Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Christopher Alexander Hunter' _publ_contact_author_address ; University of Sheffield Sheffield S3 7HF UNITED KINGDOM ; _publ_contact_author_email C.HUNTER@SHEF.AC.UK _publ_section_title ; Substituent Effects on Aromatic Stacking Interactions ; loop_ _publ_author_name C.A.Hunter H.Adams K.R.Lawson C.M.R.Low J.Perkins C.J.Urch ; J.G.Winter ; C.Zonta #F2-OMe.cif data_ilt119m _database_code_depnum_ccdc_archive 'CCDC 238547' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 F2 N O2' _chemical_formula_weight 291.29 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' F F 0.0171 0.0103 '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 4.6327(11) _cell_length_b 24.041(6) _cell_length_c 12.808(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.977(5) _cell_angle_gamma 90.00 _cell_volume 1425.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1340 _cell_measurement_theta_min 4.648 _cell_measurement_theta_max 46.634 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9535 _exptl_absorpt_correction_T_max 0.9666 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 8609 _diffrn_reflns_av_R_equivalents 0.0691 _diffrn_reflns_av_sigmaI/netI 0.1059 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.57 _reflns_number_total 3217 _reflns_number_gt 1573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0702P)^2^+0.0000P] 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 3217 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1162 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1144 _refine_ls_goodness_of_fit_ref 0.807 _refine_ls_restrained_S_all 0.807 _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 N1 N 0.4665(4) 0.65178(7) 0.16449(15) 0.0238(5) Uani 1 1 d . . . H1A H 0.2788 0.6462 0.1594 0.029 Uiso 1 1 calc R . . O1 O 0.9016(3) 0.61404(7) 0.21089(14) 0.0357(5) Uani 1 1 d . . . O2 O 0.9019(4) 0.86150(6) 0.07572(13) 0.0324(5) Uani 1 1 d . . . F1 F 0.3300(3) 0.55124(6) 0.03926(11) 0.0420(4) Uani 1 1 d . . . F2 F 0.6263(3) 0.55577(6) 0.39184(11) 0.0440(4) Uani 1 1 d . . . C1 C 0.5777(5) 0.70530(9) 0.13765(18) 0.0214(5) Uani 1 1 d . . . C2 C 0.7491(5) 0.71129(9) 0.05156(18) 0.0232(6) Uani 1 1 d . . . C3 C 0.8626(5) 0.76347(9) 0.02939(18) 0.0257(6) Uani 1 1 d . . . H3 H 0.9829 0.7680 -0.0286 0.031 Uiso 1 1 calc R . . C4 C 0.8004(5) 0.80886(9) 0.09185(19) 0.0241(6) Uani 1 1 d . . . C5 C 0.6208(5) 0.80234(9) 0.17484(19) 0.0261(6) Uani 1 1 d . . . H5 H 0.5731 0.8338 0.2156 0.031 Uiso 1 1 calc R . . C6 C 0.5093(5) 0.75099(10) 0.19973(17) 0.0231(6) Uani 1 1 d . . . C7 C 0.6369(5) 0.60988(9) 0.19705(18) 0.0238(5) Uani 1 1 d . . . C8 C 0.4859(5) 0.55564(9) 0.21470(18) 0.0240(6) Uani 1 1 d . . . C9 C 0.4869(5) 0.53011(10) 0.31098(19) 0.0285(6) Uani 1 1 d . . . C10 C 0.3434(6) 0.48095(10) 0.3300(2) 0.0347(7) Uani 1 1 d . . . H10 H 0.3466 0.4650 0.3978 0.042 Uiso 1 1 calc R . . C11 C 0.1953(6) 0.45576(11) 0.2476(2) 0.0375(7) Uani 1 1 d . . . H11 H 0.0952 0.4219 0.2588 0.045 Uiso 1 1 calc R . . C12 C 0.1905(6) 0.47884(10) 0.1497(2) 0.0353(7) Uani 1 1 d . . . H12 H 0.0891 0.4613 0.0929 0.042 Uiso 1 1 calc R . . C13 C 0.3363(6) 0.52802(10) 0.13568(19) 0.0284(6) Uani 1 1 d . . . C14 C 0.8107(6) 0.66331(10) -0.02020(19) 0.0311(6) Uani 1 1 d . . . H14A H 0.9754 0.6420 0.0085 0.047 Uiso 1 1 calc R . . H14B H 0.8563 0.6776 -0.0893 0.047 Uiso 1 1 calc R . . H14C H 0.6406 0.6392 -0.0263 0.047 Uiso 1 1 calc R . . C15 C 0.3193(5) 0.74408(10) 0.29187(19) 0.0307(6) Uani 1 1 d . . . H15A H 0.2974 0.7800 0.3268 0.046 Uiso 1 1 calc R . . H15B H 0.4077 0.7173 0.3410 0.046 Uiso 1 1 calc R . . H15C H 0.1292 0.7304 0.2678 0.046 Uiso 1 1 calc R . . C16 C 1.0960(5) 0.87015(10) -0.0069(2) 0.0330(6) Uani 1 1 d . . . H16A H 1.2660 0.8463 0.0039 0.049 Uiso 1 1 calc R . . H16B H 1.1563 0.9092 -0.0076 0.049 Uiso 1 1 calc R . . H16C H 0.9988 0.8609 -0.0739 0.049 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 N1 0.0233(11) 0.0197(10) 0.0286(12) 0.0026(9) 0.0021(9) -0.0023(9) O1 0.0212(9) 0.0323(10) 0.0537(12) 0.0094(9) 0.0043(8) -0.0018(8) O2 0.0432(11) 0.0199(9) 0.0348(11) 0.0014(8) 0.0135(8) -0.0069(8) F1 0.0661(11) 0.0330(8) 0.0264(9) 0.0041(7) -0.0049(7) -0.0100(8) F2 0.0571(10) 0.0470(10) 0.0275(9) 0.0037(7) -0.0061(7) -0.0163(8) C1 0.0240(13) 0.0195(12) 0.0209(13) 0.0021(10) 0.0026(10) -0.0023(10) C2 0.0270(13) 0.0212(13) 0.0215(14) -0.0003(10) 0.0017(11) -0.0008(11) C3 0.0291(14) 0.0246(13) 0.0237(14) 0.0003(11) 0.0070(11) -0.0004(11) C4 0.0287(13) 0.0165(12) 0.0273(14) 0.0034(10) 0.0025(11) -0.0021(11) C5 0.0300(14) 0.0222(13) 0.0265(14) -0.0035(11) 0.0053(11) 0.0020(11) C6 0.0237(13) 0.0264(13) 0.0195(13) 0.0025(10) 0.0024(10) -0.0006(11) C7 0.0247(13) 0.0240(13) 0.0232(13) 0.0014(11) 0.0051(10) -0.0041(11) C8 0.0259(13) 0.0196(12) 0.0269(14) 0.0012(11) 0.0068(11) 0.0029(11) C9 0.0308(14) 0.0283(14) 0.0265(15) -0.0020(11) 0.0026(11) -0.0012(12) C10 0.0428(16) 0.0276(14) 0.0341(16) 0.0060(12) 0.0068(13) -0.0039(13) C11 0.0428(16) 0.0232(14) 0.0468(18) 0.0066(13) 0.0062(14) -0.0057(13) C12 0.0428(16) 0.0221(14) 0.0407(17) -0.0032(12) -0.0018(13) -0.0065(12) C13 0.0386(15) 0.0237(13) 0.0231(14) 0.0033(11) 0.0046(11) 0.0039(12) C14 0.0437(16) 0.0250(13) 0.0250(14) -0.0028(11) 0.0078(12) -0.0007(12) C15 0.0348(15) 0.0301(14) 0.0277(15) -0.0015(11) 0.0090(12) 0.0006(12) C16 0.0339(15) 0.0280(14) 0.0376(16) 0.0096(12) 0.0106(12) -0.0028(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.338(3) . ? N1 C1 1.433(3) . ? O1 C7 1.237(3) . ? O2 C4 1.368(3) . ? O2 C16 1.428(3) . ? F1 C13 1.355(3) . ? F2 C9 1.351(3) . ? C1 C2 1.388(3) . ? C1 C6 1.399(3) . ? C2 C3 1.393(3) . ? C2 C14 1.508(3) . ? C3 C4 1.389(3) . ? C4 C5 1.381(3) . ? C5 C6 1.380(3) . ? C6 C15 1.506(3) . ? C7 C8 1.501(3) . ? C8 C13 1.377(3) . ? C8 C9 1.377(3) . ? C9 C10 1.382(3) . ? C10 C11 1.378(4) . ? C11 C12 1.371(4) . ? C12 C13 1.377(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 C7 N1 C1 122.5(2) . . ? C4 O2 C16 118.37(18) . . ? C2 C1 C6 121.1(2) . . ? C2 C1 N1 120.3(2) . . ? C6 C1 N1 118.58(19) . . ? C1 C2 C3 119.0(2) . . ? C1 C2 C14 122.0(2) . . ? C3 C2 C14 118.9(2) . . ? C4 C3 C2 120.2(2) . . ? O2 C4 C5 116.1(2) . . ? O2 C4 C3 124.1(2) . . ? C5 C4 C3 119.8(2) . . ? C6 C5 C4 121.3(2) . . ? C5 C6 C1 118.5(2) . . ? C5 C6 C15 120.9(2) . . ? C1 C6 C15 120.6(2) . . ? O1 C7 N1 123.7(2) . . ? O1 C7 C8 120.9(2) . . ? N1 C7 C8 115.4(2) . . ? C13 C8 C9 115.4(2) . . ? C13 C8 C7 122.2(2) . . ? C9 C8 C7 122.3(2) . . ? F2 C9 C10 118.4(2) . . ? F2 C9 C8 118.0(2) . . ? C10 C9 C8 123.5(2) . . ? C11 C10 C9 118.1(2) . . ? C12 C11 C10 121.0(2) . . ? C11 C12 C13 118.3(3) . . ? F1 C13 C12 118.5(2) . . ? F1 C13 C8 117.8(2) . . ? C12 C13 C8 123.7(2) . . ? 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 C7 N1 C1 C2 66.3(3) . . . . ? C7 N1 C1 C6 -113.9(3) . . . . ? C6 C1 C2 C3 2.4(4) . . . . ? N1 C1 C2 C3 -177.8(2) . . . . ? C6 C1 C2 C14 -176.2(2) . . . . ? N1 C1 C2 C14 3.6(4) . . . . ? C1 C2 C3 C4 -1.1(4) . . . . ? C14 C2 C3 C4 177.6(2) . . . . ? C16 O2 C4 C5 178.0(2) . . . . ? C16 O2 C4 C3 -3.4(4) . . . . ? C2 C3 C4 O2 -179.9(2) . . . . ? C2 C3 C4 C5 -1.3(4) . . . . ? O2 C4 C5 C6 -178.9(2) . . . . ? C3 C4 C5 C6 2.4(4) . . . . ? C4 C5 C6 C1 -1.2(4) . . . . ? C4 C5 C6 C15 178.6(2) . . . . ? C2 C1 C6 C5 -1.3(4) . . . . ? N1 C1 C6 C5 178.9(2) . . . . ? C2 C1 C6 C15 179.0(2) . . . . ? N1 C1 C6 C15 -0.8(3) . . . . ? C1 N1 C7 O1 3.0(4) . . . . ? C1 N1 C7 C8 -176.0(2) . . . . ? O1 C7 C8 C13 -118.1(3) . . . . ? N1 C7 C8 C13 60.9(3) . . . . ? O1 C7 C8 C9 62.1(3) . . . . ? N1 C7 C8 C9 -118.9(3) . . . . ? C13 C8 C9 F2 -178.9(2) . . . . ? C7 C8 C9 F2 1.0(3) . . . . ? C13 C8 C9 C10 -1.7(4) . . . . ? C7 C8 C9 C10 178.2(2) . . . . ? F2 C9 C10 C11 178.3(2) . . . . ? C8 C9 C10 C11 1.1(4) . . . . ? C9 C10 C11 C12 0.0(4) . . . . ? C10 C11 C12 C13 -0.3(4) . . . . ? C11 C12 C13 F1 -179.4(2) . . . . ? C11 C12 C13 C8 -0.4(4) . . . . ? C9 C8 C13 F1 -179.7(2) . . . . ? C7 C8 C13 F1 0.5(3) . . . . ? C9 C8 C13 C12 1.3(4) . . . . ? C7 C8 C13 C12 -178.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.212 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.057 # Attachment 'OCH232M.cif' data_och232m _database_code_depnum_ccdc_archive 'CCDC 615388' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Centre for Chemical Biology Department of Chemistry Krebs Institute for Biomolecular Science University of Sheffield Sheffield S3 7HF UK ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 F2 N O' _chemical_formula_weight 261.26 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9925(9) _cell_length_b 16.8092(18) _cell_length_c 18.0165(19) _cell_angle_alpha 75.543(2) _cell_angle_beta 89.972(2) _cell_angle_gamma 83.735(2) _cell_volume 2620.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2949 _cell_measurement_theta_min 4.666 _cell_measurement_theta_max 49.054 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9524 _exptl_absorpt_correction_T_max 0.9768 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16340 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.1047 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 27.55 _reflns_number_total 11440 _reflns_number_gt 4958 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+0.0000P] 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 11440 _refine_ls_number_parameters 693 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.1375 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 0.851 _refine_ls_restrained_S_all 0.876 _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 F1A F 0.5348(2) 0.91204(10) 0.14263(10) 0.0676(5) Uani 1 1 d . . . F2A F 0.69173(18) 0.64265(11) 0.28245(9) 0.0588(5) Uani 1 1 d . . . O1A O 0.37899(18) 0.73540(12) 0.17422(10) 0.0424(5) Uani 1 1 d . . . N1A N 0.5820(2) 0.72210(13) 0.10153(12) 0.0334(5) Uani 1 1 d . . . H1AA H 0.6786 0.7262 0.0976 0.040 Uiso 1 1 calc R . . C1A C 0.5067(3) 0.69396(18) 0.04437(16) 0.0377(7) Uani 1 1 d . . . C2A C 0.4611(3) 0.61515(19) 0.06214(19) 0.0497(8) Uani 1 1 d . . . C3A C 0.3893(4) 0.5917(2) 0.0039(3) 0.0748(11) Uani 1 1 d . . . H3AA H 0.3545 0.5388 0.0145 0.090 Uiso 1 1 calc R . . C4A C 0.3674(4) 0.6428(3) -0.0682(3) 0.0835(13) Uani 1 1 d . . . H4AA H 0.3201 0.6246 -0.1071 0.100 Uiso 1 1 calc R . . C5A C 0.4139(3) 0.7207(3) -0.08440(19) 0.0635(10) Uani 1 1 d . . . H5AA H 0.3992 0.7557 -0.1347 0.076 Uiso 1 1 calc R . . C6A C 0.4821(3) 0.7483(2) -0.02772(17) 0.0447(8) Uani 1 1 d . . . C7A C 0.4872(4) 0.55731(19) 0.1406(2) 0.0693(10) Uani 1 1 d . . . H7A1 H 0.5904 0.5571 0.1582 0.104 Uiso 1 1 calc R . . H7A2 H 0.4703 0.5013 0.1384 0.104 Uiso 1 1 calc R . . H7A3 H 0.4179 0.5758 0.1765 0.104 Uiso 1 1 calc R . . C8A C 0.5292(3) 0.83375(18) -0.04317(16) 0.0514(8) Uani 1 1 d . . . H8A1 H 0.4963 0.8648 -0.0952 0.077 Uiso 1 1 calc R . . H8A2 H 0.6384 0.8301 -0.0384 0.077 Uiso 1 1 calc R . . H8A3 H 0.4836 0.8621 -0.0060 0.077 Uiso 1 1 calc R . . C9A C 0.5118(3) 0.74228(16) 0.16015(14) 0.0317(6) Uani 1 1 d . . . C10A C 0.6072(3) 0.77607(17) 0.21144(14) 0.0315(6) Uani 1 1 d . . . C11A C 0.6114(3) 0.85902(18) 0.20341(16) 0.0433(7) Uani 1 1 d . . . C12A C 0.6895(3) 0.8916(2) 0.25231(18) 0.0549(9) Uani 1 1 d . . . H12A H 0.6887 0.9497 0.2444 0.066 Uiso 1 1 calc R . . C13A C 0.7689(3) 0.8374(2) 0.31302(18) 0.0555(9) Uani 1 1 d . . . H13A H 0.8229 0.8582 0.3480 0.067 Uiso 1 1 calc R . . C14A C 0.7709(3) 0.7536(2) 0.32350(16) 0.0509(8) Uani 1 1 d . . . H14A H 0.8260 0.7160 0.3651 0.061 Uiso 1 1 calc R . . C15A C 0.6915(3) 0.72585(19) 0.27249(16) 0.0393(7) Uani 1 1 d . . . F1B F 0.0806(2) 0.86138(12) -0.06269(10) 0.0709(6) Uani 1 1 d . . . F2B F 0.0913(2) 0.85757(13) 0.19704(12) 0.0802(6) Uani 1 1 d . . . O1B O -0.13571(18) 0.79096(11) 0.07304(10) 0.0411(5) Uani 1 1 d . . . N1B N 0.0851(2) 0.71025(13) 0.11018(11) 0.0325(5) Uani 1 1 d . . . H1BA H 0.1818 0.7106 0.1171 0.039 Uiso 1 1 calc R . . C1B C 0.0249(3) 0.63207(16) 0.12737(15) 0.0308(6) Uani 1 1 d . . . C2B C 0.0351(3) 0.58468(18) 0.20273(15) 0.0365(7) Uani 1 1 d . . . C3B C -0.0226(3) 0.50903(18) 0.21901(17) 0.0468(8) Uani 1 1 d . . . H3BA H -0.0167 0.4754 0.2701 0.056 Uiso 1 1 calc R . . C4B C -0.0878(3) 0.48235(19) 0.16264(19) 0.0521(8) Uani 1 1 d . . . H4BA H -0.1270 0.4305 0.1748 0.062 Uiso 1 1 calc R . . C5B C -0.0971(3) 0.52994(19) 0.08855(18) 0.0495(8) Uani 1 1 d . . . H5BA H -0.1434 0.5107 0.0500 0.059 Uiso 1 1 calc R . . C6B C -0.0397(3) 0.60622(16) 0.06873(15) 0.0370(7) Uani 1 1 d . . . C7B C 0.1063(3) 0.6138(2) 0.26527(15) 0.0531(8) Uani 1 1 d . . . H7B1 H 0.0959 0.5744 0.3147 0.080 Uiso 1 1 calc R . . H7B2 H 0.0565 0.6683 0.2667 0.080 Uiso 1 1 calc R . . H7B3 H 0.2126 0.6178 0.2551 0.080 Uiso 1 1 calc R . . C8B C -0.0489(3) 0.65643(18) -0.01337(15) 0.0514(8) Uani 1 1 d . . . H8B1 H -0.1339 0.6996 -0.0204 0.077 Uiso 1 1 calc R . . H8B2 H -0.0625 0.6203 -0.0473 0.077 Uiso 1 1 calc R . . H8B3 H 0.0438 0.6821 -0.0258 0.077 Uiso 1 1 calc R . . C9B C 0.0000(3) 0.78263(16) 0.08403(14) 0.0318(6) Uani 1 1 d . . . C10B C 0.0847(3) 0.85741(17) 0.06805(18) 0.0442(6) Uani 1 1 d U . . C11B C 0.1196(3) 0.89592(19) -0.0064(2) 0.0556(7) Uani 1 1 d U . . C12B C 0.1899(3) 0.9668(2) -0.0244(2) 0.0732(8) Uani 1 1 d U . . H12B H 0.2128 0.9920 -0.0758 0.088 Uiso 1 1 calc R . . C13B C 0.2255(4) 0.9992(2) 0.0350(3) 0.0800(9) Uani 1 1 d U . . H13B H 0.2746 1.0479 0.0237 0.096 Uiso 1 1 calc R . . C14B C 0.1945(4) 0.9655(2) 0.1090(3) 0.0755(8) Uani 1 1 d U . . H14B H 0.2197 0.9897 0.1489 0.091 Uiso 1 1 calc R . . C15B C 0.1243(3) 0.8938(2) 0.1238(2) 0.0587(7) Uani 1 1 d U . . F1C F 0.59145(19) 0.58025(10) 0.54245(11) 0.0623(5) Uani 1 1 d . . . F2C F 0.48646(16) 0.86697(9) 0.45076(8) 0.0457(4) Uani 1 1 d . . . O1C O 0.76700(18) 0.71977(11) 0.56869(11) 0.0439(5) Uani 1 1 d . . . N1C N 0.5491(2) 0.76566(12) 0.61681(11) 0.0319(5) Uani 1 1 d . . . H1CA H 0.4511 0.7741 0.6101 0.038 Uiso 1 1 calc R . . C1C C 0.6130(3) 0.78421(18) 0.68266(14) 0.0359(7) Uani 1 1 d . . . C2C C 0.5906(3) 0.86498(18) 0.69020(14) 0.0364(7) Uani 1 1 d . . . C3C C 0.6609(3) 0.8821(2) 0.75231(17) 0.0567(9) Uani 1 1 d . . . H3CA H 0.6479 0.9367 0.7591 0.068 Uiso 1 1 calc R . . C4C C 0.7492(4) 0.8210(3) 0.80422(19) 0.0821(14) Uani 1 1 d . . . H4CA H 0.7996 0.8340 0.8453 0.099 Uiso 1 1 calc R . . C5C C 0.7641(4) 0.7411(3) 0.7964(2) 0.0795(13) Uani 1 1 d . . . H5CA H 0.8238 0.6993 0.8329 0.095 Uiso 1 1 calc R . . C6C C 0.6943(3) 0.7205(2) 0.73667(17) 0.0542(9) Uani 1 1 d . . . C7C C 0.4933(3) 0.93129(16) 0.63450(15) 0.0396(7) Uani 1 1 d . . . H7C1 H 0.5196 0.9298 0.5820 0.059 Uiso 1 1 calc R . . H7C2 H 0.5086 0.9854 0.6426 0.059 Uiso 1 1 calc R . . H7C3 H 0.3881 0.9220 0.6425 0.059 Uiso 1 1 calc R . . C8C C 0.7015(4) 0.6317(2) 0.7324(2) 0.0821(12) Uani 1 1 d . . . H8C1 H 0.7728 0.6222 0.6935 0.123 Uiso 1 1 calc R . . H8C2 H 0.6022 0.6201 0.7185 0.123 Uiso 1 1 calc R . . H8C3 H 0.7343 0.5951 0.7824 0.123 Uiso 1 1 calc R . . C9C C 0.6295(3) 0.73636(15) 0.56500(15) 0.0332(6) Uani 1 1 d . . . C10C C 0.5404(3) 0.72431(17) 0.49897(15) 0.0332(6) Uani 1 1 d . . . C11C C 0.5275(3) 0.64685(19) 0.48802(18) 0.0445(7) Uani 1 1 d . . . C12C C 0.4531(3) 0.6346(2) 0.4264(2) 0.0577(9) Uani 1 1 d . . . H12C H 0.4468 0.5803 0.4211 0.069 Uiso 1 1 calc R . . C13C C 0.3873(3) 0.7022(2) 0.37219(19) 0.0600(10) Uani 1 1 d . . . H13C H 0.3350 0.6945 0.3292 0.072 Uiso 1 1 calc R . . C14C C 0.3969(3) 0.7813(2) 0.37997(16) 0.0483(8) Uani 1 1 d . . . H14C H 0.3526 0.8284 0.3427 0.058 Uiso 1 1 calc R . . C15C C 0.4724(3) 0.78970(18) 0.44313(16) 0.0372(7) Uani 1 1 d . . . F1D F 0.28239(19) 0.64062(11) 0.69119(10) 0.0655(5) Uani 1 1 d . . . F2D F 0.02225(18) 0.74239(12) 0.45657(9) 0.0603(5) Uani 1 1 d . . . O1D O 0.24581(18) 0.81745(11) 0.58465(10) 0.0372(5) Uani 1 1 d . . . N1D N 0.0008(2) 0.80753(13) 0.60886(11) 0.0321(5) Uani 1 1 d . . . H1DA H -0.0738 0.7774 0.6103 0.038 Uiso 1 1 calc R . . C1D C -0.0264(3) 0.88613(16) 0.62746(14) 0.0318(6) Uani 1 1 d . . . C2D C -0.1187(3) 0.94892(17) 0.57749(15) 0.0333(6) Uani 1 1 d . . . C3D C -0.1443(3) 1.02457(18) 0.59589(17) 0.0434(7) Uani 1 1 d . . . H3DA H -0.2059 1.0687 0.5628 0.052 Uiso 1 1 calc R . . C4D C -0.0817(3) 1.03682(19) 0.66145(18) 0.0504(8) Uani 1 1 d . . . H4DA H -0.1006 1.0889 0.6734 0.060 Uiso 1 1 calc R . . C5D C 0.0082(3) 0.9735(2) 0.70950(17) 0.0491(8) Uani 1 1 d . . . H5DA H 0.0508 0.9825 0.7545 0.059 Uiso 1 1 calc R . . C6D C 0.0381(3) 0.89649(18) 0.69395(15) 0.0382(7) Uani 1 1 d . . . C7D C -0.1851(3) 0.93641(17) 0.50562(15) 0.0417(7) Uani 1 1 d . . . H7D1 H -0.2654 0.9007 0.5187 0.063 Uiso 1 1 calc R . . H7D2 H -0.1074 0.9103 0.4784 0.063 Uiso 1 1 calc R . . H7D3 H -0.2260 0.9900 0.4727 0.063 Uiso 1 1 calc R . . C8D C 0.1342(3) 0.8275(2) 0.74859(15) 0.0529(8) Uani 1 1 d . . . H8D1 H 0.2326 0.8192 0.7266 0.079 Uiso 1 1 calc R . . H8D2 H 0.0862 0.7765 0.7572 0.079 Uiso 1 1 calc R . . H8D3 H 0.1463 0.8421 0.7975 0.079 Uiso 1 1 calc R . . C9D C 0.1357(3) 0.77881(16) 0.58942(13) 0.0307(6) Uani 1 1 d . . . C10D C 0.1486(3) 0.69408(17) 0.57484(15) 0.0333(6) Uani 1 1 d . . . C11D C 0.2248(3) 0.62710(19) 0.62623(19) 0.0490(8) Uani 1 1 d . . . C12D C 0.2431(4) 0.5488(2) 0.6156(2) 0.0717(11) Uani 1 1 d . . . H12D H 0.2967 0.5043 0.6523 0.086 Uiso 1 1 calc R . . C13D C 0.1813(4) 0.5364(2) 0.5498(3) 0.0803(13) Uani 1 1 d . . . H13D H 0.1916 0.4826 0.5412 0.096 Uiso 1 1 calc R . . C14D C 0.1054(4) 0.6006(2) 0.4969(2) 0.0684(11) Uani 1 1 d . . . H14D H 0.0629 0.5921 0.4516 0.082 Uiso 1 1 calc R . . C15D C 0.0920(3) 0.6773(2) 0.51069(18) 0.0455(8) 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 F1A 0.0733(12) 0.0435(11) 0.0789(13) 0.0018(10) -0.0270(10) -0.0152(9) F2A 0.0592(11) 0.0486(12) 0.0606(11) -0.0045(9) -0.0123(9) 0.0071(9) O1A 0.0250(10) 0.0598(14) 0.0451(11) -0.0154(10) 0.0031(8) -0.0119(9) N1A 0.0204(11) 0.0406(14) 0.0447(13) -0.0190(11) 0.0059(10) -0.0084(10) C1A 0.0223(14) 0.0502(19) 0.0478(18) -0.0243(15) 0.0008(13) -0.0068(13) C2A 0.0285(16) 0.049(2) 0.082(2) -0.0327(19) 0.0080(16) -0.0093(14) C3A 0.047(2) 0.075(3) 0.125(4) -0.063(3) -0.003(2) -0.016(2) C4A 0.050(2) 0.115(4) 0.111(4) -0.080(3) -0.018(2) -0.004(2) C5A 0.0427(19) 0.096(3) 0.059(2) -0.039(2) -0.0126(17) 0.005(2) C6A 0.0268(15) 0.062(2) 0.0510(19) -0.0275(17) -0.0004(14) -0.0011(14) C7A 0.062(2) 0.039(2) 0.109(3) -0.019(2) 0.024(2) -0.0162(17) C8A 0.0491(19) 0.054(2) 0.0454(18) -0.0073(15) -0.0011(15) 0.0042(16) C9A 0.0255(14) 0.0310(16) 0.0363(16) -0.0034(12) 0.0002(12) -0.0049(12) C10A 0.0193(13) 0.0420(18) 0.0340(15) -0.0096(13) 0.0015(11) -0.0065(12) C11A 0.0364(16) 0.044(2) 0.0481(18) -0.0054(15) -0.0057(14) -0.0108(14) C12A 0.0482(19) 0.055(2) 0.070(2) -0.0246(18) 0.0026(18) -0.0204(17) C13A 0.0384(18) 0.088(3) 0.054(2) -0.036(2) 0.0031(16) -0.0223(19) C14A 0.0320(16) 0.077(3) 0.0429(18) -0.0147(17) -0.0079(14) -0.0025(16) C15A 0.0292(15) 0.048(2) 0.0408(17) -0.0119(15) 0.0028(13) -0.0021(14) F1B 0.0819(13) 0.0630(13) 0.0601(12) -0.0032(10) 0.0215(10) -0.0026(11) F2B 0.0737(13) 0.0988(17) 0.0898(15) -0.0636(13) -0.0013(12) -0.0114(12) O1B 0.0244(10) 0.0387(12) 0.0617(13) -0.0135(9) 0.0013(9) -0.0074(8) N1B 0.0207(11) 0.0348(14) 0.0427(13) -0.0096(10) -0.0001(10) -0.0064(10) C1B 0.0213(13) 0.0338(16) 0.0391(16) -0.0113(13) 0.0002(12) -0.0058(11) C2B 0.0248(14) 0.0504(19) 0.0346(16) -0.0107(14) 0.0017(12) -0.0050(13) C3B 0.0364(16) 0.045(2) 0.0517(19) 0.0019(15) 0.0036(15) -0.0051(14) C4B 0.0434(18) 0.0357(19) 0.076(2) -0.0084(17) -0.0015(17) -0.0120(15) C5B 0.0414(17) 0.044(2) 0.066(2) -0.0209(17) -0.0185(16) -0.0038(15) C6B 0.0335(15) 0.0332(17) 0.0457(18) -0.0148(14) -0.0077(13) 0.0010(13) C7B 0.0508(19) 0.072(2) 0.0361(17) -0.0131(16) 0.0020(15) -0.0076(17) C8B 0.068(2) 0.046(2) 0.0433(18) -0.0209(15) -0.0138(16) 0.0029(16) C9B 0.0273(15) 0.0334(17) 0.0382(16) -0.0140(13) 0.0035(12) -0.0069(12) C10B 0.0233(12) 0.0326(14) 0.0830(17) -0.0252(12) 0.0112(13) -0.0061(11) C11B 0.0314(14) 0.0385(15) 0.0937(18) -0.0114(14) 0.0149(14) -0.0024(11) C12B 0.0392(15) 0.0444(16) 0.126(2) -0.0026(15) 0.0183(16) -0.0033(13) C13B 0.0401(15) 0.0426(17) 0.154(2) -0.0161(16) 0.0042(18) -0.0104(13) C14B 0.0474(16) 0.0491(17) 0.139(2) -0.0407(16) -0.0090(17) -0.0065(13) C15B 0.0348(14) 0.0464(15) 0.1049(19) -0.0368(14) 0.0025(15) -0.0066(12) F1C 0.0646(11) 0.0333(11) 0.0919(13) -0.0192(10) 0.0167(10) -0.0098(9) F2C 0.0447(9) 0.0364(10) 0.0552(10) -0.0099(8) -0.0048(8) -0.0044(8) O1C 0.0211(10) 0.0439(13) 0.0687(13) -0.0191(10) 0.0052(9) -0.0008(8) N1C 0.0208(11) 0.0329(13) 0.0404(13) -0.0075(10) 0.0030(10) 0.0001(9) C1C 0.0213(13) 0.0500(19) 0.0295(15) 0.0011(14) -0.0018(12) -0.0006(13) C2C 0.0255(14) 0.053(2) 0.0327(16) -0.0127(14) 0.0065(12) -0.0114(13) C3C 0.0390(18) 0.104(3) 0.0406(18) -0.0364(19) 0.0099(16) -0.0218(19) C4C 0.042(2) 0.178(5) 0.031(2) -0.033(3) 0.0010(16) -0.015(3) C5C 0.044(2) 0.139(4) 0.036(2) 0.004(2) -0.0063(17) 0.014(2) C6C 0.0355(17) 0.068(2) 0.0433(19) 0.0096(17) -0.0022(15) 0.0051(16) C7C 0.0396(16) 0.0366(17) 0.0481(17) -0.0188(14) 0.0096(14) -0.0098(13) C8C 0.069(2) 0.060(3) 0.088(3) 0.025(2) -0.005(2) 0.016(2) C9C 0.0275(15) 0.0233(15) 0.0473(17) -0.0056(13) 0.0046(13) -0.0043(11) C10C 0.0220(13) 0.0351(17) 0.0470(17) -0.0167(14) 0.0095(12) -0.0077(12) C11C 0.0358(16) 0.042(2) 0.061(2) -0.0216(17) 0.0160(15) -0.0114(14) C12C 0.053(2) 0.064(3) 0.076(2) -0.046(2) 0.0261(19) -0.0281(19) C13C 0.0446(19) 0.096(3) 0.059(2) -0.046(2) 0.0166(17) -0.032(2) C14C 0.0322(16) 0.072(2) 0.0459(18) -0.0220(17) 0.0060(14) -0.0114(16) C15C 0.0290(15) 0.0414(19) 0.0477(18) -0.0201(15) 0.0085(13) -0.0119(13) F1D 0.0623(12) 0.0590(13) 0.0576(12) 0.0136(9) -0.0057(10) 0.0041(9) F2D 0.0460(10) 0.0894(15) 0.0519(11) -0.0299(10) -0.0072(8) -0.0073(10) O1D 0.0202(9) 0.0409(12) 0.0515(12) -0.0123(9) 0.0009(8) -0.0057(8) N1D 0.0180(11) 0.0366(14) 0.0419(13) -0.0100(11) 0.0035(9) -0.0040(9) C1D 0.0194(13) 0.0365(17) 0.0395(16) -0.0096(13) 0.0032(12) -0.0030(12) C2D 0.0201(13) 0.0382(17) 0.0409(16) -0.0065(13) 0.0044(12) -0.0080(12) C3D 0.0294(15) 0.0374(18) 0.061(2) -0.0096(15) 0.0040(14) -0.0010(13) C4D 0.0338(17) 0.051(2) 0.076(2) -0.0346(18) 0.0095(16) -0.0059(15) C5D 0.0325(16) 0.067(2) 0.057(2) -0.0309(18) 0.0023(15) -0.0096(16) C6D 0.0261(14) 0.051(2) 0.0386(17) -0.0142(14) 0.0017(13) -0.0047(13) C7D 0.0321(15) 0.0459(19) 0.0424(17) -0.0026(14) -0.0030(13) -0.0037(13) C8D 0.0399(17) 0.078(2) 0.0390(17) -0.0148(16) -0.0086(14) 0.0030(16) C9D 0.0231(14) 0.0366(17) 0.0287(14) -0.0024(12) -0.0024(11) -0.0004(12) C10D 0.0219(13) 0.0362(17) 0.0426(16) -0.0106(13) 0.0079(12) -0.0058(12) C11D 0.0386(17) 0.045(2) 0.058(2) -0.0027(17) 0.0143(16) -0.0067(15) C12D 0.060(2) 0.034(2) 0.112(3) -0.001(2) 0.043(2) -0.0039(17) C13D 0.065(3) 0.052(3) 0.141(4) -0.048(3) 0.059(3) -0.022(2) C14D 0.053(2) 0.075(3) 0.100(3) -0.057(3) 0.031(2) -0.028(2) C15D 0.0308(16) 0.055(2) 0.057(2) -0.0234(17) 0.0104(15) -0.0097(15) _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 F1A C11A 1.359(3) . ? F2A C15A 1.365(3) . ? O1A C9A 1.232(3) . ? N1A C9A 1.327(3) . ? N1A C1A 1.434(3) . ? C1A C2A 1.390(4) . ? C1A C6A 1.391(4) . ? C2A C3A 1.392(4) . ? C2A C7A 1.505(4) . ? C3A C4A 1.367(5) . ? C4A C5A 1.380(5) . ? C5A C6A 1.391(4) . ? C6A C8A 1.500(4) . ? C9A C10A 1.511(3) . ? C10A C11A 1.370(4) . ? C10A C15A 1.376(4) . ? C11A C12A 1.377(4) . ? C12A C13A 1.378(4) . ? C13A C14A 1.372(4) . ? C14A C15A 1.364(4) . ? F1B C11B 1.352(4) . ? F2B C15B 1.356(4) . ? O1B C9B 1.224(3) . ? N1B C9B 1.341(3) . ? N1B C1B 1.438(3) . ? C1B C6B 1.388(3) . ? C1B C2B 1.390(3) . ? C2B C3B 1.390(4) . ? C2B C7B 1.504(4) . ? C3B C4B 1.364(4) . ? C4B C5B 1.372(4) . ? C5B C6B 1.398(4) . ? C6B C8B 1.506(4) . ? C9B C10B 1.507(4) . ? C10B C15B 1.366(4) . ? C10B C11B 1.388(4) . ? C11B C12B 1.376(4) . ? C12B C13B 1.368(5) . ? C13B C14B 1.354(5) . ? C14B C15B 1.388(4) . ? F1C C11C 1.363(3) . ? F2C C15C 1.359(3) . ? O1C C9C 1.236(3) . ? N1C C9C 1.337(3) . ? N1C C1C 1.435(3) . ? C1C C2C 1.391(4) . ? C1C C6C 1.391(4) . ? C2C C3C 1.392(4) . ? C2C C7C 1.498(4) . ? C3C C4C 1.380(5) . ? C4C C5C 1.376(5) . ? C5C C6C 1.381(5) . ? C6C C8C 1.508(5) . ? C9C C10C 1.502(4) . ? C10C C15C 1.377(4) . ? C10C C11C 1.382(4) . ? C11C C12C 1.366(4) . ? C12C C13C 1.376(4) . ? C13C C14C 1.384(4) . ? C14C C15C 1.370(4) . ? F1D C11D 1.360(3) . ? F2D C15D 1.364(3) . ? O1D C9D 1.234(3) . ? N1D C9D 1.336(3) . ? N1D C1D 1.438(3) . ? C1D C6D 1.389(3) . ? C1D C2D 1.396(3) . ? C2D C3D 1.388(4) . ? C2D C7D 1.497(4) . ? C3D C4D 1.379(4) . ? C4D C5D 1.374(4) . ? C5D C6D 1.389(4) . ? C6D C8D 1.507(4) . ? C9D C10D 1.504(4) . ? C10D C15D 1.367(4) . ? C10D C11D 1.381(4) . ? C11D C12D 1.370(4) . ? C12D C13D 1.380(5) . ? C13D C14D 1.366(5) . ? C14D C15D 1.365(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 C9A N1A C1A 122.6(2) . . ? C2A C1A C6A 122.6(3) . . ? C2A C1A N1A 120.0(3) . . ? C6A C1A N1A 117.4(3) . . ? C1A C2A C3A 117.0(3) . . ? C1A C2A C7A 122.0(3) . . ? C3A C2A C7A 121.0(3) . . ? C4A C3A C2A 121.8(4) . . ? C3A C4A C5A 120.1(4) . . ? C4A C5A C6A 120.6(4) . . ? C5A C6A C1A 117.9(3) . . ? C5A C6A C8A 121.6(3) . . ? C1A C6A C8A 120.5(3) . . ? O1A C9A N1A 124.9(2) . . ? O1A C9A C10A 120.0(2) . . ? N1A C9A C10A 115.0(2) . . ? C11A C10A C15A 114.5(3) . . ? C11A C10A C9A 122.9(2) . . ? C15A C10A C9A 122.5(3) . . ? F1A C11A C10A 117.5(3) . . ? F1A C11A C12A 118.3(3) . . ? C10A C11A C12A 124.1(3) . . ? C13A C12A C11A 118.0(3) . . ? C14A C13A C12A 120.7(3) . . ? C15A C14A C13A 118.1(3) . . ? F2A C15A C14A 118.7(3) . . ? F2A C15A C10A 116.7(3) . . ? C14A C15A C10A 124.6(3) . . ? C9B N1B C1B 122.8(2) . . ? C6B C1B C2B 122.4(3) . . ? C6B C1B N1B 119.4(2) . . ? C2B C1B N1B 118.2(2) . . ? C3B C2B C1B 118.0(3) . . ? C3B C2B C7B 120.6(3) . . ? C1B C2B C7B 121.4(3) . . ? C4B C3B C2B 120.9(3) . . ? C3B C4B C5B 120.4(3) . . ? C4B C5B C6B 121.2(3) . . ? C1B C6B C5B 117.1(3) . . ? C1B C6B C8B 122.8(3) . . ? C5B C6B C8B 120.1(3) . . ? O1B C9B N1B 125.3(2) . . ? O1B C9B C10B 120.1(2) . . ? N1B C9B C10B 114.7(2) . . ? C15B C10B C11B 116.2(3) . . ? C15B C10B C9B 123.0(3) . . ? C11B C10B C9B 120.7(3) . . ? F1B C11B C12B 119.8(3) . . ? F1B C11B C10B 117.3(3) . . ? C12B C11B C10B 122.9(4) . . ? C13B C12B C11B 117.1(4) . . ? C14B C13B C12B 123.4(4) . . ? C13B C14B C15B 117.0(4) . . ? F2B C15B C10B 117.4(3) . . ? F2B C15B C14B 119.2(3) . . ? C10B C15B C14B 123.4(4) . . ? C9C N1C C1C 123.9(2) . . ? C2C C1C C6C 122.6(3) . . ? C2C C1C N1C 118.7(2) . . ? C6C C1C N1C 118.7(3) . . ? C1C C2C C3C 117.5(3) . . ? C1C C2C C7C 121.8(2) . . ? C3C C2C C7C 120.8(3) . . ? C4C C3C C2C 120.9(4) . . ? C5C C4C C3C 119.9(4) . . ? C4C C5C C6C 121.4(4) . . ? C5C C6C C1C 117.5(4) . . ? C5C C6C C8C 120.8(3) . . ? C1C C6C C8C 121.7(3) . . ? O1C C9C N1C 124.6(3) . . ? O1C C9C C10C 120.4(2) . . ? N1C C9C C10C 115.1(2) . . ? C15C C10C C11C 115.4(3) . . ? C15C C10C C9C 122.4(2) . . ? C11C C10C C9C 122.2(3) . . ? F1C C11C C12C 119.4(3) . . ? F1C C11C C10C 117.4(3) . . ? C12C C11C C10C 123.2(3) . . ? C11C C12C C13C 