data_shelxl _publ_contact_author_name "Christophe M.L. Vande Velde" _publ_contact_author_address ; Karel de Grote University College Department of Applied Engineering Salesianenlaan 30 B-2660 Antwerp BELGIUM ; _publ_contact_author_email "christophe.vandevelde@kdg.be" _publ_requested_journal ? loop_ _publ_author_name _publ_author_address ? ? ? ? _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety "C16 H13 Cl N2 O3" _chemical_formula_sum 'C16 H13 Cl N2 O3' _chemical_formula_weight 316.73 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M "P21/c" _symmetry_space_group_name_Hall "-P 2ybc" loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.979(4) _cell_length_b 7.470(2) _cell_length_c 19.413(4) _cell_angle_alpha 90.00 _cell_angle_beta 133.822(12) _cell_angle_gamma 90.00 _cell_volume 1462.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2937 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 30.92 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.6755 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_process_details "SADABS 2008-1" _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 platform goniometer with Smart 1000" _diffrn_measurement_method "\w-scans" _diffrn_detector_area_resol_mean . _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 8289 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 30.98 _reflns_number_total 4193 _reflns_number_gt 2945 _reflns_threshold_expression >2sigma(I) _computing_data_collection "Bruker APEX II" _computing_cell_refinement "Bruker APEX II" _computing_data_reduction "Bruker Saint v7.66A" _computing_structure_solution "SHELXS-97 (Sheldrick, 1997)" _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. Distances in the disordered furan rings were restrained to be sensible. The highest residual electron density is now around atoms C13 and C14. ; _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^)+(0.0670P)^2^+0.6268P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4193 _refine_ls_number_parameters 220 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1762 _refine_ls_wR_factor_gt 0.1589 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.184 _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 O3 O 0.33794(15) 0.9051(3) 0.46262(11) 0.0549(4) Uani 1 1 d . . . O7 O 0.17994(19) 0.7872(2) 0.48621(12) 0.0580(5) Uani 1 1 d . . . H97 H 0.2527 0.7949 0.5038 0.087 Uiso 1 1 calc R . . Cl1 Cl -0.15964(6) 0.98222(11) 0.20543(5) 0.0674(2) Uani 1 1 d . . . C3 C 0.2343(2) 0.9359(3) 0.37932(14) 0.0399(4) Uani 1 1 d . . . C2 C 0.1053(2) 0.9460(3) 0.34724(15) 0.0396(4) Uani 1 1 d . . . N4 N 0.23697(19) 0.9629(2) 0.31060(13) 0.0436(4) Uani 1 1 d . . . C7 C 0.0965(2) 0.9262(3) 0.42042(16) 0.0442(5) Uani 1 1 d . A . H7 H 0.0052 0.8914 0.3857 0.053 Uiso 1 1 calc R . . C1 C -0.0006(2) 0.9706(3) 0.25323(16) 0.0430(5) Uani 1 1 d . . . N5 N 0.1300(2) 0.9889(3) 0.21724(14) 0.0511(5) Uani 1 1 d . . . O12 O 0.2388(6) 1.1831(8) 0.5199(5) 0.0544(15) Uani 