 1.8(4) . . . . ? C2 C1 C6 C5 -1.6(3) . . . . ? C7 C1 C6 C5 -179.9(2) . . . . ? C6 C1 C7 O1 41.7(3) . . . . ? C2 C1 C7 O1 -136.5(2) . . . . ? C6 C1 C7 C8 -135.8(2) . . . . ? C2 C1 C7 C8 46.0(3) . . . . ? O2 N1 C8 C7 179.04(19) . . . . ? O2 N1 C8 C9 2.9(3) . . . . ? O1 C7 C8 N1 -170.2(2) . . . . ? C1 C7 C8 N1 7.4(3) . . . . ? O1 C7 C8 C9 6.3(3) . . . . ? C1 C7 C8 C9 -176.12(19) . . . . ? N1 C8 C9 C10 -130.3(3) . . . . ? C7 C8 C9 C10 53.7(3) . . . . ? N1 C8 C9 C14 50.5(3) . . . . ? C7 C8 C9 C14 -125.5(2) . . . . ? C10 C9 C14 C13 0.7(3) . . . . ? C8 C9 C14 C13 180.0(2) . . . . ? C9 C14 C13 C12 -0.3(4) . . . . ? C14 C13 C12 C11 -0.2(4) . . . . ? C13 C12 C11 C10 0.1(4) . . . . ? C14 C9 C10 C11 -0.8(4) . . . . ? C8 C9 C10 C11 180.0(2) . . . . ? C12 C11 C10 C9 0.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.09 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.403 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.069 # Attachment '3 Z.cif' data_cokl6 _database_code_depnum_ccdc_archive 'CCDC 791760' #TrackingRef '3 Z.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-Bis-(4-methoxy-phenyl)-ethane-1,2-dione monooxime ; _chemical_name_common ; 1,2-Bis-(4-methoxy-phenyl)-ethane-1,2-dione monooxime ; _chemical_formula_moiety 'C16 H15 N O4' _chemical_formula_sum 'C16 H15 N O4' _chemical_formula_weight 285.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.015(1) _cell_length_b 7.3126(13) _cell_length_c 31.207(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1372.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 7766 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.64 _exptl_crystal_description splitter _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24887 _diffrn_reflns_av_R_equivalents 0.0924 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 26.49 _reflns_number_total 2847 _reflns_number_gt 2471 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker AXS)' _computing_cell_refinement SAINT-NT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0334P)^2^+4.2791P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 2847 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0733 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1662 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6354(5) 0.2379(4) 0.89462(9) 0.0238(6) Uani 1 1 d . . . O2 O 1.1914(5) 0.2720(4) 0.90275(9) 0.0273(7) Uani 1 1 d . . . H2 H 1.338(8) 0.269(6) 0.9035(13) 0.018(11) Uiso 1 1 d . . . O3 O 0.8126(5) 1.0358(4) 0.96970(9) 0.0248(7) Uani 1 1 d . . . O4 O 0.6584(5) 0.2776(4) 0.67902(9) 0.0254(7) Uani 