119.0(3) . . ? C12C C13C C14C 120.4(3) . . ? C15C C14C C13C 117.9(3) . . ? F2C C15C C14C 118.8(3) . . ? F2C C15C C10C 117.1(2) . . ? C14C C15C C10C 124.1(3) . . ? C9D N1D C1D 122.1(2) . . ? C6D C1D C2D 122.8(3) . . ? C6D C1D N1D 119.3(2) . . ? C2D C1D N1D 117.9(2) . . ? C3D C2D C1D 117.5(3) . . ? C3D C2D C7D 120.8(2) . . ? C1D C2D C7D 121.6(3) . . ? C4D C3D C2D 121.1(3) . . ? C5D C4D C3D 119.8(3) . . ? C4D C5D C6D 121.7(3) . . ? C1D C6D C5D 117.2(3) . . ? C1D C6D C8D 122.3(3) . . ? C5D C6D C8D 120.5(3) . . ? O1D C9D N1D 123.3(2) . . ? O1D C9D C10D 120.7(2) . . ? N1D C9D C10D 116.0(2) . . ? C15D C10D C11D 115.1(3) . . ? C15D C10D C9D 124.1(3) . . ? C11D C10D C9D 120.8(3) . . ? F1D C11D C12D 119.1(3) . . ? F1D C11D C10D 117.3(3) . . ? C12D C11D C10D 123.6(3) . . ? C11D C12D C13D 117.9(4) . . ? C14D C13D C12D 120.8(4) . . ? C15D C14D C13D 118.4(4) . . ? F2D C15D C14D 118.7(3) . . ? F2D C15D C10D 117.1(3) . . ? C14D C15D C10D 124.1(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 C9A N1A C1A C2A -72.8(3) . . . . ? C9A N1A C1A C6A 107.0(3) . . . . ? C6A C1A C2A C3A 0.5(4) . . . . ? N1A C1A C2A C3A -179.7(2) . . . . ? C6A C1A C2A C7A -179.4(3) . . . . ? N1A C1A C2A C7A 0.4(4) . . . . ? C1A C2A C3A C4A 1.5(5) . . . . ? C7A C2A C3A C4A -178.6(3) . . . . ? C2A C3A C4A C5A -1.5(6) . . . . ? C3A C4A C5A C6A -0.6(5) . . . . ? C4A C5A C6A C1A 2.4(5) . . . . ? C4A C5A C6A C8A -178.0(3) . . . . ? C2A C1A C6A C5A -2.4(4) . . . . ? N1A C1A C6A C5A 177.8(2) . . . . ? C2A C1A C6A C8A 178.0(3) . . . . ? N1A C1A C6A C8A -1.8(4) . . . . ? C1A N1A C9A O1A 3.8(4) . . . . ? C1A N1A C9A C10A -176.0(2) . . . . ? O1A C9A C10A C11A -84.1(3) . . . . ? N1A C9A C10A C11A 95.8(3) . . . . ? O1A C9A C10A C15A 92.6(3) . . . . ? N1A C9A C10A C15A -87.5(3) . . . . ? C15A C10A C11A F1A 177.7(2) . . . . ? C9A C10A C11A F1A -5.3(4) . . . . ? C15A C10A C11A C12A -1.4(4) . . . . ? C9A C10A C11A C12A 175.6(3) . . . . ? F1A C11A C12A C13A -178.9(2) . . . . ? C10A C11A C12A C13A 0.2(4) . . . . ? C11A C12A C13A C14A 0.7(4) . . . . ? C12A C13A C14A C15A -0.4(4) . . . . ? C13A C14A C15A F2A -179.6(2) . . . . ? C13A C14A C15A C10A -0.9(4) . . . . ? C11A C10A C15A F2A -179.5(2) . . . . ? C9A C10A C15A F2A 3.5(3) . . . . ? C11A C10A C15A C14A 1.8(4) . . . . ? C9A C10A C15A C14A -175.2(3) . . . . ? C9B N1B C1B C6B 64.0(3) . . . . ? C9B N1B C1B C2B -116.6(3) . . . . ? C6B C1B C2B C3B -0.3(4) . . . . ? N1B C1B C2B C3B -179.7(2) . . . . ? C6B C1B C2B C7B 179.7(2) . . . . ? N1B C1B C2B C7B 0.3(4) . . . . ? C1B C2B C3B C4B -0.2(4) . . . . ? C7B C2B C3B C4B 179.7(3) . . . . ? C2B C3B C4B C5B 0.2(5) . . . . ? C3B C4B C5B C6B 0.4(5) . . . . ? C2B C1B C6B C5B 0.9(4) . . . . ? N1B C1B C6B C5B -179.7(2) . . . . ? C2B C1B C6B C8B -178.9(2) . . . . ? N1B C1B C6B C8B 0.5(4) . . . . ? C4B C5B C6B C1B -0.9(4) . . . . ? C4B C5B C6B C8B 178.8(3) . . . . ? C1B N1B C9B O1B 1.2(4) . . . . ? C1B N1B C9B C10B -178.9(2) . . . . ? O1B C9B C10B C15B 97.7(3) . . . . ? N1B C9B C10B C15B -82.2(3) . . . . ? O1B C9B C10B C11B -78.7(3) . . . . ? N1B C9B C10B C11B 101.4(3) . . . . ? C15B C10B C11B F1B -179.6(3) . . . . ? C9B C10B C11B F1B -2.9(4) . . . . ? C15B C10B C11B C12B -0.1(4) . . . . ? C9B C10B C11B C12B 176.6(3) . . . . ? F1B C11B C12B C13B 179.5(3) . . . . ? C10B C11B C12B C13B 0.0(5) . . . . ? C11B C12B C13B C14B -0.3(5) . . . . ? C12B C13B C14B C15B 0.7(5) . . . . ? C11B C10B C15B F2B 179.9(2) . . . . ? C9B C10B C15B F2B 3.3(4) . . . . ? C11B C10B C15B C14B 0.5(4) . . . . ? C9B C10B C15B C14B -176.1(3) . . . . ? C13B C14B C15B F2B 179.8(3) . . . . ? C13B C14B C15B C10B -0.8(5) . . . . ? C9C N1C C1C C2C 119.1(3) . . . . ? C9C N1C C1C C6C -61.3(3) . . . . ? C6C C1C C2C C3C 3.9(4) . . . . ? N1C C1C C2C C3C -176.5(2) . . . . ? C6C C1C C2C C7C -175.3(2) . . . . ? N1C C1C C2C C7C 4.3(3) . . . . ? C1C C2C C3C C4C 0.0(4) . . . . ? C7C C2C C3C C4C 179.2(2) . . . . ? C2C C3C C4C C5C -2.4(5) . . . . ? C3C C4C C5C C6C 1.1(5) . . . . ? C4C C5C C6C C1C 2.6(5) . . . . ? C4C C5C C6C C8C -175.1(3) . . . . ? C2C C1C C6C C5C -5.2(4) . . . . ? N1C C1C C6C C5C 175.2(3) . . . . ? C2C C1C C6C C8C 172.5(3) . . . . ? N1C C1C C6C C8C -7.2(4) . . . . ? C1C N1C C9C O1C 2.0(4) . . . . ? C1C N1C C9C C10C -177.8(2) . . . . ? O1C C9C C10C C15C -109.5(3) . . . . ? N1C C9C C10C C15C 70.3(3) . . . . ? O1C C9C C10C C11C 67.1(3) . . . . ? N1C C9C C10C C11C -113.1(3) . . . . ? C15C C10C C11C F1C -179.2(2) . . . . ? C9C C10C C11C F1C 4.0(4) . . . . ? C15C C10C C11C C12C 0.1(4) . . . . ? C9C C10C C11C C12C -176.8(2) . . . . ? F1C C11C C12C C13C 179.3(2) . . . . ? C10C C11C C12C C13C 0.0(4) . . . . ? C11C C12C C13C C14C 0.2(4) . . . . ? C12C C13C C14C C15C -0.5(4) . . . . ? C13C C14C C15C F2C 178.3(2) . . . . ? C13C C14C C15C C10C 0.6(4) . . . . ? C11C C10C C15C F2C -178.1(2) . . . . ? C9C C10C C15C F2C -1.3(3) . . . . ? C11C C10C C15C C14C -0.4(4) . . . . ? C9C C10C C15C C14C 176.4(2) . . . . ? C9D N1D C1D C6D -67.9(3) . . . . ? C9D N1D C1D C2D 112.7(3) . . . . ? C6D C1D C2D C3D 0.6(4) . . . . ? N1D C1D C2D C3D -180.0(2) . . . . ? C6D C1D C2D C7D 179.2(2) . . . . ? N1D C1D C2D C7D -1.5(3) . . . . ? C1D C2D C3D C4D -0.5(4) . . . . ? C7D C2D C3D C4D -179.1(2) . . . . ? C2D C3D C4D C5D 0.3(4) . . . . ? C3D C4D C5D C6D -0.1(4) . . . . ? C2D C1D C6D C5D -0.5(4) . . . . ? N1D C1D C6D C5D -179.8(2) . . . . ? C2D C1D C6D C8D 178.3(2) . . . . ? N1D C1D C6D C8D -1.1(4) . . . . ? C4D C5D C6D C1D 0.2(4) . . . . ? C4D C5D C6D C8D -178.6(2) . . . . ? C1D N1D C9D O1D -1.3(4) . . . . ? C1D N1D C9D C10D 177.4(2) . . . . ? O1D C9D C10D C15D -107.1(3) . . . . ? N1D C9D C10D C15D 74.1(3) . . . . ? O1D C9D C10D C11D 70.8(3) . . . . ? N1D C9D C10D C11D -108.0(3) . . . . ? C15D C10D C11D F1D -179.6(2) . . . . ? C9D C10D C11D F1D 2.3(3) . . . . ? C15D C10D C11D C12D -0.5(4) . . . . ? C9D C10D C11D C12D -178.6(3) . . . . ? F1D C11D C12D C13D 178.8(3) . . . . ? C10D C11D C12D C13D -0.2(5) . . . . ? C11D C12D C13D C14D 0.5(5) . . . . ? C12D C13D C14D C15D -0.1(5) . . . . ? C13D C14D C15D F2D 177.1(3) . . . . ? C13D C14D C15D C10D -0.8(4) . . . . ? C11D C10D C15D F2D -176.8(2) . . . . ? C9D C10D C15D F2D 1.2(4) . . . . ? C11D C10D C15D C14D 1.0(4) . . . . ? C9D C10D C15D C14D 179.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.328 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.046 # Attachment 'och235.cif' data_och235 _database_code_depnum_ccdc_archive 'CCDC 615389' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 F2 N2 O' _chemical_formula_weight 304.33 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 19.880(3) _cell_length_b 9.8369(16) _cell_length_c 15.110(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2954.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3030 _cell_measurement_theta_min 4.905 _cell_measurement_theta_max 44.424 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9766 _exptl_absorpt_correction_T_max 0.9867 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 32364 _diffrn_reflns_av_R_equivalents 0.1245 _diffrn_reflns_av_sigmaI/netI 0.0861 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3536 _reflns_number_gt 2219 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0752P)^2^+3.4854P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 3536 _refine_ls_number_parameters 405 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1157 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1632 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 0.916 _refine_ls_restrained_S_all 0.916 _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 F1 F 0.37728(16) 0.6258(3) 0.2707(2) 0.0406(8) Uani 1 1 d . . . F2 F 0.58432(16) 0.4106(3) 0.2231(2) 0.0397(8) Uani 1 1 d . . . O1 O 0.45229(19) 0.2950(4) 0.3055(3) 0.0303(9) Uani 1 1 d . . . N1 N 0.4057(2) 0.3579(4) 0.1741(3) 0.0253(9) Uani 1 1 d . . . H1A H 0.4065 0.4200 0.1323 0.030 Uiso 1 1 calc R . . N2 N 0.2283(2) -0.0841(4) 0.1322(3) 0.0321(11) Uani 1 1 d . . . C1 C 0.3625(2) 0.2420(5) 0.1618(3) 0.0255(11) Uani 1 1 d . . . C2 C 0.3876(2) 0.1102(5) 0.1535(3) 0.0270(11) Uani 1 1 d . . . C3 C 0.3423(3) 0.0029(5) 0.1434(4) 0.0293(12) Uani 1 1 d . . . H3A H 0.3592 -0.0871 0.1384 0.035 Uiso 1 1 calc R . . C4 C 0.2726(3) 0.0242(5) 0.1405(4) 0.0280(11) Uani 1 1 d . . . C5 C 0.2495(3) 0.1580(5) 0.1456(4) 0.0271(11) Uani 1 1 d . . . H5A H 0.2025 0.1746 0.1415 0.033 Uiso 1 1 calc R . . C6 C 0.2929(2) 0.2679(5) 0.1563(4) 0.0256(11) Uani 1 1 d . . . C7 C 0.4617(3) 0.0843(5) 0.1573(4) 0.0335(12) Uani 1 1 d . . . H7A H 0.4853 0.1526 0.1217 0.050 Uiso 1 1 calc R . . H7B H 0.4713 -0.0065 0.1339 0.050 Uiso 1 1 calc R . . H7C H 0.4771 0.0899 0.2188 0.050 Uiso 1 1 calc R . . C8 C 0.2670(2) 0.4113(5) 0.1630(4) 0.0315(12) Uani 1 1 d . . . H8A H 0.2181 0.4115 0.1554 0.047 Uiso 1 1 calc R . . H8B H 0.2878 0.4671 0.1167 0.047 Uiso 1 1 calc R . . H8C H 0.2784 0.4487 0.2212 0.047 Uiso 1 1 calc R . . C9 C 0.4445(2) 0.3771(5) 0.2447(3) 0.0245(11) Uani 1 1 d . . . C10 C 0.4795(2) 0.5129(5) 0.2468(3) 0.0251(11) Uani 1 1 d . . . C11 C 0.4447(2) 0.6341(5) 0.2606(4) 0.0274(12) Uani 1 1 d . . . C12 C 0.4750(3) 0.7588(5) 0.2650(4) 0.0333(13) Uani 1 1 d . . . H12A H 0.4492 0.8391 0.2735 0.040 Uiso 1 1 calc R . . C13 C 0.5440(3) 0.7650(6) 0.2568(4) 0.0368(14) Uani 1 1 d . . . H13A H 0.5660 0.8505 0.2601 0.044 Uiso 1 1 calc R . . C14 C 0.5815(3) 0.6487(6) 0.2438(4) 0.0361(14) Uani 1 1 d . . . H14A H 0.6290 0.6535 0.2386 0.043 Uiso 1 1 calc R . . C15 C 0.5488(2) 0.5253(5) 0.2385(3) 0.0267(11) Uani 1 1 d . . . C16 C 0.2542(3) -0.2223(4) 0.1459(4) 0.0338(12) Uani 1 1 d . . . H16A H 0.2854 -0.2455 0.0980 0.051 Uiso 1 1 calc R . . H16B H 0.2167 -0.2868 0.1461 0.051 Uiso 1 1 calc R . . H16C H 0.2778 -0.2267 0.2027 0.051 Uiso 1 1 calc R . . C17 C 0.1580(3) -0.0640(5) 0.1558(4) 0.0364(14) Uani 1 1 d . . . H17A H 0.1549 -0.0338 0.2174 0.055 Uiso 1 1 calc R . . H17B H 0.1335 -0.1497 0.1487 0.055 Uiso 1 1 calc R . . H17C H 0.1382 0.0052 0.1170 0.055 Uiso 1 1 calc R . . F1A F 1.06983(16) 0.2793(3) 1.0138(2) 0.0408(8) Uani 1 1 d . . . F2A F 0.94434(15) 0.6796(3) 0.9752(2) 0.0336(8) Uani 1 1 d . . . O1A O 0.89802(18) 0.4116(4) 1.0530(2) 0.0298(9) Uani 1 1 d . . . N1A N 0.9331(2) 0.3117(4) 0.9248(3) 0.0227(9) Uani 1 1 d . . . H1AA H 0.9640 0.3154 0.8832 0.027 Uiso 1 1 calc R . . N2A N 0.7274(2) -0.0751(4) 0.8880(4) 0.0385(12) Uani 1 1 d . . . C1A C 0.8796(2) 0.2156(5) 0.9140(3) 0.0228(11) Uani 1 1 d . . . C2A C 0.8133(3) 0.2579(5) 0.9001(4) 0.0271(11) Uani 1 1 d . . . C3A C 0.7635(3) 0.1595(5) 0.8922(4) 0.0284(11) Uani 1 1 d . . . H3AA H 0.7182 0.1879 0.8838 0.034 Uiso 1 1 calc R . . C4A C 0.7774(3) 0.0200(5) 0.8961(4) 0.0286(12) Uani 1 1 d . . . C5A C 0.8449(3) -0.0186(5) 0.9079(3) 0.0281(12) Uani 1 1 d . . . H5AA H 0.8561 -0.1125 0.9095 0.034 Uiso 1 1 calc R . . C6A C 0.8955(2) 0.0777(5) 0.9170(3) 0.0246(11) Uani 1 1 d . . . C7A C 0.7956(3) 0.4062(5) 0.8949(4) 0.0335(12) Uani 1 1 d . . . H7A1 H 0.7508 0.4165 0.8685 0.050 Uiso 1 1 calc R . . H7A2 H 0.8288 0.4536 0.8583 0.050 Uiso 1 1 calc R . . H7A3 H 0.7955 0.4453 0.9546 0.050 Uiso 1 1 calc R . . C8A C 0.9677(3) 0.0323(5) 0.9281(4) 0.0322(13) Uani 1 1 d . . . H8A1 H 0.9692 -0.0667 0.9350 0.048 Uiso 1 1 calc R . . H8A2 H 0.9870 0.0757 0.9806 0.048 Uiso 1 1 calc R . . H8A3 H 0.9937 0.0586 0.8757 0.048 Uiso 1 1 calc R . . C9A C 0.9395(3) 0.3962(5) 0.9939(3) 0.0242(11) Uani 1 1 d . . . C10A C 1.0042(3) 0.4762(5) 0.9940(3) 0.0252(11) Uani 1 1 d . . . C11A C 1.0671(3) 0.4157(5) 1.0036(4) 0.0303(12) Uani 1 1 d . . . C12A C 1.1262(3) 0.4889(6) 1.0046(4) 0.0344(13) Uani 1 1 d . . . H12B H 1.1683 0.4442 1.0105 0.041 Uiso 1 1 calc R . . C13A C 1.1229(3) 0.6280(6) 0.9968(4) 0.0347(13) Uani 1 1 d . . . H13B H 1.1633 0.6796 0.9976 0.042 Uiso 1 1 calc R . . C14A C 1.0618(3) 0.6942(6) 0.9877(4) 0.0329(13) Uani 1 1 d . . . H14B H 1.0597 0.7904 0.9824 0.040 Uiso 1 1 calc R . . C15A C 1.0045(3) 0.6164(5) 0.9865(4) 0.0269(11) Uani 1 1 d . . . C16A C 0.6579(3) -0.0336(6) 0.8874(5) 0.0410(14) Uani 1 1 d . . . H16D H 0.6466 0.0082 0.9444 0.061 Uiso 1 1 calc R . . H16E H 0.6292 -0.1131 0.8777 0.061 Uiso 1 1 calc R . . H16F H 0.6507 0.0324 0.8398 0.061 Uiso 1 1 calc R . . C17A C 0.7429(3) -0.2195(5) 0.8929(5) 0.0384(13) Uani 1 1 d . . . H17D H 0.7755 -0.2430 0.8468 0.058 Uiso 1 1 calc R . . H17E H 0.7016 -0.2724 0.8842 0.058 Uiso 1 1 calc R . . H17F H 0.7620 -0.2405 0.9512 0.058 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 F1 0.0301(18) 0.0346(18) 0.057(2) -0.0022(16) 0.0011(16) 0.0029(14) F2 0.0306(17) 0.0371(19) 0.051(2) -0.0037(16) 0.0017(15) 0.0028(14) O1 0.035(2) 0.0248(19) 0.031(2) 0.0066(16) -0.0079(17) -0.0033(16) N1 0.026(2) 0.026(2) 0.024(2) 0.0054(18) -0.0026(18) -0.0079(17) N2 0.028(2) 0.026(2) 0.042(3) -0.005(2) 0.000(2) -0.0024(19) C1 0.027(3) 0.028(3) 0.022(3) 0.003(2) -0.003(2) -0.004(2) C2 0.027(3) 0.031(3) 0.023(3) 0.006(2) 0.000(2) 0.001(2) C3 0.031(3) 0.024(3) 0.032(3) -0.002(2) 0.000(2) -0.001(2) C4 0.033(3) 0.027(3) 0.023(3) -0.003(2) 0.002(2) -0.005(2) C5 0.025(2) 0.030(3) 0.026(3) 0.000(2) -0.002(2) 0.002(2) C6 0.026(3) 0.023(2) 0.028(3) 0.001(2) -0.006(2) -0.001(2) C7 0.027(3) 0.034(3) 0.039(3) 0.004(3) 0.002(2) 0.001(2) C8 0.026(3) 0.027(3) 0.042(3) 0.006(3) -0.001(2) 0.002(2) C9 0.025(3) 0.022(3) 0.027(3) 0.002(2) 0.001(2) -0.003(2) C10 0.024(3) 0.023(3) 0.028(3) -0.001(2) -0.001(2) -0.002(2) C11 0.022(3) 0.024(3) 0.035(3) 0.002(2) 0.001(2) -0.002(2) C12 0.044(3) 0.018(2) 0.038(3) 0.000(2) 0.001(3) -0.001(2) C13 0.044(3) 0.033(3) 0.034(3) 0.002(3) 0.003(3) -0.014(3) C14 0.032(3) 0.035(3) 0.041(4) 0.004(3) 0.004(3) -0.013(3) C15 0.029(3) 0.024(3) 0.028(3) 0.001(2) 0.002(2) -0.001(2) C16 0.035(3) 0.023(2) 0.044(3) -0.004(3) 0.000(3) -0.005(2) C17 0.030(3) 0.032(3) 0.048(4) -0.008(3) -0.002(3) -0.008(2) F1A 0.0383(19) 0.0320(17) 0.052(2) -0.0023(16) -0.0060(16) 0.0095(15) F2A 0.0272(16) 0.0238(15) 0.050(2) 0.0026(14) 0.0004(15) 0.0024(12) O1A 0.027(2) 0.032(2) 0.030(2) -0.0063(16) 0.0064(17) -0.0024(16) N1A 0.025(2) 0.0187(19) 0.024(2) -0.0021(17) 0.0036(17) -0.0039(17) N2A 0.031(3) 0.026(2) 0.059(3) -0.003(2) 0.001(3) -0.0085(19) C1A 0.026(3) 0.022(2) 0.021(3) -0.002(2) 0.001(2) -0.002(2) C2A 0.032(3) 0.022(2) 0.027(3) -0.001(2) 0.005(2) 0.000(2) C3A 0.026(3) 0.029(3) 0.030(3) -0.001(2) 0.002(2) 0.000(2) C4A 0.028(3) 0.024(2) 0.034(3) -0.003(2) -0.001(2) -0.006(2) C5A 0.035(3) 0.020(2) 0.030(3) -0.003(2) -0.002(2) 0.001(2) C6A 0.027(3) 0.026(3) 0.022(3) -0.002(2) -0.002(2) 0.003(2) C7A 0.034(3) 0.022(2) 0.044(3) 0.000(3) 0.000(3) 0.004(2) C8A 0.027(3) 0.025(3) 0.044(3) 0.001(2) -0.005(2) 0.003(2) C9A 0.026(3) 0.021(2) 0.026(3) 0.003(2) 0.002(2) -0.001(2) C10A 0.024(3) 0.028(3) 0.023(3) -0.001(2) 0.001(2) -0.004(2) C11A 0.029(3) 0.027(3) 0.035(3) -0.003(2) 0.000(2) 0.004(2) C12A 0.022(3) 0.044(3) 0.037(3) -0.003(3) -0.002(2) 0.000(2) C13A 0.025(3) 0.048(4) 0.031(3) -0.003(3) 0.003(2) -0.009(2) C14A 0.030(3) 0.030(3) 0.039(3) 0.000(2) 0.003(2) -0.007(2) C15A 0.026(3) 0.026(3) 0.028(3) -0.001(2) 0.001(2) 0.001(2) C16A 0.024(3) 0.047(3) 0.052(4) -0.004(3) 0.005(3) -0.007(3) C17A 0.047(3) 0.025(3) 0.042(3) -0.005(3) 0.003(3) -0.011(3) _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 F1 C11 1.351(6) . ? F2 C15 1.351(6) . ? O1 C9 1.232(6) . ? N1 C9 1.329(6) . ? N1 C1 1.439(6) . ? N2 C4 1.388(6) . ? N2 C17 1.457(7) . ? N2 C16 1.468(6) . ? C1 C2 1.395(7) . ? C1 C6 1.410(7) . ? C2 C3 1.396(7) . ? C2 C7 1.496(7) . ? C3 C4 1.402(7) . ? C4 C5 1.396(7) . ? C5 C6 1.394(7) . ? C6 C8 1.505(7) . ? C9 C10 1.507(7) . ? C10 C11 1.395(7) . ? C10 C15 1.389(7) . ? C11 C12 1.369(7) . ? C12 C13 1.378(8) . ? C13 C14 1.379(9) . ? C14 C15 1.378(7) . ? F1A C11A 1.351(6) . ? F2A C15A 1.359(6) . ? O1A C9A 1.225(6) . ? N1A C9A 1.341(6) . ? N1A C1A 1.433(6) . ? N2A C4A 1.371(6) . ? N2A C16A 1.440(7) . ? N2A C17A 1.456(7) . ? C1A C6A 1.394(7) . ? C1A C2A 1.398(7) . ? C2A C3A 1.390(7) . ? C2A C7A 1.503(7) . ? C3A C4A 1.402(7) . ? C4A C5A 1.406(7) . ? C5A C6A 1.388(7) . ? C6A C8A 1.513(7) . ? C9A C10A 1.507(7) . ? C10A C11A 1.393(7) . ? C10A C15A 1.384(7) . ? C11A C12A 1.379(8) . ? C12A C13A 1.375(9) . ? C13A C14A 1.385(8) . ? C14A C15A 1.373(7) . ? 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 C9 N1 C1 124.2(4) . . ? C4 N2 C17 118.8(4) . . ? C4 N2 C16 118.4(4) . . ? C17 N2 C16 115.4(4) . . ? C2 C1 C6 120.9(4) . . ? C2 C1 N1 122.3(4) . . ? C6 C1 N1 116.7(4) . . ? C1 C2 C3 118.8(5) . . ? C1 C2 C7 120.5(5) . . ? C3 C2 C7 120.7(5) . . ? C2 C3 C4 121.9(5) . . ? N2 C4 C5 121.3(5) . . ? N2 C4 C3 121.0(5) . . ? C5 C4 C3 117.7(5) . . ? C6 C5 C4 122.2(5) . . ? C5 C6 C1 118.4(4) . . ? C5 C6 C8 121.6(4) . . ? C1 C6 C8 120.1(4) . . ? O1 C9 N1 125.3(5) . . ? O1 C9 C10 120.4(5) . . ? N1 C9 C10 114.2(4) . . ? C11 C10 C15 115.5(5) . . ? C11 C10 C9 122.1(4) . . ? C15 C10 C9 122.3(4) . . ? F1 C11 C12 119.1(5) . . ? F1 C11 C10 117.2(4) . . ? C12 C11 C10 123.7(5) . . ? C11 C12 C13 118.2(5) . . ? C14 C13 C12 121.0(5) . . ? C15 C14 C13 118.9(5) . . ? F2 C15 C14 120.0(5) . . ? F2 C15 C10 117.4(4) . . ? C14 C15 C10 122.6(5) . . ? C9A N1A C1A 124.7(4) . . ? C4A N2A C16A 120.2(4) . . ? C4A N2A C17A 120.5(4) . . ? C16A N2A C17A 118.7(4) . . ? C6A C1A C2A 120.6(4) . . ? C6A C1A N1A 118.0(4) . . ? C2A C1A N1A 121.4(4) . . ? C3A C2A C1A 118.5(4) . . ? C3A C2A C7A 120.3(4) . . ? C1A C2A C7A 121.2(4) . . ? C2A C3A C4A 122.5(5) . . ? N2A C4A C3A 121.4(5) . . ? N2A C4A C5A 121.3(4) . . ? C3A C4A C5A 117.3(4) . . ? C6A C5A C4A 121.3(4) . . ? C5A C6A C1A 119.7(5) . . ? C5A C6A C8A 119.8(4) . . ? C1A C6A C8A 120.4(4) . . ? O1A C9A N1A 125.5(5) . . ? O1A C9A C10A 120.6(5) . . ? N1A C9A C10A 113.9(4) . . ? C11A C10A C15A 115.5(5) . . ? C11A C10A C9A 122.9(4) . . ? C15A C10A C9A 121.6(5) . . ? F1A C11A C12A 118.9(5) . . ? F1A C11A C10A 118.2(5) . . ? C12A C11A C10A 122.9(5) . . ? C13A C12A C11A 118.6(5) . . ? C12A C13A C14A 121.2(5) . . ? C15A C14A C13A 117.8(5) . . ? F2A C15A C14A 118.5(5) . . ? F2A C15A C10A 117.5(5) . . ? C14A C15A C10A 124.0(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 C9 N1 C1 C2 -64.3(7) . . . . ? C9 N1 C1 C6 117.2(6) . . . . ? C6 C1 C2 C3 -2.8(8) . . . . ? N1 C1 C2 C3 178.8(5) . . . . ? C6 C1 C2 C7 178.5(5) . . . . ? N1 C1 C2 C7 0.1(8) . . . . ? C1 C2 C3 C4 0.7(8) . . . . ? C7 C2 C3 C4 179.4(5) . . . . ? C17 N2 C4 C5 -18.9(8) . . . . ? C16 N2 C4 C5 -167.4(5) . . . . ? C17 N2 C4 C3 161.7(5) . . . . ? C16 N2 C4 C3 13.2(8) . . . . ? C2 C3 C4 N2 -178.8(5) . . . . ? C2 C3 C4 C5 1.8(8) . . . . ? N2 C4 C5 C6 178.3(5) . . . . ? C3 C4 C5 C6 -2.3(8) . . . . ? C4 C5 C6 C1 0.3(8) . . . . ? C4 C5 C6 C8 -179.0(5) . . . . ? C2 C1 C6 C5 2.3(8) . . . . ? N1 C1 C6 C5 -179.2(5) . . . . ? C2 C1 C6 C8 -178.3(5) . . . . ? N1 C1 C6 C8 0.2(7) . . . . ? C1 N1 C9 O1 5.4(8) . . . . ? C1 N1 C9 C10 -173.9(4) . . . . ? O1 C9 C10 C11 -109.3(6) . . . . ? N1 C9 C10 C11 70.0(7) . . . . ? O1 C9 C10 C15 68.1(7) . . . . ? N1 C9 C10 C15 -112.6(6) . . . . ? C15 C10 C11 F1 -178.7(5) . . . . ? C9 C10 C11 F1 -1.1(8) . . . . ? C15 C10 C11 C12 0.8(8) . . . . ? C9 C10 C11 C12 178.4(5) . . . . ? F1 C11 C12 C13 178.4(5) . . . . ? C10 C11 C12 C13 -1.1(9) . . . . ? C11 C12 C13 C14 0.4(9) . . . . ? C12 C13 C14 C15 0.4(9) . . . . ? C13 C14 C15 F2 178.0(5) . . . . ? C13 C14 C15 C10 -0.8(9) . . . . ? C11 C10 C15 F2 -178.6(5) . . . . ? C9 C10 C15 F2 3.8(8) . . . . ? C11 C10 C15 C14 0.2(8) . . . . ? C9 C10 C15 C14 -177.4(5) . . . . ? C9A N1A C1A C6A -113.5(6) . . . . ? C9A N1A C1A C2A 67.0(7) . . . . ? C6A C1A C2A C3A 2.0(8) . . . . ? N1A C1A C2A C3A -178.5(5) . . . . ? C6A C1A C2A C7A -178.8(5) . . . . ? N1A C1A C2A C7A 0.7(8) . . . . ? C1A C2A C3A C4A -1.1(9) . . . . ? C7A C2A C3A C4A 179.7(6) . . . . ? C16A N2A C4A C3A -8.6(9) . . . . ? C17A N2A C4A C3A -179.6(6) . . . . ? C16A N2A C4A C5A 172.1(6) . . . . ? C17A N2A C4A C5A 1.1(9) . . . . ? C2A C3A C4A N2A -179.9(6) . . . . ? C2A C3A C4A C5A -0.5(9) . . . . ? N2A C4A C5A C6A -179.3(5) . . . . ? C3A C4A C5A C6A 1.3(8) . . . . ? C4A C5A C6A C1A -0.5(8) . . . . ? C4A C5A C6A C8A -179.0(5) . . . . ? C2A C1A C6A C5A -1.2(8) . . . . ? N1A C1A C6A C5A 179.2(4) . . . . ? C2A C1A C6A C8A 177.3(5) . . . . ? N1A C1A C6A C8A -2.2(7) . . . . ? C1A N1A C9A O1A -6.6(8) . . . . ? C1A N1A C9A C10A 173.8(4) . . . . ? O1A C9A C10A C11A 115.0(6) . . . . ? N1A C9A C10A C11A -65.4(7) . . . . ? O1A C9A C10A C15A -63.5(7) . . . . ? N1A C9A C10A C15A 116.1(6) . . . . ? C15A C10A C11A F1A 178.1(5) . . . . ? C9A C10A C11A F1A -0.5(8) . . . . ? C15A C10A C11A C12A -0.7(8) . . . . ? C9A C10A C11A C12A -179.3(5) . . . . ? F1A C11A C12A C13A -178.1(5) . . . . ? C10A C11A C12A C13A 0.7(9) . . . . ? C11A C12A C13A C14A -0.2(9) . . . . ? C12A C13A C14A C15A -0.1(9) . . . . ? C13A C14A C15A F2A -178.2(5) . . . . ? C13A C14A C15A C10A 0.1(9) . . . . ? C11A C10A C15A F2A 178.6(4) . . . . ? C9A C10A C15A F2A -2.8(8) . . . . ? C11A C10A C15A C14A 0.3(8) . . . . ? C9A C10A C15A C14A 178.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.258 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.061 # Attachment 'och228m.cif' data_och228m _database_code_depnum_ccdc_archive 'CCDC 615390' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 F2 N2 O3' _chemical_formula_weight 306.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 4.6438(13) _cell_length_b 13.421(4) _cell_length_c 23.018(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.683(6) _cell_angle_gamma 90.00 _cell_volume 1433.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1970 _cell_measurement_theta_min 4.665 _cell_measurement_theta_max 46.521 _exptl_crystal_description plate _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9514 _exptl_absorpt_correction_T_max 0.9758 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6105 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 23.34 _reflns_number_total 2064 _reflns_number_gt 1518 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.0000P] 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 2064 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.981 _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 F1 F 0.1317(3) -0.19582(11) 0.21607(6) 0.0584(5) Uani 1 1 d . . . F2 F 0.4968(3) 0.08619(10) 0.12511(6) 0.0528(4) Uani 1 1 d . . . N1 N 0.6673(4) -0.40595(15) -0.09379(9) 0.0365(5) Uani 1 1 d . . . N2 N 0.2680(4) -0.17987(13) 0.09187(7) 0.0255(5) Uani 1 1 d . . . H2A H 0.0853 -0.1810 0.1004 0.031 Uiso 1 1 calc R . . O1 O 0.5769(4) -0.38451(15) -0.14295(8) 0.0602(6) Uani 1 1 d . . . O2 O 0.8487(4) -0.47085(13) -0.08331(8) 0.0481(5) Uani 1 1 d . . . O3 O 0.7095(3) -0.11526(12) 0.11453(7) 0.0397(5) Uani 1 1 d . . . C1 C 0.3605(4) -0.24114(15) 0.04534(9) 0.0228(5) Uani 1 1 d . . . C2 C 0.2591(4) -0.21821(15) -0.01109(9) 0.0250(5) Uani 1 1 d . . . C3 C 0.3564(4) -0.27554(16) -0.05651(10) 0.0266(5) Uani 1 1 d . . . H3A H 0.2886 -0.2631 -0.0954 0.032 Uiso 1 1 calc R . . C4 C 0.5526(4) -0.35081(16) -0.04434(10) 0.0265(5) Uani 1 1 d . . . C5 C 0.6478(5) -0.37517(16) 0.01128(10) 0.0290(6) Uani 1 1 d . . . H5A H 0.7800 -0.4285 0.0179 0.035 Uiso 1 1 calc R . . C6 C 0.5490(4) -0.32118(16) 0.05778(10) 0.0262(5) Uani 1 1 d . . . C7 C 0.0612(5) -0.13110(17) -0.02326(10) 0.0350(6) Uani 1 1 d . . . H7A H 0.0076 -0.1286 -0.0649 0.052 Uiso 1 1 calc R . . H7B H 0.1600 -0.0692 -0.0116 0.052 Uiso 1 1 calc R . . H7C H -0.1128 -0.1387 -0.0012 0.052 Uiso 1 1 calc R . . C8 C 0.6395(5) -0.34926(18) 0.11916(10) 0.0354(6) Uani 1 1 d . . . H8A H 0.7303 -0.4152 0.1194 0.053 Uiso 1 1 calc R . . H8B H 0.4698 -0.3509 0.1429 0.053 Uiso 1 1 calc R . . H8C H 0.7773 -0.3000 0.1352 0.053 Uiso 1 1 calc R . . C9 C 0.4516(4) -0.12052(16) 0.12297(9) 0.0257(5) Uani 1 1 d . . . C10 C 0.3186(4) -0.05769(16) 0.16826(9) 0.0240(5) Uani 1 1 d . . . C11 C 0.1599(5) -0.09512(18) 0.21262(10) 0.0354(6) Uani 1 1 d . . . C12 C 0.0312(5) -0.0365(2) 0.25305(11) 0.0474(7) Uani 1 1 d . . . H12A H -0.0753 -0.0653 0.2830 0.057 Uiso 1 1 calc R . . C13 C 0.0616(6) 0.0653(2) 0.24874(11) 0.0482(7) Uani 1 1 d . . . H13A H -0.0288 0.1073 0.2757 0.058 Uiso 1 1 calc R . . C14 C 0.2196(5) 0.1071(2) 0.20635(12) 0.0448(7) Uani 1 1 d . . . H14A H 0.2417 0.1773 0.2039 0.054 Uiso 1 1 calc R . . C15 C 0.3449(5) 0.04529(17) 0.16766(10) 0.0319(6) 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 F1 0.0847(12) 0.0397(9) 0.0530(10) 0.0042(7) 0.0266(8) -0.0156(8) F2 0.0684(10) 0.0339(8) 0.0575(10) 0.0056(7) 0.0184(8) -0.0066(8) N1 0.0424(12) 0.0281(12) 0.0402(14) -0.0058(10) 0.0135(10) 0.0056(10) N2 0.0176(9) 0.0270(10) 0.0326(11) -0.0057(8) 0.0088(8) -0.0002(8) O1 0.0847(15) 0.0678(14) 0.0287(11) -0.0064(9) 0.0090(10) 0.0293(11) O2 0.0521(11) 0.0389(11) 0.0541(12) -0.0095(9) 0.0123(9) 0.0186(9) O3 0.0199(9) 0.0437(11) 0.0561(12) -0.0183(8) 0.0085(8) -0.0009(7) C1 0.0187(11) 0.0200(12) 0.0302(13) -0.0042(10) 0.0072(9) -0.0034(9) C2 0.0226(11) 0.0205(12) 0.0326(14) -0.0009(10) 0.0076(10) -0.0032(9) C3 0.0273(12) 0.0260(13) 0.0271(13) 0.0007(10) 0.0066(10) -0.0028(10) C4 0.0266(12) 0.0214(13) 0.0326(14) -0.0062(10) 0.0114(10) -0.0006(10) C5 0.0292(12) 0.0189(12) 0.0393(15) -0.0005(10) 0.0069(10) 0.0036(10) C6 0.0254(12) 0.0212(13) 0.0323(13) 0.0004(10) 0.0048(10) -0.0005(10) C7 0.0342(14) 0.0315(14) 0.0397(15) 0.0011(11) 0.0067(11) 0.0116(11) C8 0.0421(14) 0.0278(14) 0.0366(15) -0.0003(11) 0.0045(11) 0.0073(11) C9 0.0204(12) 0.0245(12) 0.0325(13) 0.0003(10) 0.0037(10) 0.0022(10) C10 0.0195(11) 0.0252(13) 0.0273(13) -0.0037(10) 0.0011(9) 0.0012(9) C11 0.0390(14) 0.0329(15) 0.0346(14) -0.0032(12) 0.0070(11) -0.0081(12) C12 0.0429(16) 0.071(2) 0.0292(15) -0.0097(14) 0.0148(12) -0.0072(15) C13 0.0438(15) 0.060(2) 0.0404(16) -0.0287(14) 0.0006(13) 0.0098(14) C14 0.0505(16) 0.0345(15) 0.0491(17) -0.0127(13) -0.0016(14) 0.0065(13) C15 0.0296(13) 0.0309(14) 0.0352(14) -0.0033(12) 0.0027(11) 0.0028(11) _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 F1 C11 1.361(3) . ? F2 C15 1.350(3) . ? N1 O1 1.223(3) . ? N1 O2 1.228(2) . ? N1 C4 1.478(3) . ? N2 C9 1.348(3) . ? N2 C1 1.432(3) . ? O3 C9 1.224(2) . ? C1 C2 1.395(3) . ? C1 C6 1.407(3) . ? C2 C3 1.390(3) . ? C2 C7 1.505(3) . ? C3 C4 1.380(3) . ? C4 C5 1.374(3) . ? C5 C6 1.388(3) . ? C6 C8 1.503(3) . ? C9 C10 1.497(3) . ? C10 C11 1.382(3) . ? C10 C15 1.388(3) . ? C11 C12 1.377(3) . ? C12 C13 1.377(4) . ? C13 C14 1.368(4) . ? C14 C15 1.367(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 N1 O2 123.47(19) . . ? O1 N1 C4 118.3(2) . . ? O2 N1 C4 118.2(2) . . ? C9 N2 C1 122.14(17) . . ? C2 C1 C6 122.53(19) . . ? C2 C1 N2 118.02(18) . . ? C6 C1 N2 119.46(19) . . ? C3 C2 C1 118.1(2) . . ? C3 C2 C7 120.5(2) . . ? C1 C2 C7 121.41(19) . . ? C4 C3 C2 119.1(2) . . ? C5 C4 C3 122.9(2) . . ? C5 C4 N1 119.1(2) . . ? C3 C4 N1 117.9(2) . . ? C4 C5 C6 119.4(2) . . ? C5 C6 C1 117.8(2) . . ? C5 C6 C8 120.4(2) . . ? C1 C6 C8 121.79(19) . . ? O3 C9 N2 123.3(2) . . ? O3 C9 C10 121.10(19) . . ? N2 C9 C10 115.56(18) . . ? C11 C10 C15 114.8(2) . . ? C11 C10 C9 124.2(2) . . ? C15 C10 C9 121.00(19) . . ? F1 C11 C12 118.8(2) . . ? F1 C11 C10 117.4(2) . . ? C12 C11 C10 123.7(2) . . ? C11 C12 C13 118.0(2) . . ? C14 C13 C12 121.2(2) . . ? C15 C14 C13 118.3(3) . . ? F2 C15 C14 118.6(2) . . ? F2 C15 C10 117.47(19) . . ? C14 C15 C10 123.9(2) . . ? 