# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr feijun wang' _publ_contact_author_email mshi@mail.sioc.ac.cn _publ_section_title ; A Highly Efficient Kinetic Resolution of Morita-Baylis-Hillman Adducts Achieved by N-Ar Axially Chiral Pd-Complexes Catalyzed Asymmetric Allylation ; loop_ _publ_author_name 'feijun wang' 'Shengke Li' 'Mingliang Qu' 'Lian-Jun Liu' 'Mei-Xin Zhao' ; Min Shi ; # Attachment '- CCDC 798781.cif' data_z2 _database_code_depnum_ccdc_archive 'CCDC 798781' #TrackingRef '- CCDC 798781.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H21 I2 N3 O Pd' _chemical_formula_weight 763.67 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.0426(5) _cell_length_b 15.0498(9) _cell_length_c 19.5924(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2666.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.902 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 3.036 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3840 _exptl_absorpt_correction_T_max 0.7718 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 28953 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4679 _reflns_number_gt 4090 _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^)+(0.0074P)^2^+26.6450P] 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 0.06(5) _chemical_absolute_configuration ad _refine_ls_number_reflns 4679 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1067 _refine_ls_goodness_of_fit_ref 1.242 _refine_ls_restrained_S_all 1.242 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -1.3482(9) 0.5984(6) 0.7108(5) 0.050(2) Uani 1 1 d . . . I2 I -0.79291(9) 0.53394(5) 0.65112(4) 0.0447(2) Uani 1 1 d . . . Pd1 Pd -0.93946(9) 0.48402(6) 0.76310(4) 0.0341(2) Uani 1 1 d . . . I1 I -0.71030(10) 0.44490(6) 0.83529(5) 0.0582(3) Uani 1 1 d . . . N1 N -1.1390(9) 0.5220(7) 0.7205(4) 0.036(2) Uani 1 1 d . . . N2 N -1.0893(11) 0.3575(6) 0.8567(5) 0.042(2) Uani 1 1 d . . . N3 N -1.1524(10) 0.4957(6) 0.8748(5) 0.039(2) Uani 1 1 d . . . C1 C -1.1184(13) 0.6428(9) 0.9279(6) 0.043(3) Uani 1 1 d . . . C2 C -1.0507(14) 0.6043(10) 0.9870(7) 0.055(3) Uani 1 1 d . . . H2A H -1.0355 0.5433 0.9895 0.065 Uiso 1 1 calc R . . C3 C -1.0090(17) 0.6575(13) 1.0389(8) 0.068(5) Uani 1 1 d . . . H3A H -0.9623 0.6328 1.0767 0.081 Uiso 1 1 calc R . . C4 C -1.0348(18) 0.7491(14) 1.0371(9) 0.074(5) Uani 1 1 d . . . H4A H -1.0065 0.7844 1.0738 0.089 Uiso 1 1 calc R . . C5 C -1.0999(17) 0.7863(11) 0.9827(9) 0.068(5) Uani 1 1 d . . . H5A H -1.1173 0.8472 0.9825 0.081 Uiso 1 1 calc R . . C6 C -1.1431(14) 0.7339(9) 0.9250(8) 0.051(3) Uani 1 1 d . . . C7 C -1.2006(16) 0.7718(9) 0.8646(8) 0.059(4) Uani 1 1 d . . . H7A H -1.2197 