1 1 d . . . N1 N 1.1439(6) 0.2673(5) 0.85857(11) 0.0230(7) Uani 1 1 d . . . C1 C 0.7870(7) 0.5326(6) 0.90800(13) 0.0208(9) Uani 1 1 d . . . C2 C 0.9554(7) 0.6601(6) 0.89921(13) 0.0214(9) Uani 1 1 d . . . H2A H 1.0661 0.6315 0.8786 0.026 Uiso 1 1 calc R . . C3 C 0.9626(8) 0.8262(6) 0.92012(13) 0.0233(9) Uani 1 1 d . . . H3 H 1.0803 0.9097 0.9147 0.028 Uiso 1 1 calc R . . C4 C 0.7935(7) 0.8706(5) 0.94954(12) 0.0193(8) Uani 1 1 d . . . C5 C 0.6253(7) 0.7467(6) 0.95806(12) 0.0238(9) Uani 1 1 d . . . H5 H 0.5116 0.7765 0.9780 0.029 Uiso 1 1 calc R . . C6 C 0.6233(8) 0.5780(6) 0.93727(13) 0.0232(9) Uani 1 1 d . . . H6 H 0.5080 0.4931 0.9433 0.028 Uiso 1 1 calc R . . C7 C 0.7790(7) 0.3541(6) 0.88632(13) 0.0197(9) Uani 1 1 d . . . C8 C 0.9425(7) 0.3070(5) 0.85115(13) 0.0179(8) Uani 1 1 d . . . C9 C 0.8578(7) 0.2997(5) 0.80657(12) 0.0187(8) Uani 1 1 d . . . C10 C 0.6539(7) 0.3742(5) 0.79504(13) 0.0204(8) Uani 1 1 d . . . H10 H 0.5628 0.4280 0.8165 0.024 Uiso 1 1 calc R . . C11 C 0.5799(7) 0.3717(5) 0.75261(13) 0.0200(9) Uani 1 1 d . . . H11 H 0.4414 0.4254 0.7451 0.024 Uiso 1 1 calc R . . C12 C 0.7123(7) 0.2891(5) 0.72130(12) 0.0205(8) Uani 1 1 d . . . C13 C 0.9145(7) 0.2114(6) 0.73264(13) 0.0237(9) Uani 1 1 d . . . H13 H 1.0030 0.1531 0.7114 0.028 Uiso 1 1 calc R . . C14 C 0.9877(7) 0.2181(6) 0.77442(13) 0.0238(9) Uani 1 1 d . . . H14 H 1.1280 0.1668 0.7816 0.029 Uiso 1 1 calc R . . C15 C 0.6291(9) 1.0952(6) 0.99440(15) 0.0328(11) Uani 1 1 d . . . H15A H 0.6078 1.0122 1.0187 0.049 Uiso 1 1 calc R . . H15B H 0.4950 1.0955 0.9766 0.049 Uiso 1 1 calc R . . H15C H 0.6573 1.2191 1.0050 0.049 Uiso 1 1 calc R . . C16 C 0.4725(8) 0.3809(6) 0.66453(14) 0.0301(11) Uani 1 1 d . . . H16A H 0.4958 0.5104 0.6712 0.045 Uiso 1 1 calc R . . H16B H 0.3377 0.3375 0.6789 0.045 Uiso 1 1 calc R . . H16C H 0.4561 0.3657 0.6335 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0206(15) 0.0232(15) 0.0276(15) 0.0026(12) 0.0005(12) -0.0029(13) O2 0.0241(17) 0.0297(16) 0.0282(15) 0.0011(13) -0.0026(13) -0.0020(14) O3 0.0313(18) 0.0170(14) 0.0261(15) -0.0053(11) -0.0003(13) -0.0035(13) O4 0.0295(16) 0.0212(14) 0.0256(14) -0.0014(12) -0.0012(13) -0.0002(14) N1 0.0258(19) 0.0189(17) 0.0245(17) 0.0016(14) -0.0023(15) -0.0031(16) C1 0.026(2) 0.0164(19) 0.0203(18) 0.0004(15) -0.0027(17) -0.0053(17) C2 0.024(2) 0.017(2) 0.022(2) 0.0018(15) 0.0006(17) 0.0019(17) C3 0.028(2) 0.016(2) 0.026(2) -0.0003(16) -0.0010(18) -0.0015(17) C4 0.022(2) 0.0150(18) 0.0207(18) 0.0023(15) -0.0022(17) -0.0005(16) C5 0.029(2) 0.018(2) 0.024(2) 0.0022(16) 