data_wue5756 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 Cl N2 O' _chemical_formula_weight 386.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 '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 6.0519(2) _cell_length_b 10.2844(8) _cell_length_c 16.9410(8) _cell_angle_alpha 74.927(5) _cell_angle_beta 88.001(4) _cell_angle_gamma 77.262(5) _cell_volume 992.79(10) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2947 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description 'plate' _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 1.825 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.6583 _exptl_absorpt_correction_T_max 0.9143 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11836 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.56 _diffrn_reflns_theta_max 66.81 _reflns_number_total 3302 _reflns_number_gt 2883 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (NOnius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0911P)^2^+1.0295P] 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 3302 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.1945 _refine_ls_wR_factor_gt 0.1862 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 -0.7729(4) 0.8127(2) 0.85214(14) 0.0439(6) Uani 1 1 d . . . N2 N -0.9162(4) 0.7295(3) 0.88095(15) 0.0468(6) Uani 1 1 d . . . C3 C -1.0114(5) 0.6522(3) 0.83290(19) 0.0469(7) Uani 1 1 d . . . H3A H -0.8946 0.5777 0.8210 0.056 Uiso 1 1 calc R . . H3B H -1.0819 0.7134 0.7814 0.056 Uiso 1 1 calc R . . C4 C -1.1908(5) 0.5943(3) 0.89120(19) 0.0490(7) Uani 1 1 d . . . H4A H -1.3381 0.6170 0.8628 0.059 Uiso 1 1 calc R . . H4B H -1.1438 0.4938 0.9116 0.059 Uiso 1 1 calc R . . C5 C -1.2050(5) 0.6640(3) 0.96209(18) 0.0451(7) Uani 1 1 d . . . C6 C -1.3499(5) 0.6626(4) 1.0292(2) 0.0565(8) Uani 1 1 d . . . H6 H -1.4638 0.6117 1.0359 0.068 Uiso 1 1 calc R . . C7 C -1.3248(6) 0.7372(4) 1.0864(2) 0.0631(9) Uani 1 1 d . . . H7 H -1.4215 0.7359 1.1311 0.076 Uiso 1 1 calc R . . C8 C -1.1585(6) 0.8115(4) 1.0764(2) 0.0582(8) Uani 1 1 d . . . H8 H -1.1424 0.8609 1.1146 0.070 Uiso 1 1 calc R . . C9 C -1.0112(5) 0.8148(3) 1.00964(19) 0.0499(7) Uani 1 1 d . . . H9 H -0.8971 0.8654 1.0032 0.060 Uiso 1 1 calc R . . C10 C -1.0394(5) 0.7404(3) 0.95302(17) 0.0411(6) Uani 1 1 d . . . C11 C -0.6890(5) 0.8181(3) 0.77826(17) 0.0431(7) Uani 1 1 d . . . H11 H -0.7350 0.7685 0.7448 0.052 Uiso 1 1 calc R . . C12 C -0.5231(5) 0.9035(3) 0.75008(18) 0.0439(7) Uani 1 1 d . . . C13 C -0.4462(5) 0.9673(3) 0.8058(2) 0.0507(7) Uani 1 1 d . . . H13 H -0.5095 0.9586 0.8579 0.061 Uiso 1 1 calc R . . C14 C -0.2805(6) 1.0415(3) 0.7844(2) 0.0588(8) Uani 1 1 d . . . H14 H -0.2328 1.0844 0.8214 0.071 Uiso 1 1 calc R . . C15 C -0.1811(6) 1.0535(3) 0.7062(2) 0.0612(9) Uani 1 1 d . . . H15 