0.8325 0.8636 0.070 Uiso 1 1 calc R . . C8 C -1.2288(14) 0.7232(9) 0.8084(7) 0.052(3) Uani 1 1 d . . . H8A H -1.2641 0.7504 0.7690 0.063 Uiso 1 1 calc R . . C9 C -1.2038(13) 0.6290(8) 0.8097(6) 0.038(3) Uani 1 1 d . . . C10 C -1.1558(12) 0.5902(8) 0.8699(6) 0.037(3) Uani 1 1 d . . . C11 C -1.2271(13) 0.5799(7) 0.7461(6) 0.041(3) Uani 1 1 d . . . C12 C -1.3402(13) 0.5473(9) 0.6491(7) 0.051(3) Uani 1 1 d . . . H12A H -1.3192 0.5851 0.6102 0.061 Uiso 1 1 calc R . . H12B H -1.4322 0.5158 0.6409 0.061 Uiso 1 1 calc R . . C13 C -1.2126(13) 0.4817(8) 0.6619(6) 0.043(3) Uani 1 1 d . . . H13A H -1.1454 0.4824 0.6226 0.052 Uiso 1 1 calc R . . C14 C -1.2555(12) 0.3854(9) 0.6783(6) 0.042(3) Uani 1 1 d . . . C15 C -1.1878(15) 0.3152(11) 0.6468(8) 0.062(4) Uani 1 1 d . . . H15A H -1.1157 0.3250 0.6139 0.074 Uiso 1 1 calc R . . C16 C -1.2277(18) 0.2295(11) 0.6645(9) 0.067(4) Uani 1 1 d . . . H16A H -1.1828 0.1819 0.6425 0.081 Uiso 1 1 calc R . . C17 C -1.3300(18) 0.2138(11) 0.7129(9) 0.070(5) Uani 1 1 d . . . H17A H -1.3535 0.1557 0.7250 0.084 Uiso 1 1 calc R . . C18 C -1.3998(15) 0.2839(11) 0.7445(8) 0.065(4) Uani 1 1 d . . . H18A H -1.4728 0.2731 0.7769 0.078 Uiso 1 1 calc R . . C19 C -1.3622(14) 0.3703(10) 0.7284(7) 0.051(3) Uani 1 1 d . . . H19A H -1.4073 0.4177 0.7506 0.062 Uiso 1 1 calc R . . C20 C -1.0598(11) 0.4413(7) 0.8379(6) 0.035(2) Uani 1 1 d . . . C21 C -1.2025(16) 0.3571(8) 0.9055(6) 0.043(3) Uani 1 1 d . . . C22 C -1.2812(18) 0.2884(9) 0.9378(7) 0.060(4) Uani 1 1 d . . . H22A H -1.2590 0.2291 0.9291 0.072 Uiso 1 1 calc R . . C23 C -1.3893(18) 0.3108(12) 0.9815(8) 0.074(5) Uani 1 1 d . . . H23A H -1.4406 0.2663 1.0044 0.088 Uiso 1 1 calc R . . C24 C -1.4252(17) 0.3973(11) 0.9931(8) 0.067(4) Uani 1 1 d . . . H24A H -1.5003 0.4101 1.0240 0.081 Uiso 1 1 calc R . . C25 C -1.3544(14) 0.4672(12) 0.9607(6) 0.059(4) Uani 1 1 d . . . H25A H -1.3814 0.5260 0.9682 0.071 Uiso 1 1 calc R . . C26 C -1.2438(13) 0.4452(8) 0.9173(6) 0.042(3) Uani 1 1 d . . . C27 C -1.0233(15) 0.2783(8) 0.8285(7) 0.049(3) Uani 1 1 d . . . H27A H -0.9476 0.2946 0.7965 0.074 Uiso 1 1 calc R . . H27B H -1.0979 0.2440 0.8056 0.074 Uiso 1 1 calc R . . H27C H -0.9806 0.2436 0.8646 0.074 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 0.026(4) 0.062(6) 0.062(6) 0.009(5) -0.007(4) 0.013(4) I2 0.0353(4) 0.0420(4) 0.0569(5) 0.0058(4) 0.0105(4) 0.0008(4) Pd1 0.0204(4) 0.0386(5) 0.0434(4) 0.0026(4) 0.0046(4) 0.0027(4) I1 0.0301(4) 0.0722(6) 0.0724(6) 0.0104(5) -0.0072(5) 0.0079(4) N1 0.021(4) 0.048(6) 0.040(5) 0.000(5) 0.003(4) 0.011(5) N2 0.030(6) 0.042(6) 0.052(6) 0.000(5) 0.006(5) -0.002(4) N3 0.027(5) 0.034(5) 0.055(6) -0.002(4) 0.008(4) 0.012(4) C1 