0.0028(17) -0.0050(19) C6 0.025(2) 0.019(2) 0.026(2) 0.0019(16) 0.0001(18) -0.0031(17) C7 0.018(2) 0.0185(19) 0.023(2) 0.0028(16) -0.0025(16) -0.0011(16) C8 0.018(2) 0.0073(17) 0.029(2) 0.0015(15) -0.0003(16) -0.0013(15) C9 0.020(2) 0.0130(18) 0.0236(19) 0.0006(15) 0.0002(16) -0.0016(17) C10 0.022(2) 0.0142(18) 0.025(2) -0.0013(15) 0.0016(17) -0.0024(18) C11 0.022(2) 0.0078(18) 0.030(2) 0.0023(16) 0.0005(18) 0.0034(16) C12 0.027(2) 0.0100(18) 0.0246(19) -0.0018(16) 0.0021(17) -0.0052(16) C13 0.025(2) 0.016(2) 0.030(2) -0.0024(16) 0.0064(18) -0.0011(18) C14 0.019(2) 0.019(2) 0.033(2) 0.0012(18) 0.0038(18) -0.0009(17) C15 0.042(3) 0.028(2) 0.028(2) -0.0030(18) 0.005(2) -0.002(2) C16 0.033(3) 0.026(2) 0.031(2) -0.0006(19) -0.004(2) 0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.239(5) . ? O2 N1 1.408(4) . ? O2 H2 0.88(5) . ? O3 C4 1.367(5) . ? O3 C15 1.415(6) . ? O4 C12 1.361(5) . ? O4 C16 1.423(5) . ? N1 C8 1.267(5) . ? C1 C6 1.383(6) . ? C5 C6 1.394(6) . ? C6 H6 0.9500 . ? C4 C5 1.384(6) . ? C5 H5 0.9500 . ? C3 C4 1.408(6) . ? C2 C3 1.379(6) . ? C3 H3 0.9500 . ? C1 C2 1.404(6) . ? C2 H2A 0.9500 . ? C1 C7 1.471(6) . ? C7 C8 1.514(6) . ? C8 C9 1.483(5) . ? C9 C10 1.389(6) . ? C9 C14 1.405(6) . ? C10 C11 1.397(6) . ? C10 H10 0.9500 . ? C11 C12 1.397(6) . ? C11 H11 0.9500 . ? C12 C13 1.389(6) . ? C13 C14 1.377(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 N1 O2 H2 103(3) . . ? C4 O3 C15 117.1(3) . . ? C12 O4 C16 117.5(3) . . ? C8 N1 O2 111.5(3) . . ? C1 C6 C5 120.9(4) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C4 C5 C6 119.7(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? O3 C4 C5 123.5(4) . . ? O3 C4 C3 116.3(4) . . ? C3 C4 C5 120.2(4) . . ? C2 C3 C4 119.2(4) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C1 C2 C3 121.0(4) . . ? C3 C2 H2A 119.5 . . ? C1 C2 H2A 119.5 . . ? C6 C1 C2 118.9(4) . . ? C6 C1 C7 119.6(4) . . ? C2 C1 C7 121.5(4) . . ? O1 C7 C1 122.4(4) . . ? O1 C7 C8 116.6(4) . . ? C1 C7 C8 120.9(3) . . ? N1 C8 C9 119.5(4) . . ? N1 C8 C7 122.8(4) . . ? C9 C8 C7 117.7(4) . . ? C10 C9 C14 118.2(4) . . ? C10 C9 C8 122.2(4) . . ? C14 C9 C8 119.6(4) . . ? C9 C10 C11 121.4(4) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C10 C11 C12 119.1(4) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? O4 C12 C13 115.5(4) . . ? O4 C12 C11 124.7(4) . . ? C13 C12 C11 119.8(4) . . ? C14 C13 C12 120.5(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C9 120.9(4) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 C1 C6 C5 C4 -0.3(6) . . . . ? C15 O3 C4 C5 -12.0(6) . . . . ? C15 O3 C4 C3 170.8(4) . . . . ? C6 C5 C4 O3 -177.4(4) . . . . ? C6 C5 C4 C3 -0.3(6) . . . . ? O3 C4 C3 C2 178.9(4) . . . . ? C5 C4 C3 C2 1.6(6) . . . . ? C4 C3 C2 C1 -2.4(6) . . . . ? C5 C6 C1 C2 -0.5(6) . . . . ? C5 C6 C1 C7 -179.4(4) . . . . ? C3 C2 C1 C6 1.8(6) . . . . ? C3 C2 C1 C7 -179.2(4) . . . . ? C6 C1 C7 O1 -3.3(6) . . . . ? C2 C1 C7 O1 177.8(4) . . . . ? C6 C1 C7 C8 174.2(4) . . . . ? C2 C1 C7 C8 -4.7(6) . . . . ? O2 N1 C8 C9 -176.8(3) . . . . ? O2 N1 C8 C7 0.4(5) . . . . ? O1 C7 C8 N1 -107.7(5) . . . . ? C1 C7 C8 N1 74.7(5) . . . . ? O1 C7 C8 C9 69.6(5) . . . . ? C1 C7 C8 C9 -108.1(4) . . . . ? N1 C8 C9 C10 -167.4(4) . . . . ? C7 C8 C9 C10 15.3(5) . . . . ? N1 C8 C9 C14 11.5(6) . . . . ? C7 C8 C9 C14 -165.8(4) . . . . ? C14 C9 C10 C11 -1.1(6) . . . . ? C8 C9 C10 C11 177.8(4) . . . . ? C9 C10 C11 C12 1.3(6) . . . . ? C16 O4 C12 C13 -169.8(4) . . . . ? C16 O4 C12 C11 10.2(6) . . . . ? C10 C11 C12 O4 179.9(4) . . . . ? C10 C11 C12 C13 -0.1(6) . . . . ? O4 C12 C13 C14 178.8(4) . . . . ? C11 C12 C13 C14 -1.2(6) . . . . ? C12 C13 C14 C9 1.4(6) . . . . ? C10 C9 C14 C13 -0.3(6) . . . . ? C8 C9 C14 C13 -179.2(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 0.88(5) 1.83(5) 2.694(4) 168(4) 1_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.370 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.083 # Attachment '3a Z.cif' data_cokl5 _database_code_depnum_ccdc_archive 'CCDC 791761' #TrackingRef '3a Z.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-Bis-(4-methoxy-phenyl)-ethane-1,2-dione monooxime NEt3 ; _chemical_name_common ; 1,2-Bis-(4-methoxy-phenyl)-ethane-1,2-dione monooxime NEt3 ; _chemical_formula_moiety 'C16 H15 N O4, C6 H15 N' _chemical_formula_sum 'C22 H30 N2 O4' _chemical_formula_weight 386.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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 19.219(3) _cell_length_b 11.4306(12) _cell_length_c 19.510(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4286.1(9) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 7650 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 30.64 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; 1,2-Bis-(4-methoxy-phenyl)-ethane-1,2-dione monooxime NEt3 ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 66823 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6245 _reflns_number_gt 4384 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+1.8142P] 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 6245 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.02149(5) 