H -0.0671 1.1038 0.6919 0.073 Uiso 1 1 calc R . . C16 C -0.2510(6) 0.9913(3) 0.6505(2) 0.0605(9) Uani 1 1 d . . . H16 H -0.1825 0.9992 0.5993 0.073 Uiso 1 1 calc R . . C17 C -0.4230(5) 0.9168(3) 0.67004(19) 0.0484(7) Uani 1 1 d . . . C18 C -0.4850(7) 0.8546(4) 0.6060(2) 0.0617(9) Uani 1 1 d . . . O1 O -0.6821(6) 0.8503(3) 0.59425(15) 0.0773(8) Uani 1 1 d . . . C19 C -0.2815(8) 0.7936(4) 0.5562(2) 0.0736(11) Uani 1 1 d . . . H19 H -0.1325 0.7789 0.5760 0.088 Uiso 1 1 calc R . . C20 C -0.3145(7) 0.7634(4) 0.4889(2) 0.0663(10) Uani 1 1 d . . . H20 H -0.4650 0.7808 0.4699 0.080 Uiso 1 1 calc R . . C21 C -0.1321(6) 0.7029(3) 0.4390(2) 0.0639(10) Uani 1 1 d . . . C22 C 0.0978(6) 0.6539(3) 0.4667(2) 0.0564(8) Uani 1 1 d . . . H22 H 0.1431 0.6612 0.5176 0.068 Uiso 1 1 calc R . . C23 C 0.2556(5) 0.5943(3) 0.41631(18) 0.0481(7) Uani 1 1 d . . . H23 H 0.4084 0.5608 0.4333 0.058 Uiso 1 1 calc R . . C24 C 0.1830(5) 0.5851(3) 0.33980(19) 0.0500(7) Uani 1 1 d . . . C25 C -0.0392(6) 0.6324(4) 0.3128(2) 0.0637(9) Uani 1 1 d . . . H25 H -0.0840 0.6247 0.2619 0.076 Uiso 1 1 calc R . . C26 C -0.1940(6) 0.6909(4) 0.3616(2) 0.0658(9) Uani 1 1 d . . . H26 H -0.3458 0.7241 0.3432 0.079 Uiso 1 1 calc R . . Cl1 Cl 0.38059(18) 0.51196(11) 0.27596(6) 0.0774(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 N1 0.0408(12) 0.0433(13) 0.0463(13) -0.0090(10) 0.0075(10) -0.0107(10) N2 0.0487(13) 0.0503(14) 0.0470(14) -0.0151(11) 0.0106(11) -0.0209(11) C3 0.0484(16) 0.0442(15) 0.0495(17) -0.0141(13) 0.0009(13) -0.0104(13) C4 0.0475(16) 0.0429(15) 0.0555(18) -0.0074(13) -0.0037(14) -0.0130(13) C5 0.0416(15) 0.0422(15) 0.0475(16) -0.0039(12) 0.0004(12) -0.0099(12) C6 0.0458(17) 0.0598(19) 0.062(2) -0.0052(16) 0.0105(15) -0.0209(14) C7 0.059(2) 0.075(2) 0.055(2) -0.0154(17) 0.0221(16) -0.0182(17) C8 0.065(2) 0.063(2) 0.0511(18) -0.0203(15) 0.0131(15) -0.0169(16) C9 0.0507(17) 0.0509(17) 0.0515(17) -0.0144(14) 0.0092(14) -0.0181(14) C10 0.0393(14) 0.0409(14) 0.0410(15) -0.0061(12) 0.0046(11) -0.0105(11) C11 0.0399(14) 0.0425(15) 0.0447(16) -0.0108(12) 0.0050(12) -0.0052(12) C12 0.0379(14) 0.0382(14) 0.0489(16) -0.0053(12) 0.0070(12) -0.0027(11) C13 0.0469(16) 0.0508(17) 0.0522(18) -0.0107(14) 0.0066(13) -0.0101(13) C14 0.0509(18) 0.0505(18) 0.073(2) -0.0088(16) 0.0009(16) -0.0151(14) C15 0.0478(18) 0.0457(17) 0.083(2) -0.0037(17) 0.0086(17) -0.0126(14) C16 0.0521(18) 0.0458(17) 0.069(2) 0.0026(15) 0.0246(16) -0.0040(14) C17 0.0475(16) 0.0381(15) 0.0516(17) -0.0051(13) 0.0129(13) -0.0025(12) C18 0.080(3) 0.0537(19) 0.0522(19) -0.0113(15) 0.0181(18) -0.0218(17) O1 0.102(2) 0.0800(18) 0.0556(15) -0.0215(13) 0.0018(14) -0.0278(16) C19 0.092(3) 0.065(2) 0.063(2) -0.0052(18) 0.000(2) -0.029(2) C20 0.074(2) 0.057(2) 0.066(2) -0.0091(17) 