0.030(6) 0.056(8) 0.045(7) -0.007(6) 0.009(5) -0.005(6) C2 0.038(7) 0.077(10) 0.049(8) -0.004(7) 0.009(7) -0.002(7) C3 0.057(9) 0.092(13) 0.054(9) -0.010(9) 0.008(7) -0.029(9) C4 0.056(11) 0.101(15) 0.066(11) -0.024(10) 0.009(8) -0.029(10) C5 0.056(10) 0.059(10) 0.089(13) -0.005(9) 0.024(9) -0.019(8) C6 0.029(7) 0.057(9) 0.068(9) -0.005(7) 0.015(7) -0.011(6) C7 0.042(8) 0.043(7) 0.092(11) 0.002(7) 0.022(8) 0.002(7) C8 0.022(6) 0.064(9) 0.071(9) 0.006(7) 0.012(6) 0.004(6) C9 0.017(6) 0.043(6) 0.055(7) 0.003(5) 0.007(6) 0.007(6) C10 0.024(6) 0.042(7) 0.045(7) -0.011(5) 0.005(5) -0.001(5) C11 0.035(6) 0.037(6) 0.049(7) 0.022(5) 0.002(6) 0.011(5) C12 0.034(7) 0.062(8) 0.055(8) -0.005(7) -0.014(6) 0.012(6) C13 0.033(6) 0.053(7) 0.043(6) -0.004(6) 0.013(6) 0.006(6) C14 0.017(6) 0.061(8) 0.048(7) -0.014(6) -0.005(5) -0.002(5) C15 0.035(8) 0.092(11) 0.058(9) 0.000(8) 0.005(7) 0.019(8) C16 0.050(9) 0.071(10) 0.081(11) -0.011(9) -0.003(9) 0.018(8) C17 0.051(10) 0.062(10) 0.098(13) 0.008(9) -0.029(9) 0.000(8) C18 0.040(8) 0.078(11) 0.077(11) 0.002(9) 0.003(8) -0.014(7) C19 0.028(6) 0.070(9) 0.057(8) -0.015(7) 0.003(6) -0.009(6) C20 0.017(5) 0.038(6) 0.051(6) 0.007(5) -0.003(5) -0.001(5) C21 0.044(7) 0.052(7) 0.034(6) 0.005(5) 0.006(6) -0.007(7) C22 0.066(9) 0.052(8) 0.060(8) 0.010(7) 0.013(8) -0.009(8) C23 0.067(10) 0.090(13) 0.064(10) 0.007(9) 0.035(8) -0.030(9) C24 0.053(9) 0.089(12) 0.059(9) 0.005(9) 0.018(8) -0.017(9) C25 0.043(7) 0.080(10) 0.053(8) -0.012(8) 0.018(6) -0.016(7) C26 0.042(8) 0.048(7) 0.037(6) 0.003(5) 0.005(5) -0.011(6) C27 0.048(8) 0.042(7) 0.058(8) 0.000(6) 0.003(6) 0.013(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.326(13) . ? O1 C12 1.435(14) . ? I2 Pd1 2.6709(11) . ? Pd1 C20 1.935(11) . ? Pd1 N1 2.068(8) . ? Pd1 I1 2.5771(12) . ? N1 C11 1.283(14) . ? N1 C13 1.459(15) . ? N2 C20 1.341(14) . ? N2 C21 1.401(15) . ? N2 C27 1.443(15) . ? N3 C20 1.376(14) . ? N3 C26 1.398(14) . ? N3 C10 1.425(15) . ? C1 C6 1.390(19) . ? C1 C10 1.427(17) . ? C1 C2 1.431(18) . ? C2 C3 1.349(19) . ? C2 H2A 0.9300 . ? C3 C4 1.40(3) . ? C3 H3A 0.9300 . ? C4 C5 1.34(2) . ? C4 H4A 0.9300 . ? C5 C6 1.43(2) . ? C5 H5A 0.9300 . ? C6 C7 1.41(2) . ? C7 C8 1.35(2) . ? C7 H7A 0.9300 . ? C8 C9 1.436(18) . ? C8 H8A 0.9300 . ? C9 C10 1.385(16) . ? C9 C11 1.464(17) . ? C12 C13 1.539(16) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.534(17) . ? C13 H13A 0.9800 . ? C14 C15 1.368(18) . ? C14 C19 1.395(17) . ? C15 C16 1.38(2) . ? C15 H15A 0.9300 . ? C16 C17 1.35(2) . ? C16 H16A 0.9300 . ? C17 C18 1.38(2) . ? C17 H17A 0.9300 . ? C18 C19 1.38(2) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C21 C26 1.397(17) . ? C21 C22 1.406(17) . ? C22 C23 1.34(2) . ? C22 H22A 0.9300 . ? C23 C24 1.36(2) . ? C23 H23A 0.9300 . ? C24 C25 1.39(2) . ? C24 H24A 0.9300 . ? C25 C26 1.353(17) . ? C25 H25A 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? 