0.73487(8) 0.07516(5) 0.0264(2) Uani 1 1 d . . . O2 O 0.07912(5) 0.85824(8) 0.17700(5) 0.0242(2) Uani 1 1 d . . . H2 H 0.0953(11) 0.8834(18) 0.2203(11) 0.061(6) Uiso 1 1 d . . . O3 O 0.14672(5) 1.02358(9) -0.15043(5) 0.0288(2) Uani 1 1 d . . . O4 O 0.21388(5) 0.25686(8) 0.06285(5) 0.0281(2) Uani 1 1 d . . . N1 N 0.11097(6) 0.74889(9) 0.17013(5) 0.0209(2) Uani 1 1 d . . . C1 C 0.06746(6) 0.82390(10) 0.00850(6) 0.0183(2) Uani 1 1 d . . . C2 C 0.13898(6) 0.84175(10) 0.00037(6) 0.0203(2) Uani 1 1 d . . . H2A H 0.1707 0.8079 0.0320 0.024 Uiso 1 1 calc R . . C3 C 0.16370(6) 0.90838(11) -0.05339(6) 0.0217(2) Uani 1 1 d . . . H3 H 0.2124 0.9196 -0.0589 0.026 Uiso 1 1 calc R . . C4 C 0.11721(7) 0.95937(10) -0.09973(6) 0.0212(2) Uani 1 1 d . . . C5 C 0.04563(7) 0.94339(11) -0.09177(6) 0.0228(3) Uani 1 1 d . . . H5 H 0.0139 0.9785 -0.1229 0.027 Uiso 1 1 calc R . . C6 C 0.02158(7) 0.87569(11) -0.03792(6) 0.0214(2) Uani 1 1 d . . . H6 H -0.0271 0.8643 -0.0325 0.026 Uiso 1 1 calc R . . C7 C 0.04057(6) 0.75232(10) 0.06560(6) 0.0192(2) Uani 1 1 d . . . C8 C 0.09339(6) 0.69809(10) 0.11399(6) 0.0190(2) Uani 1 1 d . . . C9 C 0.12538(6) 0.58410(10) 0.09752(6) 0.0196(2) Uani 1 1 d . . . C10 C 0.10279(7) 0.51767(11) 0.04184(6) 0.0229(3) Uani 1 1 d . . . H10 H 0.0673 0.5478 0.0129 0.027 Uiso 1 1 calc R . . C11 C 0.13119(7) 0.40777(11) 0.02756(7) 0.0246(3) Uani 1 1 d . . . H11 H 0.1151 0.3636 -0.0105 0.029 Uiso 1 1 calc R . . C12 C 0.18316(6) 0.36414(10) 0.06968(7) 0.0219(3) Uani 1 1 d . . . C13 C 0.20812(7) 0.43121(11) 0.12440(7) 0.0239(3) Uani 1 1 d . . . H13 H 0.2448 0.4021 0.1523 0.029 Uiso 1 1 calc R . . C14 C 0.17968(7) 0.53926(11) 0.13790(6) 0.0230(3) Uani 1 1 d . . . H14 H 0.1970 0.5842 0.1751 0.028 Uiso 1 1 calc R . . C15 C 0.10081(8) 1.07301(14) -0.20053(8) 0.0348(3) Uani 1 1 d . . . H15A H 0.0743 1.0103 -0.2227 0.052 Uiso 1 1 calc R . . H15B H 0.1281 1.1151 -0.2351 0.052 Uiso 1 1 calc R . . H15C H 0.0687 1.1274 -0.1781 0.052 Uiso 1 1 calc R . . C16 C 0.19388(8) 0.18585(13) 0.00590(10) 0.0418(4) Uani 1 1 d . . . H16A H 0.1441 0.1682 0.0089 0.063 Uiso 1 1 calc R . . H16B H 0.2205 0.1127 0.0066 0.063 Uiso 1 1 calc R . . H16C H 0.2034 0.2279 -0.0369 0.063 Uiso 1 1 calc R . . N2 N 0.11785(6) 0.94746(9) 0.29939(5) 0.0214(2) Uani 1 1 d . . . C17 C 0.15668(8) 1.05636(12) 0.28566(8) 0.0353(3) Uani 1 1 d . . . H17A H 0.2068 1.0375 0.2814 0.042 Uiso 1 1 calc R . . H17B H 0.1511 1.1097 0.3253 0.042 Uiso 1 1 calc R . . C18 C 0.13305(9) 1.11958(13) 0.22085(9) 0.0419(4) Uani 1 1 d . . . H18A H 0.1373 1.0668 0.1815 0.063 