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 C9 N2 C1 C2 -113.0(2) . . . . ? C9 N2 C1 C6 66.8(3) . . . . ? C6 C1 C2 C3 -1.9(3) . . . . ? N2 C1 C2 C3 177.87(17) . . . . ? C6 C1 C2 C7 -179.02(19) . . . . ? N2 C1 C2 C7 0.7(3) . . . . ? C1 C2 C3 C4 -1.4(3) . . . . ? C7 C2 C3 C4 175.73(19) . . . . ? C2 C3 C4 C5 3.1(3) . . . . ? C2 C3 C4 N1 -175.88(18) . . . . ? O1 N1 C4 C5 178.8(2) . . . . ? O2 N1 C4 C5 -1.3(3) . . . . ? O1 N1 C4 C3 -2.2(3) . . . . ? O2 N1 C4 C3 177.75(19) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? N1 C4 C5 C6 177.61(19) . . . . ? C4 C5 C6 C1 -1.9(3) . . . . ? C4 C5 C6 C8 177.3(2) . . . . ? C2 C1 C6 C5 3.6(3) . . . . ? N2 C1 C6 C5 -176.16(18) . . . . ? C2 C1 C6 C8 -175.6(2) . . . . ? N2 C1 C6 C8 4.7(3) . . . . ? C1 N2 C9 O3 -1.0(3) . . . . ? C1 N2 C9 C10 177.27(18) . . . . ? O3 C9 C10 C11 -125.1(2) . . . . ? N2 C9 C10 C11 56.6(3) . . . . ? O3 C9 C10 C15 55.8(3) . . . . ? N2 C9 C10 C15 -122.4(2) . . . . ? C15 C10 C11 F1 -178.73(19) . . . . ? C9 C10 C11 F1 2.2(3) . . . . ? C15 C10 C11 C12 1.1(3) . . . . ? C9 C10 C11 C12 -178.0(2) . . . . ? F1 C11 C12 C13 -179.8(2) . . . . ? C10 C11 C12 C13 0.3(4) . . . . ? C11 C12 C13 C14 -1.3(4) . . . . ? C12 C13 C14 C15 0.8(4) . . . . ? C13 C14 C15 F2 178.8(2) . . . . ? C13 C14 C15 C10 0.8(4) . . . . ? C11 C10 C15 F2 -179.75(19) . . . . ? C9 C10 C15 F2 -0.6(3) . . . . ? C11 C10 C15 C14 -1.7(3) . . . . ? C9 C10 C15 C14 177.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.34 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.234 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.045 # Attachment 'OCH236M.cif' data_och236m _database_code_depnum_ccdc_archive 'CCDC 615391' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Centre for Chemical Biology Department of Chemistry Krebs Institute for Biomolecular Science University of Sheffield Sheffield S3 7HF UK ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H10 F5 N O' _chemical_formula_weight 315.24 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' F F 0.0171 0.0103 '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 4.7498(10) _cell_length_b 10.856(2) _cell_length_c 26.289(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.256(4) _cell_angle_gamma 90.00 _cell_volume 1354.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1971 _cell_measurement_theta_min 4.861 _cell_measurement_theta_max 54.713 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9314 _exptl_absorpt_correction_T_max 0.9717 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8113 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.56 _reflns_number_total 3051 _reflns_number_gt 1799 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.2174P] 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 3051 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_restrained_S_all 0.889 _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 F1 F 0.0512(2) 0.07278(10) 0.29436(4) 0.0360(3) Uani 1 1 d . . . F2 F -0.1695(3) 0.05892(14) 0.19899(5) 0.0613(5) Uani 1 1 d . . . F3 F -0.0182(3) 0.22307(15) 0.12790(5) 0.0678(5) Uani 1 1 d . . . F4 F 0.3616(3) 0.40256(14) 0.15248(5) 0.0639(5) Uani 1 1 d . . . F5 F 0.5801(3) 0.41948(12) 0.24807(5) 0.0540(4) Uani 1 1 d . . . O1 O 0.7175(3) 0.25701(15) 0.33065(6) 0.0407(4) Uani 1 1 d . . . N1 N 0.2879(3) 0.26681(14) 0.36570(6) 0.0244(4) Uani 1 1 d . . . H1A H 0.1054 0.2738 0.3592 0.029 Uiso 1 1 calc R . . C1 C 0.3910(4) 0.26578(18) 0.41783(7) 0.0259(4) Uani 1 1 d . . . C2 C 0.5657(4) 0.36056(19) 0.43621(7) 0.0320(5) Uani 1 1 d . . . C3 C 0.6643(5) 0.3518(2) 0.48679(9) 0.0437(6) Uani 1 1 d . . . H3A H 0.7876 0.4135 0.5003 0.052 Uiso 1 1 calc R . . C4 C 0.5876(5) 0.2562(2) 0.51752(9) 0.0463(6) Uani 1 1 d . . . H4A H 0.6580 0.2524 0.5518 0.056 Uiso 1 1 calc R . . C5 C 0.4088(4) 0.1659(2) 0.49868(8) 0.0387(5) Uani 1 1 d . . . H5A H 0.3545 0.1007 0.5203 0.046 Uiso 1 1 calc R . . C6 C 0.3065(4) 0.16870(19) 0.44843(7) 0.0293(5) Uani 1 1 d . . . C7 C 0.6452(5) 0.4693(2) 0.40443(8) 0.0418(6) Uani 1 1 d . . . H7A H 0.6901 0.5396 0.4267 0.063 Uiso 1 1 calc R . . H7B H 0.4872 0.4907 0.3810 0.063 Uiso 1 1 calc R . . H7C H 0.8101 0.4484 0.3849 0.063 Uiso 1 1 calc R . . C8 C 0.1168(5) 0.0684(2) 0.42740(8) 0.0389(5) Uani 1 1 d . . . H8A H 0.1054 0.0020 0.4525 0.058 Uiso 1 1 calc R . . H8B H 0.1932 0.0359 0.3960 0.058 Uiso 1 1 calc R . . H8C H -0.0719 0.1020 0.4200 0.058 Uiso 1 1 calc R . . C9 C 0.4591(4) 0.25744(17) 0.32674(7) 0.0246(4) Uani 1 1 d . . . C10 C 0.3181(4) 0.24841(17) 0.27450(7) 0.0243(4) Uani 1 1 d . . . C11 C 0.1264(4) 0.15729(18) 0.26063(7) 0.0266(4) Uani 1 1 d . . . C12 C 0.0148(4) 0.1490(2) 0.21161(8) 0.0360(5) Uani 1 1 d . . . C13 C 0.0931(5) 0.2314(2) 0.17559(8) 0.0410(6) Uani 1 1 d . . . C14 C 0.2835(5) 0.3223(2) 0.18773(8) 0.0400(6) Uani 1 1 d . . . C15 C 0.3952(4) 0.32932(19) 0.23686(8) 0.0331(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 F1 0.0409(7) 0.0298(7) 0.0378(7) -0.0034(5) 0.0061(5) -0.0073(5) F2 0.0598(9) 0.0673(10) 0.0554(9) -0.0228(7) -0.0147(7) -0.0214(7) F3 0.0819(12) 0.0907(12) 0.0290(8) -0.0074(7) -0.0207(7) 0.0200(9) F4 0.0859(12) 0.0652(10) 0.0416(8) 0.0226(7) 0.0163(7) 0.0066(8) F5 0.0548(9) 0.0535(9) 0.0541(9) 0.0026(7) 0.0090(7) -0.0271(7) O1 0.0151(7) 0.0715(11) 0.0353(8) -0.0112(7) -0.0022(6) 0.0037(7) N1 0.0147(7) 0.0353(10) 0.0228(8) -0.0013(7) -0.0036(6) 0.0028(6) C1 0.0185(9) 0.0352(11) 0.0236(10) -0.0048(8) -0.0038(7) 0.0059(8) C2 0.0296(11) 0.0370(12) 0.0287(11) -0.0062(9) -0.0060(8) 0.0046(9) C3 0.0455(14) 0.0439(14) 0.0406(13) -0.0084(11) -0.0126(10) -0.0038(11) C4 0.0549(15) 0.0550(16) 0.0279(12) -0.0042(11) -0.0119(10) 0.0066(12) C5 0.0352(12) 0.0510(14) 0.0295(12) 0.0053(10) -0.0025(9) 0.0057(10) C6 0.0224(10) 0.0384(12) 0.0270(11) 0.0008(9) 0.0014(8) 0.0043(8) C7 0.0466(13) 0.0364(13) 0.0417(13) -0.0054(10) -0.0054(10) -0.0078(10) C8 0.0352(12) 0.0439(14) 0.0374(13) 0.0045(10) -0.0011(9) -0.0048(10) C9 0.0164(9) 0.0300(11) 0.0274(10) -0.0049(8) -0.0001(7) 0.0007(8) C10 0.0166(9) 0.0300(11) 0.0262(10) -0.0040(8) 0.0010(7) 0.0035(8) C11 0.0212(10) 0.0279(11) 0.0308(11) -0.0043(8) 0.0013(8) 0.0017(8) C12 0.0316(11) 0.0420(13) 0.0338(12) -0.0126(10) -0.0071(9) -0.0006(9) C13 0.0461(13) 0.0523(15) 0.0238(11) -0.0067(10) -0.0084(10) 0.0147(11) C14 0.0485(14) 0.0427(14) 0.0292(12) 0.0084(10) 0.0052(10) 0.0118(11) C15 0.0303(11) 0.0343(12) 0.0350(12) -0.0001(9) 0.0058(9) -0.0018(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 F1 C11 1.334(2) . ? F2 C12 1.345(2) . ? F3 C13 1.344(2) . ? F4 C14 1.336(2) . ? F5 C15 1.340(2) . ? O1 C9 1.227(2) . ? N1 C9 1.337(2) . ? N1 C1 1.437(2) . ? C1 C6 1.394(3) . ? C1 C2 1.396(3) . ? C2 C3 1.395(3) . ? C2 C7 1.503(3) . ? C3 C4 1.373(4) . ? C4 C5 1.377(3) . ? C5 C6 1.390(3) . ? C6 C8 1.505(3) . ? C9 C10 1.507(2) . ? C10 C11 1.383(3) . ? C10 C15 1.383(3) . ? C11 C12 1.377(3) . ? C12 C13 1.365(3) . ? C13 C14 1.367(3) . ? C14 C15 1.379(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 C9 N1 C1 122.37(15) . . ? C6 C1 C2 122.55(18) . . ? C6 C1 N1 117.45(17) . . ? C2 C1 N1 119.99(18) . . ? C3 C2 C1 116.9(2) . . ? C3 C2 C7 120.09(19) . . ? C1 C2 C7 123.04(17) . . ? C4 C3 C2 121.7(2) . . ? C5 C4 C3 120.0(2) . . ? C4 C5 C6 120.9(2) . . ? C5 C6 C1 117.85(19) . . ? C5 C6 C8 121.01(19) . . ? C1 C6 C8 121.12(17) . . ? O1 C9 N1 124.93(17) . . ? O1 C9 C10 118.89(16) . . ? N1 C9 C10 116.18(15) . . ? C11 C10 C15 117.09(18) . . ? C11 C10 C9 123.43(17) . . ? C15 C10 C9 119.33(17) . . ? F1 C11 C12 118.26(18) . . ? F1 C11 C10 120.46(17) . . ? C12 C11 C10 121.25(19) . . ? F2 C12 C13 119.86(18) . . ? F2 C12 C11 120.1(2) . . ? C13 C12 C11 120.0(2) . . ? F3 C13 C12 119.7(2) . . ? F3 C13 C14 119.9(2) . . ? C12 C13 C14 120.46(19) . . ? F4 C14 C13 120.5(2) . . ? F4 C14 C15 120.4(2) . . ? C13 C14 C15 119.0(2) . . ? F5 C15 C14 118.12(19) . . ? F5 C15 C10 119.74(18) . . ? C14 C15 C10 122.13(19) . . ? 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 C9 N1 C1 C6 -116.6(2) . . . . ? C9 N1 C1 C2 64.2(2) . . . . ? C6 C1 C2 C3 2.6(3) . . . . ? N1 C1 C2 C3 -178.25(18) . . . . ? C6 C1 C2 C7 -176.5(2) . . . . ? N1 C1 C2 C7 2.6(3) . . . . ? C1 C2 C3 C4 -1.6(3) . . . . ? C7 C2 C3 C4 177.5(2) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C4 C5 C6 C8 178.5(2) . . . . ? C2 C1 C6 C5 -1.8(3) . . . . ? N1 C1 C6 C5 179.00(17) . . . . ? C2 C1 C6 C8 179.70(18) . . . . ? N1 C1 C6 C8 0.5(3) . . . . ? C1 N1 C9 O1 -6.1(3) . . . . ? C1 N1 C9 C10 174.68(17) . . . . ? O1 C9 C10 C11 123.1(2) . . . . ? N1 C9 C10 C11 -57.7(2) . . . . ? O1 C9 C10 C15 -52.4(3) . . . . ? N1 C9 C10 C15 126.92(19) . . . . ? C15 C10 C11 F1 177.16(17) . . . . ? C9 C10 C11 F1 1.6(3) . . . . ? C15 C10 C11 C12 -0.9(3) . . . . ? C9 C10 C11 C12 -176.41(18) . . . . ? F1 C11 C12 F2 1.4(3) . . . . ? C10 C11 C12 F2 179.46(18) . . . . ? F1 C11 C12 C13 -177.99(19) . . . . ? C10 C11 C12 C13 0.1(3) . . . . ? F2 C12 C13 F3 1.0(3) . . . . ? C11 C12 C13 F3 -179.61(18) . . . . ? F2 C12 C13 C14 -179.0(2) . . . . ? C11 C12 C13 C14 0.4(3) . . . . ? F3 C13 C14 F4 -0.4(3) . . . . ? C12 C13 C14 F4 179.6(2) . . . . ? F3 C13 C14 C15 180.0(2) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? F4 C14 C15 F5 0.8(3) . . . . ? C13 C14 C15 F5 -179.60(19) . . . . ? F4 C14 C15 C10 179.55(19) . . . . ? C13 C14 C15 C10 -0.9(3) . . . . ? C11 C10 C15 F5 180.00(17) . . . . ? C9 C10 C15 F5 -4.3(3) . . . . ? C11 C10 C15 C14 1.3(3) . . . . ? C9 C10 C15 C14 176.99(18) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.243 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.045 # Attachment 'JMS058.cif' data_jms058 _database_code_depnum_ccdc_archive 'CCDC 615392' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Centre for Chemical Biology Department of Chemistry Krebs Institute for Biomolecular Science University of Sheffield Sheffield S3 7HF UK ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H10 F5 N O' _chemical_formula_weight 315.24 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 12.822(4) _cell_length_b 11.499(3) _cell_length_c 9.804(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.84(2) _cell_angle_gamma 90.00 _cell_volume 1403.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 10.318 _cell_measurement_theta_max 24.309 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.139 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9138 _exptl_absorpt_correction_T_max 0.9621 _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 'SIEMENS P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 18.87 _diffrn_reflns_number 1564 _diffrn_reflns_av_R_equivalents 0.0862 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1229 _reflns_number_gt 961 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0986P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 1229 _refine_ls_number_parameters 201 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1119 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _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 N1 N 0.6562(2) 0.0500(3) 0.8154(3) 0.0504(7) Uani 1 1 d . . . H1A H 0.6751 0.0478 0.9099 0.080 Uiso 1 1 d R . . O1 O 0.7100(3) 0.0083(3) 0.6162(2) 0.0710(8) Uani 1 1 d . . . C1 C 0.7224(3) 0.0028(3) 0.7433(3) 0.0526(9) Uani 1 1 d . . . C2 C 0.8197(3) -0.0571(4) 0.8322(4) 0.0619(11) Uani 1 1 d . . . C3 C 0.9220(4) -0.0118(5) 0.8503(5) 0.0770(14) Uani 1 1 d . . . C4 C 1.0108(4) -0.0699(7) 0.9259(6) 0.102(2) Uani 1 1 d . . . C5 C 0.9987(6) -0.1745(9) 0.9844(6) 0.112(3) Uani 1 1 d . . . C6 C 0.8990(7) -0.2242(6) 0.9684(5) 0.098(2) Uani 1 1 d . . . C7 C 0.8107(4) -0.1639(5) 0.8918(4) 0.0748(14) Uani 1 1 d . . . C8 C 0.5584(3) 0.1062(3) 0.7486(3) 0.0496(8) Uani 1 1 d . . . C9 C 0.5618(4) 0.2147(4) 0.6858(4) 0.0593(10) Uani 1 1 d . . . C10 C 0.4638(5) 0.2643(4) 0.6186(4) 0.0741(13) Uani 1 1 d . . . H10A H 0.4641 0.3386 0.5740 0.080 Uiso 1 1 d R . . C11 C 0.3677(4) 0.2102(5) 0.6148(5) 0.0803(14) Uani 1 1 d . . . H11A H 0.3018 0.2464 0.5665 0.080 Uiso 1 1 d R . . C12 C 0.3666(4) 0.1053(5) 0.6803(5) 0.0759(13) Uani 1 1 d . . . H12A H 0.2993 0.0676 0.6775 0.080 Uiso 1 1 d R . . C13 C 0.4614(3) 0.0509(4) 0.7498(4) 0.0565(10) Uani 1 1 d . . . C14 C 0.4605(4) -0.0636(5) 0.8245(5) 0.0782(13) Uani 1 1 d . . . H14A H 0.3879 -0.0910 0.8099 0.117 Uiso 1 1 calc R . . H14B H 0.4906 -0.0533 0.9233 0.117 Uiso 1 1 calc R . . H14C H 0.5024 -0.1195 0.7880 0.117 Uiso 1 1 calc R . . C15 C 0.6663(5) 0.2775(4) 0.6935(5) 0.0816(14) Uani 1 1 d . . . H15A H 0.6518 0.3542 0.6549 0.122 Uiso 1 1 calc R . . H15B H 0.7080 0.2352 0.6408 0.122 Uiso 1 1 calc R . . H15C H 0.7057 0.2831 0.7898 0.122 Uiso 1 1 calc R . . F1 F 0.7137(3) -0.2146(3) 0.8730(3) 0.0950(10) Uani 1 1 d . . . F2 F 0.8861(4) -0.3293(4) 1.0207(4) 0.1452(19) Uani 1 1 d . . . F3 F 1.0846(4) -0.2336(6) 1.0570(5) 0.169(3) Uani 1 1 d . . . F4 F 1.1094(3) -0.0213(6) 0.9422(5) 0.158(2) Uani 1 1 d . . . F5 F 0.9340(3) 0.0908(3) 0.7910(4) 0.1037(11) 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 N1 0.0595(18) 0.0597(17) 0.0325(13) 0.0001(13) 0.0120(12) 0.0050(14) O1 0.0844(19) 0.096(2) 0.0336(14) -0.0038(13) 0.0164(11) 0.0189(17) C1 0.062(2) 0.060(2) 0.0359(18) -0.0049(15) 0.0125(14) 0.0043(18) C2 0.070(3) 0.079(3) 0.0378(17) -0.0098(17) 0.0158(16) 0.024(2) C3 0.069(3) 0.095(4) 0.064(3) -0.028(3) 0.012(2) 0.009(3) C4 0.063(3) 0.148(6) 0.084(4) -0.045(4) -0.003(3) 0.025(4) C5 0.108(5) 0.160(7) 0.057(3) -0.021(4) -0.002(3) 0.070(5) C6 0.137(6) 0.109(4) 0.048(2) 0.014(3) 0.023(3) 0.062(4) C7 0.091(4) 0.087(3) 0.048(2) 0.003(2) 0.021(2) 0.033(3) C8 0.059(2) 0.058(2) 0.0313(14) -0.0030(14) 0.0107(14) 0.0031(18) C9 0.079(3) 0.058(2) 0.0443(17) 0.0003(16) 0.0208(18) 0.008(2) C10 0.110(4) 0.063(2) 0.049(2) 0.0095(19) 0.019(2) 0.024(3) C11 0.077(3) 0.101(4) 0.058(2) -0.004(2) 0.006(2) 0.031(3) C12 0.057(2) 0.110(4) 0.059(2) -0.009(3) 0.0099(18) -0.001(3) C13 0.061(2) 0.067(2) 0.0413(18) -0.0052(15) 0.0115(15) -0.0038(19) C14 0.084(3) 0.082(3) 0.069(3) 0.004(2) 0.018(2) -0.025(3) C15 0.109(4) 0.067(3) 0.078(3) 0.002(2) 0.039(3) -0.013(3) F1 0.117(3) 0.091(2) 0.087(2) 0.0269(16) 0.0422(18) 0.018(2) F2 0.205(5) 0.147(3) 0.094(2) 0.056(2) 0.055(3) 0.100(3) F3 0.138(4) 0.251(6) 0.096(2) -0.007(3) -0.014(2) 0.127(4) F4 0.068(2) 0.219(6) 0.170(4) -0.083(4) -0.003(2) 0.018(3) F5 0.087(2) 0.106(2) 0.119(3) -0.029(2) 0.0257(17) -0.0156(18) _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 N1 C1 1.342(5) . ? N1 C8 1.423(5) . ? O1 C1 1.220(4) . ? C1 C2 1.507(6) . ? C2 C7 1.377(7) . ? C2 C3 1.382(7) . ? C3 F5 1.340(7) . ? C3 C4 1.374(9) . ? C4 C5 1.357(12) . ? C4 F4 1.357(9) . ? C5 F3 1.344(8) . ? C5 C6 1.375(11) . ? C6 F2 1.338(8) . ? C6 C7 1.385(8) . ? C7 F1 1.346(7) . ? C8 C13 1.400(6) . ? C8 C9 1.397(6) . ? C9 C10 1.393(7) . ? C9 C15 1.508(7) . ? C10 C11 1.373(8) . ? C11 C12 1.368(8) . ? C12 C13 1.391(7) . ? C13 C14 1.508(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C8 122.7(3) . . ? O1 C1 N1 124.9(3) . . ? O1 C1 C2 120.1(3) . . ? N1 C1 C2 114.9(3) . . ? C7 C2 C3 117.1(4) . . ? C7 C2 C1 120.8(4) . . ? C3 C2 C1 122.0(4) . . ? F5 C3 C4 119.7(5) . . ? F5 C3 C2 118.7(4) . . ? C4 C3 C2 121.6(6) . . ? C5 C4 F4 120.9(7) . . ? C5 C4 C3 119.7(6) . . ? F4 C4 C3 119.4(8) . . ? F3 C5 C4 120.7(9) . . ? F3 C5 C6 118.2(9) . . ? C4 C5 C6 121.1(5) . . ? F2 C6 C5 121.9(6) . . ? F2 C6 C7 120.0(8) . . ? C5 C6 C7 118.1(6) . . ? F1 C7 C2 119.8(4) . . ? F1 C7 C6 117.8(6) . . ? C2 C7 C6 122.4(6) . . ? C13 C8 C9 122.1(4) . . ? C13 C8 N1 118.5(3) . . ? C9 C8 N1 119.5(3) . . ? C10 C9 C8 117.0(4) . . ? C10 C9 C15 121.2(4) . . ? C8 C9 C15 121.8(4) . . ? C11 C10 C9 121.9(4) . . ? C12 C11 C10 119.8(4) . . ? C11 C12 C13 121.3(4) . . ? C12 C13 C8 117.7(4) . . ? C12 C13 C14 121.6(4) . . ? C8 C13 C14 120.7(4) . . ? 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 C8 N1 C1 O1 4.3(6) . . . . ? C8 N1 C1 C2 -177.6(4) . . . . ? O1 C1 C2 C7 -107.2(5) . . . . ? N1 C1 C2 C7 74.6(5) . . . . ? O1 C1 C2 C3 68.7(6) . . . . ? N1 C1 C2 C3 -109.5(4) . . . . ? C7 C2 C3 F5 178.6(4) . . . . ? C1 C2 C3 F5 2.5(6) . . . . ? C7 C2 C3 C4 -0.8(6) . . . . ? C1 C2 C3 C4 -176.8(4) . . . . ? F5 C3 C4 C5 -179.2(5) . . . . ? C2 C3 C4 C5 0.1(7) . . . . ? F5 C3 C4 F4 1.5(7) . . . . ? C2 C3 C4 F4 -179.2(4) . . . . ? F4 C4 C5 F3 -1.7(9) . . . . ? C3 C4 C5 F3 179.0(4) . . . . ? F4 C4 C5 C6 180.0(5) . . . . ? C3 C4 C5 C6 0.6(8) . . . . ? F3 C5 C6 F2 -1.1(7) . . . . ? C4 C5 C6 F2 177.3(5) . . . . ? F3 C5 C6 C7 -179.1(4) . . . . ? C4 C5 C6 C7 -0.7(8) . . . . ? C3 C2 C7 F1 -177.3(4) . . . . ? C1 C2 C7 F1 -1.2(5) . . . . ? C3 C2 C7 C6 0.7(6) . . . . ? C1 C2 C7 C6 176.8(4) . . . . ? F2 C6 C7 F1 0.0(6) . . . . ? C5 C6 C7 F1 178.1(4) . . . . ? F2 C6 C7 C2 -178.0(4) . . . . ? C5 C6 C7 C2 0.0(7) . . . . ? C1 N1 C8 C13 108.9(4) . . . . ? C1 N1 C8 C9 -72.0(4) . . . . ? C13 C8 C9 C10 -2.6(5) . . . . ? N1 C8 C9 C10 178.3(3) . . . . ? C13 C8 C9 C15 175.7(4) . . . . ? N1 C8 C9 C15 -3.4(5) . . . . ? C8 C9 C10 C11 0.6(6) . . . . ? C15 C9 C10 C11 -177.7(4) . . . . ? C9 C10 C11 C12 1.1(7) . . . . ? C10 C11 C12 C13 -0.9(7) . . . . ? C11 C12 C13 C8 -1.0(6) . . . . ? C11 C12 C13 C14 178.9(4) . . . . ? C9 C8 C13 C12 2.8(5) . . . . ? N1 C8 C13 C12 -178.0(3) . . . . ? C9 C8 C13 C14 -177.1(4) . . . . ? N1 C8 C13 C14 2.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.172 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.072 # Attachment 'och38m.cif' data_och38m _database_code_depnum_ccdc_archive 'CCDC 615393' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H15 F5 N2 O' _chemical_formula_weight 358.31 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' F F 0.0171 0.0103 '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 4.7538(19) _cell_length_b 10.885(7) _cell_length_c 30.402(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.10(4) _cell_angle_gamma 90.00 _cell_volume 1572.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 571(2) _cell_measurement_reflns_used 33 _cell_measurement_theta_min 1.99 _cell_measurement_theta_max 28.41 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9668 _exptl_absorpt_correction_T_max 0.9865 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 571(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 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10171 _diffrn_reflns_av_R_equivalents 0.1948 _diffrn_reflns_av_sigmaI/netI 0.4035 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 28.41 _reflns_number_total 3741 _reflns_number_gt 775 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.0000P] 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 3741 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3101 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1584 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 0.690 _refine_ls_restrained_S_all 0.690 _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 -0.1907(7) 0.2381(3) 0.31878(10) 0.0572(11) Uani 1 1 d . . . F1 F 0.4596(6) 0.4195(2) 0.28855(8) 0.0545(9) Uani 1 1 d . . . F2 F 0.6640(7) 0.4299(3) 0.20621(9) 0.0777(11) Uani 1 1 d . . . F3 F 0.5046(7) 0.2616(3) 0.14531(9) 0.0815(11) Uani 1 1 d . . . F4 F 0.1253(7) 0.0852(3) 0.16589(9) 0.0773(11) Uani 1 1 d . . . F5 F -0.0759(6) 0.0739(3) 0.24792(9) 0.0686(10) Uani 1 1 d . . . N1 N 0.2448(8) 0.2241(3) 0.34982(12) 0.0394(11) Uani 1 1 d . . . H1 H 0.4213 0.2182 0.3445 0.047 Uiso 1 1 calc R . . N2 N -0.1118(9) 0.2260(4) 0.52504(13) 0.0617(14) Uani 1 1 d . . . C1 C 0.0640(11) 0.2363(4) 0.31578(15) 0.0371(13) Uani 1 1 d . . . C2 C 0.1584(9) 0.2204(4) 0.39450(15) 0.0337(13) Uani 1 1 d . . . C3 C -0.0212(10) 0.1301(4) 0.40962(16) 0.0360(13) Uani 1 1 d . . . C4 C -0.1096(10) 0.1327(4) 0.45260(16) 0.0448(15) Uani 1 1 d . . . H4 H -0.2296 0.0716 0.4625 0.054 Uiso 1 1 calc R . . C5 C -0.0206(11) 0.2270(5) 0.48198(15) 0.0451(14) Uani 1 1 d . . . C6 C 0.1706(10) 0.3135(4) 0.46668(16) 0.0446(14) Uani 1 1 d . . . H6 H 0.2406 0.3732 0.4858 0.053 Uiso 1 1 calc R . . C7 C 0.2581(9) 0.3122(4) 0.42353(16) 0.0376(13) Uani 1 1 d . . . C8 C 0.1913(10) 0.2449(4) 0.27089(15) 0.0330(12) Uani 1 1 d . . . C9 C 0.3783(11) 0.3346(5) 0.25930(16) 0.0402(14) Uani 1 1 d . . . C10 C 0.4829(11) 0.3416(5) 0.21697(18) 0.0481(15) Uani 1 1 d . . . C11 C 0.3994(11) 0.2578(5) 0.18609(17) 0.0452(15) Uani 1 1 d . . . C12 C 0.2089(12) 0.1684(5) 0.19606(17) 0.0525(16) Uani 1 1 d . . . C13 C 0.1083(11) 0.1611(5) 0.23852(17) 0.0443(14) Uani 1 1 d . . . C14 C -0.1157(10) 0.0221(4) 0.38133(14) 0.0531(15) Uani 1 1 d . . . H14A H -0.2829 0.0441 0.3650 0.080 Uiso 1 1 calc R . . H14B H -0.1544 -0.0471 0.3998 0.080 Uiso 1 1 calc R . . H14C H 0.0305 0.0011 0.3613 0.080 Uiso 1 1 calc R . . C15 C 0.4624(10) 0.4074(4) 0.40785(15) 0.0522(15) Uani 1 1 d . . . H15A H 0.5089 0.4625 0.4315 0.078 Uiso 1 1 calc R . . H15B H 0.3785 0.4527 0.3839 0.078 Uiso 1 1 calc R . . H15C H 0.6303 0.3676 0.3981 0.078 Uiso 1 1 calc R . . C16 C -0.3309(10) 0.1421(4) 0.53811(14) 0.0590(17) Uani 1 1 d . . . H16A H -0.4949 0.1543 0.5197 0.089 Uiso 1 1 calc R . . H16B H -0.3771 0.1571 0.5682 0.089 Uiso 1 1 calc R . . H16C H -0.2659 0.0591 0.5350 0.089 Uiso 1 1 calc R . . C17 C -0.0273(12) 0.3225(4) 0.55450(15) 0.0664(17) Uani 1 1 d . . . H17A H 0.1720 0.3180 0.5599 0.100 Uiso 1 1 calc R . . H17B H -0.1238 0.3137 0.5818 0.100 Uiso 1 1 calc R . . H17C H -0.0736 0.4006 0.5416 0.100 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 0.028(2) 0.091(3) 0.052(2) 0.013(2) 0.0078(18) 0.006(2) F1 0.062(2) 0.0559(19) 0.0454(19) 0.0004(17) -0.0002(16) -0.0086(17) F2 0.075(2) 0.093(3) 0.065(2) 0.0254(19) 0.0151(18) -0.024(2) F3 0.102(3) 0.103(3) 0.0404(19) 0.0101(18) 0.0196(18) 0.016(2) F4 0.107(3) 0.077(2) 0.048(2) -0.0138(19) -0.0076(19) 0.003(2) F5 0.070(2) 0.072(2) 0.064(2) 0.0015(18) -0.0081(18) -0.025(2) N1 0.026(2) 0.058(3) 0.034(2) 0.005(2) 0.009(2) 0.008(2) N2 0.059(3) 0.089(4) 0.037(3) -0.006(3) 0.018(3) -0.021(3) C1 0.031(3) 0.047(4) 0.034(3) 0.004(3) 0.007(3) 0.004(3) C2 0.022(3) 0.052(4) 0.028(3) 0.005(3) 0.009(2) 0.009(3) C3 0.030(3) 0.039(3) 0.039(3) 0.005(3) 0.002(3) 0.006(3) C4 0.043(4) 0.052(4) 0.040(3) 0.007(3) 0.005(3) -0.001(3) C5 0.045(3) 0.067(4) 0.024(3) 0.007(3) 0.007(3) 0.007(3) C6 0.039(3) 0.056(4) 0.038(3) 0.000(3) 0.003(3) -0.008(3) C7 0.026(3) 0.049(4) 0.038(3) 0.000(3) 0.001(3) 0.005(3) C8 0.025(3) 0.043(3) 0.031(3) 0.004(3) 0.013(2) 0.004(3) C9 0.036(4) 0.046(4) 0.039(4) 0.006(3) 0.000(3) 0.008(3) C10 0.036(4) 0.063(4) 0.045(4) 0.019(3) 0.008(3) -0.005(3) C11 0.047(4) 0.063(4) 0.027(3) 0.005(3) 0.014(3) 0.003(3) C12 0.057(4) 0.068(4) 0.032(4) -0.008(3) -0.015(3) 0.010(4) C13 0.041(4) 0.043(4) 0.050(4) 0.003(3) -0.002(3) -0.010(3) C14 0.047(4) 0.063(4) 0.050(3) 0.007(3) 0.007(3) 0.002(3) C15 0.048(4) 0.058(4) 0.051(3) -0.003(3) 0.015(3) -0.007(3) C16 0.055(4) 0.080(4) 0.043(4) 0.003(3) 0.011(3) 0.000(4) C17 0.088(5) 0.069(4) 0.042(3) -0.009(3) 0.009(3) 0.001(4) _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 C1 1.217(5) . ? F1 C9 1.334(5) . ? F2 C10 1.335(5) . ? F3 C11 1.346(5) . ? F4 C12 1.343(5) . ? F5 C13 1.326(5) . ? N1 C1 1.339(5) . ? N1 C2 1.427(5) . ? N2 C5 1.387(5) . ? N2 C17 1.433(5) . ? N2 C16 1.447(5) . ? C1 C8 1.506(6) . ? C2 C3 1.386(6) . ? C2 C7 1.409(6) . ? C3 C4 1.381(6) . ? C3 C14 1.519(6) . ? C4 C5 1.420(6) . ? C5 C6 1.395(6) . ? C6 C7 1.384(6) . ? C7 C15 1.504(5) . ? C8 C9 1.372(6) . ? C8 C13 1.393(6) . ? C9 C10 1.391(6) . ? C10 C11 1.362(6) . ? C11 C12 1.368(6) . ? C12 C13 1.387(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 123.1(4) . . ? C5 N2 C17 119.7(5) . . ? C5 N2 C16 120.2(5) . . ? C17 N2 C16 119.1(4) . . ? O1 C1 N1 124.6(4) . . ? O1 C1 C8 119.0(5) . . ? N1 C1 C8 116.3(4) . . ? C3 C2 C7 119.8(4) . . ? C3 C2 N1 121.7(5) . . ? C7 C2 N1 118.4(4) . . ? C4 C3 C2 120.0(5) . . ? C4 C3 C14 117.4(4) . . ? C2 C3 C14 122.6(4) . . ? C3 C4 C5 121.2(5) . . ? N2 C5 C6 122.5(5) . . ? N2 C5 C4 119.6(5) . . ? C6 C5 C4 117.8(4) . . ? C7 C6 C5 121.3(5) . . ? C6 C7 C2 119.8(5) . . ? C6 C7 C15 120.1(5) . . ? C2 C7 C15 120.1(4) . . ? C9 C8 C13 117.4(5) . . ? C9 C8 C1 123.4(5) . . ? C13 C8 C1 119.1(5) . . ? F1 C9 C8 120.2(4) . . ? F1 C9 C10 118.4(5) . . ? C8 C9 C10 121.4(5) . . ? F2 C10 C11 119.6(5) . . ? F2 C10 C9 120.6(5) . . ? C11 C10 C9 119.8(5) . . ? F3 C11 C10 120.4(5) . . ? F3 C11 C12 119.0(5) . . ? C10 C11 C12 120.6(5) . . ? F4 C12 C11 121.1(5) . . ? F4 C12 C13 119.6(6) . . ? C11 C12 C13 119.2(6) . . ? F5 C13 C12 118.8(5) . . ? F5 C13 C8 119.7(5) . . ? C12 C13 C8 121.4(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 C2 N1 C1 O1 -4.6(8) . . . . ? C2 N1 C1 C8 177.1(4) . . . . ? C1 N1 C2 C3 60.5(6) . . . . ? C1 N1 C2 C7 -118.9(5) . . . . ? C7 C2 C3 C4 2.2(6) . . . . ? N1 C2 C3 C4 -177.2(4) . . . . ? C7 C2 C3 C14 -174.4(4) . . . . ? N1 C2 C3 C14 6.2(7) . . . . ? C2 C3 C4 C5 0.2(7) . . . . ? C14 C3 C4 C5 177.0(4) . . . . ? C17 N2 C5 C6 5.3(7) . . . . ? C16 N2 C5 C6 173.9(5) . . . . ? C17 N2 C5 C4 -178.6(4) . . . . ? C16 N2 C5 C4 -10.1(7) . . . . ? C3 C4 C5 N2 -179.4(5) . . . . ? C3 C4 C5 C6 -3.2(7) . . . . ? N2 C5 C6 C7 180.0(4) . . . . ? C4 C5 C6 C7 3.8(7) . . . . ? C5 C6 C7 C2 -1.5(7) . . . . ? C5 C6 C7 C15 179.4(4) . . . . ? C3 C2 C7 C6 -1.6(6) . . . . ? N1 C2 C7 C6 177.8(4) . . . . ? C3 C2 C7 C15 177.5(4) . . . . ? N1 C2 C7 C15 -3.1(6) . . . . ? O1 C1 C8 C9 122.5(6) . . . . ? N1 C1 C8 C9 -59.1(7) . . . . ? O1 C1 C8 C13 -54.8(7) . . . . ? N1 C1 C8 C13 123.6(5) . . . . ? C13 C8 C9 F1 178.2(4) . . . . ? C1 C8 C9 F1 0.9(7) . . . . ? C13 C8 C9 C10 -0.4(7) . . . . ? C1 C8 C9 C10 -177.7(5) . . . . ? F1 C9 C10 F2 1.1(7) . . . . ? C8 C9 C10 F2 179.7(4) . . . . ? F1 C9 C10 C11 -178.6(4) . . . . ? C8 C9 C10 C11 0.0(7) . . . . ? F2 C10 C11 F3 2.0(7) . . . . ? C9 C10 C11 F3 -178.3(4) . . . . ? F2 C10 C11 C12 -178.4(5) . . . . ? C9 C10 C11 C12 1.3(7) . . . . ? F3 C11 C12 F4 -0.3(7) . . . . ? C10 C11 C12 F4 -179.9(5) . . . . ? F3 C11 C12 C13 177.4(4) . . . . ? C10 C11 C12 C13 -2.2(8) . . . . ? F4 C12 C13 F5 -2.1(7) . . . . ? C11 C12 C13 F5 -179.9(5) . . . . ? F4 C12 C13 C8 179.5(4) . . . . ? C11 C12 C13 C8 1.8(8) . . . . ? C9 C8 C13 F5 -178.8(4) . . . . ? C1 C8 C13 F5 -1.4(7) . . . . ? C9 C8 C13 C12 -0.5(7) . . . . ? C1 C8 C13 C12 176.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.292 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.065 # Attachment 'OCH237M.cif' data_och237m _database_code_depnum_ccdc_archive 'CCDC 615394' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Centre for Chemical Biology Department of Chemistry Krebs Institute for Biomolecular Science University of Sheffield Sheffield S3 7HF UK ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H9 F5 N2 O3' _chemical_formula_weight 360.24 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.6658(8) _cell_length_b 13.056(2) _cell_length_c 13.473(2) _cell_angle_alpha 63.577(3) _cell_angle_beta 85.102(3) _cell_angle_gamma 84.119(3) _cell_volume 730.