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 O1 C12 106.6(9) . . ? C20 Pd1 N1 84.7(4) . . ? C20 Pd1 I1 87.7(3) . . ? N1 Pd1 I1 170.4(2) . . ? C20 Pd1 I2 174.0(3) . . ? N1 Pd1 I2 91.3(2) . . ? I1 Pd1 I2 96.67(4) . . ? C11 N1 C13 107.9(9) . . ? C11 N1 Pd1 124.8(8) . . ? C13 N1 Pd1 126.9(7) . . ? C20 N2 C21 109.7(10) . . ? C20 N2 C27 126.1(10) . . ? C21 N2 C27 124.0(10) . . ? C20 N3 C26 110.4(9) . . ? C20 N3 C10 124.8(10) . . ? C26 N3 C10 124.8(10) . . ? C6 C1 C10 118.5(12) . . ? C6 C1 C2 120.1(13) . . ? C10 C1 C2 121.4(12) . . ? C3 C2 C1 119.3(15) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 121.3(17) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C5 C4 C3 120.4(16) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C4 C5 C6 121.2(16) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C1 C6 C7 119.4(13) . . ? C1 C6 C5 117.8(15) . . ? C7 C6 C5 122.7(14) . . ? C8 C7 C6 122.4(13) . . ? C8 C7 H7A 118.8 . . ? C6 C7 H7A 118.8 . . ? C7 C8 C9 119.5(13) . . ? C7 C8 H8A 120.3 . . ? C9 C8 H8A 120.3 . . ? C10 C9 C8 118.8(12) . . ? C10 C9 C11 123.8(10) . . ? C8 C9 C11 117.4(11) . . ? C9 C10 N3 119.0(11) . . ? C9 C10 C1 121.2(11) . . ? N3 C10 C1 119.6(11) . . ? N1 C11 O1 116.8(11) . . ? N1 C11 C9 125.9(11) . . ? O1 C11 C9 117.2(10) . . ? O1 C12 C13 104.1(9) . . ? O1 C12 H12A 110.9 . . ? C13 C12 H12A 110.9 . . ? O1 C12 H12B 110.9 . . ? C13 C12 H12B 110.9 . . ? H12A C12 H12B 109.0 . . ? N1 C13 C14 110.1(10) . . ? N1 C13 C12 101.8(9) . . ? C14 C13 C12 116.7(10) . . ? N1 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? C15 C14 C19 120.0(14) . . ? C15 C14 C13 121.5(11) . . ? C19 C14 C13 118.5(11) . . ? C14 C15 C16 119.4(14) . . ? C14 C15 H15A 120.3 . . ? C16 C15 H15A 120.3 . . ? C17 C16 C15 121.3(15) . . ? C17 C16 H16A 119.3 . . ? C15 C16 H16A 119.3 . . ? C16 C17 C18 119.8(16) . . ? C16 C17 H17A 120.1 . . ? C18 C17 H17A 120.1 . . ? C17 C18 C19 120.4(15) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C18 C19 C14 119.0(14) . . ? C18 C19 H19A 120.5 . . ? C14 C19 H19A 120.5 . . ? N2 C20 N3 107.1(10) . . ? N2 C20 Pd1 129.2(9) . . ? N3 C20 Pd1 122.8(8) . . ? C26 C21 N2 107.7(10) . . ? C26 C21 C22 119.3(12) . . ? N2 C21 C22 132.9(12) . . ? C23 C22 C21 118.1(14) . . ? C23 C22 H22A 121.0 . . ? C21 C22 H22A 121.0 . . ? C22 C23 C24 121.4(14) . . ? C22 C23 H23A 119.3 . . ? C24 C23 H23A 119.3 . . ? C23 C24 C25 122.6(15) . . ? C23 C24 H24A 118.7 . . ? C25 C24 H24A 118.7 . . ? C26 C25 