Uiso 1 1 calc R . . H18B H 0.1622 1.1887 0.2135 0.063 Uiso 1 1 calc R . . H18C H 0.0844 1.1438 0.2260 0.063 Uiso 1 1 calc R . . C19 C 0.04911(7) 0.97444(12) 0.32988(7) 0.0280(3) Uani 1 1 d . . . H19A H 0.0258 1.0349 0.3017 0.034 Uiso 1 1 calc R . . H19B H 0.0561 1.0072 0.3763 0.034 Uiso 1 1 calc R . . C20 C 0.00210(8) 0.86835(13) 0.33487(7) 0.0320(3) Uani 1 1 d . . . H20A H 0.0037 0.8247 0.2917 0.048 Uiso 1 1 calc R . . H20B H -0.0457 0.8938 0.3438 0.048 Uiso 1 1 calc R . . H20C H 0.0179 0.8179 0.3724 0.048 Uiso 1 1 calc R . . C21 C 0.15837(8) 0.87139(13) 0.34625(7) 0.0318(3) Uani 1 1 d . . . H21A H 0.1266 0.8142 0.3680 0.038 Uiso 1 1 calc R . . H21B H 0.1789 0.9201 0.3831 0.038 Uiso 1 1 calc R . . C22 C 0.21602(7) 0.80594(13) 0.30985(7) 0.0304(3) Uani 1 1 d . . . H22D H 0.1959 0.7553 0.2745 0.046 Uiso 1 1 calc R . . H22E H 0.2416 0.7580 0.3430 0.046 Uiso 1 1 calc R . . H22F H 0.2479 0.8621 0.2885 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0214(5) 0.0337(5) 0.0240(5) 0.0013(4) -0.0018(4) -0.0052(4) O2 0.0303(5) 0.0222(4) 0.0202(4) -0.0054(3) -0.0048(4) 0.0056(4) O3 0.0232(5) 0.0343(5) 0.0289(5) 0.0120(4) 0.0024(4) 0.0012(4) O4 0.0253(5) 0.0223(4) 0.0367(5) -0.0082(4) 0.0065(4) -0.0007(4) N1 0.0250(5) 0.0195(5) 0.0182(5) -0.0024(4) -0.0010(4) 0.0016(4) C1 0.0201(6) 0.0188(5) 0.0160(5) -0.0033(4) -0.0015(4) -0.0004(4) C2 0.0192(6) 0.0209(5) 0.0208(6) -0.0010(4) -0.0034(5) 0.0016(4) C3 0.0166(6) 0.0226(6) 0.0258(6) -0.0005(5) -0.0007(5) 0.0004(5) C4 0.0228(6) 0.0204(5) 0.0204(6) 0.0002(4) 0.0016(5) 0.0005(5) C5 0.0197(6) 0.0283(6) 0.0204(6) 0.0028(5) -0.0030(5) 0.0026(5) C6 0.0177(6) 0.0270(6) 0.0194(6) -0.0009(5) -0.0015(5) 0.0001(5) C7 0.0217(6) 0.0197(5) 0.0162(5) -0.0040(4) -0.0032(4) -0.0011(5) C8 0.0201(6) 0.0210(5) 0.0158(5) 0.0001(4) -0.0009(4) -0.0020(4) C9 0.0220(6) 0.0203(5) 0.0163(5) -0.0012(4) 0.0005(4) -0.0028(5) C10 0.0232(6) 0.0278(6) 0.0176(6) -0.0039(5) -0.0016(5) -0.0013(5) C11 0.0245(6) 0.0284(6) 0.0208(6) -0.0092(5) 0.0023(5) -0.0045(5) C12 0.0201(6) 0.0210(5) 0.0245(6) -0.0035(5) 0.0084(5) -0.0036(5) C13 0.0242(6) 0.0252(6) 0.0225(6) -0.0003(5) -0.0018(5) 0.0010(5) C14 0.0268(6) 0.0229(6) 0.0192(6) -0.0032(5) -0.0035(5) -0.0012(5) C15 0.0295(7) 0.0455(8) 0.0293(7) 0.0159(6) 0.0017(6) 0.0040(6) C16 0.0272(7) 0.0342(7) 0.0639(11) -0.0286(8) 0.0061(7) -0.0031(6) N2 0.0245(5) 0.0209(5) 0.0187(5) -0.0025(4) -0.0014(4) 0.0016(4) C17 0.0392(8) 0.0275(7) 0.0393(8) -0.0067(6) -0.0022(7) -0.0090(6) C18 0.0508(10) 0.0238(7) 0.0512(10) 0.0064(7) 0.0001(8) -0.0064(7) C19 0.0319(7) 