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1959 _cell_measurement_theta_min 5.824 _cell_measurement_theta_max 54.117 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9286 _exptl_absorpt_correction_T_max 0.9678 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5148 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.55 _reflns_number_total 3155 _reflns_number_gt 2269 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.3304P] 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 3155 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 0.888 _refine_ls_restrained_S_all 0.888 _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 F1 F 1.0686(3) 0.30138(10) 0.46203(10) 0.0376(3) Uani 1 1 d . . . F2 F 0.8492(3) 0.10141(11) 0.51540(11) 0.0512(4) Uani 1 1 d . . . F3 F 0.5105(3) 0.07977(11) 0.37128(12) 0.0500(4) Uani 1 1 d . . . F4 F 0.4058(3) 0.26054(12) 0.17140(11) 0.0450(4) Uani 1 1 d . . . F5 F 0.6407(3) 0.45951(10) 0.11421(10) 0.0355(3) Uani 1 1 d . . . O1 O 1.2318(3) 0.50332(11) 0.27568(12) 0.0303(3) Uani 1 1 d . . . O2 O 1.3234(3) 1.05893(13) 0.10063(13) 0.0407(4) Uani 1 1 d . . . O3 O 1.0027(4) 1.06111(13) 0.22511(14) 0.0448(4) Uani 1 1 d . . . N1 N 0.7832(3) 0.59095(13) 0.22928(13) 0.0224(3) Uani 1 1 d . . . H1A H 0.6002 0.5658 0.2676 0.027 Uiso 1 1 d R . . N2 N 1.1254(4) 1.01702(13) 0.16816(14) 0.0292(4) Uani 1 1 d . . . C1 C 0.8629(4) 0.70172(15) 0.21008(15) 0.0206(4) Uani 1 1 d . . . C2 C 1.0567(4) 0.75927(15) 0.12157(15) 0.0232(4) Uani 1 1 d . . . C3 C 1.1432(4) 0.86322(15) 0.10963(16) 0.0246(4) Uani 1 1 d . . . H3A H 1.2796 0.9036 0.0523 0.030 Uiso 1 1 calc R . . C4 C 1.0289(4) 0.90711(15) 0.18194(16) 0.0243(4) Uani 1 1 d . . . C5 C 0.8273(4) 0.85337(15) 0.26583(16) 0.0239(4) Uani 1 1 d . . . H5A H 0.7475 0.8879 0.3119 0.029 Uiso 1 1 calc R . . C6 C 0.7423(4) 0.74744(15) 0.28191(15) 0.0219(4) Uani 1 1 d . . . C7 C 1.1648(5) 0.71417(17) 0.03883(17) 0.0311(5) Uani 1 1 d . . . H7A H 1.2765 0.7716 -0.0216 0.047 Uiso 1 1 calc R . . H7B H 1.0004 0.6982 0.0086 0.047 Uiso 1 1 calc R . . H7C H 1.2878 0.6434 0.0757 0.047 Uiso 1 1 calc R . . C8 C 0.5310(4) 0.68350(17) 0.37531(16) 0.0282(4) Uani 1 1 d . . . H8A H 0.3640 0.6693 0.3449 0.042 Uiso 1 1 calc R . . H8B H 0.4673 0.7294 0.4152 0.042 Uiso 1 1 calc R . . H8C H 0.6245 0.6102 0.4265 0.042 Uiso 1 1 calc R . . C9 C 0.9774(4) 0.49974(15) 0.26259(15) 0.0217(4) Uani 1 1 d . . . C10 C 0.8593(4) 0.38756(15) 0.28658(15) 0.0220(4) Uani 1 1 d . . . C11 C 0.9119(4) 0.29294(16) 0.38707(16) 0.0269(4) Uani 1 1 d . . . C12 C 0.7983(5) 0.18943(17) 0.41586(18) 0.0332(5) Uani 1 1 d . . . C13 C 0.6278(5) 0.17853(17) 0.34317(19) 0.0338(5) Uani 1 1 d . . . C14 C 0.5747(4) 0.26974(18) 0.24164(17) 0.0307(5) Uani 1 1 d . . . C15 C 0.6926(4) 0.37260(16) 0.21437(16) 0.0255(4) 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 F1 0.0389(7) 0.0353(7) 0.0344(7) -0.0093(5) -0.0084(5) -0.0080(5) F2 0.0660(10) 0.0264(7) 0.0460(8) -0.0011(6) 0.0012(7) -0.0116(6) F3 0.0612(9) 0.0348(7) 0.0620(9) -0.0269(7) 0.0193(7) -0.0289(6) F4 0.0453(8) 0.0584(9) 0.0518(8) -0.0399(7) 0.0040(6) -0.0217(6) F5 0.0427(7) 0.0345(7) 0.0316(6) -0.0155(5) -0.0053(5) -0.0053(5) O1 0.0167(7) 0.0255(7) 0.0472(9) -0.0142(6) -0.0007(6) -0.0043(5) O2 0.0420(9) 0.0312(8) 0.0492(9) -0.0172(7) 0.0123(8) -0.0179(7) O3 0.0576(11) 0.0332(8) 0.0529(10) -0.0280(8) 0.0116(8) -0.0120(7) N1 0.0171(8) 0.0209(8) 0.0306(8) -0.0124(6) 0.0020(6) -0.0054(6) N2 0.0326(10) 0.0205(8) 0.0342(9) -0.0110(7) -0.0029(8) -0.0041(7) C1 0.0176(9) 0.0187(9) 0.0271(9) -0.0107(7) -0.0039(7) -0.0017(7) C2 0.0223(9) 0.0204(9) 0.0257(9) -0.0090(8) -0.0009(7) -0.0008(7) C3 0.0236(10) 0.0213(9) 0.0266(9) -0.0082(8) 0.0018(8) -0.0049(7) C4 0.0243(10) 0.0182(9) 0.0304(10) -0.0098(8) -0.0049(8) -0.0024(7) C5 0.0218(9) 0.0237(9) 0.0289(10) -0.0140(8) -0.0021(8) -0.0007(7) C6 0.0166(9) 0.0235(9) 0.0254(9) -0.0106(8) -0.0028(7) -0.0006(7) C7 0.0361(12) 0.0278(10) 0.0292(10) -0.0133(8) 0.0062(9) -0.0047(8) C8 0.0233(10) 0.0327(11) 0.0328(10) -0.0181(9) 0.0047(8) -0.0078(8) C9 0.0182(9) 0.0227(9) 0.0256(9) -0.0119(7) 0.0028(7) -0.0050(7) C10 0.0158(9) 0.0220(9) 0.0301(10) -0.0140(8) 0.0044(7) -0.0029(7) C11 0.0217(10) 0.0282(10) 0.0321(10) -0.0147(8) 0.0028(8) -0.0041(7) C12 0.0368(12) 0.0234(10) 0.0342(11) -0.0088(9) 0.0076(9) -0.0061(8) C13 0.0354(12) 0.0255(10) 0.0468(12) -0.0219(10) 0.0154(10) -0.0144(8) C14 0.0250(10) 0.0387(12) 0.0419(12) -0.0298(10) 0.0078(9) -0.0102(8) C15 0.0254(10) 0.0243(10) 0.0291(10) -0.0145(8) 0.0038(8) -0.0031(7) _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 F1 C11 1.345(2) . ? F2 C12 1.343(2) . ? F3 C13 1.334(2) . ? F4 C14 1.334(2) . ? F5 C15 1.343(2) . ? O1 C9 1.224(2) . ? O2 N2 1.224(2) . ? O3 N2 1.224(2) . ? N1 C9 1.346(2) . ? N1 C1 1.434(2) . ? N2 C4 1.476(2) . ? C1 C6 1.401(2) . ? C1 C2 1.401(3) . ? C2 C3 1.392(3) . ? C2 C7 1.507(3) . ? C3 C4 1.381(3) . ? C4 C5 1.379(3) . ? C5 C6 1.396(3) . ? C6 C8 1.508(3) . ? C9 C10 1.505(2) . ? C10 C15 1.385(3) . ? C10 C11 1.388(3) . ? C11 C12 1.379(3) . ? C12 C13 1.376(3) . ? C13 C14 1.378(3) . ? C14 C15 1.385(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 C9 N1 C1 120.93(15) . . ? O3 N2 O2 123.68(17) . . ? O3 N2 C4 118.04(16) . . ? O2 N2 C4 118.28(16) . . ? C6 C1 C2 122.83(16) . . ? C6 C1 N1 117.91(16) . . ? C2 C1 N1 119.26(15) . . ? C3 C2 C1 117.68(17) . . ? C3 C2 C7 119.94(17) . . ? C1 C2 C7 122.36(16) . . ? C4 C3 C2 119.40(17) . . ? C5 C4 C3 123.03(17) . . ? C5 C4 N2 118.56(16) . . ? C3 C4 N2 118.42(17) . . ? C4 C5 C6 118.93(17) . . ? C5 C6 C1 118.02(17) . . ? C5 C6 C8 120.75(16) . . ? C1 C6 C8 121.22(16) . . ? O1 C9 N1 124.51(16) . . ? O1 C9 C10 120.33(16) . . ? N1 C9 C10 115.15(16) . . ? C15 C10 C11 116.78(17) . . ? C15 C10 C9 123.73(17) . . ? C11 C10 C9 119.47(16) . . ? F1 C11 C12 117.68(18) . . ? F1 C11 C10 120.16(16) . . ? C12 C11 C10 122.11(18) . . ? F2 C12 C13 120.72(18) . . ? F2 C12 C11 119.8(2) . . ? C13 C12 C11 119.50(19) . . ? F3 C13 C12 120.0(2) . . ? F3 C13 C14 119.7(2) . . ? C12 C13 C14 120.25(18) . . ? F4 C14 C13 120.66(17) . . ? F4 C14 C15 120.15(19) . . ? C13 C14 C15 119.16(18) . . ? F5 C15 C10 119.98(16) . . ? F5 C15 C14 117.85(17) . . ? C10 C15 C14 122.17(18) . . ? 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 C9 N1 C1 C6 -112.58(19) . . . . ? C9 N1 C1 C2 67.2(2) . . . . ? C6 C1 C2 C3 3.7(3) . . . . ? N1 C1 C2 C3 -176.04(16) . . . . ? C6 C1 C2 C7 -174.47(18) . . . . ? N1 C1 C2 C7 5.8(3) . . . . ? C1 C2 C3 C4 -2.2(3) . . . . ? C7 C2 C3 C4 176.03(18) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C2 C3 C4 N2 179.56(16) . . . . ? O3 N2 C4 C5 -6.7(3) . . . . ? O2 N2 C4 C5 173.25(17) . . . . ? O3 N2 C4 C3 172.83(18) . . . . ? O2 N2 C4 C3 -7.2(3) . . . . ? C3 C4 C5 C6 2.7(3) . . . . ? N2 C4 C5 C6 -177.78(16) . . . . ? C4 C5 C6 C1 -1.2(3) . . . . ? C4 C5 C6 C8 177.67(17) . . . . ? C2 C1 C6 C5 -2.0(3) . . . . ? N1 C1 C6 C5 177.78(16) . . . . ? C2 C1 C6 C8 179.11(17) . . . . ? N1 C1 C6 C8 -1.1(3) . . . . ? C1 N1 C9 O1 -2.4(3) . . . . ? C1 N1 C9 C10 176.23(15) . . . . ? O1 C9 C10 C15 -131.2(2) . . . . ? N1 C9 C10 C15 50.1(2) . . . . ? O1 C9 C10 C11 50.2(2) . . . . ? N1 C9 C10 C11 -128.46(18) . . . . ? C15 C10 C11 F1 -179.09(16) . . . . ? C9 C10 C11 F1 -0.4(3) . . . . ? C15 C10 C11 C12 -1.7(3) . . . . ? C9 C10 C11 C12 176.94(17) . . . . ? F1 C11 C12 F2 -0.8(3) . . . . ? C10 C11 C12 F2 -178.16(17) . . . . ? F1 C11 C12 C13 177.61(17) . . . . ? C10 C11 C12 C13 0.2(3) . . . . ? F2 C12 C13 F3 0.1(3) . . . . ? C11 C12 C13 F3 -178.24(18) . . . . ? F2 C12 C13 C14 179.39(18) . . . . ? C11 C12 C13 C14 1.0(3) . . . . ? F3 C13 C14 F4 0.4(3) . . . . ? C12 C13 C14 F4 -178.88(18) . . . . ? F3 C13 C14 C15 178.63(17) . . . . ? C12 C13 C14 C15 -0.7(3) . . . . ? C11 C10 C15 F5 -177.92(16) . . . . ? C9 C10 C15 F5 3.5(3) . . . . ? C11 C10 C15 C14 2.1(3) . . . . ? C9 C10 C15 C14 -176.48(17) . . . . ? F4 C14 C15 F5 -2.7(3) . . . . ? C13 C14 C15 F5 179.06(17) . . . . ? F4 C14 C15 C10 177.24(16) . . . . ? C13 C14 C15 C10 -1.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.415 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.053 # Attachment 'OCH234M.cif' data_och234m _database_code_depnum_ccdc_archive 'CCDC 615395' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Centre for Chemical Biology Department of Chemistry Krebs Institute for Biomolecular Science University of Sheffield Sheffield S3 7HF UK ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 F5 N O2' _chemical_formula_weight 345.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.7637(11) _cell_length_b 10.695(3) _cell_length_c 14.616(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.579(5) _cell_angle_gamma 90.00 _cell_volume 739.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1346 _cell_measurement_theta_min 4.721 _cell_measurement_theta_max 50.790 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9379 _exptl_absorpt_correction_T_max 0.9829 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4474 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0591 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.52 _reflns_number_total 1760 _reflns_number_gt 1204 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 1760 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 0.917 _refine_ls_restrained_S_all 0.917 _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 F1 F 0.0008(5) 0.9302(2) 0.92179(14) 0.0336(6) Uani 1 1 d . . . F2 F -0.1324(6) 0.9377(3) 1.09559(16) 0.0522(8) Uani 1 1 d . . . F3 F 0.0854(6) 0.7674(3) 1.22072(15) 0.0544(8) Uani 1 1 d . . . F4 F 0.4477(6) 0.5889(3) 1.17217(16) 0.0498(7) Uani 1 1 d . . . F5 F 0.5788(5) 0.5794(2) 0.99881(16) 0.0435(7) Uani 1 1 d . . . O1 O 0.6337(5) 0.7475(3) 0.85097(17) 0.0370(7) Uani 1 1 d . . . O2 O 0.4200(6) 0.7748(3) 0.42669(17) 0.0397(7) Uani 1 1 d . . . N1 N 0.1747(6) 0.7375(3) 0.78862(19) 0.0245(7) Uani 1 1 d . . . H1A H -0.0015 0.7301 0.8006 0.029 Uiso 1 1 calc R . . C1 C 0.2328(7) 0.7404(4) 0.6943(2) 0.0238(8) Uani 1 1 d . . . C2 C 0.3929(8) 0.6458(4) 0.6600(2) 0.0272(8) Uani 1 1 d . . . C3 C 0.4576(8) 0.6561(4) 0.5695(2) 0.0285(9) Uani 1 1 d . . . H3A H 0.5682 0.5931 0.5450 0.034 Uiso 1 1 calc R . . C4 C 0.3630(8) 0.7563(4) 0.5155(2) 0.0301(9) Uani 1 1 d . . . C5 C 0.1900(8) 0.8460(4) 0.5491(2) 0.0292(9) Uani 1 1 d . . . H5A H 0.1154 0.9119 0.5101 0.035 Uiso 1 1 calc R . . C6 C 0.1249(8) 0.8400(4) 0.6397(2) 0.0267(9) Uani 1 1 d . . . C7 C 0.4927(10) 0.5330(4) 0.7160(3) 0.0400(11) Uani 1 1 d . . . H7A H 0.5263 0.4638 0.6746 0.060 Uiso 1 1 calc R . . H7B H 0.3482 0.5084 0.7551 0.060 Uiso 1 1 calc R . . H7C H 0.6686 0.5532 0.7547 0.060 Uiso 1 1 calc R . . C8 C -0.0544(9) 0.9404(4) 0.6766(3) 0.0358(10) Uani 1 1 d . . . H8A H -0.2335 0.9041 0.6906 0.054 Uiso 1 1 calc R . . H8B H -0.0925 1.0064 0.6303 0.054 Uiso 1 1 calc R . . H8C H 0.0462 0.9761 0.7328 0.054 Uiso 1 1 calc R . . C9 C 0.3814(7) 0.7459(4) 0.8591(2) 0.0237(8) Uani 1 1 d . . . C10 C 0.2879(7) 0.7524(4) 0.9539(2) 0.0225(7) Uani 1 1 d . . . C11 C 0.1076(8) 0.8433(3) 0.9816(2) 0.0251(8) Uani 1 1 d . . . C12 C 0.0425(9) 0.8482(4) 1.0704(3) 0.0312(9) Uani 1 1 d . . . C13 C 0.1539(9) 0.7633(4) 1.1343(2) 0.0350(10) Uani 1 1 d . . . C14 C 0.3373(9) 0.6723(4) 1.1092(3) 0.0326(9) Uani 1 1 d . . . C15 C 0.4017(8) 0.6685(4) 1.0207(3) 0.0300(9) Uani 1 1 d . . . C16 C 0.6230(9) 0.6947(4) 0.3922(3) 0.0367(10) Uani 1 1 d . . . H16A H 0.8029 0.7008 0.4318 0.055 Uiso 1 1 calc R . . H16B H 0.6505 0.7200 0.3294 0.055 Uiso 1 1 calc R . . H16C H 0.5551 0.6082 0.3917 0.055 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 F1 0.0400(14) 0.0332(13) 0.0275(11) -0.0004(11) 0.0028(10) 0.0072(12) F2 0.0570(17) 0.0636(18) 0.0380(14) -0.0146(15) 0.0142(12) 0.0204(16) F3 0.0684(17) 0.076(2) 0.0214(12) -0.0038(13) 0.0172(11) -0.0033(16) F4 0.0674(18) 0.0475(16) 0.0316(13) 0.0135(12) -0.0074(12) 0.0003(14) F5 0.0464(17) 0.0435(14) 0.0392(13) -0.0015(12) -0.0011(11) 0.0197(13) O1 0.0227(13) 0.0600(19) 0.0297(14) -0.0070(14) 0.0085(11) -0.0042(14) O2 0.0498(17) 0.0534(19) 0.0185(13) 0.0059(14) 0.0152(12) 0.0057(16) N1 0.0200(14) 0.0360(18) 0.0185(14) -0.0002(14) 0.0072(11) -0.0012(15) C1 0.0225(17) 0.031(2) 0.0186(17) -0.0028(17) 0.0058(13) -0.0046(18) C2 0.029(2) 0.031(2) 0.0215(19) -0.0006(17) 0.0051(15) -0.0009(18) C3 0.031(2) 0.032(2) 0.0235(19) -0.0043(17) 0.0094(16) 0.0008(18) C4 0.0329(19) 0.039(2) 0.0197(18) -0.0017(19) 0.0060(15) -0.007(2) C5 0.030(2) 0.034(2) 0.024(2) 0.0009(18) 0.0032(15) -0.0005(19) C6 0.0229(19) 0.033(2) 0.0248(19) -0.0033(18) 0.0060(15) -0.0052(18) C7 0.054(3) 0.038(2) 0.030(2) 0.004(2) 0.0154(19) 0.011(2) C8 0.037(2) 0.039(2) 0.032(2) -0.001(2) 0.0090(17) 0.002(2) C9 0.0237(18) 0.0266(19) 0.0210(17) -0.0016(16) 0.0030(13) -0.0016(17) C10 0.0192(15) 0.0283(18) 0.0205(17) -0.0043(15) 0.0043(12) -0.0009(16) C11 0.0288(19) 0.026(2) 0.0204(19) -0.0027(17) 0.0039(15) -0.0015(18) C12 0.031(2) 0.036(2) 0.028(2) -0.0083(19) 0.0077(16) 0.0004(19) C13 0.046(2) 0.042(3) 0.0178(18) -0.0044(19) 0.0068(16) -0.008(2) C14 0.038(2) 0.034(2) 0.025(2) 0.0041(18) -0.0014(16) -0.0030(19) C15 0.031(2) 0.029(2) 0.030(2) -0.0042(18) 0.0028(16) 0.0006(18) C16 0.038(2) 0.049(2) 0.025(2) -0.006(2) 0.0115(17) -0.005(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 F1 C11 1.336(4) . ? F2 C12 1.348(5) . ? F3 C13 1.341(4) . ? F4 C14 1.345(5) . ? F5 C15 1.336(4) . ? O1 C9 1.221(4) . ? O2 C4 1.370(4) . ? O2 C16 1.427(5) . ? N1 C9 1.344(4) . ? N1 C1 1.437(4) . ? C1 C6 1.393(5) . ? C1 C2 1.394(5) . ? C2 C3 1.396(5) . ? C2 C7 1.504(6) . ? C3 C4 1.376(6) . ? C4 C5 1.391(5) . ? C5 C6 1.395(5) . ? C6 C8 1.510(5) . ? C9 C10 1.505(5) . ? C10 C15 1.389(5) . ? C10 C11 1.388(5) . ? C11 C12 1.370(5) . ? C12 C13 1.366(6) . ? C13 C14 1.385(6) . ? C14 C15 1.364(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O2 C16 117.6(3) . . ? C9 N1 C1 121.9(3) . . ? C6 C1 C2 121.9(3) . . ? C6 C1 N1 117.8(3) . . ? C2 C1 N1 120.2(3) . . ? C3 C2 C1 118.2(4) . . ? C3 C2 C7 119.2(3) . . ? C1 C2 C7 122.5(3) . . ? C4 C3 C2 120.8(3) . . ? O2 C4 C3 124.7(3) . . ? O2 C4 C5 115.1(3) . . ? C3 C4 C5 120.1(3) . . ? C6 C5 C4 120.6(4) . . ? C1 C6 C5 118.1(3) . . ? C1 C6 C8 121.7(3) . . ? C5 C6 C8 120.1(4) . . ? O1 C9 N1 124.7(3) . . ? O1 C9 C10 119.2(3) . . ? N1 C9 C10 116.1(3) . . ? C15 C10 C11 116.8(3) . . ? C15 C10 C9 119.0(3) . . ? C11 C10 C9 124.0(4) . . ? F1 C11 C12 118.8(3) . . ? F1 C11 C10 119.9(3) . . ? C12 C11 C10 121.2(4) . . ? F2 C12 C13 119.3(3) . . ? F2 C12 C11 120.0(4) . . ? C13 C12 C11 120.6(4) . . ? F3 C13 C12 120.3(4) . . ? F3 C13 C14 120.1(4) . . ? C12 C13 C14 119.6(3) . . ? F4 C14 C15 121.1(4) . . ? F4 C14 C13 119.6(3) . . ? C15 C14 C13 119.3(4) . . ? F5 C15 C14 117.7(4) . . ? F5 C15 C10 119.9(3) . . ? C14 C15 C10 122.4(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 C9 N1 C1 C6 -116.2(4) . . . . ? C9 N1 C1 C2 63.7(5) . . . . ? C6 C1 C2 C3 3.4(5) . . . . ? N1 C1 C2 C3 -176.4(3) . . . . ? C6 C1 C2 C7 -175.4(4) . . . . ? N1 C1 C2 C7 4.7(6) . . . . ? C1 C2 C3 C4 -0.7(6) . . . . ? C7 C2 C3 C4 178.2(4) . . . . ? C16 O2 C4 C3 -9.2(6) . . . . ? C16 O2 C4 C5 172.6(3) . . . . ? C2 C3 C4 O2 178.9(4) . . . . ? C2 C3 C4 C5 -3.0(6) . . . . ? O2 C4 C5 C6 -177.7(3) . . . . ? C3 C4 C5 C6 4.1(6) . . . . ? C2 C1 C6 C5 -2.4(5) . . . . ? N1 C1 C6 C5 177.5(3) . . . . ? C2 C1 C6 C8 178.4(4) . . . . ? N1 C1 C6 C8 -1.7(5) . . . . ? C4 C5 C6 C1 -1.4(5) . . . . ? C4 C5 C6 C8 177.8(4) . . . . ? C1 N1 C9 O1 -5.4(6) . . . . ? C1 N1 C9 C10 175.1(4) . . . . ? O1 C9 C10 C15 -52.3(6) . . . . ? N1 C9 C10 C15 127.2(4) . . . . ? O1 C9 C10 C11 123.0(4) . . . . ? N1 C9 C10 C11 -57.5(5) . . . . ? C15 C10 C11 F1 177.0(3) . . . . ? C9 C10 C11 F1 1.7(6) . . . . ? C15 C10 C11 C12 -1.0(6) . . . . ? C9 C10 C11 C12 -176.4(4) . . . . ? F1 C11 C12 F2 1.7(6) . . . . ? C10 C11 C12 F2 179.8(4) . . . . ? F1 C11 C12 C13 -178.1(4) . . . . ? C10 C11 C12 C13 -0.1(6) . . . . ? F2 C12 C13 F3 1.3(6) . . . . ? C11 C12 C13 F3 -178.9(4) . . . . ? F2 C12 C13 C14 -178.9(4) . . . . ? C11 C12 C13 C14 0.9(6) . . . . ? F3 C13 C14 F4 -0.4(6) . . . . ? C12 C13 C14 F4 179.8(4) . . . . ? F3 C13 C14 C15 179.1(4) . . . . ? C12 C13 C14 C15 -0.6(6) . . . . ? F4 C14 C15 F5 -0.2(6) . . . . ? C13 C14 C15 F5 -179.8(4) . . . . ? F4 C14 C15 C10 179.1(4) . . . . ? C13 C14 C15 C10 -0.5(6) . . . . ? C11 C10 C15 F5 -179.4(3) . . . . ? C9 C10 C15 F5 -3.8(6) . . . . ? C11 C10 C15 C14 1.3(6) . . . . ? C9 C10 C15 C14 176.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.271 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.057 # Attachment 'OCH27A.cif' data_och27a _database_code_depnum_ccdc_archive 'CCDC 615396' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 N2 O' _chemical_formula_weight 296.40 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 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 9.181(9) _cell_length_b 19.20(2) _cell_length_c 19.68(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3468(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 25.02 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.135 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9557 _exptl_absorpt_correction_T_max 0.9724 _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 'SIEMENS P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_reflns_number 3889 _diffrn_reflns_av_R_equivalents 0.0783 _diffrn_reflns_av_sigmaI/netI 0.0930 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3059 _reflns_number_gt 1423 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0749P)^2^+0.0000P] 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 3059 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1752 _refine_ls_R_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.1921 _refine_ls_wR_factor_gt 0.1497 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.5633(3) 0.09603(13) 0.30081(12) 0.0573(7) Uani 1 1 d . . . N1 N 0.3212(3) 0.10371(14) 0.28347(14) 0.0479(8) Uani 1 1 d . . . H1 H 0.2500 0.0900 0.2584 0.057 Uiso 1 1 calc R . . N2 N 0.1695(4) 0.28772(16) 0.49642(18) 0.0676(10) Uani 1 1 d . . . C1 C 0.4542(4) 0.07936(18) 0.26861(18) 0.0452(9) Uani 1 1 d . . . C2 C 0.2882(4) 0.15095(18) 0.33804(19) 0.0453(9) Uani 1 1 d . . . C3 C 0.2524(4) 0.22081(18) 0.3231(2) 0.0509(10) Uani 1 1 d . . . C4 C 0.2137(4) 0.26468(19) 0.3766(2) 0.0568(11) Uani 1 1 d . . . H4 H 0.1907 0.3108 0.3667 0.068 Uiso 1 1 calc R . . C5 C 0.2077(4) 0.24300(19) 0.4439(2) 0.0537(10) Uani 1 1 d . . . C6 C 0.2447(4) 0.17250(19) 0.45639(19) 0.0538(10) Uani 1 1 d . . . H6 H 0.2418 0.1560 0.5008 0.065 Uiso 1 1 calc R . . C7 C 0.2850(4) 0.12733(17) 0.40505(19) 0.0455(9) Uani 1 1 d . . . C8 C 0.4606(4) 0.02814(18) 0.21045(19) 0.0495(10) Uani 1 1 d . . . C9 C 0.5009(5) -0.0417(2) 0.2244(2) 0.0666(12) Uani 1 1 d . . . C10 C 0.5062(5) -0.0881(2) 0.1700(3) 0.0877(15) Uani 1 1 d . . . H10 H 0.5311 -0.1343 0.1781 0.105 Uiso 1 1 calc R . . C11 C 0.4758(6) -0.0675(3) 0.1052(3) 0.0875(16) Uani 1 1 d . . . H11 H 0.4799 -0.0994 0.0697 0.105 Uiso 1 1 calc R . . C12 C 0.4389(5) 0.0010(3) 0.0924(2) 0.0778(14) Uani 1 1 d . . . H12 H 0.4189 0.0148 0.0481 0.093 Uiso 1 1 calc R . . C13 C 0.4310(4) 0.0495(2) 0.1440(2) 0.0567(11) Uani 1 1 d . . . C14 C 0.2523(5) 0.2475(2) 0.2518(2) 0.0768(13) Uani 1 1 d . . . H14A H 0.2216 0.2953 0.2515 0.115 Uiso 1 1 calc R . . H14B H 0.1864 0.2203 0.2248 0.115 Uiso 1 1 calc R . . H14C H 0.3487 0.2441 0.2332 0.115 Uiso 1 1 calc R . . C15 C 0.3209(4) 0.05200(17) 0.4217(2) 0.0642(12) Uani 1 1 d . . . H15A H 0.2630 0.0217 0.3938 0.096 Uiso 1 1 calc R . . H15B H 0.3001 0.0431 0.4687 0.096 Uiso 1 1 calc R . . H15C H 0.4223 0.0435 0.4131 0.096 Uiso 1 1 calc R . . C16 C 0.5369(6) -0.0650(2) 0.2953(2) 0.0948(17) Uani 1 1 d . . . H16A H 0.5521 -0.1144 0.2956 0.142 Uiso 1 1 calc R . . H16B H 0.4577 -0.0535 0.3251 0.142 Uiso 1 1 calc R . . H16C H 0.6238 -0.0419 0.3104 0.142 Uiso 1 1 calc R . . C17 C 0.3958(4) 0.1245(2) 0.1268(2) 0.0709(13) Uani 1 1 d . . . H17A H 0.4083 0.1318 0.0789 0.106 Uiso 1 1 calc R . . H17B H 0.4601 0.1548 0.1514 0.106 Uiso 1 1 calc R . . H17C H 0.2969 0.1344 0.1392 0.106 Uiso 1 1 calc R . . C18 C 0.1236(5) 0.2596(2) 0.5602(2) 0.0798(14) Uani 1 1 d . . . H18A H 0.0408 0.2299 0.5532 0.120 Uiso 1 1 calc R . . H18B H 0.0973 0.2969 0.5902 0.120 Uiso 1 1 calc R . . H18C H 0.2016 0.2332 0.5799 0.120 Uiso 1 1 calc R . . C19 C 0.1267(5) 0.3583(2) 0.4801(2) 0.0818(14) Uani 1 1 d . . . H19A H 0.2018 0.3801 0.4537 0.123 Uiso 1 1 calc R . . H19B H 0.1120 0.3841 0.5213 0.123 Uiso 1 1 calc R . . H19C H 0.0378 0.3575 0.4544 0.123 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 0.0334(14) 0.0744(18) 0.0642(17) -0.0085(15) -0.0033(13) -0.0024(13) N1 0.0321(16) 0.0525(18) 0.059(2) -0.0092(16) -0.0012(15) -0.0015(14) N2 0.090(3) 0.0509(19) 0.062(2) -0.0109(19) 0.011(2) 0.0069(19) C1 0.035(2) 0.049(2) 0.052(2) 0.0041(19) 0.003(2) -0.0027(19) C2 0.034(2) 0.047(2) 0.056(3) -0.008(2) -0.0003(18) -0.0026(18) C3 0.046(2) 0.050(2) 0.056(3) 0.003(2) 0.002(2) -0.0020(19) C4 0.057(3) 0.043(2) 0.071(3) -0.001(2) 0.006(2) 0.004(2) C5 0.052(2) 0.049(2) 0.059(3) -0.004(2) 0.003(2) 0.001(2) C6 0.052(2) 0.060(3) 0.050(2) -0.001(2) -0.001(2) -0.001(2) C7 0.039(2) 0.047(2) 0.050(2) -0.003(2) -0.0003(19) -0.0033(18) C8 0.036(2) 0.049(2) 0.064(3) -0.012(2) 0.007(2) -0.0036(18) C9 0.070(3) 0.052(3) 0.078(3) -0.005(3) 0.011(3) -0.001(2) C10 0.100(4) 0.055(3) 0.108(4) -0.022(3) 0.030(3) -0.006(3) C11 0.089(4) 0.087(4) 0.086(4) -0.031(3) 0.023(3) -0.014(3) C12 0.068(3) 0.096(4) 0.069(3) -0.015(3) 0.004(3) -0.002(3) C13 0.042(2) 0.076(3) 0.052(3) -0.013(2) 0.009(2) -0.005(2) C14 0.094(4) 0.059(2) 0.077(3) 0.006(2) 0.010(3) 0.005(3) C15 0.069(3) 0.048(2) 0.076(3) 0.007(2) 0.000(2) 0.007(2) C16 0.122(4) 0.057(3) 0.106(4) 0.011(3) 0.021(4) 0.020(3) C17 0.062(3) 0.092(3) 0.059(3) 0.010(3) 0.005(2) 0.009(3) C18 0.098(4) 0.070(3) 0.071(3) -0.016(3) 0.018(3) 0.001(3) C19 0.093(3) 0.056(3) 0.097(4) -0.012(3) 0.015(3) 0.013(3) _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 C1 1.228(4) . ? N1 C1 1.340(4) . ? N1 C2 1.438(4) . ? N2 C5 1.389(5) . ? N2 C18 1.429(5) . ? N2 C19 1.447(5) . ? C1 C8 1.510(5) . ? C2 C7 1.395(5) . ? C2 C3 1.412(5) . ? C3 C4 1.394(5) . ? C3 C14 1.494(5) . ? C4 C5 1.390(5) . ? C5 C6 1.417(5) . ? C6 C7 1.382(5) . ? C7 C15 1.519(5) . ? C8 C13 1.397(5) . ? C8 C9 1.417(5) . ? C9 C10 1.394(6) . ? C9 C16 1.501(6) . ? C10 C11 1.365(6) . ? C11 C12 1.381(6) . ? C12 C13 1.379(5) . ? C13 C17 1.513(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 125.1(3) . . ? C5 N2 C18 119.6(3) . . ? C5 N2 C19 118.8(4) . . ? C18 N2 C19 117.9(3) . . ? O1 C1 N1 122.7(3) . . ? O1 C1 C8 121.9(3) . . ? N1 C1 C8 115.4(3) . . ? C7 C2 C3 120.0(3) . . ? C7 C2 N1 120.4(3) . . ? C3 C2 N1 119.5(3) . . ? C4 C3 C2 118.4(4) . . ? C4 C3 C14 120.1(3) . . ? C2 C3 C14 121.4(3) . . ? C3 C4 C5 123.3(4) . . ? N2 C5 C4 122.3(4) . . ? N2 C5 C6 121.4(4) . . ? C4 C5 C6 116.3(4) . . ? C7 C6 C5 122.4(4) . . ? C6 C7 C2 119.5(3) . . ? C6 C7 C15 119.8(4) . . ? C2 C7 C15 120.6(3) . . ? C13 C8 C9 120.7(4) . . ? C13 C8 C1 120.7(3) . . ? C9 C8 C1 118.6(4) . . ? C10 C9 C8 117.7(4) . . ? C10 C9 C16 121.0(4) . . ? C8 C9 C16 121.3(4) . . ? C11 C10 C9 121.7(5) . . ? C10 C11 C12 119.7(5) . . ? C13 C12 C11 121.5(5) . . ? C12 C13 C8 118.7(4) . . ? C12 C13 C17 119.2(4) . . ? C8 C13 C17 122.0(4) . . ? 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 C2 N1 C1 O1 -0.6(5) . . . . ? C2 N1 C1 C8 177.8(3) . . . . ? C1 N1 C2 C7 -75.4(5) . . . . ? C1 N1 C2 C3 107.6(4) . . . . ? C7 C2 C3 C4 -0.2(5) . . . . ? N1 C2 C3 C4 176.8(3) . . . . ? C7 C2 C3 C14 -178.9(3) . . . . ? N1 C2 C3 C14 -1.9(5) . . . . ? C2 C3 C4 C5 -0.4(6) . . . . ? C14 C3 C4 C5 178.3(4) . . . . ? C18 N2 C5 C4 161.6(4) . . . . ? C19 N2 C5 C4 3.5(6) . . . . ? C18 N2 C5 C6 -19.2(6) . . . . ? C19 N2 C5 C6 -177.3(4) . . . . ? C3 C4 C5 N2 179.7(4) . . . . ? C3 C4 C5 C6 0.5(6) . . . . ? N2 C5 C6 C7 -179.1(3) . . . . ? C4 C5 C6 C7 0.1(5) . . . . ? C5 C6 C7 C2 -0.8(5) . . . . ? C5 C6 C7 C15 -179.0(3) . . . . ? C3 C2 C7 C6 0.8(5) . . . . ? N1 C2 C7 C6 -176.2(3) . . . . ? C3 C2 C7 C15 179.0(3) . . . . ? N1 C2 C7 C15 2.0(5) . . . . ? O1 C1 C8 C13 -113.9(4) . . . . ? N1 C1 C8 C13 67.8(4) . . . . ? O1 C1 C8 C9 64.6(5) . . . . ? N1 C1 C8 C9 -113.8(4) . . . . ? C13 C8 C9 C10 -1.5(6) . . . . ? C1 C8 C9 C10 -180.0(4) . . . . ? C13 C8 C9 C16 178.4(4) . . . . ? C1 C8 C9 C16 -0.1(6) . . . . ? C8 C9 C10 C11 0.8(7) . . . . ? C16 C9 C10 C11 -179.0(5) . . . . ? C9 C10 C11 C12 0.1(7) . . . . ? C10 C11 C12 C13 -0.4(7) . . . . ? C11 C12 C13 C8 -0.3(6) . . . . ? C11 C12 C13 C17 177.6(4) . . . . ? C9 C8 C13 C12 1.3(6) . . . . ? C1 C8 C13 C12 179.7(3) . . . . ? C9 C8 C13 C17 -176.5(4) . . . . ? C1 C8 C13 C17 1.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.203 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.044 # Attachment 'OCH45.cif' data_och45 _database_code_depnum_ccdc_archive 'CCDC 615397' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N2 O3' _chemical_formula_weight 298.33 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 22.145(3) _cell_length_b 4.8085(6) _cell_length_c 14.6170(18) _cell_angle_alpha 90.00 _cell_angle_beta 95.725(3) _cell_angle_gamma 90.00 _cell_volume 1548.