0.66 1 d PD A 1 C12 C 0.2186(19) 1.214(2) 0.4992(16) 0.074(7) Uani 0.34 1 d PD A 2 H12 H 0.2657 1.2133 0.4815 0.089 Uiso 0.34 1 calc PR A 2 C21 C 0.3936(2) 0.7706(3) 0.32592(16) 0.0460(5) Uani 1 1 d . . . C8 C 0.3633(2) 0.9553(3) 0.33577(19) 0.0522(6) Uani 1 1 d . . . H8A H 0.4315(15) 0.9939(9) 0.3985(14) 0.063 Uiso 1 1 calc R . . H8B H 0.3594(3) 1.0328(18) 0.2963(9) 0.063 Uiso 1 1 calc R . . C11 C 0.1222(2) 1.0981(3) 0.46895(16) 0.0466(5) Uani 1 1 d D . . C6 C 0.0158(2) 0.9923(3) 0.18996(16) 0.0508(5) Uani 1 1 d . . . H6 H -0.0592 1.0098 0.1255 0.061 Uiso 1 1 calc R . . C26 C 0.3453(3) 0.7129(4) 0.23946(19) 0.0629(7) Uani 1 1 d . . . H26 H 0.2944 0.7902 0.1874 0.075 Uiso 1 1 calc R . . C22 C 0.4684(3) 0.6548(4) 0.4017(2) 0.0649(7) Uani 1 1 d . . . H22 H 0.5027 0.6921 0.4609 0.078 Uiso 1 1 calc R . . C15 C 0.0476(6) 1.1830(9) 0.4785(6) 0.068(3) Uani 0.66 1 d PD A 2 H15 H -0.0380 1.1521 0.4491 0.081 Uiso 0.66 1 calc PR A 2 O15 O 0.0565(10) 1.1670(13) 0.4903(10) 0.081(5) Uani 0.34 1 d PD A 1 C14 C 0.1206(3) 1.3239(4) 0.5397(2) 0.0784(10) Uani 1 1 d D . . H14 H 0.0910 1.4094 0.5562 0.094 Uiso 1 1 calc R A 1 C13 C 0.2351(4) 1.3305(4) 0.5599(2) 0.0789(9) Uani 1 1 d D A . H13 H 0.2995 1.4193 0.5948 0.095 Uiso 1 1 calc R B 1 C24 C 0.4437(4) 0.4291(5) 0.3040(3) 0.0808(10) Uani 1 1 d . . . H24 H 0.4601 0.3135 0.2965 0.097 Uiso 1 1 calc R . . C25 C 0.3707(4) 0.5435(5) 0.2286(3) 0.0796(9) Uani 1 1 d . . . H25 H 0.3381 0.5069 0.1698 0.096 Uiso 1 1 calc R . . C23 C 0.4934(4) 0.4835(5) 0.3912(3) 0.0832(10) Uani 1 1 d . . . H23 H 0.5436 0.4053 0.4429 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 O3 0.0404(8) 0.0720(12) 0.0367(8) -0.0025(8) 0.0208(7) 0.0017(8) O7 0.0759(12) 0.0452(9) 0.0548(10) 0.0072(8) 0.0459(10) 0.0031(9) Cl1 0.0408(3) 0.0855(5) 0.0615(4) 0.0075(3) 0.0301(3) 0.0125(3) C3 0.0412(10) 0.0372(10) 0.0371(10) -0.0043(8) 0.0254(9) -0.0018(8) C2 0.0427(10) 0.0356(10) 0.0391(10) -0.0014(8) 0.0278(9) 0.0003(8) N4 0.0444(9) 0.0439(10) 0.0428(9) -0.0017(8) 0.0303(8) -0.0024(8) C7 0.0485(11) 0.0427(11) 0.0435(11) -0.0019(9) 0.0326(10) -0.0041(9) C1 0.0401(10) 0.0390(10) 0.0419(10) 0.0003(8) 0.0254(9) 0.0046(8) N5 0.0568(12) 0.0541(11) 0.0425(10) 0.0033(8) 0.0345(9) 0.0021(9) O12 0.053(2) 0.062(2) 0.054(3) -0.018(3) 0.040(2) -0.015(2) C12 0.073(9) 0.091(12) 0.056(9) 0.000(7) 0.044(8) -0.002(7) C21 0.0395(10) 0.0557(13) 0.0485(11) -0.0035(10) 0.0327(10) -0.0071(9) C8 0.0491(12) 0.0561(14) 0.0582(14) -0.0086(11) 0.0397(12) -0.0126(10) C11 0.0566(13) 0.0449(12) 0.0454(11) 0.0023(10) 0.0380(11) 0.0028(10) C6 0.0495(12) 0.0553(13) 0.0357(10) 0.0057(10) 0.0250(10) 0.0085(10) C26 0.0658(16) 0.0664(17) 0.0521(14) -0.0035(13) 0.0392(13) -0.0028(13) C22 0.0611(15) 0.088(2) 0.0577(15) 0.0133(14) 0.0458(13) 0.0167(14) C15 0.066(4) 0.084(6) 0.061(3) 0.025(4) 0.047(3) 0.023(4) O15 0.121(10) 0.075(7) 0.123(10) -0.032(7) 0.112(9) -0.027(7) C14 0.118(3) 0.0607(17) 0.0721(19) 0.0008(15) 0.072(2) 0.0226(18) C13 0.104(3) 0.0656(19) 