0.0124(18) -0.0223(18) C21 0.057(2) 0.0356(16) 0.092(3) -0.0062(16) 0.0346(19) -0.0129(14) C22 0.081(2) 0.0495(17) 0.0442(17) -0.0139(14) 0.0185(16) -0.0253(16) C23 0.0500(17) 0.0475(16) 0.0480(17) -0.0112(13) 0.0086(13) -0.0158(13) C24 0.0596(19) 0.0442(16) 0.0512(17) -0.0157(13) 0.0133(14) -0.0197(14) C25 0.063(2) 0.066(2) 0.065(2) -0.0120(17) -0.0003(17) -0.0262(17) C26 0.059(2) 0.060(2) 0.074(2) -0.0064(18) 0.0053(18) -0.0195(17) Cl1 0.0953(7) 0.0805(7) 0.0667(6) -0.0385(5) 0.0286(5) -0.0220(5) _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 C11 1.326(4) . ? N1 N2 1.343(3) . ? N2 C10 1.425(4) . ? N2 C3 1.482(4) . ? C3 C4 1.553(4) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 C5 1.542(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C5 C10 1.386(4) . ? C5 C6 1.411(4) . ? C6 C7 1.414(5) . ? C6 H6 0.9400 . ? C7 C8 1.373(5) . ? C7 H7 0.9400 . ? C8 C9 1.414(4) . ? C8 H8 0.9400 . ? C9 C10 1.409(4) . ? C9 H9 0.9400 . ? C11 C12 1.464(4) . ? C11 H11 0.9400 . ? C12 C13 1.425(4) . ? C12 C17 1.452(4) . ? C13 C14 1.373(4) . ? C13 H13 0.9400 . ? C14 C15 1.424(5) . ? C14 H14 0.9400 . ? C15 C16 1.392(5) . ? C15 H15 0.9400 . ? C16 C17 1.405(5) . ? C16 H16 0.9400 . ? C17 C18 1.491(5) . ? C18 O1 1.228(5) . ? C18 C19 1.576(6) . ? C19 C20 1.289(5) . ? C19 H19 0.9400 . ? C20 C21 1.493(5) . ? C20 H20 0.9400 . ? C21 C26 1.419(6) . ? C21 C22 1.422(5) . ? C22 C23 1.404(4) . ? C22 H22 0.9400 . ? C23 C24 1.416(4) . ? C23 H23 0.9400 . ? C24 C25 1.376(5) . ? C24 Cl1 1.761(3) . ? C25 C26 1.371(5) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? 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 C11 N1 N2 119.4(2) . . ? N1 N2 C10 120.0(2) . . ? N1 N2 C3 124.9(2) . . ? C10 N2 C3 112.8(2) . . ? N2 C3 C4 102.4(2) . . ? N2 C3 H3A 111.3 . . ? C4 C3 H3A 111.3 . . ? N2 C3 H3B 111.3 . . ? C4 C3 H3B 111.3 . . ? H3A C3 H3B 109.2 . . ? C5 C4 C3 105.5(2) . . ? C5 C4 H4A 110.6 . . ? C3 C4 H4A 110.6 . . ? C5 C4 H4B 110.6 . . ? C3 C4 H4B 110.6 . . ? H4A C4 H4B 108.8 . . ? C10 C5 C6 118.8(3) . . ? C10 C5 C4 109.0(3) . . ? C6 C5 C4 132.1(3) . . ? C5 C6 C7 120.3(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 119.8(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 121.0(3) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 118.4(3) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C5 C10 C9 121.6(3) . . ? C5 C10 N2 109.5(2) . . ? C9 C10 N2 128.9(3) . . ? N1 C11 C12 118.4(3) . . ? N1 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? C13 C12 C17 119.1(3) . . ? C13 C12 C11 118.3(3) . . ? C17 C12 C11 122.4(3) . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 120.0(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 120.7(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C12 118.8(3) . . ? C16 C17 C18 116.3(3) . . ? C12 C17 C18 125.0(3) . . ? O1 C18 C17 121.5(3) . . ? O1 C18 C19 122.9(3) . . ? C17 C18 C19 115.6(3) . . ? C20 C19 C18 121.6(4) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C19 C20 C21 125.0(4) . . ? C19 C20 H20 117.5 . . ? C21 C20 H20 117.5 . . ? C26 C21 C22 119.2(3) . . ? C26 C21 C20 118.0(3) . . ? C22 C21 C20 122.8(4) . . ? C23 C22 C21 118.5(3) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? C22 C23 C24 119.6(3) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C25 C24 C23 122.1(3) . . ? C25 C24 Cl1 118.1(3) . . ? C23 C24 Cl1 119.8(2) . . ? C26 C25 C24 118.6(3) . . ? C26 C25 H25 120.7 . . ? C24 C25 H25 120.7 . . ? C25 C26 C21 122.0(3) . . ? C25 C26 H26 119.0 . . ? C21 C26 H26 119.0 . . ? 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 C11 N1 N2 C10 -168.6(2) . . . . ? C11 N1 N2 C3 -7.1(4) . . . . ? N1 N2 C3 C4 -171.4(2) . . . . ? C10 N2 C3 C4 -8.7(3) . . . . ? N2 C3 C4 C5 8.5(3) . . . . ? C3 C4 C5 C10 -6.1(3) . . . . ? C3 C4 C5 C6 173.5(3) . . . . ? C10 C5 C6 C7 -0.5(5) . . . . ? C4 C5 C6 C7 179.9(3) . . . . ? C5 C6 C7 C8 0.1(5) . . . . ? C6 C7 C8 C9 0.0(5) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C6 C5 C10 C9 0.9(4) . . . . ? C4 C5 C10 C9 -179.5(3) . . . . ? C6 C5 C10 N2 -178.9(3) . . . . ? C4 C5 C10 N2 0.8(3) . . . . ? C8 C9 C10 C5 -0.8(5) . . . . ? C8 C9 C10 N2 179.0(3) . . . . ? N1 N2 C10 C5 168.9(2) . . . . ? C3 N2 C10 C5 5.4(3) . . . . ? N1 N2 C10 C9 -10.8(5) . . . . ? C3 N2 C10 C9 -174.4(3) . . . . ? N2 N1 C11 C12 -176.5(2) . . . . ? N1 C11 C12 C13 5.0(4) . . . . ? N1 C11 C12 C17 -179.5(3) . . . . ? C17 C12 C13 C14 0.4(4) . . . . ? C11 C12 C13 C14 176.0(3) . . . . ? C12 C13 C14 C15 -1.0(5) . . . . ? C13 C14 C15 C16 0.4(5) . . . . ? C14 C15 C16 C17 0.7(5) . . . . ? C15 C16 C17 C12 -1.3(4) . . . . ? C15 C16 C17 C18 179.9(3) . . . . ? C13 C12 C17 C16 0.7(4) . . . . ? C11 C12 C17 C16 -174.7(3) . . . . ? C13 C12 C17 C18 179.4(3) . . . . ? C11 C12 C17 C18 4.0(4) . . . . ? C16 C17 C18 O1 -142.8(3) . . . . ? C12 C17 C18 O1 38.5(5) . . . . ? C16 C17 C18 C19 38.1(4) . . . . ? C12 C17 C18 C19 -140.6(3) . . . . ? O1 C18 C19 C20 15.6(6) . . . . ? C17 C18 C19 C20 -165.4(3) . . . . ? C18 C19 C20 C21 -178.8(3) . . . . ? C19 C20 C21 C26 -172.6(3) . . . . ? C19 C20 C21 C22 9.1(5) . . . . ? C26 C21 C22 C23 -0.4(4) . . . . ? C20 C21 C22 C23 177.8(3) . . . . ? C21 C22 C23 C24 0.3(4) . . . . ? C22 C23 C24 C25 -0.3(5) . . . . ? C22 C23 C24 Cl1 179.4(2) . . . . ? C23 C24 C25 C26 0.4(5) . . . . ? Cl1 C24 C25 C26 -179.3(3) . . . . ? C24 C25 C26 C21 -0.5(5) . . . . ? C22 C21 C26 C25 0.5(5) . . . . ? C20 C21 C26 C25 -177.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 66.81 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 1.272 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.054