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 0.92 _cell_measurement_theta_max 28.32 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9739 _exptl_absorpt_correction_T_max 0.9991 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9629 _diffrn_reflns_av_R_equivalents 0.1267 _diffrn_reflns_av_sigmaI/netI 0.2176 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 0.92 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3691 _reflns_number_gt 1134 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0753P)^2^+0.0000P] 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 3691 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2274 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1910 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 0.794 _refine_ls_restrained_S_all 0.794 _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 N1 N -0.24031(13) 0.5520(6) 0.41341(19) 0.0338(8) Uani 1 1 d . . . H1 H -0.2504 0.7227 0.4206 0.041 Uiso 1 1 calc R . . N2 N 0.00575(15) 0.3907(8) 0.3631(2) 0.0450(9) Uani 1 1 d . . . O1 O -0.27469(11) 0.1100(5) 0.41202(19) 0.0501(8) Uani 1 1 d . . . O2 O 0.03440(12) 0.2024(7) 0.4047(2) 0.0598(9) Uani 1 1 d . . . O3 O 0.02848(12) 0.5562(6) 0.3126(2) 0.0512(8) Uani 1 1 d . . . C1 C -0.28419(16) 0.3606(8) 0.4141(3) 0.0355(9) Uani 1 1 d . . . C2 C -0.17844(15) 0.4973(7) 0.4018(2) 0.0299(9) Uani 1 1 d . . . C3 C -0.14220(16) 0.3330(7) 0.4648(3) 0.0341(9) Uani 1 1 d . . . C4 C -0.08163(16) 0.2924(8) 0.4491(3) 0.0362(10) Uani 1 1 d . . . H4 H -0.0567 0.1788 0.4880 0.043 Uiso 1 1 calc R . . C5 C -0.05912(16) 0.4214(8) 0.3757(3) 0.0357(10) Uani 1 1 d . . . C6 C -0.09431(16) 0.5841(8) 0.3145(3) 0.0380(10) Uani 1 1 d . . . H6 H -0.0774 0.6695 0.2659 0.046 Uiso 1 1 calc R . . C7 C -0.15511(16) 0.6202(7) 0.3256(3) 0.0339(9) Uani 1 1 d . . . C8 C -0.34770(16) 0.4730(7) 0.4160(3) 0.0361(10) Uani 1 1 d . . . C9 C -0.38935(17) 0.4137(8) 0.3396(3) 0.0421(10) Uani 1 1 d . . . C10 C -0.44810(18) 0.5182(9) 0.3376(3) 0.0581(13) Uani 1 1 d . . . H10 H -0.4763 0.4817 0.2875 0.070 Uiso 1 1 calc R . . C11 C -0.46427(19) 0.6753(11) 0.4096(4) 0.0691(15) Uani 1 1 d . . . H11 H -0.5033 0.7476 0.4073 0.083 Uiso 1 1 calc R . . C12 C -0.4241(2) 0.7269(10) 0.4843(4) 0.0675(14) Uani 1 1 d . . . H12 H -0.4365 0.8295 0.5331 0.081 Uiso 1 1 calc R . . C13 C -0.36474(17) 0.6287(8) 0.4890(3) 0.0437(11) Uani 1 1 d . . . C14 C -0.16483(16) 0.2066(8) 0.5487(3) 0.0443(11) Uani 1 1 d . . . H14A H -0.1971 0.3185 0.5681 0.066 Uiso 1 1 calc R . . H14B H -0.1323 0.1981 0.5972 0.066 Uiso 1 1 calc R . . H14C H -0.1796 0.0222 0.5347 0.066 Uiso 1 1 calc R . . C15 C -0.19477(18) 0.7900(9) 0.2567(3) 0.0525(12) Uani 1 1 d . . . H15A H -0.2075 0.9561 0.2858 0.079 Uiso 1 1 calc R . . H15B H -0.2298 0.6830 0.2344 0.079 Uiso 1 1 calc R . . H15C H -0.1723 0.8390 0.2063 0.079 Uiso 1 1 calc R . . C16 C -0.37307(18) 0.2368(9) 0.2608(3) 0.0576(12) Uani 1 1 d . . . H16A H -0.3727 0.0446 0.2787 0.086 Uiso 1 1 calc R . . H16B H -0.3336 0.2887 0.2448 0.086 Uiso 1 1 calc R . . H16C H -0.4025 0.2641 0.2088 0.086 Uiso 1 1 calc R . . C17 C -0.32144(18) 0.6897(9) 0.5730(3) 0.0557(12) Uani 1 1 d . . . H17A H -0.2971 0.5282 0.5887 0.084 Uiso 1 1 calc R . . H17B H -0.3441 0.7374 0.6234 0.084 Uiso 1 1 calc R . . H17C H -0.2956 0.8423 0.5602 0.084 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 N1 0.0323(18) 0.0234(18) 0.046(2) -0.0032(15) 0.0050(15) 0.0043(14) N2 0.036(2) 0.052(2) 0.048(2) -0.010(2) 0.0046(17) 0.0061(19) O1 0.0464(18) 0.0233(16) 0.080(2) 0.0007(15) 0.0016(15) 0.0034(13) O2 0.0430(18) 0.072(2) 0.065(2) 0.0142(18) 0.0075(15) 0.0217(16) O3 0.0397(17) 0.0500(19) 0.066(2) 0.0024(16) 0.0169(15) -0.0049(14) C1 0.038(2) 0.031(2) 0.037(2) 0.0010(19) 0.0026(18) -0.001(2) C2 0.029(2) 0.026(2) 0.035(2) -0.0037(18) 0.0026(18) -0.0009(17) C3 0.037(2) 0.033(2) 0.033(2) -0.0019(19) 0.0046(19) 0.0040(18) C4 0.036(2) 0.034(2) 0.038(2) 0.0021(19) 0.0011(18) 0.0073(18) C5 0.029(2) 0.037(2) 0.041(3) -0.006(2) 0.0027(19) 0.0036(18) C6 0.037(2) 0.038(2) 0.041(2) 0.002(2) 0.0093(19) 0.0021(19) C7 0.035(2) 0.028(2) 0.039(2) 0.0010(19) 0.0034(18) 0.0029(18) C8 0.031(2) 0.031(2) 0.047(3) -0.001(2) 0.0077(19) 0.0016(18) C9 0.035(2) 0.032(2) 0.059(3) 0.002(2) 0.002(2) -0.0053(19) C10 0.038(3) 0.053(3) 0.081(4) -0.002(3) -0.007(2) -0.002(2) C11 0.030(3) 0.083(4) 0.094(4) -0.018(3) 0.003(3) 0.010(2) C12 0.044(3) 0.081(4) 0.079(4) -0.025(3) 0.015(3) 0.007(3) C13 0.037(2) 0.046(3) 0.048(3) -0.001(2) 0.006(2) 0.001(2) C14 0.043(2) 0.049(3) 0.041(3) 0.003(2) 0.0047(19) 0.008(2) C15 0.049(3) 0.060(3) 0.050(3) 0.017(2) 0.012(2) 0.008(2) C16 0.055(3) 0.058(3) 0.057(3) -0.010(3) -0.004(2) 0.001(2) C17 0.055(3) 0.067(3) 0.048(3) -0.005(2) 0.016(2) 0.002(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 N1 C1 1.339(4) . ? N1 C2 1.422(4) . ? N2 O3 1.227(4) . ? N2 O2 1.231(4) . ? N2 C5 1.474(4) . ? O1 C1 1.224(4) . ? C1 C8 1.510(5) . ? C2 C3 1.403(5) . ? C2 C7 1.405(5) . ? C3 C4 1.397(5) . ? C3 C14 1.500(5) . ? C4 C5 1.375(5) . ? C5 C6 1.372(5) . ? C6 C7 1.383(5) . ? C7 C15 1.508(5) . ? C8 C13 1.387(5) . ? C8 C9 1.405(5) . ? C9 C10 1.392(5) . ? C9 C16 1.504(5) . ? C10 C11 1.372(6) . ? C11 C12 1.361(6) . ? C12 C13 1.392(5) . ? C13 C17 1.509(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 125.6(3) . . ? O3 N2 O2 123.5(3) . . ? O3 N2 C5 118.3(3) . . ? O2 N2 C5 118.2(4) . . ? O1 C1 N1 123.4(3) . . ? O1 C1 C8 121.0(3) . . ? N1 C1 C8 115.6(3) . . ? C3 C2 C7 121.7(3) . . ? C3 C2 N1 121.4(3) . . ? C7 C2 N1 116.9(3) . . ? C4 C3 C2 117.8(3) . . ? C4 C3 C14 118.8(3) . . ? C2 C3 C14 123.3(3) . . ? C5 C4 C3 119.6(3) . . ? C6 C5 C4 122.7(3) . . ? C6 C5 N2 118.2(4) . . ? C4 C5 N2 119.1(3) . . ? C5 C6 C7 119.4(4) . . ? C6 C7 C2 118.7(3) . . ? C6 C7 C15 119.9(3) . . ? C2 C7 C15 121.4(3) . . ? C13 C8 C9 120.9(4) . . ? C13 C8 C1 122.2(4) . . ? C9 C8 C1 116.9(3) . . ? C10 C9 C8 118.8(4) . . ? C10 C9 C16 118.9(4) . . ? C8 C9 C16 122.3(3) . . ? C11 C10 C9 119.8(4) . . ? C12 C11 C10 121.1(4) . . ? C11 C12 C13 121.0(4) . . ? C8 C13 C12 118.3(4) . . ? C8 C13 C17 122.1(3) . . ? C12 C13 C17 119.6(4) . . ? 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 C2 N1 C1 O1 6.1(6) . . . . ? C2 N1 C1 C8 -172.9(3) . . . . ? C1 N1 C2 C3 -61.8(5) . . . . ? C1 N1 C2 C7 119.4(4) . . . . ? C7 C2 C3 C4 -0.5(5) . . . . ? N1 C2 C3 C4 -179.1(3) . . . . ? C7 C2 C3 C14 177.8(3) . . . . ? N1 C2 C3 C14 -0.9(5) . . . . ? C2 C3 C4 C5 2.5(5) . . . . ? C14 C3 C4 C5 -175.9(3) . . . . ? C3 C4 C5 C6 -2.0(6) . . . . ? C3 C4 C5 N2 176.3(3) . . . . ? O3 N2 C5 C6 15.9(5) . . . . ? O2 N2 C5 C6 -164.9(3) . . . . ? O3 N2 C5 C4 -162.5(3) . . . . ? O2 N2 C5 C4 16.6(5) . . . . ? C4 C5 C6 C7 -0.6(6) . . . . ? N2 C5 C6 C7 -178.9(3) . . . . ? C5 C6 C7 C2 2.6(5) . . . . ? C5 C6 C7 C15 -177.8(3) . . . . ? C3 C2 C7 C6 -2.0(5) . . . . ? N1 C2 C7 C6 176.7(3) . . . . ? C3 C2 C7 C15 178.3(3) . . . . ? N1 C2 C7 C15 -3.0(5) . . . . ? O1 C1 C8 C13 117.6(4) . . . . ? N1 C1 C8 C13 -63.4(5) . . . . ? O1 C1 C8 C9 -62.6(5) . . . . ? N1 C1 C8 C9 116.4(4) . . . . ? C13 C8 C9 C10 1.1(6) . . . . ? C1 C8 C9 C10 -178.7(3) . . . . ? C13 C8 C9 C16 -177.7(4) . . . . ? C1 C8 C9 C16 2.6(5) . . . . ? C8 C9 C10 C11 -0.2(6) . . . . ? C16 C9 C10 C11 178.6(4) . . . . ? C9 C10 C11 C12 -1.3(7) . . . . ? C10 C11 C12 C13 1.8(8) . . . . ? C9 C8 C13 C12 -0.6(6) . . . . ? C1 C8 C13 C12 179.2(4) . . . . ? C9 C8 C13 C17 178.5(4) . . . . ? C1 C8 C13 C17 -1.8(6) . . . . ? C11 C12 C13 C8 -0.9(7) . . . . ? C11 C12 C13 C17 -180.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.220 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.073 data_hazel3m _database_code_depnum_ccdc_archive 'CCDC 615398' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Centre for Chemical Biology Department of Chemistry Krebs Institute for Biomolecular Science University of Sheffield Sheffield S3 7HF UK ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 N4 O6' _chemical_formula_weight 462.46 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 15.0670(17) _cell_length_b 12.8503(14) _cell_length_c 15.5065(17) _cell_angle_alpha 90.00 _cell_angle_beta 105.241(2) _cell_angle_gamma 90.00 _cell_volume 2896.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7229 _cell_measurement_theta_min 4.604 _cell_measurement_theta_max 53.113 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.060 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9681 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 32125 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.56 _reflns_number_total 6616 _reflns_number_gt 4462 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.0000P] 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 6616 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1335 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.62609(8) 0.40229(8) 0.37637(8) 0.0360(3) Uani 1 1 d . . . O2 O 0.97889(13) 0.41441(14) 0.73170(12) 0.0769(6) Uani 1 1 d . . . O3 O 1.05235(10) 0.52591(16) 0.67235(12) 0.0745(5) Uani 1 1 d . . . O4 O 0.37499(8) 0.29380(8) 0.11856(8) 0.0313(3) Uani 1 1 d . . . O5 O 0.21696(10) 0.08397(10) -0.29878(9) 0.0453(4) Uani 1 1 d . . . O6 O 0.08252(9) 0.14058(11) -0.29676(9) 0.0471(4) Uani 1 1 d . . . N1 N 0.65536(9) 0.57199(9) 0.41423(9) 0.0247(3) Uani 1 1 d . . . H1A H 0.6370 0.6370 0.4048 0.030 Uiso 1 1 calc R . . N2 N 0.98215(13) 0.48056(15) 0.67553(12) 0.0516(5) Uani 1 1 d . . . N3 N 0.32780(9) 0.41596(10) 0.01090(9) 0.0281(3) Uani 1 1 d . . . H3A H 0.3261 0.4827 -0.0022 0.034 Uiso 1 1 calc R . . N4 N 0.16643(11) 0.14075(11) -0.26897(9) 0.0346(4) Uani 1 1 d . . . C1 C 0.48202(11) 0.44891(11) 0.23044(11) 0.0242(3) Uani 1 1 d . . . H1B H 0.5066 0.3804 0.2370 0.029 Uiso 1 1 calc R . . C2 C 0.40586(10) 0.47137(11) 0.16032(10) 0.0226(3) Uani 1 1 d . . . C3 C 0.36758(11) 0.57057(11) 0.15317(11) 0.0254(4) Uani 1 1 d . . . H3B H 0.3144 0.5860 0.1064 0.030 Uiso 1 1 calc R . . C4 C 0.40684(11) 0.64634(11) 0.21397(11) 0.0260(4) Uani 1 1 d . . . H4A H 0.3803 0.7139 0.2087 0.031 Uiso 1 1 calc R . . C5 C 0.48425(11) 0.62567(12) 0.28261(11) 0.0261(4) Uani 1 1 d . . . H5A H 0.5111 0.6790 0.3236 0.031 Uiso 1 1 calc R . . C6 C 0.52284(10) 0.52616(11) 0.29148(10) 0.0235(3) Uani 1 1 d . . . C7 C 0.60501(11) 0.49555(12) 0.36394(11) 0.0254(4) Uani 1 1 d . . . C8 C 0.73736(10) 0.54955(11) 0.48196(10) 0.0228(3) Uani 1 1 d . . . C9 C 0.73278(11) 0.49033(12) 0.55670(11) 0.0282(4) Uani 1 1 d . . . C10 C 0.81506(13) 0.46729(13) 0.61950(11) 0.0329(4) Uani 1 1 d . . . H10A H 0.8149 0.4255 0.6700 0.039 Uiso 1 1 calc R . . C11 C 0.89642(12) 0.50511(14) 0.60819(12) 0.0344(4) Uani 1 1 d . . . C12 C 0.90054(11) 0.56627(13) 0.53701(12) 0.0325(4) Uani 1 1 d . . . H12A H 0.9580 0.5925 0.5322 0.039 Uiso 1 1 calc R . . C13 C 0.82055(11) 0.58970(12) 0.47198(11) 0.0264(4) Uani 1 1 d . . . C14 C 0.64320(13) 0.45560(15) 0.57192(13) 0.0407(5) Uani 1 1 d . . . H14A H 0.5951 0.5061 0.5452 0.061 Uiso 1 1 calc R . . H14B H 0.6492 0.4507 0.6363 0.061 Uiso 1 1 calc R . . H14C H 0.6267 0.3873 0.5442 0.061 Uiso 1 1 calc R . . C15 C 0.82286(13) 0.65497(14) 0.39275(13) 0.0363(4) Uani 1 1 d . . . H15A H 0.7833 0.7160 0.3905 0.054 Uiso 1 1 calc R . . H15B H 0.8007 0.6140 0.3380 0.054 Uiso 1 1 calc R . . H15C H 0.8861 0.6777 0.3978 0.054 Uiso 1 1 calc R . . C16 C 0.36767(10) 0.38613(12) 0.09500(11) 0.0242(3) Uani 1 1 d . . . C17 C 0.28772(11) 0.34296(11) -0.05860(10) 0.0251(4) Uani 1 1 d . . . C18 C 0.34455(11) 0.28072(13) -0.09481(11) 0.0296(4) Uani 1 1 d . . . C19 C 0.30392(12) 0.21447(12) -0.16488(11) 0.0292(4) Uani 1 1 d . . . H19A H 0.3408 0.1718 -0.1917 0.035 Uiso 1 1 calc R . . C20 C 0.20950(12) 0.21161(12) -0.19484(10) 0.0279(4) Uani 1 1 d . . . C21 C 0.15265(12) 0.27370(12) -0.15999(11) 0.0291(4) Uani 1 1 d . . . H21A H 0.0878 0.2702 -0.1832 0.035 Uiso 1 1 calc R . . C22 C 0.19203(11) 0.34170(12) -0.09011(11) 0.0278(4) Uani 1 1 d . . . C23 C 0.44780(12) 0.28536(16) -0.06147(14) 0.0446(5) Uani 1 1 d . . . H23A H 0.4682 0.3577 -0.0617 0.067 Uiso 1 1 calc R . . H23B H 0.4754 0.2436 -0.1006 0.067 Uiso 1 1 calc R . . H23C H 0.4670 0.2578 -0.0005 0.067 Uiso 1 1 calc R . . C24 C 0.13247(13) 0.41086(15) -0.05128(13) 0.0405(5) Uani 1 1 d . . . H24A H 0.1427 0.3954 0.0125 0.061 Uiso 1 1 calc R . . H24B H 0.0677 0.3987 -0.0822 0.061 Uiso 1 1 calc R . . H24C H 0.1480 0.4838 -0.0587 0.061 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 0.0377(7) 0.0192(6) 0.0390(7) 0.0014(5) -0.0111(5) 0.0025(5) O2 0.0784(12) 0.0734(11) 0.0571(11) 0.0125(9) -0.0205(9) 0.0292(9) O3 0.0287(8) 0.1107(15) 0.0697(12) -0.0129(11) -0.0127(8) 0.0127(9) O4 0.0357(6) 0.0175(5) 0.0331(7) 0.0001(5) -0.0045(5) 0.0000(5) O5 0.0610(9) 0.0400(7) 0.0365(8) -0.0134(6) 0.0157(7) -0.0058(7) O6 0.0395(8) 0.0516(8) 0.0412(8) -0.0109(6) -0.0054(6) -0.0089(6) N1 0.0263(7) 0.0170(6) 0.0252(7) 0.0010(5) -0.0032(6) 0.0009(5) N2 0.0439(11) 0.0568(11) 0.0421(10) -0.0090(9) -0.0100(8) 0.0223(9) N3 0.0343(8) 0.0182(6) 0.0268(7) 0.0008(5) -0.0005(6) -0.0016(6) N4 0.0487(10) 0.0297(8) 0.0227(8) -0.0004(6) 0.0048(7) -0.0087(7) C1 0.0260(8) 0.0163(7) 0.0270(9) 0.0015(6) 0.0013(7) 0.0007(6) C2 0.0233(8) 0.0188(7) 0.0235(8) 0.0010(6) 0.0020(6) -0.0022(6) C3 0.0239(8) 0.0231(8) 0.0257(8) 0.0025(6) 0.0004(7) 0.0033(6) C4 0.0291(9) 0.0176(7) 0.0293(9) 0.0013(6) 0.0039(7) 0.0034(6) C5 0.0288(9) 0.0196(7) 0.0273(9) -0.0016(6) 0.0028(7) -0.0029(6) C6 0.0228(8) 0.0193(7) 0.0257(8) 0.0030(6) 0.0016(6) -0.0011(6) C7 0.0279(8) 0.0205(8) 0.0247(8) 0.0003(6) 0.0015(7) -0.0011(6) C8 0.0233(8) 0.0207(7) 0.0202(8) -0.0030(6) -0.0016(6) 0.0010(6) C9 0.0351(9) 0.0215(8) 0.0261(9) 0.0010(6) 0.0048(7) 0.0012(7) C10 0.0467(11) 0.0251(8) 0.0222(9) 0.0010(7) 0.0007(8) 0.0077(7) C11 0.0303(9) 0.0343(9) 0.0304(10) -0.0093(7) -0.0063(8) 0.0134(7) C12 0.0238(8) 0.0323(9) 0.0377(10) -0.0074(8) 0.0017(7) 0.0006(7) C13 0.0282(8) 0.0208(8) 0.0285(9) -0.0032(6) 0.0046(7) 0.0008(6) C14 0.0416(11) 0.0453(11) 0.0366(10) 0.0095(9) 0.0127(9) -0.0052(9) C15 0.0347(10) 0.0319(9) 0.0450(11) 0.0059(8) 0.0152(8) -0.0035(7) C16 0.0217(8) 0.0207(8) 0.0265(8) 0.0011(6) -0.0002(6) -0.0002(6) C17 0.0338(9) 0.0184(7) 0.0200(8) 0.0021(6) 0.0013(7) -0.0019(6) C18 0.0299(9) 0.0297(9) 0.0281(9) 0.0018(7) 0.0056(7) -0.0020(7) C19 0.0375(10) 0.0258(8) 0.0251(9) 0.0015(7) 0.0096(7) 0.0012(7) C20 0.0387(10) 0.0230(8) 0.0189(8) 0.0010(6) 0.0020(7) -0.0039(7) C21 0.0300(9) 0.0281(8) 0.0250(9) 0.0030(7) -0.0001(7) -0.0001(7) C22 0.0302(9) 0.0240(8) 0.0255(9) 0.0027(6) 0.0007(7) 0.0033(7) C23 0.0334(10) 0.0535(12) 0.0470(12) -0.0127(10) 0.0106(9) -0.0080(9) C24 0.0341(10) 0.0440(11) 0.0387(11) -0.0076(9) 0.0011(8) 0.0106(8) _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 1.2418(18) . ? O2 N2 1.227(3) . ? O3 N2 1.220(2) . ? O4 C16 1.2377(18) . ? O5 N4 1.2290(19) . ? O6 N4 1.2237(19) . ? N1 C7 1.3555(19) . ? N1 C8 1.4250(19) . ? N1 H1A 0.8800 . ? N2 C11 1.466(2) . ? N3 C16 1.340(2) . ? N3 C17 1.4366(19) . ? N3 H3A 0.8800 . ? N4 C20 1.476(2) . ? C1 C2 1.388(2) . ? C1 C6 1.398(2) . ? C1 H1B 0.9500 . ? C2 C3 1.392(2) . ? C2 C16 1.500(2) . ? C3 C4 1.376(2) . ? C3 H3B 0.9500 . ? C4 C5 1.382(2) . ? C4 H4A 0.9500 . ? C5 C6 1.397(2) . ? C5 H5A 0.9500 . ? C6 C7 1.489(2) . ? C8 C13 1.401(2) . ? C8 C9 1.403(2) . ? C9 C10 1.392(2) . ? C9 C14 1.498(2) . ? C10 C11 1.372(3) . ? C10 H10A 0.9500 . ? C11 C12 1.370(3) . ? C12 C13 1.386(2) . ? C12 H12A 0.9500 . ? C13 C15 1.495(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 C18 1.393(2) . ? C17 C22 1.395(2) . ? C18 C19 1.389(2) . ? C18 C23 1.506(2) . ? C19 C20 1.376(2) . ? C19 H19A 0.9500 . ? C20 C21 1.380(2) . ? C21 C22 1.397(2) . ? C21 H21A 0.9500 . ? C22 C24 1.497(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 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 C7 N1 C8 121.54(12) . . ? C7 N1 H1A 119.2 . . ? C8 N1 H1A 119.2 . . ? O3 N2 O2 123.82(18) . . ? O3 N2 C11 118.64(19) . . ? O2 N2 C11 117.54(19) . . ? C16 N3 C17 122.39(13) . . ? C16 N3 H3A 118.8 . . ? C17 N3 H3A 118.8 . . ? O6 N4 O5 123.46(15) . . ? O6 N4 C20 118.50(15) . . ? O5 N4 C20 118.03(15) . . ? C2 C1 C6 120.59(14) . . ? C2 C1 H1B 119.7 . . ? C6 C1 H1B 119.7 . . ? C1 C2 C3 119.53(14) . . ? C1 C2 C16 117.94(13) . . ? C3 C2 C16 122.53(13) . . ? C4 C3 C2 119.94(14) . . ? C4 C3 H3B 120.0 . . ? C2 C3 H3B 120.0 . . ? C3 C4 C5 121.02(14) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C4 C5 C6 119.80(14) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? C5 C6 C1 119.07(14) . . ? C5 C6 C7 123.92(14) . . ? C1 C6 C7 116.99(13) . . ? O1 C7 N1 121.90(14) . . ? O1 C7 C6 119.99(13) . . ? N1 C7 C6 118.10(13) . . ? C13 C8 C9 122.05(14) . . ? C13 C8 N1 118.14(14) . . ? C9 C8 N1 119.80(14) . . ? C10 C9 C8 117.71(16) . . ? C10 C9 C14 119.99(16) . . ? C8 C9 C14 122.26(15) . . ? C11 C10 C9 119.76(16) . . ? C11 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? C12 C11 C10 122.51(15) . . ? C12 C11 N2 118.65(18) . . ? C10 C11 N2 118.83(18) . . ? C11 C12 C13 119.74(16) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C12 C13 C8 118.14(15) . . ? C12 C13 C15 121.07(16) . . ? C8 C13 C15 120.79(14) . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C16 N3 122.93(14) . . ? O4 C16 C2 120.80(14) . . ? N3 C16 C2 116.26(13) . . ? C18 C17 C22 122.68(14) . . ? C18 C17 N3 119.70(14) . . ? C22 C17 N3 117.53(14) . . ? C19 C18 C17 118.42(15) . . ? C19 C18 C23 119.72(16) . . ? C17 C18 C23 121.85(15) . . ? C20 C19 C18 118.96(16) . . ? C20 C19 H19A 120.5 . . ? C18 C19 H19A 120.5 . . ? C19 C20 C21 123.04(15) . . ? C19 C20 N4 118.89(15) . . ? C21 C20 N4 118.06(15) . . ? C20 C21 C22 118.97(15) . . ? C20 C21 H21A 120.5 . . ? C22 C21 H21A 120.5 . . ? C17 C22 C21 117.91(15) . . ? C17 C22 C24 121.70(15) . . ? C21 C22 C24 120.39(15) . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 C6 C1 C2 C3 -2.8(2) . . . . ? C6 C1 C2 C16 177.54(15) . . . . ? C1 C2 C3 C4 1.8(2) . . . . ? C16 C2 C3 C4 -178.55(15) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C4 C5 C6 C1 -0.1(2) . . . . ? C4 C5 C6 C7 -178.85(15) . . . . ? C2 C1 C6 C5 2.0(2) . . . . ? C2 C1 C6 C7 -179.23(15) . . . . ? C8 N1 C7 O1 2.5(3) . . . . ? C8 N1 C7 C6 -176.94(14) . . . . ? C5 C6 C7 O1 167.97(16) . . . . ? C1 C6 C7 O1 -10.8(2) . . . . ? C5 C6 C7 N1 -12.6(2) . . . . ? C1 C6 C7 N1 168.62(15) . . . . ? C7 N1 C8 C13 116.74(17) . . . . ? C7 N1 C8 C9 -64.4(2) . . . . ? C13 C8 C9 C10 -3.4(2) . . . . ? N1 C8 C9 C10 177.76(14) . . . . ? C13 C8 C9 C14 174.20(16) . . . . ? N1 C8 C9 C14 -4.6(2) . . . . ? C8 C9 C10 C11 2.0(2) . . . . ? C14 C9 C10 C11 -175.71(16) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C9 C10 C11 N2 179.52(15) . . . . ? O3 N2 C11 C12 9.4(3) . . . . ? O2 N2 C11 C12 -170.08(18) . . . . ? O3 N2 C11 C10 -169.70(18) . . . . ? O2 N2 C11 C10 10.9(3) . . . . ? C10 C11 C12 C13 -1.7(3) . . . . ? N2 C11 C12 C13 179.33(15) . . . . ? C11 C12 C13 C8 0.2(2) . . . . ? C11 C12 C13 C15 -179.10(15) . . . . ? C9 C8 C13 C12 2.4(2) . . . . ? N1 C8 C13 C12 -178.83(14) . . . . ? C9 C8 C13 C15 -178.33(15) . . . . ? N1 C8 C13 C15 0.5(2) . . . . ? C17 N3 C16 O4 1.8(2) . . . . ? C17 N3 C16 C2 -179.57(14) . . . . ? C1 C2 C16 O4 29.3(2) . . . . ? C3 C2 C16 O4 -150.31(16) . . . . ? C1 C2 C16 N3 -149.29(15) . . . . ? C3 C2 C16 N3 31.1(2) . . . . ? C16 N3 C17 C18 -73.9(2) . . . . ? C16 N3 C17 C22 109.29(18) . . . . ? C22 C17 C18 C19 -0.3(2) . . . . ? N3 C17 C18 C19 -176.92(14) . . . . ? C22 C17 C18 C23 178.31(16) . . . . ? N3 C17 C18 C23 1.7(2) . . . . ? C17 C18 C19 C20 -1.0(2) . . . . ? C23 C18 C19 C20 -179.65(16) . . . . ? C18 C19 C20 C21 1.7(2) . . . . ? C18 C19 C20 N4 -179.66(14) . . . . ? O6 N4 C20 C19 -178.16(15) . . . . ? O5 N4 C20 C19 2.7(2) . . . . ? O6 N4 C20 C21 0.5(2) . . . . ? O5 N4 C20 C21 -178.56(15) . . . . ? C19 C20 C21 C22 -1.0(2) . . . . ? N4 C20 C21 C22 -179.68(14) . . . . ? C18 C17 C22 C21 1.0(2) . . . . ? N3 C17 C22 C21 177.65(14) . . . . ? C18 C17 C22 C24 -178.78(16) . . . . ? N3 C17 C22 C24 -2.1(2) . . . . ? C20 C21 C22 C17 -0.3(2) . . . . ? C20 C21 C22 C24 179.44(16) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.290 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.043 # Attachment 'OCH166A.cif' data_och166a _database_code_depnum_ccdc_archive 'CCDC 615399' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Centre for Chemical Biology Department of Chemistry Krebs Institute for Biomolecular Science University of Sheffield Sheffield S3 7HF UK ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 N3 O5' _chemical_formula_weight 343.34 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)/n 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 4.634(3) _cell_length_b 12.208(6) _cell_length_c 29.098(16) _cell_angle_alpha 90.00 _cell_angle_beta 92.433(11) _cell_angle_gamma 90.00 _cell_volume 1644.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 29 _cell_measurement_theta_min 1.40 _cell_measurement_theta_max 28.46 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9576 _exptl_absorpt_correction_T_max 0.9948 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10231 _diffrn_reflns_av_R_equivalents 0.2731 _diffrn_reflns_av_sigmaI/netI 0.4846 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 28.46 _reflns_number_total 3998 _reflns_number_gt 846 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.0000P] 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 3998 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3382 _refine_ls_R_factor_gt 0.0754 _refine_ls_wR_factor_ref 0.2433 _refine_ls_wR_factor_gt 0.1585 _refine_ls_goodness_of_fit_ref 0.766 _refine_ls_restrained_S_all 0.766 _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 0.3215(9) 0.8632(3) 0.13144(17) 0.0492(13) Uani 1 1 d . . . O2 O 1.2278(11) 1.3258(4) 0.17260(19) 0.0645(16) Uani 1 1 d . . . O3 O 1.3220(12) 1.2380(4) 0.2360(2) 0.0671(17) Uani 1 1 d . . . O4 O 0.5027(11) 0.2929(4) 0.07900(17) 0.0532(15) Uani 1 1 d . . . O5 O 0.1506(10) 0.3628(4) 0.03775(18) 0.0566(15) Uani 1 1 d . . . N1 N 0.7567(10) 0.7926(4) 0.11406(17) 0.0320(13) Uani 1 1 d . . . H1A H 0.9415 0.8072 0.1116 0.038 Uiso 1 1 calc R . . N2 N 1.2109(14) 1.2446(5) 0.1971(3) 0.0523(18) Uani 1 1 d . . . N3 N 0.3677(13) 0.3711(5) 0.0638(2) 0.0415(15) Uani 1 1 d . . . C1 C 0.5883(13) 0.8726(5) 0.1304(2) 0.0315(16) Uani 1 1 d . . . C2 C 0.7396(12) 0.9730(5) 0.1469(3) 0.0320(16) Uani 1 1 d . . . C3 C 0.8378(13) 1.0502(5) 0.1160(2) 0.0339(17) Uani 1 1 d . . . C4 C 0.9897(13) 1.1424(5) 0.1327(3) 0.0414(18) Uani 1 1 d . . . H4A H 1.0552 1.1968 0.1123 0.050 Uiso 1 1 calc R . . C5 C 1.0418(13) 1.1518(5) 0.1800(3) 0.0396(18) Uani 1 1 d . . . C6 C 0.9377(13) 1.0781(5) 0.2108(3) 0.0416(18) Uani 1 1 d . . . H6A H 0.9716 1.0880 0.2430 0.050 Uiso 1 1 calc R . . C7 C 0.7809(13) 0.9880(5) 0.1938(2) 0.0337(16) Uani 1 1 d . . . C8 C 0.6576(12) 0.6856(5) 0.1003(2) 0.0294(16) Uani 1 1 d . . . C9 C 0.7670(12) 0.5967(5) 0.1249(2) 0.0322(16) Uani 1 1 d . . . C10 C 0.6776(13) 0.4914(5) 0.1124(2) 0.0354(17) Uani 1 1 d . . . H10A H 0.7524 0.4288 0.1282 0.042 Uiso 1 1 calc R . . C11 C 0.4736(13) 0.4812(5) 0.0757(2) 0.0348(17) Uani 1 1 d . . . C12 C 0.3639(13) 0.5697(5) 0.0519(2) 0.0369(17) Uani 1 1 d . . . H12A H 0.2199 0.5595 0.0281 0.044 Uiso 1 1 calc R . . C13 C 0.4631(13) 0.6746(5) 0.0627(2) 0.0342(17) Uani 1 1 d . . . C14 C 0.7913(15) 1.0370(5) 0.0650(2) 0.047(2) Uani 1 1 d . . . H14A H 0.8883 0.9703 0.0550 0.071 Uiso 1 1 calc R . . H14B H 0.8713 1.1006 0.0493 0.071 Uiso 1 1 calc R . . H14C H 0.5839 1.0316 0.0572 0.071 Uiso 1 1 calc R . . C15 C 0.6574(14) 0.9077(5) 0.2278(2) 0.0466(19) Uani 1 1 d . . . H15A H 0.4493 0.9201 0.2297 0.070 Uiso 1 1 calc R . . H15B H 0.7520 0.9186 0.2583 0.070 Uiso 1 1 calc R . . H15C H 0.6916 0.8325 0.2175 0.070 Uiso 1 1 calc R . . C16 C 0.9825(12) 0.6109(5) 0.1652(2) 0.0376(17) Uani 1 1 d . . . H16A H 1.1518 0.6509 0.1551 0.056 Uiso 1 1 calc R . . H16B H 1.0425 0.5387 0.1769 0.056 Uiso 1 1 calc R . . H16C H 0.8924 0.6522 0.1897 0.056 Uiso 1 1 calc R . . C17 C 0.3640(14) 0.7691(5) 0.0333(2) 0.047(2) Uani 1 1 d . . . H17A H 0.2467 0.8186 0.0513 0.071 Uiso 1 1 calc R . . H17B H 0.2480 0.7418 0.0067 0.071 Uiso 1 1 calc R . . H17C H 0.5323 0.8087 0.0225 0.071 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 0.023(2) 0.040(3) 0.085(4) -0.009(3) 0.003(2) -0.002(2) O2 0.079(4) 0.041(3) 0.074(4) -0.005(3) 0.011(3) -0.016(3) O3 0.067(4) 0.061(4) 0.070(4) -0.016(3) -0.026(3) -0.003(3) O4 0.062(4) 0.035(3) 0.063(4) -0.005(3) 0.009(3) -0.007(3) O5 0.044(3) 0.051(3) 0.074(4) -0.014(3) -0.010(3) -0.012(3) N1 0.028(3) 0.032(3) 0.036(3) -0.004(3) 0.008(3) -0.003(3) N2 0.055(4) 0.030(4) 0.071(6) -0.015(4) -0.003(4) -0.008(3) N3 0.042(4) 0.035(4) 0.048(4) -0.007(3) 0.016(3) -0.007(3) C1 0.026(4) 0.027(4) 0.042(4) -0.004(3) -0.004(3) -0.001(3) C2 0.015(3) 0.031(4) 0.050(5) 0.007(4) 0.005(3) 0.008(3) C3 0.025(3) 0.033(4) 0.044(5) -0.003(4) 0.006(3) 0.003(3) C4 0.047(4) 0.022(4) 0.055(5) 0.002(4) 0.006(4) -0.003(3) C5 0.029(4) 0.037(4) 0.052(5) -0.010(4) -0.002(3) 0.001(3) C6 0.033(4) 0.045(4) 0.047(5) -0.008(4) 0.009(4) 0.004(4) C7 0.031(4) 0.033(4) 0.037(5) 0.001(3) 0.003(3) 0.003(3) C8 0.022(3) 0.027(4) 0.039(5) -0.003(3) 0.007(3) -0.005(3) C9 0.028(4) 0.035(4) 0.034(4) 0.000(3) 0.010(3) -0.001(3) C10 0.031(4) 0.030(4) 0.046(5) 0.001(3) 0.011(3) -0.002(3) C11 0.026(4) 0.031(4) 0.047(5) -0.003(4) 0.004(4) -0.007(3) C12 0.035(4) 0.038(4) 0.037(5) -0.008(3) 0.001(3) -0.004(3) C13 0.030(4) 0.035(4) 0.037(4) 0.000(3) 0.005(3) -0.001(3) C14 0.073(5) 0.026(4) 0.043(5) 0.004(4) 0.007(4) -0.006(4) C15 0.048(4) 0.051(4) 0.042(5) 0.009(4) 0.004(4) 0.008(4) C16 0.024(3) 0.037(4) 0.051(5) 0.001(4) -0.001(3) 0.001(3) C17 0.042(4) 0.047(4) 0.053(5) 0.005(4) -0.001(4) 0.002(4) _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 C1 1.243(6) . ? O2 N2 1.225(7) . ? O3 N2 1.227(8) . ? O4 N3 1.214(6) . ? O5 N3 1.237(7) . ? N1 C1 1.349(7) . ? N1 C8 1.436(7) . ? N2 C5 1.453(8) . ? N3 C11 1.468(8) . ? C1 C2 1.481(8) . ? C2 C7 1.384(9) . ? C2 C3 1.391(8) . ? C3 C4 1.402(8) . ? C3 C14 1.502(9) . ? C4 C5 1.394(9) . ? C5 C6 1.372(9) . ? C6 C7 1.396(8) . ? C7 C15 1.522(8) . ? C8 C9 1.384(8) . ? C8 C13 1.395(9) . ? C9 C10 1.394(8) . ? C9 C16 1.518(8) . ? C10 C11 1.401(9) . ? C11 C12 1.369(9) . ? C12 C13 1.392(8) . ? C13 C17 1.497(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C8 125.0(5) . . ? O3 N2 O2 123.7(7) . . ? O3 N2 C5 117.6(7) . . ? O2 N2 C5 118.7(7) . . ? O4 N3 O5 123.5(6) . . ? O4 N3 C11 118.1(6) . . ? O5 N3 C11 118.3(6) . . ? O1 C1 N1 122.2(6) . . ? O1 C1 C2 121.7(6) . . ? N1 C1 C2 116.1(5) . . ? C7 C2 C3 120.7(6) . . ? C7 C2 C1 118.2(6) . . ? C3 C2 C1 121.0(7) . . ? C2 C3 C4 119.6(7) . . ? C2 C3 C14 121.9(6) . . ? C4 C3 C14 118.5(6) . . ? C5 C4 C3 118.1(7) . . ? C6 C5 C4 122.7(6) . . ? C6 C5 N2 119.3(7) . . ? C4 C5 N2 118.0(7) . . ? C5 C6 C7 118.5(7) . . ? C2 C7 C6 120.1(6) . . ? C2 C7 C15 121.1(6) . . ? C6 C7 C15 118.8(6) . . ? C9 C8 C13 122.7(6) . . ? C9 C8 N1 117.7(6) . . ? C13 C8 N1 119.6(6) . . ? C8 C9 C10 119.4(6) . . ? C8 C9 C16 121.6(6) . . ? C10 C9 C16 119.0(6) . . ? C9 C10 C11 117.7(6) . . ? C12 C11 C10 122.6(6) . . ? C12 C11 N3 119.3(6) . . ? C10 C11 N3 118.0(6) . . ? C11 C12 C13 120.0(6) . . ? C12 C13 C8 117.5(6) . . ? C12 C13 C17 119.4(6) . . ? C8 C13 C17 123.2(6) . . ? 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 C8 N1 C1 O1 -6.2(10) . . . . ? C8 N1 C1 C2 174.1(6) . . . . ? O1 C1 C2 C7 77.3(8) . . . . ? N1 C1 C2 C7 -103.0(7) . . . . ? O1 C1 C2 C3 -102.7(7) . . . . ? N1 C1 C2 C3 77.0(8) . . . . ? C7 C2 C3 C4 2.3(9) . . . . ? C1 C2 C3 C4 -177.6(6) . . . . ? C7 C2 C3 C14 -178.9(6) . . . . ? C1 C2 C3 C14 1.1(9) . . . . ? C2 C3 C4 C5 1.3(9) . . . . ? C14 C3 C4 C5 -177.5(6) . . . . ? C3 C4 C5 C6 -3.5(9) . . . . ? C3 C4 C5 N2 177.1(5) . . . . ? O3 N2 C5 C6 20.0(9) . . . . ? O2 N2 C5 C6 -157.9(6) . . . . ? O3 N2 C5 C4 -160.7(6) . . . . ? O2 N2 C5 C4 21.5(9) . . . . ? C4 C5 C6 C7 2.1(9) . . . . ? N2 C5 C6 C7 -178.6(6) . . . . ? C3 C2 C7 C6 -3.9(9) . . . . ? C1 C2 C7 C6 176.1(5) . . . . ? C3 C2 C7 C15 176.1(5) . . . . ? C1 C2 C7 C15 -4.0(8) . . . . ? C5 C6 C7 C2 1.7(9) . . . . ? C5 C6 C7 C15 -178.3(5) . . . . ? C1 N1 C8 C9 -116.6(6) . . . . ? C1 N1 C8 C13 65.0(8) . . . . ? C13 C8 C9 C10 -1.1(9) . . . . ? N1 C8 C9 C10 -179.5(5) . . . . ? C13 C8 C9 C16 178.9(5) . . . . ? N1 C8 C9 C16 0.5(8) . . . . ? C8 C9 C10 C11 -1.4(8) . . . . ? C16 C9 C10 C11 178.6(5) . . . . ? C9 C10 C11 C12 0.7(9) . . . . ? C9 C10 C11 N3 -177.1(5) . . . . ? O4 N3 C11 C12 166.6(6) . . . . ? O5 N3 C11 C12 -11.4(9) . . . . ? O4 N3 C11 C10 -15.6(8) . . . . ? O5 N3 C11 C10 166.5(5) . . . . ? C10 C11 C12 C13 2.6(10) . . . . ? N3 C11 C12 C13 -179.7(5) . . . . ? C11 C12 C13 C8 -4.9(9) . . . . ? C11 C12 C13 C17 173.7(6) . . . . ? C9 C8 C13 C12 4.3(9) . . . . ? N1 C8 C13 C12 -177.3(5) . . . . ? C9 C8 C13 C17 -174.3(6) . . . . ? N1 C8 C13 C17 4.1(9) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 28.46 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.347 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.079 # Attachment 'OCH24T.cif' data_och24t _database_code_depnum_ccdc_archive 'CCDC 615400' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Centre for Chemical Biology Department of Chemistry Krebs Institute for Biomolecular Science University of Sheffield Sheffield S3 7HF UK ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H18 N2 O3' _chemical_formula_weight 370.39 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.939(3) _cell_length_b 12.274(2) _cell_length_c 8.5993(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1787.