0.0689(18) -0.0212(15) 0.0608(19) -0.0234(18) C24 0.095(2) 0.0615(18) 0.123(3) -0.0058(19) 0.089(3) -0.0025(17) C25 0.091(2) 0.077(2) 0.073(2) -0.0181(17) 0.0574(19) -0.0089(18) C23 0.090(2) 0.085(2) 0.107(3) 0.042(2) 0.081(2) 0.0362(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 O3 C3 1.234(2) . ? O7 C7 1.417(3) . ? O7 H97 0.8200 . ? Cl1 C1 1.719(2) . ? C3 N4 1.376(3) . ? C3 C2 1.445(3) . ? C2 C1 1.347(3) . ? C2 C7 1.515(3) . ? N4 N5 1.344(3) . ? N4 C8 1.472(3) . ? C7 C11 1.483(3) . ? C7 H7 0.9800 . ? C1 C6 1.406(3) . ? N5 C6 1.288(3) . ? O12 C11 1.344(4) . ? O12 C13 1.369(4) . ? C12 C13 1.352(5) . ? C12 C11 1.346(5) . ? C12 C14 2.160(9) . ? C12 H12 0.9300 . ? C21 C22 1.369(4) . ? C21 C26 1.375(3) . ? C21 C8 1.494(4) . ? C8 H8A 0.9312 . ? C8 H8B 0.9312 . ? C11 O15 1.344(5) . ? C11 C15 1.339(4) . ? C6 H6 0.9300 . ? C26 C25 1.370(4) . ? C26 H26 0.9300 . ? C22 C23 1.377(5) . ? C22 H22 0.9300 . ? C15 C14 1.372(5) . ? C15 H15 0.9300 . ? O15 C14 1.381(5) . ? C14 C13 1.359(4) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? C24 C25 1.358(5) . ? C24 C23 1.374(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C23 H23 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 O7 H97 109.5 . . ? O3 C3 N4 120.2(2) . . ? O3 C3 C2 123.9(2) . . ? N4 C3 C2 115.99(18) . . ? C1 C2 C3 117.6(2) . . ? C1 C2 C7 123.8(2) . . ? C3 C2 C7 118.52(18) . . ? N5 N4 C3 125.25(19) . . ? N5 N4 C8 114.35(19) . . ? C3 N4 C8 120.32(19) . . ? O7 C7 C11 112.10(19) . . ? O7 C7 C2 111.49(18) . . ? C11 C7 C2 111.73(18) . . ? O7 C7 H7 107.1 . . ? C11 C7 H7 107.1 . . ? C2 C7 H7 107.1 . . ? C2 C1 C6 120.5(2) . . ? C2 C1 Cl1 122.39(19) . . ? C6 C1 Cl1 117.05(18) . . ? C6 N5 N4 117.55(19) . . ? C11 O12 C13 107.1(3) . . ? C13 C12 C11 108.0(5) . . ? C13 C12 H12 126.0 . . ? C11 C12 H12 126.0 . . ? C22 C21 C26 118.5(3) . . ? C22 C21 C8 121.3(2) . . ? C26 C21 C8 120.2(2) . . ? N4 C8 C21 112.00(19) . . ? N4 C8 H8A 109.2 . . ? C21 C8 H8A 109.2 . . ? N4 C8 H8B 109.2 . . ? C21 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? O15 C11 O12 109.4(3) . . ? O12 C11 C15 109.8(3) . . ? O15 C11 C12 108.2(5) . . ? C15 C11 C12 106.1(6) . . ? O15 C11 C7 127.7(3) . . ? O12 C11 C7 120.9(2) . . ? C15 C11 C7 129.0(3) . . ? C12 C11 C7 124.1(4) . . ? N5 C6 C1 122.9(2) . . ? N5 C6 H6 118.5 . . ? C1 C6 H6 118.5 . . ? C25 C26 C21 121.2(3) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? C21 C22 C23 120.8(3) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C11 C15 C14 107.4(4) . . ? C11 C15 H15 126.3 . . ? C14 C15 H15 126.3 . . ? C11 O15 C14 106.6(4) . . ? C13 C14 C15 107.4(3) . . ? C13 C14 O15 107.4(3) . . ? C13 C14 H14 126.3 . . ? C15 C14 H14 125.6 . . ? O15 C14 H14 126.3 . . ? C12 C14 H14 158.9 . . ? C12 C13 C14 105.6(5) . . ? C14 C13 O12 107.9(3) . . ? C12 C13 H13 126.1 . . ? C14 C13 H13 126.1 . . ? O12 C13 H13 126.1 . . ? C25 C24 C23 120.3(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 119.8(3) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C24 C23 C22 119.5(3) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? 