C24 116.4(15) . . ? C26 C25 H25A 121.8 . . ? C24 C25 H25A 121.8 . . ? C25 C26 C21 122.3(12) . . ? C25 C26 N3 132.7(13) . . ? C21 C26 N3 105.0(10) . . ? N2 C27 H27A 109.5 . . ? N2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 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 C20 Pd1 N1 C11 63.3(10) . . . . ? I1 Pd1 N1 C11 25(2) . . . . ? I2 Pd1 N1 C11 -121.2(9) . . . . ? C20 Pd1 N1 C13 -108.9(9) . . . . ? I1 Pd1 N1 C13 -146.8(13) . . . . ? I2 Pd1 N1 C13 66.6(9) . . . . ? C6 C1 C2 C3 -1.1(19) . . . . ? C10 C1 C2 C3 175.9(12) . . . . ? C1 C2 C3 C4 2(2) . . . . ? C2 C3 C4 C5 -1(2) . . . . ? C3 C4 C5 C6 -1(2) . . . . ? C10 C1 C6 C7 -1.5(19) . . . . ? C2 C1 C6 C7 175.7(12) . . . . ? C10 C1 C6 C5 -177.7(11) . . . . ? C2 C1 C6 C5 -0.6(18) . . . . ? C4 C5 C6 C1 2(2) . . . . ? C4 C5 C6 C7 -174.6(14) . . . . ? C1 C6 C7 C8 -2(2) . . . . ? C5 C6 C7 C8 174.0(13) . . . . ? C6 C7 C8 C9 2(2) . . . . ? C7 C8 C9 C10 2.1(19) . . . . ? C7 C8 C9 C11 -176.2(12) . . . . ? C8 C9 C10 N3 170.5(10) . . . . ? C11 C9 C10 N3 -11.3(18) . . . . ? C8 C9 C10 C1 -5.6(18) . . . . ? C11 C9 C10 C1 172.5(11) . . . . ? C20 N3 C10 C9 66.9(16) . . . . ? C26 N3 C10 C9 -112.4(13) . . . . ? C20 N3 C10 C1 -116.9(13) . . . . ? C26 N3 C10 C1 63.8(16) . . . . ? C6 C1 C10 C9 5.3(18) . . . . ? C2 C1 C10 C9 -171.8(11) . . . . ? C6 C1 C10 N3 -170.8(11) . . . . ? C2 C1 C10 N3 12.1(18) . . . . ? C13 N1 C11 O1 -8.8(14) . . . . ? Pd1 N1 C11 O1 177.8(7) . . . . ? C13 N1 C11 C9 173.1(11) . . . . ? Pd1 N1 C11 C9 -0.3(16) . . . . ? C12 O1 C11 N1 -2.5(14) . . . . ? C12 O1 C11 C9 175.8(10) . . . . ? C10 C9 C11 N1 -45.1(18) . . . . ? C8 C9 C11 N1 133.0(12) . . . . ? C10 C9 C11 O1 136.7(12) . . . . ? C8 C9 C11 O1 -45.1(15) . . . . ? C11 O1 C12 C13 11.9(12) . . . . ? C11 N1 C13 C14 -109.4(10) . . . . ? Pd1 N1 C13 C14 63.8(11) . . . . ? C11 N1 C13 C12 15.1(12) . . . . ? Pd1 N1 C13 C12 -171.7(8) . . . . ? O1 C12 C13 N1 -16.0(12) . . . . ? O1 C12 C13 C14 103.8(12) . . . . ? N1 C13 C14 C15 -111.4(13) . . . . ? C12 C13 C14 C15 133.3(12) . . . . ? N1 C13 C14 C19 66.2(13) . . . . ? C12 C13 C14 C19 -49.1(15) . . . . ? C19 C14 C15 C16 1(2) . . . . ? C13 C14 C15 C16 178.4(12) . . . . ? C14 C15 C16 C17 -1(2) . . . . ? C15 C16 C17 C18 2(2) . . . . ? C16 C17 C18 C19 -2(2) . . . . ? C17 C18 C19 C14 2(2) . . . . ? C15 C14 C19 C18 -1(2) . . . . ? C13 C14 C19 C18 -178.8(12) . . . . ? C21 N2 C20 N3 0.6(13) . . . . ? C27 N2 C20 N3 176.7(11) . . . . ? C21 N2 C20 Pd1 -169.1(8) . . . . ? C27 N2 C20 Pd1 7.0(18) . . . . ? C26 N3 C20 N2 -0.7(13) . . . . ? C10 N3 C20 N2 179.9(11) . . . . ? C26 N3 C20 Pd1 169.8(8) . . . . ? C10 N3 C20 Pd1 -9.6(16) . . . . ? N1 Pd1 C20 N2 109.4(11) . . . . ? I1 