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 423(2) _cell_measurement_reflns_used 230 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 22.3 _exptl_crystal_description NEEDLE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9614 _exptl_absorpt_correction_T_max 0.9818 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 423(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 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11334 _diffrn_reflns_av_R_equivalents 0.0933 _diffrn_reflns_av_sigmaI/netI 0.0801 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2310 _reflns_number_gt 1486 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0992P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 2310 _refine_ls_number_parameters 255 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0906 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 0.816 _refine_ls_restrained_S_all 0.816 _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 N1 N 0.26718(16) 0.2528(2) 0.3506(4) 0.0311(7) Uani 1 1 d . . . H1A H 0.2541 0.2980 0.2786 0.037 Uiso 1 1 calc R . . N2 N 0.2742(2) 0.3760(2) 0.9799(4) 0.0358(8) Uani 1 1 d . . . O1 O 0.30873(17) 0.08153(19) 0.4062(3) 0.0442(7) Uani 1 1 d . . . O3 O 0.33678(18) 0.4045(2) 1.0387(4) 0.0524(8) Uani 1 1 d . . . O4 O 0.21317(17) 0.36503(19) 1.0550(3) 0.0401(7) Uani 1 1 d . . . C1 C 0.2849(2) 0.1481(3) 0.3110(4) 0.0305(8) Uani 1 1 d . . . C2 C 0.2745(2) 0.1201(3) 0.1415(4) 0.0292(8) Uani 1 1 d . . . C3 C 0.1978(2) 0.1026(2) 0.0827(4) 0.0297(8) Uani 1 1 d . . . C4 C 0.1281(2) 0.1094(3) 0.1770(5) 0.0371(9) Uani 1 1 d . . . H4A H 0.1331 0.1234 0.2828 0.045 Uiso 1 1 calc R . . C5 C 0.0550(2) 0.0956(3) 0.1146(5) 0.0420(10) Uani 1 1 d . . . H5A H 0.0106 0.1018 0.1776 0.050 Uiso 1 1 calc R . . C6 C 0.0461(2) 0.0719(3) -0.0461(5) 0.0444(10) Uani 1 1 d . . . H6A H -0.0040 0.0625 -0.0878 0.053 Uiso 1 1 calc R . . C7 C 0.1103(2) 0.0628(3) -0.1386(5) 0.0383(9) Uani 1 1 d . . . H7A H 0.1034 0.0475 -0.2437 0.046 Uiso 1 1 calc R . . C8 C 0.1884(2) 0.0762(3) -0.0788(5) 0.0314(8) Uani 1 1 d . . . C9 C 0.2547(2) 0.0651(3) -0.1726(4) 0.0330(8) Uani 1 1 d . . . H9A H 0.2482 0.0485 -0.2773 0.040 Uiso 1 1 calc R . . C10 C 0.3309(2) 0.0783(2) -0.1131(4) 0.0319(8) Uani 1 1 d . . . C11 C 0.3988(2) 0.0639(3) -0.2091(5) 0.0373(9) Uani 1 1 d . . . H11A H 0.3924 0.0443 -0.3128 0.045 Uiso 1 1 calc R . . C12 C 0.4724(2) 0.0786(3) -0.1510(5) 0.0442(10) Uani 1 1 d . . . H12A H 0.5161 0.0671 -0.2144 0.053 Uiso 1 1 calc R . . C13 C 0.4833(2) 0.1111(3) 0.0052(5) 0.0436(10) Uani 1 1 d . . . H13A H 0.5341 0.1233 0.0423 0.052 Uiso 1 1 calc R . . C14 C 0.4204(2) 0.1248(3) 0.1022(5) 0.0373(9) Uani 1 1 d . . . H14A H 0.4288 0.1451 0.2051 0.045 Uiso 1 1 calc R . . C15 C 0.3412(2) 0.1081(2) 0.0467(5) 0.0299(8) Uani 1 1 d . . . C16 C 0.2698(2) 0.2898(3) 0.5086(4) 0.0272(8) Uani 1 1 d . . . C17 C 0.3427(2) 0.3005(3) 0.5836(4) 0.0295(8) Uani 1 1 d . . . C18 C 0.3433(2) 0.3314(3) 0.7380(4) 0.0315(8) Uani 1 1 d . . . H18A H 0.3908 0.3394 0.7909 0.038 Uiso 1 1 calc R . . C19 C 0.2729(2) 0.3502(3) 0.8127(4) 0.0292(8) Uani 1 1 d . . . C20 C 0.2008(2) 0.3432(3) 0.7392(4) 0.0306(8) Uani 1 1 d . . . H20A H 0.1545 0.3580 0.7931 0.037 Uiso 1 1 calc R . . C21 C 0.19839(19) 0.3137(3) 0.5837(4) 0.0295(8) Uani 1 1 d . . . C22 C 0.1205(2) 0.3054(3) 0.5026(5) 0.0419(10) Uani 1 1 d . . . H22A H 0.1037 0.2307 0.5011 0.063 Uiso 1 1 calc R . . H22B H 0.1257 0.3314 0.3978 0.063 Uiso 1 1 calc R . . H22C H 0.0821 0.3486 0.5567 0.063 Uiso 1 1 calc R . . C23 C 0.4194(2) 0.2796(3) 0.5010(5) 0.0412(10) Uani 1 1 d . . . H23A H 0.4615 0.3154 0.5554 0.062 Uiso 1 1 calc R . . H23B H 0.4163 0.3073 0.3968 0.062 Uiso 1 1 calc R . . H23C H 0.4294 0.2026 0.4979 0.062 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 N1 0.0390(17) 0.0291(14) 0.0252(15) -0.0006(12) -0.0005(14) 0.0048(12) N2 0.052(2) 0.0303(16) 0.0250(16) -0.0017(12) -0.0047(15) 0.0048(14) O1 0.0734(19) 0.0306(13) 0.0288(14) 0.0012(11) -0.0085(14) 0.0024(12) O3 0.0519(17) 0.0684(18) 0.0368(16) -0.0186(15) -0.0153(15) 0.0044(15) O4 0.0569(18) 0.0363(13) 0.0272(14) 0.0025(12) 0.0043(13) 0.0053(12) C1 0.0365(19) 0.0295(18) 0.0255(18) -0.0026(14) 0.0024(15) -0.0041(15) C2 0.036(2) 0.0238(15) 0.028(2) -0.0015(14) -0.0026(16) 0.0012(13) C3 0.038(2) 0.0226(15) 0.0286(19) -0.0011(14) 0.0006(16) 0.0004(13) C4 0.043(2) 0.0334(18) 0.035(2) -0.0033(16) 0.0022(18) 0.0002(16) C5 0.037(2) 0.041(2) 0.048(3) -0.0035(18) 0.0050(19) 0.0009(17) C6 0.039(2) 0.041(2) 0.054(3) -0.0026(19) -0.008(2) 0.0049(17) C7 0.046(2) 0.0352(19) 0.034(2) -0.0024(15) -0.0098(18) 0.0018(16) C8 0.0367(19) 0.0250(16) 0.033(2) -0.0007(14) -0.0009(16) -0.0014(14) C9 0.048(2) 0.0265(17) 0.0243(17) -0.0024(14) -0.0023(16) 0.0005(14) C10 0.043(2) 0.0231(16) 0.030(2) -0.0007(15) 0.0049(16) -0.0016(14) C11 0.048(2) 0.0353(19) 0.0282(18) -0.0029(15) 0.0074(17) -0.0004(16) C12 0.045(2) 0.045(2) 0.042(2) 0.0016(18) 0.015(2) -0.0023(18) C13 0.035(2) 0.047(2) 0.049(3) 0.0023(19) 0.0002(19) -0.0033(16) C14 0.040(2) 0.0362(19) 0.035(2) 0.0000(16) -0.0008(18) 0.0010(15) C15 0.0364(19) 0.0231(15) 0.0302(19) -0.0012(14) 0.0009(16) 0.0012(13) C16 0.037(2) 0.0216(15) 0.0234(17) 0.0007(13) 0.0023(16) 0.0013(13) C17 0.0318(19) 0.0236(16) 0.033(2) 0.0018(14) 0.0014(16) 0.0005(13) C18 0.0332(19) 0.0289(17) 0.032(2) -0.0016(15) -0.0060(16) 0.0007(14) C19 0.042(2) 0.0235(16) 0.0225(17) 0.0006(13) -0.0025(16) 0.0004(14) C20 0.0342(19) 0.0305(17) 0.0272(18) -0.0040(15) 0.0051(16) 0.0021(14) C21 0.0297(19) 0.0254(15) 0.0335(19) -0.0021(15) -0.0019(16) 0.0010(14) C22 0.036(2) 0.049(2) 0.040(2) -0.0144(18) -0.0028(18) 0.0048(17) C23 0.033(2) 0.045(2) 0.045(2) -0.0054(18) 0.0022(18) -0.0045(15) _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 N1 C1 1.363(4) . ? N1 C16 1.433(5) . ? N2 O3 1.226(4) . ? N2 O4 1.226(4) . ? N2 C19 1.472(4) . ? O1 C1 1.225(4) . ? C1 C2 1.508(5) . ? C2 C15 1.401(5) . ? C2 C3 1.410(5) . ? C3 C8 1.435(6) . ? C3 C4 1.434(5) . ? C4 C5 1.360(6) . ? C5 C6 1.421(6) . ? C6 C7 1.351(6) . ? C7 C8 1.428(5) . ? C8 C9 1.390(5) . ? C9 C10 1.398(5) . ? C10 C11 1.426(5) . ? C10 C15 1.432(6) . ? C11 C12 1.356(6) . ? C12 C13 1.413(6) . ? C13 C14 1.364(5) . ? C14 C15 1.439(5) . ? C16 C17 1.400(5) . ? C16 C21 1.402(5) . ? C17 C18 1.381(5) . ? C17 C23 1.503(5) . ? C18 C19 1.373(5) . ? C19 C20 1.377(5) . ? C20 C21 1.386(5) . ? C21 C22 1.496(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C16 121.9(3) . . ? O3 N2 O4 122.9(3) . . ? O3 N2 C19 118.5(3) . . ? O4 N2 C19 118.6(3) . . ? O1 C1 N1 122.3(3) . . ? O1 C1 C2 122.2(3) . . ? N1 C1 C2 115.5(3) . . ? C15 C2 C3 121.2(3) . . ? C15 C2 C1 119.5(3) . . ? C3 C2 C1 119.3(3) . . ? C2 C3 C8 118.9(3) . . ? C2 C3 C4 123.1(3) . . ? C8 C3 C4 117.9(3) . . ? C5 C4 C3 121.3(4) . . ? C4 C5 C6 120.4(4) . . ? C7 C6 C5 120.3(4) . . ? C6 C7 C8 121.5(4) . . ? C9 C8 C3 119.6(3) . . ? C9 C8 C7 121.9(4) . . ? C3 C8 C7 118.5(3) . . ? C8 C9 C10 121.6(3) . . ? C9 C10 C11 121.2(3) . . ? C9 C10 C15 119.5(3) . . ? C11 C10 C15 119.3(3) . . ? C12 C11 C10 120.8(4) . . ? C11 C12 C13 120.5(4) . . ? C14 C13 C12 121.0(4) . . ? C13 C14 C15 120.5(4) . . ? C2 C15 C14 123.0(3) . . ? C2 C15 C10 119.1(3) . . ? C14 C15 C10 117.9(3) . . ? C17 C16 C21 121.9(3) . . ? C17 C16 N1 119.6(3) . . ? C21 C16 N1 118.5(3) . . ? C18 C17 C16 118.3(3) . . ? C18 C17 C23 119.7(3) . . ? C16 C17 C23 122.0(3) . . ? C19 C18 C17 119.3(3) . . ? C18 C19 C20 123.0(3) . . ? C18 C19 N2 118.7(3) . . ? C20 C19 N2 118.3(3) . . ? C19 C20 C21 119.1(3) . . ? C20 C21 C16 118.3(3) . . ? C20 C21 C22 119.6(3) . . ? C16 C21 C22 122.1(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 C16 N1 C1 O1 -4.6(5) . . . . ? C16 N1 C1 C2 176.3(3) . . . . ? O1 C1 C2 C15 -73.5(4) . . . . ? N1 C1 C2 C15 105.5(4) . . . . ? O1 C1 C2 C3 104.1(4) . . . . ? N1 C1 C2 C3 -76.8(4) . . . . ? C15 C2 C3 C8 -2.5(4) . . . . ? C1 C2 C3 C8 179.9(3) . . . . ? C15 C2 C3 C4 177.3(3) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C2 C3 C4 C5 177.7(3) . . . . ? C8 C3 C4 C5 -2.6(5) . . . . ? C3 C4 C5 C6 1.3(5) . . . . ? C4 C5 C6 C7 -0.1(6) . . . . ? C5 C6 C7 C8 0.2(6) . . . . ? C2 C3 C8 C9 2.1(4) . . . . ? C4 C3 C8 C9 -177.7(3) . . . . ? C2 C3 C8 C7 -177.6(3) . . . . ? C4 C3 C8 C7 2.6(4) . . . . ? C6 C7 C8 C9 178.8(3) . . . . ? C6 C7 C8 C3 -1.6(5) . . . . ? C3 C8 C9 C10 0.4(5) . . . . ? C7 C8 C9 C10 -180.0(3) . . . . ? C8 C9 C10 C11 178.3(3) . . . . ? C8 C9 C10 C15 -2.4(5) . . . . ? C9 C10 C11 C12 179.0(3) . . . . ? C15 C10 C11 C12 -0.3(5) . . . . ? C10 C11 C12 C13 -1.6(6) . . . . ? C11 C12 C13 C14 2.3(6) . . . . ? C12 C13 C14 C15 -1.0(6) . . . . ? C3 C2 C15 C14 -179.7(3) . . . . ? C1 C2 C15 C14 -2.1(5) . . . . ? C3 C2 C15 C10 0.5(5) . . . . ? C1 C2 C15 C10 178.1(3) . . . . ? C13 C14 C15 C2 179.4(3) . . . . ? C13 C14 C15 C10 -0.8(5) . . . . ? C9 C10 C15 C2 2.0(5) . . . . ? C11 C10 C15 C2 -178.8(3) . . . . ? C9 C10 C15 C14 -177.8(3) . . . . ? C11 C10 C15 C14 1.4(4) . . . . ? C1 N1 C16 C17 70.0(4) . . . . ? C1 N1 C16 C21 -109.6(4) . . . . ? C21 C16 C17 C18 2.6(5) . . . . ? N1 C16 C17 C18 -177.0(3) . . . . ? C21 C16 C17 C23 -177.2(3) . . . . ? N1 C16 C17 C23 3.1(5) . . . . ? C16 C17 C18 C19 0.2(5) . . . . ? C23 C17 C18 C19 -179.9(3) . . . . ? C17 C18 C19 C20 -2.2(5) . . . . ? C17 C18 C19 N2 176.0(3) . . . . ? O3 N2 C19 C18 16.7(5) . . . . ? O4 N2 C19 C18 -161.3(3) . . . . ? O3 N2 C19 C20 -165.0(3) . . . . ? O4 N2 C19 C20 17.0(5) . . . . ? C18 C19 C20 C21 1.4(5) . . . . ? N2 C19 C20 C21 -176.8(3) . . . . ? C19 C20 C21 C16 1.4(5) . . . . ? C19 C20 C21 C22 179.7(3) . . . . ? C17 C16 C21 C20 -3.5(5) . . . . ? N1 C16 C21 C20 176.2(3) . . . . ? C17 C16 C21 C22 178.3(3) . . . . ? N1 C16 C21 C22 -2.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.356 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.080 # Attachment 'OCH265M.cif' data_och265m _database_code_depnum_ccdc_archive 'CCDC 615401' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 F5 N O' _chemical_formula_weight 329.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 11.1542(10) _cell_length_b 8.4970(7) _cell_length_c 31.528(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.122(2) _cell_angle_gamma 90.00 _cell_volume 2976.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6766 _cell_measurement_theta_min 4.677 _cell_measurement_theta_max 50.744 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9481 _exptl_absorpt_correction_T_max 0.9582 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 32644 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6781 _reflns_number_gt 4429 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+0.6168P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(7) _refine_ls_number_reflns 6781 _refine_ls_number_parameters 841 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.5339(3) 0.8235(4) 0.52077(11) 0.0482(9) Uani 1 1 d . . . N1 N 0.3785(3) 0.6756(4) 0.49352(13) 0.0399(9) Uani 1 1 d . . . C1 C 0.4467(3) 0.5315(5) 0.49963(14) 0.0326(9) Uani 1 1 d . . . C2 C 0.4516(4) 0.4561(6) 0.53856(14) 0.0390(11) Uani 1 1 d . . . C3 C 0.5164(4) 0.3160(6) 0.54356(15) 0.0422(11) Uani 1 1 d . . . H3 H 0.5225 0.2635 0.5703 0.051 Uiso 1 1 calc R . . C4 C 0.5718(4) 0.2531(5) 0.50993(16) 0.0389(10) Uani 1 1 d . . . H4 H 0.6155 0.1574 0.5136 0.047 Uiso 1 1 calc R . . C5 C 0.5640(4) 0.3284(5) 0.47130(15) 0.0381(10) Uani 1 1 d . . . H5 H 0.6030 0.2840 0.4485 0.046 Uiso 1 1 calc R . . C6 C 0.5005(4) 0.4680(5) 0.46466(14) 0.0334(9) Uani 1 1 d . . . C7 C 0.4298(4) 0.8112(5) 0.50648(13) 0.0314(9) Uani 1 1 d . . . C8 C 0.3489(4) 0.9539(5) 0.50251(15) 0.0349(10) Uani 1 1 d . . . C9 C 0.3386(4) 1.0457(5) 0.46615(15) 0.0390(11) Uani 1 1 d . . . C10 C 0.2692(4) 1.1781(6) 0.46308(16) 0.0447(12) Uani 1 1 d . . . C11 C 0.2056(4) 1.2188(6) 0.4966(2) 0.0528(14) Uani 1 1 d . . . C12 C 0.2144(5) 1.1310(6) 0.53330(19) 0.0536(14) Uani 1 1 d . . . C13 C 0.2860(4) 0.9990(6) 0.53580(16) 0.0417(11) Uani 1 1 d . . . C14 C 0.4882(4) 0.5475(6) 0.42185(15) 0.0462(12) Uani 1 1 d . . . H14A H 0.5526 0.5114 0.4050 0.069 Uiso 1 1 calc R . . H14B H 0.4940 0.6617 0.4257 0.069 Uiso 1 1 calc R . . H14C H 0.4099 0.5210 0.4069 0.069 Uiso 1 1 calc R . . C15 C 0.3898(5) 0.5227(7) 0.57542(17) 0.0579(14) Uani 1 1 d . . . H15A H 0.3998 0.4499 0.5996 0.087 Uiso 1 1 calc R . . H15B H 0.3038 0.5367 0.5668 0.087 Uiso 1 1 calc R . . H15C H 0.4257 0.6246 0.5838 0.087 Uiso 1 1 calc R . . C16 C 0.2546(5) 0.6643(7) 0.4733(2) 0.078(2) Uani 1 1 d . . . H16A H 0.1977 0.6724 0.4951 0.117 Uiso 1 1 calc R . . H16B H 0.2438 0.5630 0.4586 0.117 Uiso 1 1 calc R . . H16C H 0.2400 0.7500 0.4527 0.117 Uiso 1 1 calc R . . F1 F 0.3984(3) 1.0052(3) 0.43285(9) 0.0516(7) Uani 1 1 d . . . F2 F 0.2594(3) 1.2680(3) 0.42780(10) 0.0604(8) Uani 1 1 d . . . F3 F 0.1345(3) 1.3479(4) 0.49439(14) 0.0842(12) Uani 1 1 d . . . F4 F 0.1521(3) 1.1726(4) 0.56602(13) 0.0857(12) Uani 1 1 d . . . F5 F 0.2941(3) 0.9138(3) 0.57171(10) 0.0580(8) Uani 1 1 d . . . O1A O 1.0294(3) 0.8275(5) 0.52126(10) 0.0503(9) Uani 1 1 d . . . N1A N 0.8800(3) 0.7807(4) 0.46958(11) 0.0342(8) Uani 1 1 d . . . C1A C 0.9446(4) 0.8550(5) 0.43774(13) 0.0306(9) Uani 1 1 d . . . C2A C 1.0002(4) 0.7620(5) 0.40835(13) 0.0331(9) Uani 1 1 d . . . C3A C 1.0637(4) 0.8389(6) 0.37833(14) 0.0385(10) Uani 1 1 d . . . H3A H 1.1044 0.7786 0.3587 0.046 Uiso 1 1 calc R . . C4A C 1.0685(4) 1.0014(6) 0.37663(14) 0.0391(11) Uani 1 1 d . . . H4A H 1.1113 1.0516 0.3557 0.047 Uiso 1 1 calc R . . C5A C 1.0117(4) 1.0900(6) 0.40513(14) 0.0382(10) Uani 1 1 d . . . H5A H 1.0156 1.2016 0.4037 0.046 Uiso 1 1 calc R . . C6A C 0.9484(4) 1.0200(5) 0.43614(14) 0.0360(10) Uani 1 1 d . . . C7A C 0.9297(4) 0.7760(5) 0.50969(13) 0.0337(10) Uani 1 1 d . . . C8A C 0.8530(4) 0.7021(5) 0.54157(13) 0.0315(9) Uani 1 1 d . . . C9A C 0.7811(4) 0.7931(6) 0.56506(14) 0.0376(10) Uani 1 1 d . . . C10A C 0.7131(4) 0.7285(7) 0.59454(14) 0.0480(13) Uani 1 1 d . . . C11A C 0.7189(5) 0.5723(8) 0.60255(15) 0.0521(13) Uani 1 1 d . . . C12A C 0.7906(5) 0.4781(6) 0.58066(16) 0.0506(13) Uani 1 1 d . . . C13A C 0.8574(4) 0.5427(6) 0.54994(15) 0.0410(11) Uani 1 1 d . . . C14A C 0.8847(5) 1.1175(6) 0.46696(17) 0.0512(13) Uani 1 1 d . . . H14D H 0.9293 1.1129 0.4952 0.077 Uiso 1 1 calc R . . H14E H 0.8032 1.0763 0.4687 0.077 Uiso 1 1 calc R . . H14F H 0.8800 1.2269 0.4571 0.077 Uiso 1 1 calc R . . C15A C 0.9932(5) 0.5863(6) 0.40953(16) 0.0450(11) Uani 1 1 d . . . H15D H 0.9189 0.5514 0.3933 0.067 Uiso 1 1 calc R . . H15E H 0.9932 0.5510 0.4391 0.067 Uiso 1 1 calc R . . H15F H 1.0627 0.5414 0.3969 0.067 Uiso 1 1 calc R . . C16A C 0.7599(4) 0.7184(7) 0.45659(16) 0.0536(14) Uani 1 1 d . . . H16D H 0.7585 0.6051 0.4623 0.080 Uiso 1 1 calc R . . H16E H 0.7405 0.7370 0.4261 0.080 Uiso 1 1 calc R . . H16F H 0.7005 0.7715 0.4727 0.080 Uiso 1 1 calc R . . F1A F 0.7747(2) 0.9491(3) 0.55784(9) 0.0519(7) Uani 1 1 d . . . F2A F 0.6393(3) 0.8191(5) 0.61560(9) 0.0713(10) Uani 1 1 d . . . F3A F 0.6562(3) 0.5075(5) 0.63240(9) 0.0793(11) Uani 1 1 d . . . F4A F 0.7999(3) 0.3226(4) 0.58899(12) 0.0762(10) Uani 1 1 d . . . F5A F 0.9271(3) 0.4499(3) 0.52806(11) 0.0613(8) Uani 1 1 d . . . O1B O 1.0352(3) 0.8159(4) 0.77202(10) 0.0490(9) Uani 1 1 d . . . N1B N 0.8752(3) 0.8238(5) 0.72363(11) 0.0361(9) Uani 1 1 d . . . C1B C 0.9442(4) 0.7696(6) 0.68988(13) 0.0366(10) Uani 1 1 d . . . C2B C 0.9891(4) 0.8812(7) 0.66263(14) 0.0460(12) Uani 1 1 d . . . C3B C 1.0546(5) 0.8239(10) 0.63040(15) 0.0657(19) Uani 1 1 d . . . H3B H 1.0875 0.8960 0.6116 0.079 Uiso 1 1 calc R . . C4B C 1.0727(5) 0.6646(11) 0.62520(19) 0.079(2) Uani 1 1 d . . . H4B H 1.1164 0.6279 0.6026 0.095 Uiso 1 1 calc R . . C5B C 1.0271(5) 0.5585(9) 0.6530(2) 0.072(2) Uani 1 1 d . . . H5B H 1.0417 0.4492 0.6497 0.086 Uiso 1 1 calc R . . C6B C 0.9605(4) 0.6088(7) 0.68549(16) 0.0484(13) Uani 1 1 d . . . C7B C 0.9286(4) 0.8400(5) 0.76235(13) 0.0339(10) Uani 1 1 d . . . C8B C 0.8488(4) 0.8902(6) 0.79645(13) 0.0400(11) Uani 1 1 d . . . C9B C 0.7940(5) 0.7807(8) 0.82014(16) 0.0575(15) Uani 1 1 d . . . C10B C 0.7234(6) 0.8221(12) 0.85177(18) 0.089(3) Uani 1 1 d . . . C11B C 0.7068(5) 0.9795(12) 0.85969(18) 0.082(2) Uani 1 1 d . . . C12B C 0.7602(5) 1.0906(10) 0.83785(17) 0.0671(19) Uani 1 1 d . . . C13B C 0.8301(4) 1.0471(7) 0.80581(15) 0.0490(13) Uani 1 1 d . . . C14B C 0.9685(6) 1.0525(7) 0.66773(19) 0.0649(16) Uani 1 1 d . . . H14G H 1.0287 1.1115 0.6534 0.097 Uiso 1 1 calc R . . H14H H 0.9754 1.0791 0.6981 0.097 Uiso 1 1 calc R . . H14I H 0.8878 1.0798 0.6550 0.097 Uiso 1 1 calc R . . C15B C 0.9082(6) 0.4950(7) 0.7154(2) 0.0711(17) Uani 1 1 d . . . H15G H 0.9208 0.3870 0.7058 0.107 Uiso 1 1 calc R . . H15H H 0.8217 0.5148 0.7158 0.107 Uiso 1 1 calc R . . H15I H 0.9479 0.5089 0.7442 0.107 Uiso 1 1 calc R . . C16B C 0.7464(4) 0.8528(8) 0.71205(16) 0.0586(16) Uani 1 1 d . . . H16G H 0.7105 0.9002 0.7363 0.088 Uiso 1 1 calc R . . H16H H 0.7059 0.7529 0.7045 0.088 Uiso 1 1 calc R . . H16I H 0.7369 0.9245 0.6876 0.088 Uiso 1 1 calc R . . F1B F 0.8080(4) 0.6273(5) 0.81152(10) 0.0847(13) Uani 1 1 d . . . F2B F 0.6695(5) 0.7113(8) 0.87322(12) 0.151(3) Uani 1 1 d . . . F3B F 0.6373(3) 1.0188(8) 0.89082(12) 0.135(2) Uani 1 1 d . . . F4B F 0.7460(4) 1.2429(6) 0.84683(11) 0.0999(16) Uani 1 1 d . . . F5B F 0.8824(3) 1.1579(4) 0.78369(9) 0.0666(9) Uani 1 1 d . . . O1C O 0.5303(3) 0.8219(4) 0.77762(11) 0.0429(8) Uani 1 1 d . . . N1C N 0.4291(4) 0.8313(5) 0.75876(13) 0.0484(10) Uani 1 1 d . . . C1C C 0.4483(4) 1.1078(5) 0.74689(14) 0.0328(9) Uani 1 1 d . . . C2C C 0.5068(4) 1.1671(5) 0.71284(14) 0.0377(10) Uani 1 1 d . . . C3C C 0.5705(4) 1.3077(6) 0.71959(18) 0.0491(13) Uani 1 1 d . . . H3C H 0.6106 1.3520 0.6971 0.059 Uiso 1 1 calc R . . C4C C 0.5760(4) 1.3828(6) 0.7581(2) 0.0550(14) Uani 1 1 d . . . H4C H 0.6214 1.4770 0.7622 0.066 Uiso 1 1 calc R . . C5C C 0.5167(4) 1.3236(6) 0.79115(18) 0.0500(13) Uani 1 1 d . . . H5C H 0.5201 1.3781 0.8175 0.060 Uiso 1 1 calc R . . C6C C 0.4519(4) 1.1846(5) 0.78585(15) 0.0405(11) Uani 1 1 d . . . C7C C 0.3810(3) 0.9635(4) 0.74113(11) 0.0175(7) Uani 1 1 d . . . C8C C 0.3488(4) 0.6879(5) 0.75527(14) 0.0324(9) Uani 1 1 d . . . C9C C 0.2861(4) 0.6433(6) 0.78886(16) 0.0440(11) Uani 1 1 d . . . C10C C 0.2156(5) 0.5101(7) 0.7870(2) 0.0609(16) Uani 1 1 d . . . C11C C 0.2097(5) 0.4180(6) 0.7513(2) 0.0574(15) Uani 1 1 d . . . C12C C 0.2719(4) 0.4583(6) 0.71762(17) 0.0477(13) Uani 1 1 d . . . C13C C 0.3397(4) 0.5927(5) 0.71968(15) 0.0401(11) Uani 1 1 d . . . C14C C 0.3865(5) 1.1210(7) 0.82185(16) 0.0539(13) Uani 1 1 d . . . H14J H 0.3866 1.2001 0.8445 0.081 Uiso 1 1 calc R . . H14K H 0.4269 1.0254 0.8331 0.081 Uiso 1 1 calc R . . H14L H 0.3033 1.0960 0.8114 0.081 Uiso 1 1 calc R . . C15C C 0.4982(4) 1.0848(6) 0.67041(15) 0.0496(13) Uani 1 1 d . . . H15J H 0.4991 0.9706 0.6749 0.074 Uiso 1 1 calc R . . H15K H 0.5668 1.1151 0.6548 0.074 Uiso 1 1 calc R . . H15L H 0.4231 1.1151 0.6539 0.074 Uiso 1 1 calc R . . C16C C 0.2626(4) 0.9690(6) 0.71737(17) 0.0496(13) Uani 1 1 d . . . H16J H 0.2582 0.8889 0.6949 0.074 Uiso 1 1 calc R . . H16K H 0.2498 1.0733 0.7045 0.074 Uiso 1 1 calc R . . H16L H 0.2004 0.9485 0.7367 0.074 Uiso 1 1 calc R . . F1C F 0.2917(3) 0.7326(4) 0.82387(9) 0.0593(8) Uani 1 1 d . . . F2C F 0.1533(4) 0.4704(4) 0.81949(15) 0.0939(13) Uani 1 1 d . . . F3C F 0.1429(3) 0.2871(4) 0.74970(15) 0.0890(13) Uani 1 1 d . . . F4C F 0.2657(3) 0.3670(4) 0.68223(12) 0.0701(10) Uani 1 1 d . . . F5C F 0.3992(3) 0.6313(3) 0.68595(9) 0.0533(7) 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 O1 0.0259(17) 0.0426(19) 0.074(2) -0.0042(16) -0.0084(16) -0.0007(13) N1 0.0249(19) 0.031(2) 0.063(3) -0.0048(18) -0.0028(17) 0.0025(15) C1 0.0198(19) 0.028(2) 0.049(3) -0.0018(19) -0.0015(17) 0.0012(16) C2 0.030(2) 0.043(3) 0.045(3) -0.003(2) 0.006(2) 0.0007(19) C3 0.038(3) 0.046(3) 0.042(3) 0.005(2) 0.001(2) -0.004(2) C4 0.030(2) 0.029(2) 0.057(3) 0.004(2) 0.004(2) 0.0043(18) C5 0.033(2) 0.040(3) 0.042(2) -0.004(2) 0.0046(19) 0.0035(19) C6 0.029(2) 0.030(2) 0.040(2) -0.0016(18) -0.0017(18) -0.0015(17) C7 0.026(2) 0.031(2) 0.037(2) -0.0006(18) 0.0037(18) -0.0021(17) C8 0.023(2) 0.030(2) 0.051(3) -0.005(2) 0.0013(19) -0.0066(17) C9 0.028(2) 0.038(3) 0.050(3) 0.000(2) -0.002(2) -0.0063(19) C10 0.033(2) 0.037(3) 0.063(3) 0.009(2) -0.005(2) -0.008(2) C11 0.028(2) 0.026(3) 0.104(5) 0.007(3) 0.008(3) 0.0022(19) C12 0.043(3) 0.042(3) 0.080(4) -0.004(3) 0.026(3) 0.004(2) C13 0.039(3) 0.034(3) 0.053(3) 0.002(2) 0.013(2) -0.001(2) C14 0.040(3) 0.049(3) 0.049(3) 0.009(2) -0.001(2) 0.000(2) C15 0.051(3) 0.068(4) 0.057(3) -0.006(3) 0.022(3) 0.010(3) C16 0.035(3) 0.048(3) 0.146(6) -0.018(4) -0.027(3) 0.005(2) F1 0.0579(18) 0.0505(17) 0.0469(16) 0.0019(13) 0.0074(14) -0.0011(13) F2 0.0528(18) 0.0444(17) 0.081(2) 0.0200(16) -0.0105(16) -0.0044(14) F3 0.058(2) 0.0426(19) 0.157(4) 0.020(2) 0.032(2) 0.0225(15) F4 0.087(3) 0.058(2) 0.122(3) 0.002(2) 0.065(2) 0.0192(18) F5 0.0641(19) 0.0506(17) 0.0637(19) 0.0033(15) 0.0303(15) 0.0052(15) O1A 0.0294(17) 0.083(3) 0.0378(18) 0.0038(16) -0.0030(14) -0.0156(16) N1A 0.0276(18) 0.046(2) 0.0288(18) -0.0006(16) 0.0008(14) -0.0063(16) C1A 0.024(2) 0.039(2) 0.028(2) -0.0001(18) 0.0008(16) -0.0009(18) C2A 0.031(2) 0.038(2) 0.030(2) -0.0007(19) 0.0017(17) -0.0017(19) C3A 0.034(2) 0.049(3) 0.032(2) -0.001(2) 0.0055(19) -0.002(2) C4A 0.029(2) 0.055(3) 0.033(2) 0.008(2) 0.0038(19) -0.009(2) C5A 0.031(2) 0.040(3) 0.042(3) 0.007(2) -0.0035(19) -0.004(2) C6A 0.024(2) 0.045(3) 0.039(2) 0.001(2) -0.0011(18) 0.0010(19) C7A 0.029(2) 0.038(2) 0.034(2) -0.0050(18) 0.0024(18) 0.0013(18) C8A 0.024(2) 0.044(3) 0.026(2) 0.0032(18) -0.0020(16) -0.0016(18) C9A 0.032(2) 0.051(3) 0.028(2) -0.003(2) -0.0038(18) -0.001(2) C10A 0.039(3) 0.077(4) 0.028(2) -0.012(2) 0.004(2) -0.005(3) C11A 0.046(3) 0.081(4) 0.030(2) 0.015(3) 0.003(2) -0.010(3) C12A 0.050(3) 0.050(3) 0.049(3) 0.021(2) -0.009(2) -0.008(2) C13A 0.030(2) 0.046(3) 0.046(3) 0.000(2) 0.001(2) 0.004(2) C14A 0.049(3) 0.043(3) 0.062(3) -0.011(2) 0.010(3) 0.006(2) C15A 0.048(3) 0.042(3) 0.045(3) -0.005(2) 0.004(2) -0.001(2) C16A 0.035(3) 0.081(4) 0.043(3) 0.005(3) -0.003(2) -0.023(3) F1A 0.0484(16) 0.0503(18) 0.0575(17) -0.0132(14) 0.0071(13) 0.0031(13) F2A 0.0588(19) 0.118(3) 0.0398(16) -0.0242(18) 0.0175(14) 0.0037(19) F3A 0.066(2) 0.130(3) 0.0426(17) 0.0338(19) 0.0083(16) -0.024(2) F4A 0.070(2) 0.064(2) 0.091(3) 0.0360(19) -0.0079(19) -0.0084(17) F5A 0.0562(19) 0.0486(18) 0.080(2) -0.0030(16) 0.0135(16) 0.0137(14) O1B 0.0274(17) 0.081(3) 0.0378(17) -0.0079(17) -0.0007(13) 0.0029(16) N1B 0.0251(18) 0.056(2) 0.0274(18) -0.0043(16) 0.0042(14) 0.0033(16) C1B 0.023(2) 0.057(3) 0.029(2) -0.005(2) 0.0020(17) -0.0004(19) C2B 0.031(2) 0.082(4) 0.025(2) 0.002(2) -0.0015(19) -0.006(2) C3B 0.037(3) 0.137(6) 0.024(2) -0.005(3) 0.005(2) -0.017(3) C4B 0.038(3) 0.154(8) 0.044(3) -0.032(4) 0.003(3) 0.018(4) C5B 0.041(3) 0.103(5) 0.066(4) -0.040(4) -0.018(3) 0.031(3) C6B 0.036(3) 0.061(3) 0.046(3) -0.014(2) -0.007(2) 0.014(2) C7B 0.027(2) 0.045(3) 0.030(2) 0.0010(19) 0.0026(17) -0.0028(19) C8B 0.024(2) 0.071(3) 0.024(2) -0.006(2) 0.0003(17) -0.004(2) C9B 0.050(3) 0.090(5) 0.033(3) -0.010(3) 0.007(2) -0.033(3) C10B 0.055(4) 0.178(9) 0.036(3) -0.020(4) 0.015(3) -0.065(5) C11B 0.032(3) 0.178(8) 0.036(3) -0.041(4) 0.003(2) -0.010(4) C12B 0.041(3) 0.124(6) 0.034(3) -0.027(3) -0.008(2) 0.025(3) C13B 0.035(3) 0.079(4) 0.031(3) -0.004(3) -0.002(2) 0.015(3) C14B 0.062(4) 0.070(4) 0.061(4) 0.014(3) -0.006(3) -0.014(3) C15B 0.062(4) 0.049(3) 0.100(5) 0.002(3) -0.010(3) -0.003(3) C16B 0.030(2) 0.106(5) 0.040(3) -0.013(3) 0.001(2) 0.007(3) F1B 0.114(3) 0.093(3) 0.0492(19) -0.0031(18) 0.0161(19) -0.062(2) F2B 0.143(4) 0.257(7) 0.063(2) -0.039(3) 0.057(3) -0.142(5) F3B 0.050(2) 0.294(7) 0.066(2) -0.080(3) 0.0265(19) -0.016(3) F4B 0.097(3) 0.141(4) 0.055(2) -0.040(2) -0.0259(19) 0.079(3) F5B 0.094(3) 0.059(2) 0.0465(18) 0.0036(15) 0.0059(17) 0.0236(18) O1C 0.0242(16) 0.0428(19) 0.060(2) 0.0069(16) -0.0043(14) 0.0019(13) N1C 0.045(3) 0.054(3) 0.047(2) 0.001(2) 0.011(2) 0.002(2) C1C 0.028(2) 0.029(2) 0.041(2) 0.0049(19) 0.0006(18) 0.0039(17) C2C 0.029(2) 0.038(3) 0.046(3) 0.009(2) 0.0045(19) 0.0044(19) C3C 0.032(3) 0.045(3) 0.070(4) 0.025(3) 0.006(2) -0.002(2) C4C 0.034(3) 0.041(3) 0.088(4) 0.002(3) -0.012(3) -0.004(2) C5C 0.043(3) 0.046(3) 0.058(3) -0.007(2) -0.013(2) 0.003(2) C6C 0.037(2) 0.039(3) 0.044(3) 0.000(2) -0.003(2) 0.005(2) C7C 0.0140(16) 0.0149(18) 0.0235(18) 0.0041(14) 0.0001(13) 0.0006(13) C8C 0.025(2) 0.027(2) 0.045(2) 0.0082(19) 0.0042(18) 0.0037(16) C9C 0.044(3) 0.034(3) 0.057(3) 0.003(2) 0.017(2) 0.005(2) C10C 0.041(3) 0.043(3) 0.104(5) 0.024(3) 0.034(3) 0.002(2) C11C 0.036(3) 0.031(3) 0.104(5) -0.002(3) 0.003(3) -0.003(2) C12C 0.042(3) 0.030(3) 0.069(3) -0.003(2) -0.009(3) 0.004(2) C13C 0.035(2) 0.033(3) 0.052(3) 0.006(2) 0.002(2) 0.008(2) C14C 0.066(4) 0.055(3) 0.041(3) -0.007(2) 0.009(3) 0.004(3) C15C 0.046(3) 0.055(3) 0.049(3) 0.015(2) 0.010(2) 0.010(2) C16C 0.031(2) 0.046(3) 0.069(3) 0.009(2) -0.012(2) 0.000(2) F1C 0.072(2) 0.0557(18) 0.0547(18) 0.0070(15) 0.0304(16) 0.0007(15) F2C 0.097(3) 0.062(2) 0.134(3) 0.026(2) 0.072(3) -0.010(2) F3C 0.058(2) 0.0356(18) 0.173(4) 0.003(2) 0.011(2) -0.0127(15) F4C 0.067(2) 0.0430(18) 0.094(2) -0.0168(17) -0.0257(18) 0.0071(15) F5C 0.068(2) 0.0463(17) 0.0457(16) 0.0005(13) 0.0073(14) 0.0091(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.212(5) . ? N1 C7 1.334(5) . ? N1 C1 1.445(5) . ? N1 C16 1.472(6) . ? C1 C6 1.409(6) . ? C1 C2 1.381(6) . ? C2 C3 1.395(7) . ? C2 C15 1.513(6) . ? C3 C4 1.381(7) . ? C4 C5 1.372(6) . ? C5 C6 1.388(6) . ? C6 C14 1.504(6) . ? C7 C8 1.510(6) . ? C8 C13 1.368(6) . ? C8 C9 1.383(6) . ? C9 F1 1.338(5) . ? C9 C10 1.364(7) . ? C10 F2 1.346(6) . ? C10 C11 1.369(8) . ? C11 F3 1.352(5) . ? C11 C12 1.372(8) . ? C12 F4 1.342(6) . ? C12 C13 1.375(7) . ? C13 F5 1.340(6) . ? O1A C7A 1.220(5) . ? N1A C7A 1.335(5) . ? N1A C1A 1.434(5) . ? N1A C16A 1.464(5) . ? C1A C2A 1.404(6) . ? C1A C6A 1.403(6) . ? C2A C3A 1.394(6) . ? C2A C15A 1.495(7) . ? C3A C4A 1.383(7) . ? C4A C5A 1.371(7) . ? C5A C6A 1.390(6) . ? C6A C14A 1.503(6) . ? C7A C8A 1.513(6) . ? C8A C13A 1.380(7) . ? C8A C9A 1.377(6) . ? C9A F1A 1.346(5) . ? C9A C10A 1.366(7) . ? C10A F2A 1.345(6) . ? C10A C11A 