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 O3 C3 C2 C1 -176.3(2) . . . . ? N4 C3 C2 C1 3.6(3) . . . . ? O3 C3 C2 C7 2.9(3) . . . . ? N4 C3 C2 C7 -177.12(18) . . . . ? O3 C3 N4 N5 176.7(2) . . . . ? C2 C3 N4 N5 -3.3(3) . . . . ? O3 C3 N4 C8 0.0(3) . . . . ? C2 C3 N4 C8 -179.94(19) . . . . ? C1 C2 C7 O7 136.8(2) . . . . ? C3 C2 C7 O7 -42.3(3) . . . . ? C1 C2 C7 C11 -96.8(3) . . . . ? C3 C2 C7 C11 84.0(2) . . . . ? C3 C2 C1 C6 -2.4(3) . . . . ? C7 C2 C1 C6 178.4(2) . . . . ? C3 C2 C1 Cl1 179.17(16) . . . . ? C7 C2 C1 Cl1 0.0(3) . . . . ? C3 N4 N5 C6 1.4(3) . . . . ? C8 N4 N5 C6 178.2(2) . . . . ? N5 N4 C8 C21 -87.0(2) . . . . ? C3 N4 C8 C21 90.0(2) . . . . ? C22 C21 C8 N4 -92.5(3) . . . . ? C26 C21 C8 N4 86.9(3) . . . . ? C13 O12 C11 O15 -11.6(10) . . . . ? C13 O12 C11 C15 -2.3(8) . . . . ? C13 O12 C11 C12 76.6(15) . . . . ? C13 O12 C11 C7 -176.6(3) . . . . ? C13 C12 C11 O15 15(2) . . . . ? C14 C12 C11 O15 2.2(11) . . . . ? C13 C12 C11 O12 -81.8(16) . . . . ? C14 C12 C11 O12 -94.9(12) . . . . ? C13 C12 C11 C15 24(2) . . . . ? C14 C12 C11 C15 11.2(9) . . . . ? C13 C12 C11 C7 -164.9(9) . . . . ? C14 C12 C11 C7 -178.0(5) . . . . ? O7 C7 C11 O15 -96.6(10) . . . . ? C2 C7 C11 O15 137.4(9) . . . . ? O7 C7 C11 O12 65.3(5) . . . . ? C2 C7 C11 O12 -60.6(5) . . . . ? O7 C7 C11 C15 -107.7(6) . . . . ? C2 C7 C11 C15 126.3(6) . . . . ? O7 C7 C11 C12 83.6(15) . . . . ? C2 C7 C11 C12 -42.3(15) . . . . ? N4 N5 C6 C1 0.2(4) . . . . ? C2 C1 C6 N5 0.4(4) . . . . ? Cl1 C1 C6 N5 178.97(19) . . . . ? C22 C21 C26 C25 0.1(4) . . . . ? C8 C21 C26 C25 -179.3(3) . . . . ? C26 C21 C22 C23 -0.8(4) . . . . ? C8 C21 C22 C23 178.7(3) . . . . ? O15 C11 C15 C14 87(2) . . . . ? O12 C11 C15 C14 -1.7(9) . . . . ? C12 C11 C15 C14 -17.8(14) . . . . ? C7 C11 C15 C14 172.0(3) . . . . ? O12 C11 O15 C14 13.1(13) . . . . ? C15 C11 O15 C14 -81(2) . . . . ? C12 C11 O15 C14 -3.4(18) . . . . ? C7 C11 O15 C14 176.8(5) . . . . ? C11 C15 C14 C13 5.1(8) . . . . ? C11 C15 C14 O15 -86(2) . . . . ? C11 C15 C14 C12 11.2(9) . . . . ? C11 O15 C14 C13 -9.5(12) . . . . ? C11 O15 C14 C15 82(2) . . . . ? C11 O15 C14 C12 2.1(11) . . . . ? C11 C12 C14 C13 159(2) . . . . ? C13 C12 C14 C15 -170.3(14) . . . . ? C11 C12 C14 C15 -11.1(9) . . . . ? C13 C12 C14 O15 -161.4(14) . . . . ? C11 C12 C14 O15 -2.1(11) . . . . ? C11 C12 C13 C14 -21(2) . . . . ? C11 C12 C13 O12 79.7(15) . . . . ? C14 C12 C13 O12 100.6(16) . . . . ? C15 C14 C13 C12 9.6(13) . . . . ? O15 C14 C13 C12 18.6(14) . . . . ? C15 C14 C13 O12 -6.5(7) . . . . ? O15 C14 C13 O12 2.5(9) . . . . ? C12 C14 C13 O12 -16.1(15) . . . . ? C11 O12 C13 C12 -78.6(16) . . . . ? C11 O12 C13 C14 5.4(7) . . . . ? C23 C24 C25 C26 -0.8(5) . . . . ? C21 C26 C25 C24 0.7(5) . . . . ? C25 C24 C23 C22 0.2(5) . . . . ? C21 C22 C23 C24 0.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.390 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.055