Pd1 C20 N2 -76.5(10) . . . . ? I2 Pd1 C20 N2 61(3) . . . . ? N1 Pd1 C20 N3 -58.8(9) . . . . ? I1 Pd1 C20 N3 115.3(9) . . . . ? I2 Pd1 C20 N3 -108(3) . . . . ? C20 N2 C21 C26 -0.3(14) . . . . ? C27 N2 C21 C26 -176.5(11) . . . . ? C20 N2 C21 C22 174.8(15) . . . . ? C27 N2 C21 C22 -1(2) . . . . ? C26 C21 C22 C23 -3(2) . . . . ? N2 C21 C22 C23 -177.7(15) . . . . ? C21 C22 C23 C24 2(3) . . . . ? C22 C23 C24 C25 0(3) . . . . ? C23 C24 C25 C26 -1(2) . . . . ? C24 C25 C26 C21 0(2) . . . . ? C24 C25 C26 N3 177.6(13) . . . . ? N2 C21 C26 C25 178.0(11) . . . . ? C22 C21 C26 C25 2(2) . . . . ? N2 C21 C26 N3 -0.1(13) . . . . ? C22 C21 C26 N3 -176.0(12) . . . . ? C20 N3 C26 C25 -177.3(13) . . . . ? C10 N3 C26 C25 2(2) . . . . ? C20 N3 C26 C21 0.5(13) . . . . ? C10 N3 C26 C21 179.9(11) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.814 _refine_diff_density_min -1.033 _refine_diff_density_rms 0.164 # Attachment '- CCDC 822886.cif' data_z1 _database_code_depnum_ccdc_archive 'CCDC 822886' #TrackingRef '- CCDC 822886.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 Cl N O3' _chemical_formula_weight 341.78 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.1242(5) _cell_length_b 6.2039(3) _cell_length_c 13.0579(6) _cell_angle_alpha 90.00 _cell_angle_beta 111.5220(10) _cell_angle_gamma 90.00 _cell_volume 838.34(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.244 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8960 _exptl_absorpt_correction_T_max 0.9259 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 9791 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2798 _reflns_number_gt 2492 _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^)+(0.0395P)^2^+0.1247P] 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 -0.02(7) _chemical_absolute_configuration ad _refine_ls_number_reflns 2798 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.027 _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 0.34216(6) 0.65657(15) 0.79144(6) 0.0899(3) Uani 1 1 d . . . O1 O -0.32601(19) 1.6815(4) 1.05294(18) 0.1002(7) Uani 1 1 d . . . O2 O -0.13182(18) 1.6922(3) 1.05709(17) 0.0926(6) Uani 1 1 d . . . O3 O -0.37811(19) 0.4711(3) 0.64647(17) 0.0909(6) Uani 1 1 d . . . N1 N -0.23841(19) 1.6089(4) 1.02836(16) 0.0685(5) Uani 1 1 d . . . C1 C -0.18595(18) 1.1472(4) 0.87179(15) 0.0558(5) Uani 1 1 d . . . H1A H -0.1191 1.0865 0.8549 0.067 Uiso 1 1 calc R . . C2 C -0.16237(19) 1.3275(4) 0.93701(16) 0.0579(6) Uani 1 1 d . . . H2A H -0.0807 1.3902 0.9634 0.069 Uiso 1 1 calc R . . C3 C -0.26193(19) 1.4140(4) 0.96269(16) 0.0534(5) Uani 1 1 d . . . C4 C -0.3822(2) 1.3198(4) 0.92789(18) 0.0609(6) Uani 1 1 d . . . H4A