1.351(8) . ? C11A F3A 1.340(6) . ? C11A C12A 1.362(8) . ? C12A F4A 1.349(6) . ? C12A C13A 1.386(7) . ? C13A F5A 1.340(5) . ? O1B C7B 1.218(5) . ? N1B C7B 1.317(5) . ? N1B C1B 1.444(5) . ? N1B C16B 1.471(6) . ? C1B C6B 1.387(7) . ? C1B C2B 1.401(7) . ? C2B C3B 1.391(7) . ? C2B C14B 1.484(8) . ? C3B C4B 1.380(10) . ? C4B C5B 1.386(10) . ? C5B C6B 1.385(8) . ? C6B C15B 1.505(8) . ? C7B C8B 1.517(6) . ? C8B C9B 1.370(7) . ? C8B C13B 1.385(8) . ? C9B F1B 1.344(8) . ? C9B C10B 1.371(9) . ? C10B F2B 1.333(8) . ? C10B C11B 1.377(12) . ? C11B F3B 1.346(6) . ? C11B C12B 1.339(11) . ? C12B F4B 1.337(9) . ? C12B C13B 1.381(7) . ? C13B F5B 1.336(6) . ? O1C N1C 1.230(5) . ? N1C C7C 1.344(5) . ? N1C C8C 1.510(6) . ? C1C C6C 1.388(6) . ? C1C C2C 1.399(6) . ? C1C C7C 1.440(6) . ? C2C C3C 1.397(7) . ? C2C C15C 1.505(7) . ? C3C C4C 1.369(8) . ? C4C C5C 1.377(8) . ? C5C C6C 1.387(7) . ? C6C C14C 1.504(7) . ? C7C C16C 1.460(5) . ? C8C C9C 1.373(6) . ? C8C C13C 1.380(7) . ? C9C F1C 1.336(6) . ? C9C C10C 1.377(7) . ? C10C F2C 1.332(6) . ? C10C C11C 1.367(9) . ? C11C F3C 1.337(6) . ? C11C C12C 1.364(8) . ? C12C F4C 1.356(6) . ? C12C C13C 1.367(7) . ? C13C F5C 1.344(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C1 119.0(3) . . ? C7 N1 C16 123.3(4) . . ? C1 N1 C16 117.7(4) . . ? C6 C1 C2 122.2(4) . . ? C6 C1 N1 118.4(4) . . ? C2 C1 N1 119.3(4) . . ? C3 C2 C1 118.4(4) . . ? C3 C2 C15 120.0(4) . . ? C1 C2 C15 121.6(4) . . ? C4 C3 C2 120.4(4) . . ? C5 C4 C3 120.2(4) . . ? C4 C5 C6 121.6(4) . . ? C5 C6 C1 117.2(4) . . ? C5 C6 C14 121.6(4) . . ? C1 C6 C14 121.3(4) . . ? O1 C7 N1 124.0(4) . . ? O1 C7 C8 120.5(4) . . ? N1 C7 C8 115.5(3) . . ? C13 C8 C9 117.9(4) . . ? C13 C8 C7 120.3(4) . . ? C9 C8 C7 121.8(4) . . ? F1 C9 C10 118.4(4) . . ? F1 C9 C8 119.6(4) . . ? C10 C9 C8 121.9(5) . . ? F2 C10 C9 122.1(5) . . ? F2 C10 C11 119.0(5) . . ? C9 C10 C11 118.9(5) . . ? F3 C11 C10 120.5(5) . . ? F3 C11 C12 118.9(5) . . ? C10 C11 C12 120.7(4) . . ? F4 C12 C13 120.6(5) . . ? F4 C12 C11 120.1(5) . . ? C13 C12 C11 119.3(5) . . ? F5 C13 C12 119.0(4) . . ? F5 C13 C8 119.8(4) . . ? C12 C13 C8 121.3(5) . . ? C7A N1A C1A 118.9(3) . . ? C7A N1A C16A 123.1(4) . . ? C1A N1A C16A 117.9(3) . . ? C2A C1A C6A 121.5(4) . . ? C2A C1A N1A 119.6(4) . . ? C6A C1A N1A 118.9(4) . . ? C3A C2A C1A 117.7(4) . . ? C3A C2A C15A 121.1(4) . . ? C1A C2A C15A 121.2(4) . . ? C4A C3A C2A 121.2(4) . . ? C3A C4A C5A 120.1(4) . . ? C6A C5A C4A 121.3(4) . . ? C5A C6A C1A 118.1(4) . . ? C5A C6A C14A 121.2(4) . . ? C1A C6A C14A 120.7(4) . . ? O1A C7A N1A 124.2(4) . . ? O1A C7A C8A 120.3(4) . . ? N1A C7A C8A 115.5(3) . . ? C13A C8A C9A 117.4(4) . . ? C13A C8A C7A 121.5(4) . . ? C9A C8A C7A 121.0(4) . . ? F1A C9A C10A 119.1(4) . . ? F1A C9A C8A 119.1(4) . . ? C10A C9A C8A 121.7(5) . . ? F2A C10A C11A 119.4(5) . . ? F2A C10A C9A 120.5(5) . . ? C11A C10A C9A 120.1(5) . . ? F3A C11A C12A 118.8(5) . . ? F3A C11A C10A 121.0(5) . . ? C12A C11A C10A 120.2(5) . . ? F4A C12A C11A 121.0(5) . . ? F4A C12A C13A 119.1(5) . . ? C11A C12A C13A 119.9(5) . . ? F5A C13A C8A 119.4(4) . . ? F5A C13A C12A 120.0(5) . . ? C8A C13A C12A 120.7(4) . . ? C7B N1B C1B 119.3(3) . . ? C7B N1B C16B 124.3(3) . . ? C1B N1B C16B 116.4(3) . . ? C6B C1B C2B 123.3(4) . . ? C6B C1B N1B 118.1(4) . . ? C2B C1B N1B 118.6(4) . . ? C3B C2B C1B 116.8(6) . . ? C3B C2B C14B 121.2(5) . . ? C1B C2B C14B 122.0(4) . . ? C4B C3B C2B 121.5(6) . . ? C3B C4B C5B 119.8(5) . . ? C4B C5B C6B 121.2(6) . . ? C5B C6B C1B 117.5(6) . . ? C5B C6B C15B 121.9(6) . . ? C1B C6B C15B 120.6(5) . . ? O1B C7B N1B 124.4(4) . . ? O1B C7B C8B 119.4(4) . . ? N1B C7B C8B 116.2(4) . . ? C9B C8B C13B 117.0(5) . . ? C9B C8B C7B 120.9(5) . . ? C13B C8B C7B 122.1(4) . . ? F1B C9B C10B 118.7(6) . . ? F1B C9B C8B 118.9(5) . . ? C10B C9B C8B 122.4(7) . . ? F2B C10B C9B 120.2(8) . . ? F2B C10B C11B 121.3(7) . . ? C9B C10B C11B 118.4(6) . . ? F3B C11B C12B 120.8(8) . . ? F3B C11B C10B 118.0(8) . . ? C12B C11B C10B 121.2(5) . . ? F4B C12B C11B 120.4(6) . . ? F4B C12B C13B 120.0(7) . . ? C11B C12B C13B 119.6(7) . . ? F5B C13B C12B 119.6(6) . . ? F5B C13B C8B 119.1(4) . . ? C12B C13B C8B 121.3(6) . . ? O1C N1C C7C 124.7(4) . . ? O1C N1C C8C 119.7(4) . . ? C7C N1C C8C 115.6(4) . . ? C6C C1C C2C 122.0(4) . . ? C6C C1C C7C 119.1(4) . . ? C2C C1C C7C 118.9(4) . . ? C1C C2C C3C 117.2(4) . . ? C1C C2C C15C 121.2(4) . . ? C3C C2C C15C 121.6(4) . . ? C4C C3C C2C 121.0(5) . . ? C3C C4C C5C 121.0(5) . . ? C4C C5C C6C 120.0(5) . . ? C5C C6C C1C 118.8(5) . . ? C5C C6C C14C 119.9(5) . . ? C1C C6C C14C 121.4(4) . . ? N1C C7C C1C 118.4(3) . . ? N1C C7C C16C 123.3(4) . . ? C1C C7C C16C 118.3(3) . . ? C9C C8C C13C 117.4(4) . . ? C9C C8C N1C 120.4(4) . . ? C13C C8C N1C 122.1(4) . . ? F1C C9C C8C 119.4(4) . . ? F1C C9C C10C 119.1(5) . . ? C8C C9C C10C 121.5(5) . . ? F2C C10C C11C 119.9(5) . . ? F2C C10C C9C 120.7(6) . . ? C11C C10C C9C 119.5(5) . . ? F3C C11C C10C 119.6(6) . . ? F3C C11C C12C 120.0(6) . . ? C10C C11C C12C 120.4(5) . . ? F4C C12C C11C 120.3(5) . . ? F4C C12C C13C 120.3(5) . . ? C11C C12C C13C 119.4(5) . . ? F5C C13C C8C 119.7(4) . . ? F5C C13C C12C 118.4(5) . . ? C8C C13C C12C 121.9(5) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.350 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.045 # Attachment 'och276m.cif' data_och276m _database_code_depnum_ccdc_archive 'CCDC 615402' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H34 Cl2 N2 O4' _chemical_formula_weight 533.47 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 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 15.436(8) _cell_length_b 11.833(6) _cell_length_c 16.617(9) _cell_angle_alpha 90.00 _cell_angle_beta 111.728(9) _cell_angle_gamma 90.00 _cell_volume 2820(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 590 _cell_measurement_theta_min 1.42 _cell_measurement_theta_max 25.00 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9440 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker smart1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 19579 _diffrn_reflns_av_R_equivalents 0.2662 _diffrn_reflns_av_sigmaI/netI 0.2367 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4965 _reflns_number_gt 1845 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker smart' _computing_cell_refinement 'Bruker smart' _computing_data_reduction 'Bruker saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1462P)^2^+0.0000P] 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 4965 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2092 _refine_ls_R_factor_gt 0.0950 _refine_ls_wR_factor_ref 0.2908 _refine_ls_wR_factor_gt 0.2357 _refine_ls_goodness_of_fit_ref 0.866 _refine_ls_restrained_S_all 0.866 _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 Cl1 Cl 0.17224(13) 0.39561(16) 0.16403(11) 0.0588(6) Uani 1 1 d . . . Cl2 Cl 0.98703(15) 0.0391(2) 1.21863(14) 0.0988(10) Uani 1 1 d . . . N1 N 0.3396(3) 0.1190(4) 0.4795(3) 0.0348(13) Uani 1 1 d . . . H1 H 0.3266 0.0463 0.4745 0.042 Uiso 1 1 calc R . . N2 N 0.6534(3) -0.0361(4) 0.9053(3) 0.0366(13) Uani 1 1 d . . . H2 H 0.6235 -0.1007 0.8996 0.044 Uiso 1 1 calc R . . O1 O 0.6645(3) 0.1313(4) 0.8445(3) 0.0489(13) Uani 1 1 d . . . O2 O 0.4223(3) 0.2563(3) 0.5683(3) 0.0387(11) Uani 1 1 d . . . C1 C 0.5035(4) 0.0917(5) 0.6996(4) 0.0325(15) Uani 1 1 d . . . H1A H 0.5422 0.1541 0.6992 0.039 Uiso 1 1 calc R . . C2 C 0.5309(4) 0.0186(5) 0.7702(4) 0.0297(14) Uani 1 1 d . . . C3 C 0.4735(4) -0.0714(5) 0.7707(4) 0.0352(16) Uani 1 1 d . . . H3 H 0.4915 -0.1221 0.8184 0.042 Uiso 1 1 calc R . . C4 C 0.3898(4) -0.0876(5) 0.7017(4) 0.0349(16) Uani 1 1 d . . . H4 H 0.3503 -0.1487 0.7026 0.042 Uiso 1 1 calc R . . C5 C 0.3641(4) -0.0154(5) 0.6320(4) 0.0326(15) Uani 1 1 d . . . H5 H 0.3069 -0.0273 0.5847 0.039 Uiso 1 1 calc R . . C6 C 0.4209(4) 0.0749(5) 0.6300(4) 0.0288(14) Uani 1 1 d . . . C7 C 0.3944(4) 0.1581(5) 0.5576(4) 0.0339(15) Uani 1 1 d . . . C8 C 0.3006(4) 0.1885(5) 0.4034(4) 0.0350(15) Uani 1 1 d . . . C9 C 0.2053(4) 0.2057(5) 0.3715(4) 0.0360(16) Uani 1 1 d . . . C10 C 0.1657(5) 0.2695(5) 0.2957(4) 0.0425(17) Uani 1 1 d . . . H10 H 0.1002 0.2817 0.2718 0.051 Uiso 1 1 calc R . . C11 C 0.2223(4) 0.3146(5) 0.2558(4) 0.0375(16) Uani 1 1 d . . . C12 C 0.3169(5) 0.2956(5) 0.2890(4) 0.0419(17) Uani 1 1 d . . . H12 H 0.3545 0.3263 0.2602 0.050 Uiso 1 1 calc R . . C13 C 0.3583(4) 0.2326(5) 0.3634(4) 0.0353(16) Uani 1 1 d . . . C14 C 0.6215(4) 0.0423(6) 0.8431(4) 0.0368(16) Uani 1 1 d . . . C15 C 0.7351(4) -0.0170(5) 0.9811(4) 0.0380(16) Uani 1 1 d . . . C16 C 0.8222(4) -0.0426(5) 0.9784(4) 0.0413(17) Uani 1 1 d . . . C17 C 0.8994(4) -0.0245(6) 1.0524(5) 0.051(2) Uani 1 1 d . . . H17 H 0.9598 -0.0396 1.0522 0.061 Uiso 1 1 calc R . . C18 C 0.8904(5) 0.0152(6) 1.1264(5) 0.053(2) Uani 1 1 d . . . C19 C 0.8049(5) 0.0362(6) 1.1288(5) 0.053(2) Uani 1 1 d . . . H19 H 0.8000 0.0636 1.1806 0.063 Uiso 1 1 calc R . . C20 C 0.7252(4) 0.0182(5) 1.0570(4) 0.0418(17) Uani 1 1 d . . . C21 C 0.6290(5) 0.0401(7) 1.0572(5) 0.061(2) Uani 1 1 d . . . H21A H 0.6339 0.0654 1.1148 0.091 Uiso 1 1 calc R . . H21B H 0.5922 -0.0297 1.0422 0.091 Uiso 1 1 calc R . . H21C H 0.5983 0.0987 1.0144 0.091 Uiso 1 1 calc R . . C22 C 0.8309(5) -0.0841(7) 0.8961(4) 0.062(2) Uani 1 1 d . . . H22A H 0.8209 -0.0210 0.8555 0.092 Uiso 1 1 calc R . . H22B H 0.7841 -0.1428 0.8700 0.092 Uiso 1 1 calc R . . H22C H 0.8934 -0.1156 0.9092 0.092 Uiso 1 1 calc R . . C23 C 0.1441(5) 0.1595(6) 0.4167(4) 0.0487(19) Uani 1 1 d . . . H23A H 0.1433 0.0768 0.4137 0.073 Uiso 1 1 calc R . . H23B H 0.0805 0.1885 0.3883 0.073 Uiso 1 1 calc R . . H23C H 0.1687 0.1834 0.4775 0.073 Uiso 1 1 calc R . . C24 C 0.4613(4) 0.2098(6) 0.3983(4) 0.0460(18) Uani 1 1 d . . . H24A H 0.4890 0.2422 0.3591 0.069 Uiso 1 1 calc R . . H24B H 0.4721 0.1281 0.4029 0.069 Uiso 1 1 calc R . . H24C H 0.4899 0.2443 0.4558 0.069 Uiso 1 1 calc R . . C2S C 0.9365(9) 0.3434(11) 1.0082(8) 0.149(5) Uiso 1 1 d . . . H2S1 H 0.9943 0.3372 0.9968 0.223 Uiso 1 1 calc R . . H2S2 H 0.9495 0.3265 1.0693 0.223 Uiso 1 1 calc R . . H2S3 H 0.9119 0.4204 0.9952 0.223 Uiso 1 1 calc R . . C1S C 0.8719(7) 0.2678(8) 0.9568(6) 0.089(3) Uiso 1 1 d . . . H1S1 H 0.8991 0.1911 0.9692 0.107 Uiso 1 1 calc R . . H1S2 H 0.8613 0.2849 0.8955 0.107 Uiso 1 1 calc R . . O1S O 0.7841(3) 0.2661(4) 0.9659(3) 0.0544(13) Uiso 1 1 d . . . H1S H 0.7923 0.2639 1.0188 0.065 Uiso 1 1 calc R . . O2S O 0.2745(4) 0.8974(5) 0.4332(4) 0.0806(17) Uiso 1 1 d . . . H2S H 0.2216 0.9251 0.4241 0.097 Uiso 1 1 calc R . . C3S C 0.2784(7) 0.8576(9) 0.3524(6) 0.093(3) Uiso 1 1 d . . . H3S1 H 0.3101 0.9152 0.3298 0.112 Uiso 1 1 calc R . . H3S2 H 0.3164 0.7878 0.3635 0.112 Uiso 1 1 calc R . . C4S C 0.1923(9) 0.8355(12) 0.2903(8) 0.152(5) Uiso 1 1 d . . . H4S1 H 0.1567 0.7876 0.3150 0.227 Uiso 1 1 calc R . . H4S2 H 0.1999 0.7965 0.2413 0.227 Uiso 1 1 calc R . . H4S3 H 0.1589 0.9067 0.2703 0.227 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 Cl1 0.0630(13) 0.0651(13) 0.0468(11) 0.0157(10) 0.0188(9) -0.0003(10) Cl2 0.0630(15) 0.151(3) 0.0613(15) -0.0013(15) -0.0021(11) -0.0387(15) N1 0.037(3) 0.032(3) 0.038(3) -0.001(3) 0.016(3) -0.001(3) N2 0.036(3) 0.030(3) 0.037(3) 0.007(3) 0.006(3) -0.003(2) O1 0.043(3) 0.033(3) 0.057(3) 0.011(2) 0.002(2) -0.012(2) O2 0.046(3) 0.029(3) 0.037(3) -0.004(2) 0.011(2) 0.000(2) C1 0.029(4) 0.031(4) 0.041(4) -0.007(3) 0.017(3) 0.000(3) C2 0.029(3) 0.025(3) 0.035(4) -0.002(3) 0.012(3) 0.000(3) C3 0.035(4) 0.034(4) 0.039(4) 0.002(3) 0.018(3) 0.001(3) C4 0.030(4) 0.036(4) 0.040(4) -0.005(3) 0.015(3) -0.007(3) C5 0.026(3) 0.035(4) 0.036(4) -0.009(3) 0.011(3) -0.001(3) C6 0.022(3) 0.029(3) 0.035(4) -0.002(3) 0.010(3) 0.004(3) C7 0.034(4) 0.032(4) 0.038(4) -0.011(3) 0.016(3) 0.001(3) C8 0.038(4) 0.035(4) 0.033(4) -0.002(3) 0.014(3) -0.003(3) C9 0.040(4) 0.037(4) 0.032(4) 0.002(3) 0.015(3) -0.006(3) C10 0.045(4) 0.041(4) 0.037(4) 0.008(3) 0.010(3) -0.001(3) C11 0.044(4) 0.044(4) 0.024(3) 0.006(3) 0.013(3) -0.002(3) C12 0.043(4) 0.045(4) 0.039(4) -0.002(4) 0.017(3) -0.010(3) C13 0.037(4) 0.031(4) 0.041(4) -0.008(3) 0.018(3) -0.006(3) C14 0.025(4) 0.040(4) 0.042(4) -0.002(3) 0.009(3) 0.003(3) C15 0.033(4) 0.031(4) 0.046(4) 0.005(3) 0.010(3) -0.006(3) C16 0.030(4) 0.034(4) 0.051(4) -0.002(3) 0.004(3) -0.008(3) C17 0.020(4) 0.064(5) 0.060(5) 0.012(4) 0.004(3) -0.009(3) C18 0.040(4) 0.060(5) 0.047(5) 0.004(4) 0.001(4) -0.013(4) C19 0.054(5) 0.055(5) 0.046(5) 0.005(4) 0.015(4) -0.013(4) C20 0.043(4) 0.040(4) 0.044(4) 0.006(3) 0.018(3) 0.001(3) C21 0.054(5) 0.080(6) 0.055(5) 0.005(4) 0.027(4) 0.010(4) C22 0.047(5) 0.082(6) 0.058(5) -0.010(4) 0.023(4) 0.004(4) C23 0.046(4) 0.055(5) 0.051(4) 0.003(4) 0.025(4) -0.006(4) C24 0.042(4) 0.047(4) 0.052(4) 0.000(4) 0.021(3) 0.001(4) _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 Cl1 C11 1.723(6) . ? Cl2 C18 1.721(7) . ? N1 C7 1.343(7) . ? N1 C8 1.441(7) . ? N2 C14 1.340(7) . ? N2 C15 1.432(7) . ? O1 C14 1.240(7) . ? O2 C7 1.229(7) . ? C1 C6 1.384(8) . ? C1 C2 1.392(8) . ? C2 C3 1.387(8) . ? C2 C14 1.499(8) . ? C3 C4 1.387(8) . ? C4 C5 1.374(8) . ? C5 C6 1.390(8) . ? C6 C7 1.489(8) . ? C8 C9 1.383(8) . ? C8 C13 1.394(8) . ? C9 C10 1.399(8) . ? C9 C23 1.511(8) . ? C10 C11 1.385(8) . ? C11 C12 1.376(8) . ? C12 C13 1.382(8) . ? C13 C24 1.501(8) . ? C15 C20 1.391(9) . ? C15 C16 1.395(8) . ? C16 C17 1.376(8) . ? C16 C22 1.505(9) . ? C17 C18 1.371(9) . ? C18 C19 1.358(9) . ? C19 C20 1.376(9) . ? C20 C21 1.508(9) . ? C2S C1S 1.377(13) . ? C1S O1S 1.418(10) . ? O2S C3S 1.445(9) . ? C3S C4S 1.372(13) . ? 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 C7 N1 C8 124.1(5) . . ? C14 N2 C15 121.5(5) . . ? C6 C1 C2 120.9(6) . . ? C3 C2 C1 119.2(6) . . ? C3 C2 C14 123.1(6) . . ? C1 C2 C14 117.7(5) . . ? C2 C3 C4 120.2(6) . . ? C5 C4 C3 120.1(6) . . ? C4 C5 C6 120.7(6) . . ? C1 C6 C5 119.0(6) . . ? C1 C6 C7 118.2(5) . . ? C5 C6 C7 122.8(5) . . ? O2 C7 N1 121.8(6) . . ? O2 C7 C6 122.1(6) . . ? N1 C7 C6 116.0(6) . . ? C9 C8 C13 122.6(6) . . ? C9 C8 N1 117.4(5) . . ? C13 C8 N1 120.0(6) . . ? C8 C9 C10 118.2(6) . . ? C8 C9 C23 122.0(6) . . ? C10 C9 C23 119.8(6) . . ? C11 C10 C9 119.7(6) . . ? C12 C11 C10 120.6(6) . . ? C12 C11 Cl1 120.5(5) . . ? C10 C11 Cl1 118.9(5) . . ? C11 C12 C13 121.2(6) . . ? C12 C13 C8 117.6(6) . . ? C12 C13 C24 121.0(6) . . ? C8 C13 C24 121.4(6) . . ? O1 C14 N2 122.1(6) . . ? O1 C14 C2 120.5(6) . . ? N2 C14 C2 117.4(6) . . ? C20 C15 C16 121.7(6) . . ? C20 C15 N2 119.2(6) . . ? C16 C15 N2 118.9(6) . . ? C17 C16 C15 117.6(6) . . ? C17 C16 C22 121.6(6) . . ? C15 C16 C22 120.7(6) . . ? C18 C17 C16 120.9(6) . . ? C19 C18 C17 120.7(6) . . ? C19 C18 Cl2 118.4(6) . . ? C17 C18 Cl2 120.8(6) . . ? C18 C19 C20 120.9(7) . . ? C19 C20 C15 118.0(6) . . ? C19 C20 C21 122.5(7) . . ? C15 C20 C21 119.5(6) . . ? C2S C1S O1S 116.4(9) . . ? C4S C3S O2S 113.5(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.549 _refine_diff_density_min -0.623 _refine_diff_density_rms 0.092 # Attachment 'och277m.cif' data_och277m _database_code_depnum_ccdc_archive 'CCDC 615403' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 N2 O3' _chemical_formula_weight 312.36 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)/n 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 7.123(3) _cell_length_b 16.792(8) _cell_length_c 13.785(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.881(9) _cell_angle_gamma 90.00 _cell_volume 1607.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 501 _cell_measurement_theta_min 5.721 _cell_measurement_theta_max 50.544 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9629 _exptl_absorpt_correction_T_max 0.9894 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7085 _diffrn_reflns_av_R_equivalents 0.2415 _diffrn_reflns_av_sigmaI/netI 0.5909 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3478 _reflns_number_gt 822 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.0000P] 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 3478 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3108 _refine_ls_R_factor_gt 0.0758 _refine_ls_wR_factor_ref 0.2135 _refine_ls_wR_factor_gt 0.1534 _refine_ls_goodness_of_fit_ref 0.740 _refine_ls_restrained_S_all 0.740 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3758(6) 0.3437(3) 0.1512(3) 0.0235(12) Uani 1 1 d . . . N2 N 0.3609(8) 0.4333(4) 0.6030(4) 0.0367(15) Uani 1 1 d . . . O1 O 0.0654(5) 0.3105(2) 0.1500(3) 0.0326(11) Uani 1 1 d . . . O2 O 0.4798(6) 0.3951(3) 0.6655(3) 0.0437(13) Uani 1 1 d . . . O3 O 0.2736(6) 0.4912(3) 0.6239(3) 0.0496(14) Uani 1 1 d . . . C1 C 0.2592(7) 0.3593(3) 0.3030(4) 0.0207(14) Uani 1 1 d . . . C2 C 0.3351(8) 0.3040(3) 0.3808(4) 0.0229(14) Uani 1 1 d . . . C3 C 0.3715(7) 0.3298(3) 0.4782(4) 0.0233(15) Uani 1 1 d . . . H3A H 0.4290 0.2952 0.5310 0.028 Uiso 1 1 calc R . . C4 C 0.3231(8) 0.4066(4) 0.4973(4) 0.0239(14) Uani 1 1 d . . . C5 C 0.2385(8) 0.4585(3) 0.4254(4) 0.0280(16) Uani 1 1 d . . . H5A H 0.2014 0.5099 0.4430 0.034 Uiso 1 1 calc R . . C6 C 0.2067(8) 0.4365(4) 0.3267(4) 0.0260(15) Uani 1 1 d . . . C7 C 0.2257(8) 0.3339(3) 0.1950(4) 0.0273(16) Uani 1 1 d . . . C8 C 0.3580(7) 0.3248(4) 0.0467(4) 0.0258(15) Uani 1 1 d . . . C9 C 0.3260(7) 0.3872(3) -0.0231(4) 0.0210(14) Uani 1 1 d . . . C10 C 0.3331(8) 0.3706(4) -0.1211(4) 0.0308(16) Uani 1 1 d . . . H10A H 0.3125 0.4121 -0.1691 0.037 Uiso 1 1 calc R . . C11 C 0.3697(8) 0.2944(4) -0.1491(4) 0.0304(16) Uani 1 1 d . . . H11A H 0.3770 0.2839 -0.2159 0.036 Uiso 1 1 calc R . . C12 C 0.3958(7) 0.2335(4) -0.0807(4) 0.0299(16) Uani 1 1 d . . . H12A H 0.4157 0.1808 -0.1014 0.036 Uiso 1 1 calc R . . C13 C 0.3935(7) 0.2479(4) 0.0185(4) 0.0255(15) Uani 1 1 d . . . C14 C 0.4296(8) 0.1815(3) 0.0938(4) 0.0339(16) Uani 1 1 d . . . H14A H 0.5348 0.1966 0.1497 0.051 Uiso 1 1 calc R . . H14B H 0.4650 0.1330 0.0626 0.051 Uiso 1 1 calc R . . H14C H 0.3126 0.1717 0.1182 0.051 Uiso 1 1 calc R . . C15 C 0.2710(8) 0.4690(3) 0.0069(4) 0.0354(17) Uani 1 1 d . . . H15A H 0.2619 0.5058 -0.0492 0.053 Uiso 1 1 calc R . . H15B H 0.3693 0.4881 0.0637 0.053 Uiso 1 1 calc R . . H15C H 0.1463 0.4662 0.0256 0.053 Uiso 1 1 calc R . . C16 C 0.5663(7) 0.3724(4) 0.2039(4) 0.0303(16) Uani 1 1 d . . . H16A H 0.5762 0.4297 0.1923 0.045 Uiso 1 1 calc R . . H16B H 0.6665 0.3442 0.1791 0.045 Uiso 1 1 calc R . . H16C H 0.5830 0.3625 0.2754 0.045 Uiso 1 1 calc R . . C17 C 0.3741(8) 0.2189(3) 0.3569(4) 0.0315(16) Uani 1 1 d . . . H17A H 0.4728 0.2175 0.3176 0.047 Uiso 1 1 calc R . . H17B H 0.2553 0.1946 0.3188 0.047 Uiso 1 1 calc R . . H17C H 0.4194 0.1892 0.4189 0.047 Uiso 1 1 calc R . . C18 C 0.1184(9) 0.4948(4) 0.2449(4) 0.0363(17) Uani 1 1 d . . . H18A H 0.0660 0.5406 0.2741 0.054 Uiso 1 1 calc R . . H18B H 0.0147 0.4684 0.1970 0.054 Uiso 1 1 calc R . . H18C H 0.2175 0.5130 0.2108 0.054 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 N1 0.023(3) 0.030(3) 0.017(3) 0.003(2) 0.004(2) 0.003(2) N2 0.045(4) 0.043(4) 0.025(3) -0.006(3) 0.015(3) -0.014(3) O1 0.025(2) 0.043(3) 0.028(2) -0.007(2) 0.0042(19) -0.003(2) O2 0.058(3) 0.053(3) 0.018(2) 0.004(2) 0.003(2) -0.005(3) O3 0.060(3) 0.048(3) 0.039(3) -0.022(3) 0.007(2) 0.010(3) C1 0.018(3) 0.026(4) 0.020(3) -0.004(3) 0.007(2) -0.001(3) C2 0.020(3) 0.021(4) 0.028(3) 0.005(3) 0.009(3) 0.007(3) C3 0.016(3) 0.031(4) 0.022(3) 0.005(3) 0.003(2) -0.003(3) C4 0.024(3) 0.025(4) 0.023(3) 0.003(3) 0.005(3) -0.006(3) C5 0.031(4) 0.025(4) 0.030(4) -0.007(3) 0.011(3) -0.008(3) C6 0.027(3) 0.025(4) 0.025(3) 0.007(3) 0.005(3) -0.001(3) C7 0.020(3) 0.031(4) 0.026(3) -0.003(3) -0.004(3) 0.010(3) C8 0.019(3) 0.035(4) 0.023(3) -0.006(3) 0.002(3) -0.008(3) C9 0.011(3) 0.021(4) 0.030(3) 0.004(3) 0.001(2) -0.001(3) C10 0.031(4) 0.034(5) 0.026(4) 0.003(3) 0.004(3) -0.005(3) C11 0.025(3) 0.041(5) 0.024(3) 0.000(3) 0.004(3) -0.003(3) C12 0.019(3) 0.036(5) 0.035(4) -0.012(3) 0.007(3) -0.003(3) C13 0.019(3) 0.032(4) 0.025(3) 0.001(3) 0.003(3) -0.003(3) C14 0.032(4) 0.024(4) 0.046(4) -0.009(3) 0.009(3) 0.002(3) C15 0.039(4) 0.039(5) 0.027(4) 0.002(3) 0.004(3) 0.002(3) C16 0.025(3) 0.041(5) 0.024(3) 0.000(3) 0.003(3) -0.006(3) C17 0.035(4) 0.029(4) 0.029(4) 0.000(3) 0.002(3) 0.000(3) C18 0.055(4) 0.029(4) 0.026(4) 0.007(3) 0.011(3) 0.014(4) _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 N1 C7 1.350(7) . ? N1 C8 1.453(6) . ? N1 C16 1.470(6) . ? N2 O3 1.223(6) . ? N2 O2 1.243(6) . ? N2 C4 1.490(7) . ? O1 C7 1.236(6) . ? C1 C6 1.408(7) . ? C1 C2 1.431(7) . ? C1 C7 1.515(7) . ? C2 C3 1.379(7) . ? C2 C17 1.506(7) . ? C3 C4 1.376(7) . ? C3 H3A 0.9500 . ? C4 C5 1.356(7) . ? C5 C6 1.380(7) . ? C5 H5A 0.9500 . ? C6 C18 1.520(7) . ? C8 C13 1.387(7) . ? C8 C9 1.406(7) . ? C9 C10 1.391(7) . ? C9 C15 1.511(7) . ? C10 C11 1.378(8) . ? C10 H10A 0.9500 . ? C11 C12 1.375(7) . ? C11 H11A 0.9500 . ? C12 C13 1.392(7) . ? C12 H12A 0.9500 . ? C13 C14 1.506(7) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 C7 N1 C8 121.0(4) . . ? C7 N1 C16 123.7(4) . . ? C8 N1 C16 115.3(4) . . ? O3 N2 O2 123.4(5) . . ? O3 N2 C4 118.6(6) . . ? O2 N2 C4 118.0(6) . . ? C6 C1 C2 120.0(5) . . ? C6 C1 C7 119.7(5) . . ? C2 C1 C7 120.2(5) . . ? C3 C2 C1 118.9(5) . . ? C3 C2 C17 120.5(5) . . ? C1 C2 C17 120.7(5) . . ? C4 C3 C2 118.7(5) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C5 C4 C3 123.5(5) . . ? C5 C4 N2 118.4(6) . . ? C3 C4 N2 118.1(5) . . ? C4 C5 C6 119.8(6) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? C5 C6 C1 118.8(5) . . ? C5 C6 C18 120.6(6) . . ? C1 C6 C18 120.6(5) . . ? O1 C7 N1 123.3(5) . . ? O1 C7 C1 120.6(5) . . ? N1 C7 C1 116.0(5) . . ? C13 C8 C9 121.0(5) . . ? C13 C8 N1 119.9(5) . . ? C9 C8 N1 118.7(5) . . ? C10 C9 C8 118.6(5) . . ? C10 C9 C15 121.1(5) . . ? C8 C9 C15 120.2(5) . . ? C11 C10 C9 120.6(6) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C12 C11 C10 120.2(5) . . ? C12 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? C11 C12 C13 121.0(6) . . ? C11 C12 H12A 119.5 . . ? C13 C12 H12A 119.5 . . ? C8 C13 C12 118.6(6) . . ? C8 C13 C14 120.7(5) . . ? C12 C13 C14 120.7(6) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C9 C15 H15A 109.5 . . ? C9 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C9 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C2 C17 H17A 109.5 . . ? C2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C6 C18 H18A 109.5 . . ? C6 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C6 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.254 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.070 # Attachment 'OCH52.cif' data_och52 _database_code_depnum_ccdc_archive 'CCDC 615404' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 N O' _chemical_formula_weight 163.21 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)/n 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 7.984(8) _cell_length_b 16.218(14) _cell_length_c 8.171(8) _cell_angle_alpha 90.00 _cell_angle_beta 112.95(15) _cell_angle_gamma 90.00 _cell_volume 974.3(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 237 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 22.37 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.113 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9773 _exptl_absorpt_correction_T_max 0.9914 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'siemens P4' _diffrn_measurement_method 'OMEGA SCANS' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1918 _diffrn_reflns_av_R_equivalents 0.0857 _diffrn_reflns_av_sigmaI/netI 0.1048 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1697 _reflns_number_gt 710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SIEMENS XSCANS' _computing_cell_refinement 'SIEMENS XSCANS' _computing_data_reduction 'SIEMENS XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.1534P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.001(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1697 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2053 _refine_ls_R_factor_gt 0.0930 _refine_ls_wR_factor_ref 0.3073 _refine_ls_wR_factor_gt 0.2273 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.3810(5) 0.1903(2) 0.6027(5) 0.0740(13) Uani 1 1 d . . . N1 N 0.1413(5) 0.2734(2) 0.4525(5) 0.0575(12) Uani 1 1 d . . . H1A H 0.0482 0.2797 0.3545 0.069 Uiso 1 1 calc R . . C1 C 0.1743(6) 0.3342(3) 0.5860(7) 0.0602(14) Uani 1 1 d . . . C2 C 0.2171(7) 0.4151(4) 0.5490(8) 0.0740(17) Uani 1 1 d . . . C3 C 0.2424(9) 0.4758(4) 0.6734(12) 0.109(3) Uani 1 1 d . . . H3A H 0.2670 0.5295 0.6501 0.131 Uiso 1 1 calc R . . C4 C 0.2311(10) 0.4567(6) 0.8333(13) 0.121(3) Uani 1 1 d . . . H4A H 0.2527 0.4975 0.9190 0.146 Uiso 1 1 calc R . . C5 C 0.1877(9) 0.3770(6) 0.8686(9) 0.105(2) Uani 1 1 d . . . H5A H 0.1792 0.3657 0.9767 0.126 Uiso 1 1 calc R . . C6 C 0.1574(7) 0.3151(4) 0.7455(8) 0.0736(17) Uani 1 1 d . . . C7 C 0.1065(9) 0.2289(4) 0.7824(9) 0.099(2) Uani 1 1 d . . . H7A H 0.2148 0.1964 0.8364 0.149 Uiso 1 1 calc R . . H7B H 0.0288 0.2036 0.6728 0.149 Uiso 1 1 calc R . . H7C H 0.0438 0.2321 0.8613 0.149 Uiso 1 1 calc R . . C8 C 0.2374(9) 0.4343(4) 0.3781(10) 0.105(3) Uani 1 1 d . . . H8A H 0.2593 0.4922 0.3728 0.158 Uiso 1 1 calc R . . H8B H 0.1279 0.4192 0.2798 0.158 Uiso 1 1 calc R . . H8C H 0.3379 0.4036 0.3725 0.158 Uiso 1 1 calc R . . C9 C 0.2491(6) 0.2049(3) 0.4696(6) 0.0551(14) Uani 1 1 d . . . C10 C 0.1907(7) 0.1497(3) 0.3108(7) 0.0777(18) Uani 1 1 d . . . H10A H 0.2942 0.1357 0.2842 0.117 Uiso 1 1 calc R . . H10B H 0.1021 0.1777 0.2108 0.117 Uiso 1 1 calc R . . H10C H 0.1382 0.1004 0.3351 0.117 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 0.064(2) 0.069(2) 0.067(2) -0.0068(18) 0.0015(18) 0.0132(18) N1 0.048(2) 0.055(3) 0.057(2) 0.002(2) 0.0064(18) -0.0024(19) C1 0.045(3) 0.055(3) 0.066(3) -0.002(3) 0.006(2) 0.006(2) C2 0.060(3) 0.055(3) 0.089(4) 0.003(3) 0.010(3) 0.008(3) C3 0.095(5) 0.064(4) 0.136(6) -0.025(5) 0.008(5) 0.009(3) C4 0.099(5) 0.098(6) 0.138(7) -0.061(6) 0.015(5) 0.012(5) C5 0.082(5) 0.133(7) 0.090(5) -0.032(5) 0.022(4) 0.008(5) C6 0.057(3) 0.080(4) 0.075(4) -0.008(3) 0.016(3) 0.005(3) C7 0.098(5) 0.108(6) 0.102(5) 0.008(4) 0.050(4) -0.010(4) C8 0.101(5) 0.065(4) 0.136(6) 0.023(4) 0.031(5) -0.008(3) C9 0.049(3) 0.053(3) 0.053(3) 0.005(2) 0.009(2) -0.002(2) C10 0.069(3) 0.070(4) 0.076(4) -0.011(3) 0.008(3) 0.000(3) _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 C9 1.206(5) . ? N1 C9 1.379(6) . ? N1 C1 1.417(7) . ? C1 C6 1.396(8) . ? C1 C2 1.418(7) . ? C2 C3 1.372(9) . ? C2 C8 1.499(9) . ? C3 C4 1.379(11) . ? C4 C5 1.397(11) . ? C5 C6 1.374(9) . ? C6 C7 1.519(8) . ? C9 C10 1.493(7) . ? 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 C9 N1 C1 124.2(4) . . ? C6 C1 N1 120.5(5) . . ? C6 C1 C2 121.6(5) . . ? N1 C1 C2 117.8(5) . . ? C3 C2 C1 118.9(7) . . ? C3 C2 C8 120.2(7) . . ? C1 C2 C8 120.9(5) . . ? C2 C3 C4 119.7(7) . . ? C3 C4 C5 121.1(7) . . ? C6 C5 C4 120.8(8) . . ? C5 C6 C1 117.9(6) . . ? C5 C6 C7 120.8(7) . . ? C1 C6 C7 121.3(5) . . ? O1 C9 N1 122.7(4) . . ? O1 C9 C10 122.2(5) . . ? N1 C9 C10 115.1(4) . . ? 