0.0281(6) 0.0240(6) -0.0046(5) 0.0013(5) 0.0073(6) C20 0.0304(7) 0.0368(7) 0.0289(7) 0.0083(6) 0.0057(6) 0.0038(6) C21 0.0353(8) 0.0390(8) 0.0212(6) 0.0003(6) -0.0036(6) 0.0108(6) C22 0.0264(7) 0.0362(7) 0.0284(7) -0.0047(6) -0.0057(5) 0.0069(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2238(15) . ? O2 N1 1.3982(13) . ? O2 H2 0.95(2) . ? O3 C4 1.3561(15) . ? O3 C15 1.4329(17) . ? O4 C12 1.3675(15) . ? O4 C16 1.4286(17) . ? N1 C8 1.2850(15) . ? C5 C6 1.3843(17) . ? C1 C6 1.3959(17) . ? C6 H6 0.9500 . ? C4 C5 1.3963(18) . ? C5 H5 0.9500 . ? C3 C4 1.3983(17) . ? C2 C3 1.3806(17) . ? C3 H3 0.9500 . ? C1 C2 1.3986(17) . ? C2 H2A 0.9500 . ? C1 C7 1.4756(17) . ? C7 C8 1.5185(16) . ? C8 C9 1.4762(16) . ? C9 C10 1.3946(16) . ? C9 C14 1.4045(17) . ? C10 C11 1.3978(18) . ? C10 H10 0.9500 . ? C11 C12 1.3861(19) . ? C11 H11 0.9500 . ? C12 C13 1.3993(18) . ? C13 C14 1.3761(17) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N2 C17 1.4758(17) . ? N2 C19 1.4812(17) . ? N2 C21 1.4828(17) . ? C17 C18 1.526(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.515(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.5139(19) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22D 0.9800 . ? C22 H22E 0.9800 . ? C22 H22F 0.9800 . ? 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 N1 O2 H2 102.3(12) . . ? C4 O3 C15 116.97(10) . . ? C12 O4 C16 117.97(11) . . ? C8 N1 O2 111.75(10) . . ? C1 C6 C5 121.24(12) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? C4 C5 C6 119.11(11) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? O3 C4 C5 124.33(11) . . ? O3 C4 C3 115.46(11) . . ? C3 C4 C5 120.21(11) . . ? C2 C3 C4 120.08(12) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C1 C2 C3 120.32(11) . . ? C3 C2 H2A 119.8 . . ? C1 C2 H2A 119.8 . . ? C6 C1 C2 119.04(11) . . ? C6 C1 C7 120.25(11) . . ? C2 C1 C7 120.71(11) . . ? O1 C7 C1 123.15(11) . . ? O1 C7 C8 119.35(11) . . ? C1 C7 C8 117.49(10) . . ? N1 C8 C9 118.35(11) . . ? N1 C8 C7 121.42(11) . . ? C9 C8 C7 120.23(10) . . ? C10 C9 C14 118.00(11) . . ? C10 C9 C8 121.36(11) . . ? C14 C9 C8 120.63(11) . . ? C9 C10 C11 121.53(12) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C12 C11 C10 119.12(11) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? O4 C12 C11 125.17(11) . . ? O4 C12 C13 114.68(12) . . ? C11 C12 C13 120.15(11) . . ? C14 C13 C12 120.10(12) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C9 121.02(11) . . ? C13 C14 H14 119.5 . . ? C9 C14 H14 119.5 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C17 N2 C19 110.38(11) . . ? C17 N2 C21 109.93(11) . . ? C19 N2 C21 110.05(10) . . ? N2 C17 C18 113.55(12) . . ? N2 C17 H17A 108.9 . . ? C18 C17 H17A 108.9 . . ? N2 C17 H17B 108.9 . . ? C18 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 C20 113.01(11) . . ? N2 C19 H19A 109.0 . . ? C20 C19 H19A 109.0 . . ? N2 C19 H19B 109.0 . . ? C20 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C21 C22 112.64(11) . . ? N2 C21 H21A 109.1 . . ? C22 C21 H21A 109.1 . . ? N2 C21 H21B 109.1 . . ? C22 C21 H21B 109.1 . . ? H21A C21 H21B 107.8 . . ? C21 C22 H22D 109.5 . . ? C21 C22 H22E 109.5 . . ? H22D C22 H22E 109.5 . . ? C21 C22 H22F 109.5 . . ? H22D C22 H22F 109.5 . . ? H22E C22 H22F 109.5 . . ? 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 C1 C6 C5 C4 0.32(19) . . . . ? C15 O3 C4 C5 -3.09(18) . . . . ? C15 O3 C4 C3 177.43(12) . . . . ? C6 C5 C4 O3 179.94(12) . . . . ? C6 C5 C4 C3 -0.61(19) . . . . ? O3 C4 C3 C2 179.66(11) . . . . ? C5 C4 C3 C2 0.15(18) . . . . ? C4 C3 C2 C1 0.59(18) . . . . ? C5 C6 C1 C2 0.40(18) . . . . ? C5 C6 C1 C7 179.86(11) . . . . ? C3 C2 C1 C6 -0.86(18) . . . . ? C3 C2 C1 C7 179.69(11) . . . . ? C6 C1 C7 O1 0.01(18) . . . . ? C2 C1 C7 O1 179.45(11) . . . . ? C6 C1 C7 C8 179.71(10) . . . . ? C2 C1 C7 C8 -0.84(16) . . . . ? O2 N1 C8 C9 177.06(10) . . . . ? O2 N1 C8 C7 -3.52(16) . . . . ? O1 C7 C8 N1 -85.72(15) . . . . ? C1 C7 C8 N1 94.56(14) . . . . ? O1 C7 C8 C9 93.69(14) . . . . ? C1 C7 C8 C9 -86.03(13) . . . . ? N1 C8 C9 C10 172.30(12) . . . . ? C7 C8 C9 C10 -7.12(17) . . . . ? N1 C8 C9 C14 -7.58(18) . . . . ? C7 C8 C9 C14 172.99(11) . . . . ? C14 C9 C10 C11 2.27(19) . . . . ? C8 C9 C10 C11 -177.62(11) . . . . ? C9 C10 C11 C12 -0.20(19) . . . . ? C16 O4 C12 C11 3.49(18) . . . . ? C16 O4 C12 C13 -176.63(12) . . . . ? C10 C11 C12 O4 177.91(11) . . . . ? C10 C11 C12 C13 -1.96(19) . . . . ? O4 C12 C13 C14 -177.88(11) . . . . ? C11 C12 C13 C14 2.01(19) . . . . ? C12 C13 C14 C9 0.14(19) . . . . ? C10 C9 C14 C13 -2.23(19) . . . . ? C8 C9 C14 C13 177.65(12) . . . . ? C19 N2 C17 C18 -78.57(15) . . . . ? C21 N2 C17 C18 159.85(13) . . . . ? C17 N2 C19 C20 170.90(12) . . . . ? C21 N2 C19 C20 -67.58(14) . . . . ? C17 N2 C21 C22 -78.72(15) . . . . ? C19 N2 C21 C22 159.49(12) . . . . ? 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 N2 0.95(2) 1.76(2) 2.7011(14) 171.9(19) . C22 H22D N1 0.98 2.61 3.4544(18) 144.4 . C2 H2A O4 0.95 2.37 3.2288(16) 149.9 8_665 C11 H11 O1 0.95 2.47 3.3347(16) 151.6 5_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.354 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.048