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 C9 N1 C1 C6 -67.3(7) . . . . ? C9 N1 C1 C2 115.3(5) . . . . ? C6 C1 C2 C3 0.0(7) . . . . ? N1 C1 C2 C3 177.4(5) . . . . ? C6 C1 C2 C8 179.1(5) . . . . ? N1 C1 C2 C8 -3.5(7) . . . . ? C1 C2 C3 C4 1.9(9) . . . . ? C8 C2 C3 C4 -177.2(6) . . . . ? C2 C3 C4 C5 -2.3(11) . . . . ? C3 C4 C5 C6 0.9(11) . . . . ? C4 C5 C6 C1 1.0(9) . . . . ? C4 C5 C6 C7 -178.8(6) . . . . ? N1 C1 C6 C5 -178.8(5) . . . . ? C2 C1 C6 C5 -1.5(8) . . . . ? N1 C1 C6 C7 1.0(7) . . . . ? C2 C1 C6 C7 178.3(5) . . . . ? C1 N1 C9 O1 1.0(8) . . . . ? C1 N1 C9 C10 -179.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.287 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.053 # Attachment 'och86m.cif' data_och86m _database_code_depnum_ccdc_archive 'CCDC 615405' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 N2 O2' _chemical_formula_weight 344.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.403(14) _cell_length_b 13.41(3) _cell_length_c 18.84(3) _cell_angle_alpha 76.34(14) _cell_angle_beta 80.3(2) _cell_angle_gamma 88.66(16) _cell_volume 1791(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 69 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 22.76 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9661 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11517 _diffrn_reflns_av_R_equivalents 0.0897 _diffrn_reflns_av_sigmaI/netI 0.2241 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 28.25 _reflns_number_total 8157 _reflns_number_gt 2620 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0936P)^2^+0.0000P] 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 8157 _refine_ls_number_parameters 473 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2151 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.2235 _refine_ls_wR_factor_gt 0.1436 _refine_ls_goodness_of_fit_ref 0.809 _refine_ls_restrained_S_all 0.809 _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 N1A N 0.2269(4) 0.4764(2) -0.03576(18) 0.0311(8) Uani 1 1 d . . . N2A N 0.1304(4) 0.7961(2) 0.07408(17) 0.0330(8) Uani 1 1 d . . . H2AA H 0.0211 0.7763 0.0698 0.040 Uiso 1 1 calc R . . O1A O 0.4357(4) 0.7721(2) 0.05027(16) 0.0438(8) Uani 1 1 d . . . C1A C 0.2449(5) 0.6520(3) 0.0220(2) 0.0282(9) Uani 1 1 d . . . C2A C 0.2749(5) 0.5544(3) 0.0641(2) 0.0283(9) Uani 1 1 d . . . C3A C 0.3198(6) 0.5360(3) 0.1372(2) 0.0349(10) Uani 1 1 d . . . H3AA H 0.3266 0.5921 0.1595 0.042 Uiso 1 1 calc R . . C4A C 0.3529(6) 0.4396(3) 0.1753(2) 0.0371(11) Uani 1 1 d . . . H4AA H 0.3823 0.4294 0.2237 0.045 Uiso 1 1 calc R . . C5A C 0.3442(6) 0.3546(3) 0.1439(2) 0.0405(11) Uani 1 1 d . . . H5AA H 0.3682 0.2877 0.1710 0.049 Uiso 1 1 calc R . . C6A C 0.3012(6) 0.3681(3) 0.0745(2) 0.0395(11) Uani 1 1 d . . . H6AA H 0.2964 0.3103 0.0538 0.047 Uiso 1 1 calc R . . C7A C 0.2633(5) 0.4677(3) 0.0324(2) 0.0292(9) Uani 1 1 d . . . C8A C 0.1977(5) 0.5701(3) -0.0761(2) 0.0336(10) Uani 1 1 d . . . C9A C 0.1624(6) 0.5790(3) -0.1499(2) 0.0410(11) Uani 1 1 d . . . H9AA H 0.1596 0.5193 -0.1686 0.049 Uiso 1 1 calc R . . C10A C 0.1327(6) 0.6732(4) -0.1935(2) 0.0459(12) Uani 1 1 d . . . H10A H 0.1101 0.6781 -0.2424 0.055 Uiso 1 1 calc R . . C11A C 0.1351(6) 0.7629(3) -0.1669(2) 0.0445(12) Uani 1 1 d . . . H11A H 0.1149 0.8276 -0.1980 0.053 Uiso 1 1 calc R . . C12A C 0.1661(6) 0.7577(3) -0.0973(2) 0.0418(11) Uani 1 1 d . . . H12A H 0.1632 0.8188 -0.0799 0.050 Uiso 1 1 calc R . . C13A C 0.2033(5) 0.6618(3) -0.0491(2) 0.0325(10) Uani 1 1 d . . . C14A C 0.2767(6) 0.7457(3) 0.0504(2) 0.0319(10) Uani 1 1 d . . . C15A C 0.1456(6) 0.8818(3) 0.1064(2) 0.0362(11) Uani 1 1 d . . . C16A C 0.2178(6) 0.9764(3) 0.0613(3) 0.0417(11) Uani 1 1 d . . . C17A C 0.2387(6) 1.0561(3) 0.0956(3) 0.0492(13) Uani 1 1 d . . . H17A H 0.2879 1.1206 0.0666 0.059 Uiso 1 1 calc R . . C18A C 0.1881(7) 1.0416(4) 0.1716(3) 0.0545(13) Uani 1 1 d . . . H18A H 0.2050 1.0960 0.1944 0.065 Uiso 1 1 calc R . . C19A C 0.1134(6) 0.9494(3) 0.2146(3) 0.0490(13) Uani 1 1 d . . . H19A H 0.0753 0.9416 0.2663 0.059 Uiso 1 1 calc R . . C20A C 0.0935(6) 0.8674(3) 0.1827(2) 0.0389(11) Uani 1 1 d . . . C21A C 0.0176(6) 0.7651(3) 0.2305(2) 0.0497(12) Uani 1 1 d . . . H21A H -0.0887 0.7451 0.2119 0.075 Uiso 1 1 calc R . . H21B H -0.0197 0.7711 0.2817 0.075 Uiso 1 1 calc R . . H21C H 0.1121 0.7130 0.2287 0.075 Uiso 1 1 calc R . . C22A C 0.2691(6) 0.9927(3) -0.0216(2) 0.0496(13) Uani 1 1 d . . . H22A H 0.3291 1.0602 -0.0423 0.074 Uiso 1 1 calc R . . H22B H 0.1583 0.9896 -0.0431 0.074 Uiso 1 1 calc R . . H22C H 0.3532 0.9391 -0.0332 0.074 Uiso 1 1 calc R . . N1B N 0.2598(4) 0.4604(2) 0.50666(18) 0.0331(8) Uani 1 1 d . . . N2B N 0.3901(5) 0.8457(2) 0.41487(18) 0.0363(9) Uani 1 1 d . . . H2BA H 0.4908 0.8127 0.4242 0.044 Uiso 1 1 calc R . . O1B O 0.0888(4) 0.8297(2) 0.40878(16) 0.0430(8) Uani 1 1 d . . . C1B C 0.2470(5) 0.6760(3) 0.4506(2) 0.0316(10) Uani 1 1 d . . . C2B C 0.1513(5) 0.6293(3) 0.5221(2) 0.0289(9) Uani 1 1 d . . . C3B C 0.0532(5) 0.6843(3) 0.5705(2) 0.0346(10) Uani 1 1 d . . . H3BA H 0.0476 0.7569 0.5552 0.041 Uiso 1 1 calc R . . C4B C -0.0338(6) 0.6352(3) 0.6388(2) 0.0385(11) Uani 1 1 d . . . H4BA H -0.1028 0.6737 0.6699 0.046 Uiso 1 1 calc R . . C5B C -0.0232(6) 0.5267(3) 0.6644(2) 0.0373(11) Uani 1 1 d . . . H5BA H -0.0814 0.4935 0.7128 0.045 Uiso 1 1 calc R . . C6B C 0.0696(6) 0.4715(3) 0.6197(2) 0.0349(10) Uani 1 1 d . . . H6BA H 0.0736 0.3990 0.6365 0.042 Uiso 1 1 calc R . . C7B C 0.1620(5) 0.5199(3) 0.5474(2) 0.0302(10) Uani 1 1 d . . . C8B C 0.3488(5) 0.5054(3) 0.4386(2) 0.0296(10) Uani 1 1 d . . . C9B C 0.4482(6) 0.4423(3) 0.3962(2) 0.0380(11) Uani 1 1 d . . . H9BA H 0.4497 0.3703 0.4161 0.046 Uiso 1 1 calc R . . C10B C 0.5419(6) 0.4832(3) 0.3271(2) 0.0429(12) Uani 1 1 d . . . H10B H 0.6125 0.4399 0.3002 0.051 Uiso 1 1 calc R . . C11B C 0.5351(6) 0.5903(3) 0.2947(2) 0.0427(11) Uani 1 1 d . . . H11B H 0.5978 0.6172 0.2458 0.051 Uiso 1 1 calc R . . C12B C 0.4409(6) 0.6543(3) 0.3326(2) 0.0365(10) Uani 1 1 d . . . H12B H 0.4367 0.7254 0.3099 0.044 Uiso 1 1 calc R . . C13B C 0.3468(5) 0.6150(3) 0.4072(2) 0.0317(10) Uani 1 1 d . . . C14B C 0.2327(6) 0.7913(3) 0.4223(2) 0.0316(10) Uani 1 1 d . . . C15B C 0.3963(6) 0.9568(3) 0.3919(2) 0.0386(11) Uani 1 1 d . . . C16B C 0.4907(6) 1.0024(3) 0.3204(3) 0.0431(12) Uani 1 1 d . . . C17B C 0.4965(6) 1.1092(3) 0.2993(3) 0.0509(13) Uani 1 1 d . . . H17B H 0.5576 1.1422 0.2512 0.061 Uiso 1 1 calc R . . C18B C 0.4162(7) 1.1681(3) 0.3461(3) 0.0545(14) Uani 1 1 d . . . H18B H 0.4203 1.2408 0.3298 0.065 Uiso 1 1 calc R . . C19B C 0.3289(6) 1.1216(3) 0.4172(3) 0.0466(12) Uani 1 1 d . . . H19B H 0.2770 1.1631 0.4496 0.056 Uiso 1 1 calc R . . C20B C 0.3166(6) 1.0150(3) 0.4416(3) 0.0400(11) Uani 1 1 d . . . C21B C 0.2246(6) 0.9648(3) 0.5189(2) 0.0474(12) Uani 1 1 d . . . H21D H 0.1967 1.0170 0.5476 0.071 Uiso 1 1 calc R . . H21E H 0.3065 0.9139 0.5427 0.071 Uiso 1 1 calc R . . H21F H 0.1107 0.9306 0.5167 0.071 Uiso 1 1 calc R . . C22B C 0.5767(6) 0.9399(3) 0.2683(3) 0.0533(13) Uani 1 1 d . . . H22D H 0.6485 0.9850 0.2245 0.080 Uiso 1 1 calc R . . H22E H 0.4808 0.9044 0.2531 0.080 Uiso 1 1 calc R . . H22F H 0.6573 0.8892 0.2930 0.080 Uiso 1 1 calc R . . O2W O -0.2219(4) 0.6996(2) 0.09514(15) 0.0417(8) Uani 1 1 d . . . HO2A H -0.2148 0.6440 0.0807 0.050 Uiso 1 1 d R . . HO2B H -0.3329 0.7182 0.0983 0.050 Uiso 1 1 d R . . O1W O 0.7274(4) 0.7540(2) 0.43262(16) 0.0472(8) Uani 1 1 d . . . HO1A H 0.7288 0.6910 0.4547 0.057 Uiso 1 1 d R . . HO1B H 0.8379 0.7755 0.4196 0.057 Uiso 1 1 d 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 N1A 0.0226(19) 0.033(2) 0.037(2) -0.0093(17) 0.0013(16) 0.0000(15) N2A 0.029(2) 0.0285(18) 0.041(2) -0.0100(17) -0.0012(16) -0.0037(16) O1A 0.0350(19) 0.0357(17) 0.060(2) -0.0137(15) -0.0033(15) -0.0038(14) C1A 0.014(2) 0.036(2) 0.035(2) -0.015(2) 0.0043(18) -0.0028(17) C2A 0.020(2) 0.029(2) 0.034(2) -0.011(2) 0.0032(18) -0.0016(17) C3A 0.043(3) 0.029(2) 0.034(3) -0.013(2) -0.002(2) -0.003(2) C4A 0.039(3) 0.036(2) 0.034(2) -0.007(2) 0.000(2) -0.002(2) C5A 0.043(3) 0.032(2) 0.041(3) -0.005(2) 0.004(2) 0.001(2) C6A 0.049(3) 0.027(2) 0.041(3) -0.014(2) 0.006(2) -0.007(2) C7A 0.017(2) 0.030(2) 0.038(3) -0.008(2) 0.0005(18) -0.0010(17) C8A 0.023(2) 0.040(3) 0.036(3) -0.012(2) 0.0027(19) -0.0013(19) C9A 0.039(3) 0.045(3) 0.039(3) -0.018(2) 0.003(2) -0.001(2) C10A 0.040(3) 0.062(3) 0.035(3) -0.010(3) -0.007(2) 0.002(2) C11A 0.040(3) 0.046(3) 0.043(3) -0.005(2) -0.003(2) 0.002(2) C12A 0.045(3) 0.036(3) 0.040(3) -0.006(2) 0.001(2) -0.003(2) C13A 0.025(2) 0.033(2) 0.037(3) -0.008(2) 0.0032(19) -0.0028(19) C14A 0.028(3) 0.028(2) 0.037(3) -0.0038(19) -0.002(2) -0.0002(19) C15A 0.036(3) 0.024(2) 0.051(3) -0.014(2) -0.008(2) 0.0008(19) C16A 0.044(3) 0.029(2) 0.052(3) -0.007(2) -0.011(2) 0.004(2) C17A 0.054(3) 0.024(2) 0.067(4) -0.008(2) -0.006(3) -0.005(2) C18A 0.059(4) 0.040(3) 0.071(4) -0.029(3) -0.009(3) 0.004(3) C19A 0.053(3) 0.043(3) 0.054(3) -0.022(3) -0.003(2) 0.002(2) C20A 0.040(3) 0.033(2) 0.044(3) -0.012(2) -0.004(2) 0.000(2) C21A 0.055(3) 0.043(3) 0.047(3) -0.011(2) 0.007(2) -0.006(2) C22A 0.053(3) 0.028(2) 0.061(3) -0.001(2) -0.002(3) -0.009(2) N1B 0.035(2) 0.0299(19) 0.034(2) -0.0076(17) -0.0033(17) -0.0063(16) N2B 0.030(2) 0.0282(19) 0.048(2) -0.0051(17) -0.0047(17) -0.0007(16) O1B 0.0337(19) 0.0385(17) 0.054(2) -0.0023(15) -0.0123(15) 0.0005(14) C1B 0.033(3) 0.030(2) 0.033(2) -0.009(2) -0.006(2) -0.0034(19) C2B 0.024(2) 0.029(2) 0.035(2) -0.009(2) -0.0065(19) 0.0014(18) C3B 0.034(3) 0.031(2) 0.038(3) -0.006(2) -0.007(2) -0.001(2) C4B 0.034(3) 0.040(3) 0.042(3) -0.012(2) -0.005(2) -0.001(2) C5B 0.031(3) 0.043(3) 0.033(3) -0.002(2) -0.001(2) -0.001(2) C6B 0.035(3) 0.031(2) 0.036(3) -0.002(2) -0.007(2) -0.002(2) C7B 0.033(3) 0.029(2) 0.031(2) -0.011(2) -0.0077(19) 0.0005(19) C8B 0.023(2) 0.032(2) 0.037(3) -0.011(2) -0.0082(19) -0.0005(18) C9B 0.036(3) 0.033(2) 0.050(3) -0.018(2) -0.008(2) -0.003(2) C10B 0.042(3) 0.044(3) 0.049(3) -0.025(2) -0.003(2) 0.000(2) C11B 0.042(3) 0.051(3) 0.035(3) -0.013(2) 0.001(2) -0.012(2) C12B 0.032(3) 0.041(3) 0.036(3) -0.007(2) -0.004(2) -0.008(2) C13B 0.031(3) 0.030(2) 0.035(2) -0.008(2) -0.008(2) -0.0037(19) C14B 0.031(3) 0.032(2) 0.030(2) -0.0051(19) -0.004(2) -0.002(2) C15B 0.034(3) 0.024(2) 0.053(3) 0.002(2) -0.010(2) -0.007(2) C16B 0.036(3) 0.037(3) 0.051(3) -0.002(2) -0.002(2) 0.000(2) C17B 0.046(3) 0.036(3) 0.063(3) 0.001(3) -0.003(3) -0.001(2) C18B 0.062(4) 0.021(2) 0.077(4) -0.001(3) -0.016(3) 0.000(2) C19B 0.033(3) 0.035(3) 0.073(4) -0.014(3) -0.010(2) -0.001(2) C20B 0.033(3) 0.031(3) 0.056(3) -0.011(2) -0.007(2) 0.000(2) C21B 0.046(3) 0.044(3) 0.056(3) -0.019(2) -0.008(2) 0.003(2) C22B 0.043(3) 0.043(3) 0.061(3) 0.001(3) 0.008(2) -0.001(2) O2W 0.0313(17) 0.0400(16) 0.0564(19) -0.0195(15) -0.0030(14) 0.0025(13) O1W 0.0274(18) 0.0342(16) 0.074(2) -0.0007(15) -0.0074(15) -0.0029(13) _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 N1A C7A 1.334(5) . ? N1A C8A 1.339(6) . ? N2A C14A 1.332(5) . ? N2A C15A 1.436(5) . ? O1A C14A 1.237(5) . ? C1A C2A 1.396(6) . ? C1A C13A 1.399(6) . ? C1A C14A 1.514(6) . ? C2A C3A 1.435(6) . ? C2A C7A 1.438(6) . ? C3A C4A 1.361(6) . ? C4A C5A 1.410(6) . ? C5A C6A 1.367(6) . ? C6A C7A 1.431(6) . ? C8A C9A 1.436(6) . ? C8A C13A 1.441(6) . ? C9A C10A 1.370(6) . ? C10A C11A 1.410(7) . ? C11A C12A 1.354(6) . ? C12A C13A 1.439(6) . ? C15A C20A 1.392(6) . ? C15A C16A 1.409(7) . ? C16A C17A 1.396(6) . ? C16A C22A 1.509(7) . ? C17A C18A 1.386(7) . ? C18A C19A 1.378(7) . ? C19A C20A 1.392(6) . ? C20A C21A 1.514(7) . ? N1B C8B 1.345(6) . ? N1B C7B 1.350(5) . ? N2B C14B 1.359(6) . ? N2B C15B 1.449(6) . ? O1B C14B 1.212(5) . ? C1B C13B 1.404(6) . ? C1B C2B 1.416(6) . ? C1B C14B 1.518(7) . ? C2B C3B 1.404(6) . ? C2B C7B 1.437(6) . ? C3B C4B 1.358(6) . ? C4B C5B 1.425(6) . ? C5B C6B 1.343(6) . ? C6B C7B 1.426(6) . ? C8B C9B 1.410(6) . ? C8B C13B 1.449(6) . ? C9B C10B 1.362(6) . ? C10B C11B 1.425(7) . ? C11B C12B 1.350(6) . ? C12B C13B 1.442(6) . ? C15B C20B 1.404(6) . ? C15B C16B 1.411(7) . ? C16B C17B 1.392(7) . ? C16B C22B 1.493(6) . ? C17B C18B 1.372(6) . ? C18B C19B 1.391(7) . ? C19B C20B 1.394(7) . ? C20B C21B 1.504(7) . ? 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 C7A N1A C8A 118.4(4) . . ? C14A N2A C15A 122.0(4) . . ? C2A C1A C13A 118.9(4) . . ? C2A C1A C14A 119.6(4) . . ? C13A C1A C14A 121.1(4) . . ? C1A C2A C3A 123.4(4) . . ? C1A C2A C7A 118.5(4) . . ? C3A C2A C7A 118.1(4) . . ? C4A C3A C2A 121.2(4) . . ? C3A C4A C5A 120.8(4) . . ? C6A C5A C4A 120.2(4) . . ? C5A C6A C7A 121.3(4) . . ? N1A C7A C6A 118.5(4) . . ? N1A C7A C2A 123.0(4) . . ? C6A C7A C2A 118.5(4) . . ? N1A C8A C9A 118.1(4) . . ? N1A C8A C13A 123.0(4) . . ? C9A C8A C13A 118.9(4) . . ? C10A C9A C8A 120.4(4) . . ? C9A C10A C11A 120.9(4) . . ? C12A C11A C10A 120.6(4) . . ? C11A C12A C13A 121.6(4) . . ? C1A C13A C12A 124.3(4) . . ? C1A C13A C8A 118.1(4) . . ? C12A C13A C8A 117.6(4) . . ? O1A C14A N2A 123.1(4) . . ? O1A C14A C1A 119.0(4) . . ? N2A C14A C1A 117.9(4) . . ? C20A C15A C16A 121.7(4) . . ? C20A C15A N2A 118.4(4) . . ? C16A C15A N2A 119.9(4) . . ? C17A C16A C15A 118.0(4) . . ? C17A C16A C22A 120.3(4) . . ? C15A C16A C22A 121.6(4) . . ? C18A C17A C16A 120.3(5) . . ? C19A C18A C17A 121.0(5) . . ? C18A C19A C20A 120.5(5) . . ? C15A C20A C19A 118.6(4) . . ? C15A C20A C21A 121.1(4) . . ? C19A C20A C21A 120.3(4) . . ? C8B N1B C7B 118.6(4) . . ? C14B N2B C15B 121.6(4) . . ? C13B C1B C2B 119.6(4) . . ? C13B C1B C14B 121.8(4) . . ? C2B C1B C14B 118.5(4) . . ? C3B C2B C1B 123.7(4) . . ? C3B C2B C7B 118.3(4) . . ? C1B C2B C7B 117.9(4) . . ? C4B C3B C2B 121.0(4) . . ? C3B C4B C5B 121.0(4) . . ? C6B C5B C4B 119.7(4) . . ? C5B C6B C7B 121.1(4) . . ? N1B C7B C6B 118.1(4) . . ? N1B C7B C2B 123.0(4) . . ? C6B C7B C2B 118.8(4) . . ? N1B C8B C9B 118.0(4) . . ? N1B C8B C13B 123.1(4) . . ? C9B C8B C13B 118.8(4) . . ? C10B C9B C8B 120.9(4) . . ? C9B C10B C11B 120.6(4) . . ? C12B C11B C10B 121.1(4) . . ? C11B C12B C13B 120.1(4) . . ? C1B C13B C12B 123.9(4) . . ? C1B C13B C8B 117.7(4) . . ? C12B C13B C8B 118.4(4) . . ? O1B C14B N2B 123.9(4) . . ? O1B C14B C1B 121.0(4) . . ? N2B C14B C1B 115.1(4) . . ? C20B C15B C16B 122.3(4) . . ? C20B C15B N2B 119.8(4) . . ? C16B C15B N2B 117.8(4) . . ? C17B C16B C15B 117.2(4) . . ? C17B C16B C22B 120.8(4) . . ? C15B C16B C22B 122.0(4) . . ? C18B C17B C16B 121.7(5) . . ? C17B C18B C19B 120.2(4) . . ? C18B C19B C20B 120.9(5) . . ? C19B C20B C15B 117.5(4) . . ? C19B C20B C21B 121.0(4) . . ? C15B C20B C21B 121.5(4) . . ? 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 C13A C1A C2A C3A 179.5(4) . . . . ? C14A C1A C2A C3A 5.6(6) . . . . ? C13A C1A C2A C7A 0.6(5) . . . . ? C14A C1A C2A C7A -173.3(3) . . . . ? C1A C2A C3A C4A -178.1(4) . . . . ? C7A C2A C3A C4A 0.8(6) . . . . ? C2A C3A C4A C5A 0.1(6) . . . . ? C3A C4A C5A C6A -0.3(6) . . . . ? C4A C5A C6A C7A -0.4(6) . . . . ? C8A N1A C7A C6A -177.7(4) . . . . ? C8A N1A C7A C2A -0.8(5) . . . . ? C5A C6A C7A N1A 178.3(4) . . . . ? C5A C6A C7A C2A 1.2(6) . . . . ? C1A C2A C7A N1A 0.6(6) . . . . ? C3A C2A C7A N1A -178.3(3) . . . . ? C1A C2A C7A C6A 177.5(3) . . . . ? C3A C2A C7A C6A -1.4(5) . . . . ? C7A N1A C8A C9A 178.7(3) . . . . ? C7A N1A C8A C13A -0.2(6) . . . . ? N1A C8A C9A C10A -179.7(4) . . . . ? C13A C8A C9A C10A -0.7(6) . . . . ? C8A C9A C10A C11A -0.3(6) . . . . ? C9A C10A C11A C12A -0.3(7) . . . . ? C10A C11A C12A C13A 2.0(7) . . . . ? C2A C1A C13A C12A 178.7(4) . . . . ? C14A C1A C13A C12A -7.5(6) . . . . ? C2A C1A C13A C8A -1.5(5) . . . . ? C14A C1A C13A C8A 172.3(4) . . . . ? C11A C12A C13A C1A 176.8(4) . . . . ? C11A C12A C13A C8A -3.0(6) . . . . ? N1A C8A C13A C1A 1.4(6) . . . . ? C9A C8A C13A C1A -177.6(3) . . . . ? N1A C8A C13A C12A -178.8(4) . . . . ? C9A C8A C13A C12A 2.2(6) . . . . ? C15A N2A C14A O1A -4.5(6) . . . . ? C15A N2A C14A C1A 175.9(4) . . . . ? C2A C1A C14A O1A 72.3(5) . . . . ? C13A C1A C14A O1A -101.4(5) . . . . ? C2A C1A C14A N2A -108.1(5) . . . . ? C13A C1A C14A N2A 78.2(5) . . . . ? C14A N2A C15A C20A -105.9(5) . . . . ? C14A N2A C15A C16A 72.0(5) . . . . ? C20A C15A C16A C17A 0.9(6) . . . . ? N2A C15A C16A C17A -176.8(4) . . . . ? C20A C15A C16A C22A -178.2(4) . . . . ? N2A C15A C16A C22A 4.0(6) . . . . ? C15A C16A C17A C18A -0.4(7) . . . . ? C22A C16A C17A C18A 178.7(4) . . . . ? C16A C17A C18A C19A -1.2(7) . . . . ? C17A C18A C19A C20A 2.3(7) . . . . ? C16A C15A C20A C19A 0.2(6) . . . . ? N2A C15A C20A C19A 178.0(4) . . . . ? C16A C15A C20A C21A -179.5(4) . . . . ? N2A C15A C20A C21A -1.7(6) . . . . ? C18A C19A C20A C15A -1.8(7) . . . . ? C18A C19A C20A C21A 177.9(4) . . . . ? C13B C1B C2B C3B 177.7(4) . . . . ? C14B C1B C2B C3B -4.4(6) . . . . ? C13B C1B C2B C7B 0.5(6) . . . . ? C14B C1B C2B C7B 178.4(3) . . . . ? C1B C2B C3B C4B -179.1(4) . . . . ? C7B C2B C3B C4B -1.8(6) . . . . ? C2B C3B C4B C5B 2.1(6) . . . . ? C3B C4B C5B C6B -2.0(6) . . . . ? C4B C5B C6B C7B 1.6(6) . . . . ? C8B N1B C7B C6B -179.5(4) . . . . ? C8B N1B C7B C2B -1.2(5) . . . . ? C5B C6B C7B N1B 177.0(4) . . . . ? C5B C6B C7B C2B -1.4(6) . . . . ? C3B C2B C7B N1B -176.8(4) . . . . ? C1B C2B C7B N1B 0.6(6) . . . . ? C3B C2B C7B C6B 1.4(5) . . . . ? C1B C2B C7B C6B 178.8(4) . . . . ? C7B N1B C8B C9B -179.1(3) . . . . ? C7B N1B C8B C13B 0.8(5) . . . . ? N1B C8B C9B C10B -179.7(4) . . . . ? C13B C8B C9B C10B 0.5(6) . . . . ? C8B C9B C10B C11B -2.8(6) . . . . ? C9B C10B C11B C12B 2.2(6) . . . . ? C10B C11B C12B C13B 0.7(6) . . . . ? C2B C1B C13B C12B 176.7(4) . . . . ? C14B C1B C13B C12B -1.1(6) . . . . ? C2B C1B C13B C8B -0.8(5) . . . . ? C14B C1B C13B C8B -178.7(4) . . . . ? C11B C12B C13B C1B 179.5(4) . . . . ? C11B C12B C13B C8B -3.0(6) . . . . ? N1B C8B C13B C1B 0.2(6) . . . . ? C9B C8B C13B C1B -180.0(3) . . . . ? N1B C8B C13B C12B -177.5(4) . . . . ? C9B C8B C13B C12B 2.4(5) . . . . ? C15B N2B C14B O1B 2.0(6) . . . . ? C15B N2B C14B C1B -176.9(3) . . . . ? C13B C1B C14B O1B 111.1(5) . . . . ? C2B C1B C14B O1B -66.8(5) . . . . ? C13B C1B C14B N2B -70.0(5) . . . . ? C2B C1B C14B N2B 112.1(4) . . . . ? C14B N2B C15B C20B 73.4(5) . . . . ? C14B N2B C15B C16B -109.2(5) . . . . ? C20B C15B C16B C17B -2.4(6) . . . . ? N2B C15B C16B C17B -179.6(4) . . . . ? C20B C15B C16B C22B 179.4(4) . . . . ? N2B C15B C16B C22B 2.1(6) . . . . ? C15B C16B C17B C18B 0.9(7) . . . . ? C22B C16B C17B C18B 179.2(4) . . . . ? C16B C17B C18B C19B 1.2(7) . . . . ? C17B C18B C19B C20B -1.9(7) . . . . ? C18B C19B C20B C15B 0.4(6) . . . . ? C18B C19B C20B C21B 179.1(4) . . . . ? C16B C15B C20B C19B 1.8(6) . . . . ? N2B C15B C20B C19B 179.0(4) . . . . ? C16B C15B C20B C21B -176.9(4) . . . . ? N2B C15B C20B C21B 0.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 0.406 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.099 # Attachment 'SHELXL.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 615406' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H12 F4 N2 O2' _chemical_formula_weight 388.32 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.261(4) _cell_length_b 9.225(4) _cell_length_c 32.382(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.503(11) _cell_angle_gamma 90.00 _cell_volume 3348(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 150 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 25.53 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 0.9870 _exptl_absorpt_correction_T_max 0.9961 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'bruker smart' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3053 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 25.53 _reflns_number_total 3053 _reflns_number_gt 2322 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+5.9945P] 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 3053 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 F1 F -0.03897(13) -0.09146(16) 0.41782(4) 0.0394(4) Uani 1 1 d . . . F2 F 0.25030(13) 0.04244(15) 0.32967(4) 0.0381(4) Uani 1 1 d . . . F3 F 0.12029(13) -0.23553(16) 0.62008(4) 0.0419(4) Uani 1 1 d . . . F4 F 0.44943(13) 0.02487(16) 0.68085(4) 0.0410(4) Uani 1 1 d . . . O1 O 0.19823(16) -0.17668(17) 0.44640(5) 0.0343(4) Uani 1 1 d . . . O2 O 0.32384(15) 0.17258(17) 0.61541(5) 0.0330(4) Uani 1 1 d . . . N1 N 0.18225(18) 0.0324(2) 0.40920(6) 0.0315(5) Uani 1 1 d . . . H11 H 0.2009 0.1227 0.4084 0.038 Uiso 1 1 calc R . . N2 N 0.31518(18) -0.0726(2) 0.60789(6) 0.0311(5) Uani 1 1 d . . . H12 H 0.3263 -0.1453 0.5921 0.037 Uiso 1 1 calc R . . C1 C 0.1110(2) -0.0288(2) 0.37534(7) 0.0297(5) Uani 1 1 d . . . C2 C 0.0028(2) -0.0967(3) 0.37990(7) 0.0326(6) Uani 1 1 d . . . C3 C -0.0641(2) -0.1642(3) 0.34791(7) 0.0347(6) Uani 1 1 d . . . H1 H -0.1348 -0.2113 0.3523 0.042 Uiso 1 1 calc R . . C4 C -0.0233(2) -0.1600(3) 0.30880(8) 0.0353(6) Uani 1 1 d . . . H2 H -0.0665 -0.2068 0.2868 0.042 Uiso 1 1 calc R . . C5 C 0.0805(2) -0.0874(3) 0.30206(7) 0.0346(6) Uani 1 1 d . . . H3 H 0.1055 -0.0807 0.2756 0.041 Uiso 1 1 calc R . . C6 C 0.1458(2) -0.0254(3) 0.33549(7) 0.0314(5) Uani 1 1 d . . . C7 C 0.2220(2) -0.0472(3) 0.44286(7) 0.0316(6) Uani 1 1 d . . . C8 C 0.2974(2) 0.0324(2) 0.47584(7) 0.0295(5) Uani 1 1 d . . . C9 C 0.3816(2) 0.1343(3) 0.46583(7) 0.0323(6) Uani 1 1 d . . . H4 H 0.3909 0.1543 0.4382 0.039 Uiso 1 1 calc R . . C10 C 0.4514(2) 0.2059(3) 0.49707(7) 0.0343(6) Uani 1 1 d . . . H5 H 0.5099 0.2706 0.4904 0.041 Uiso 1 1 calc R . . C11 C 0.4338(2) 0.1808(3) 0.53808(7) 0.0326(6) Uani 1 1 d . . . H6 H 0.4781 0.2324 0.5589 0.039 Uiso 1 1 calc R . . C12 C 0.3502(2) 0.0786(2) 0.54855(7) 0.0290(5) Uani 1 1 d . . . C13 C 0.2838(2) 0.0020(2) 0.51739(7) 0.0298(5) Uani 1 1 d . . . H7 H 0.2306 -0.0692 0.5242 0.036 Uiso 1 1 calc R . . C14 C 0.3294(2) 0.0639(3) 0.59323(7) 0.0298(5) Uani 1 1 d . . . C15 C 0.2826(2) -0.0985(2) 0.64837(7) 0.0298(5) Uani 1 1 d . . . C16 C 0.1828(2) -0.1810(3) 0.65434(7) 0.0321(6) Uani 1 1 d . . . C17 C 0.1450(2) -0.2096(3) 0.69269(8) 0.0370(6) Uani 1 1 d . . . H8 H 0.0774 -0.2656 0.6952 0.044 Uiso 1 1 calc R . . C18 C 0.2098(2) -0.1531(3) 0.72733(8) 0.0378(6) Uani 1 1 d . . . H9 H 0.1853 -0.1703 0.7535 0.045 Uiso 1 1 calc R . . C19 C 0.3114(2) -0.0707(3) 0.72340(7) 0.0358(6) Uani 1 1 d . . . H10 H 0.3550 -0.0321 0.7467 0.043 Uiso 1 1 calc R . . C20 C 0.3460(2) -0.0474(3) 0.68423(7) 0.0320(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 F1 0.0393(9) 0.0450(9) 0.0350(8) 0.0009(6) 0.0096(6) -0.0039(7) F2 0.0371(8) 0.0415(8) 0.0363(8) 0.0002(6) 0.0070(6) -0.0085(7) F3 0.0404(9) 0.0448(9) 0.0397(8) -0.0026(7) -0.0004(7) -0.0103(7) F4 0.0371(9) 0.0421(8) 0.0428(8) 0.0022(6) -0.0010(6) -0.0104(7) O1 0.0430(11) 0.0263(9) 0.0332(9) 0.0009(7) 0.0018(7) -0.0007(8) O2 0.0364(10) 0.0300(9) 0.0332(9) -0.0020(7) 0.0058(7) -0.0007(8) N1 0.0369(12) 0.0282(10) 0.0293(10) 0.0018(8) 0.0019(9) -0.0045(9) N2 0.0366(12) 0.0288(10) 0.0285(10) -0.0021(8) 0.0058(9) -0.0016(9) C1 0.0314(13) 0.0274(12) 0.0299(12) 0.0008(9) 0.0006(10) 0.0011(11) C2 0.0364(14) 0.0316(13) 0.0305(12) 0.0035(10) 0.0067(10) 0.0034(11) C3 0.0291(14) 0.0326(13) 0.0420(14) 0.0020(11) 0.0014(11) -0.0003(11) C4 0.0346(14) 0.0331(13) 0.0367(13) -0.0005(10) -0.0043(11) 0.0013(11) C5 0.0385(15) 0.0352(14) 0.0299(13) 0.0008(10) 0.0028(11) 0.0030(12) C6 0.0294(13) 0.0296(13) 0.0354(13) 0.0010(10) 0.0038(10) -0.0009(11) C7 0.0330(14) 0.0339(14) 0.0287(12) -0.0004(10) 0.0071(10) 0.0043(11) C8 0.0298(13) 0.0262(12) 0.0326(12) 0.0007(9) 0.0031(10) 0.0065(10) C9 0.0313(14) 0.0351(13) 0.0311(12) 0.0030(10) 0.0065(10) 0.0017(11) C10 0.0302(14) 0.0343(14) 0.0386(14) 0.0008(10) 0.0043(11) -0.0040(11) C11 0.0320(14) 0.0324(13) 0.0330(13) -0.0010(10) 0.0010(10) -0.0003(11) C12 0.0268(13) 0.0280(12) 0.0322(12) -0.0001(9) 0.0032(10) 0.0029(10) C13 0.0291(13) 0.0271(12) 0.0338(13) 0.0014(10) 0.0059(10) 0.0026(10) C14 0.0252(13) 0.0314(13) 0.0326(12) 0.0017(10) 0.0014(10) -0.0002(10) C15 0.0320(14) 0.0249(12) 0.0326(13) 0.0010(9) 0.0032(10) 0.0010(10) C16 0.0331(14) 0.0292(13) 0.0332(13) 0.0004(10) -0.0012(10) -0.0005(11) C17 0.0332(14) 0.0330(13) 0.0458(15) 0.0031(11) 0.0088(12) -0.0010(11) C18 0.0473(17) 0.0332(13) 0.0342(13) 0.0033(11) 0.0107(12) 0.0048(12) C19 0.0433(16) 0.0313(13) 0.0324(13) -0.0025(10) 0.0013(11) 0.0010(12) C20 0.0308(13) 0.0279(12) 0.0374(13) 0.0006(10) 0.0035(10) -0.0022(11) _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 F1 C2 1.357(3) . ? F2 C6 1.362(3) . ? F3 C16 1.353(3) . ? F4 C20 1.355(3) . ? O1 C7 1.232(3) . ? O2 C14 1.239(3) . ? N1 C7 1.354(3) . ? N1 C1 1.413(3) . ? N1 H11 0.8600 . ? N2 C14 1.360(3) . ? N2 C15 1.415(3) . ? N2 H12 0.8600 . ? C1 C6 1.385(3) . ? C1 C2 1.390(3) . ? C2 C3 1.370(3) . ? C3 C4 1.389(3) . ? C3 H1 0.9300 . ? C4 C5 1.382(4) . ? C4 H2 0.9300 . ? C5 C6 1.373(3) . ? C5 H3 0.9300 . ? C7 C8 1.492(3) . ? C8 C9 1.395(3) . ? C8 C13 1.397(3) . ? C9 C10 1.387(3) . ? C9 H4 0.9300 . ? C10 C11 1.381(3) . ? C10 H5 0.9300 . ? C11 C12 1.397(3) . ? C11 H6 0.9300 . ? C12 C13 1.390(3) . ? C12 C14 1.494(3) . ? C13 H7 0.9300 . ? C15 C16 1.386(3) . ? C15 C20 1.386(3) . ? C16 C17 1.376(3) . ? C17 C18 1.381(4) . ? C17 H8 0.9300 . ? C18 C19 1.388(4) . ? C18 H9 0.9300 . ? C19 C20 1.379(3) . ? C19 H10 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 C7 N1 C1 121.8(2) . . ? C7 N1 H11 119.1 . . ? C1 N1 H11 119.1 . . ? C14 N2 C15 121.95(19) . . ? C14 N2 H12 119.0 . . ? C15 N2 H12 119.0 . . ? C6 C1 C2 116.0(2) . . ? C6 C1 N1 121.6(2) . . ? C2 C1 N1 122.4(2) . . ? F1 C2 C3 119.1(2) . . ? F1 C2 C1 117.6(2) . . ? C3 C2 C1 123.2(2) . . ? C2 C3 C4 118.1(2) . . ? C2 C3 H1 121.0 . . ? C4 C3 H1 121.0 . . ? C5 C4 C3 121.1(2) . . ? C5 C4 H2 119.5 . . ? C3 C4 H2 119.5 . . ? C6 C5 C4 118.3(2) . . ? C6 C5 H3 120.9 . . ? C4 C5 H3 120.9 . . ? F2 C6 C5 119.1(2) . . ? F2 C6 C1 117.7(2) . . ? C5 C6 C1 123.2(2) . . ? O1 C7 N1 122.9(2) . . ? O1 C7 C8 121.6(2) . . ? N1 C7 C8 115.5(2) . . ? C9 C8 C13 119.9(2) . . ? C9 C8 C7 121.2(2) . . ? C13 C8 C7 118.9(2) . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H4 120.0 . . ? C8 C9 H4 120.0 . . ? C11 C10 C9 119.9(2) . . ? C11 C10 H5 120.0 . . ? C9 C10 H5 120.0 . . ? C10 C11 C12 120.6(2) . . ? C10 C11 H6 119.7 . . ? C12 C11 H6 119.7 . . ? C13 C12 C11 119.7(2) . . ? C13 C12 C14 122.3(2) . . ? C11 C12 C14 117.9(2) . . ? C12 C13 C8 119.8(2) . . ? C12 C13 H7 120.1 . . ? C8 C13 H7 120.1 . . ? O2 C14 N2 122.2(2) . . ? O2 C14 C12 120.6(2) . . ? N2 C14 C12 117.2(2) . . ? C16 C15 C20 115.4(2) . . ? C16 C15 N2 120.5(2) . . ? C20 C15 N2 124.1(2) . . ? F3 C16 C17 119.1(2) . . ? F3 C16 C15 117.1(2) . . ? C17 C16 C15 123.8(2) . . ? C16 C17 C18 118.4(2) . . ? C16 C17 H8 120.8 . . ? C18 C17 H8 120.8 . . ? C17 C18 C19 120.5(2) . . ? C17 C18 H9 119.7 . . ? C19 C18 H9 119.7 . . ? C20 C19 C18 118.5(2) . . ? C20 C19 H10 120.7 . . ? C18 C19 H10 120.7 . . ? F4 C20 C19 118.2(2) . . ? F4 C20 C15 118.5(2) . . ? C19 C20 C15 123.3(2) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.53 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.217 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.050