H -0.4475 1.3776 0.9480 0.073 Uiso 1 1 calc R . . C5 C -0.4041(2) 1.1393(5) 0.86311(17) 0.0617(6) Uani 1 1 d . . . H5A H -0.4846 1.0729 0.8405 0.074 Uiso 1 1 calc R . . C6 C -0.3082(2) 1.0532(4) 0.83036(16) 0.0527(5) Uani 1 1 d . . . C7 C -0.33870(19) 0.8678(4) 0.75572(17) 0.0569(5) Uani 1 1 d . . . H7A H -0.3930 0.7648 0.7674 0.068 Uiso 1 1 calc R . . C8 C -0.29851(19) 0.8279(3) 0.67327(16) 0.0515(5) Uani 1 1 d . . . C9 C -0.3498(2) 0.6298(4) 0.60563(19) 0.0643(6) Uani 1 1 d . . . C10 C -0.3695(3) 0.6364(5) 0.48641(19) 0.0791(7) Uani 1 1 d . . . H10A H -0.4570 0.6844 0.4455 0.095 Uiso 1 1 calc R . . H10B H -0.3614 0.4910 0.4624 0.095 Uiso 1 1 calc R . . C11 C -0.2770(3) 0.7809(5) 0.45709(18) 0.0787(8) Uani 1 1 d . . . H11A H -0.1931 0.7119 0.4791 0.094 Uiso 1 1 calc R . . H11B H -0.3087 0.8019 0.3780 0.094 Uiso 1 1 calc R . . C12 C -0.2633(2) 0.9960(4) 0.51322(17) 0.0651(6) Uani 1 1 d . . . H12A H -0.3470 1.0662 0.4898 0.078 Uiso 1 1 calc R . . H12B H -0.2057 1.0865 0.4915 0.078 Uiso 1 1 calc R . . C13 C -0.2098(2) 0.9720(3) 0.63899(16) 0.0525(5) Uani 1 1 d . . . H13A H -0.2097 1.1150 0.6709 0.063 Uiso 1 1 calc R . . C14 C -0.0711(2) 0.8897(3) 0.68085(15) 0.0495(5) Uani 1 1 d . . . C15 C -0.0338(2) 0.6960(4) 0.73384(19) 0.0648(6) Uani 1 1 d . . . H15A H -0.0954 0.6106 0.7469 0.078 Uiso 1 1 calc R . . C16 C 0.0926(2) 0.6238(4) 0.7685(2) 0.0688(6) Uani 1 1 d . . . H16A H 0.1153 0.4919 0.8043 0.083 Uiso 1 1 calc R . . C17 C 0.1826(2) 0.7464(4) 0.74987(17) 0.0617(6) Uani 1 1 d . . . C18 C 0.1510(3) 0.9437(6) 0.7022(2) 0.0878(9) Uani 1 1 d . . . H18A H 0.2143 1.0304 0.6926 0.105 Uiso 1 1 calc R . . C19 C 0.0244(3) 1.0153(4) 0.6678(2) 0.0783(8) Uani 1 1 d . . . H19A H 0.0035 1.1506 0.6355 0.094 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 0.0525(3) 0.1231(6) 0.0945(4) -0.0019(5) 0.0277(3) 0.0058(4) O1 0.0862(12) 0.0919(16) 0.1378(16) -0.0278(14) 0.0590(12) 0.0113(12) O2 0.0749(12) 0.0896(15) 0.1164(14) -0.0304(12) 0.0386(11) -0.0119(11) O3 0.0966(14) 0.0579(11) 0.1049(14) -0.0005(11) 0.0212(11) -0.0207(11) N1 0.0648(12) 0.0709(15) 0.0746(11) -0.0040(10) 0.0311(10) 0.0090(11) C1 0.0431(10) 0.0723(14) 0.0543(10) -0.0046(12) 0.0206(8) 0.0038(11) C2 0.0411(10) 0.0782(16) 0.0538(11) -0.0024(11) 0.0169(9) 0.0010(11) C3 0.0518(12) 0.0607(14) 0.0504(10) 0.0047(10) 0.0219(9) 0.0081(10) C4 0.0490(12) 0.0747(16) 0.0675(13) 0.0053(12) 0.0314(10) 0.0108(11) C5 0.0459(11) 0.0737(16) 0.0705(12) 0.0056(13) 0.0272(9) -0.0022(12) C6 0.0451(11) 0.0624(14) 0.0530(11) 0.0082(10) 0.0206(9) 0.0022(9) C7 0.0456(11) 0.0602(14) 0.0632(12) 0.0062(10) 0.0181(9) -0.0022(10) C8 0.0458(11) 0.0464(12) 0.0581(11) 0.0046(9) 0.0141(9) 0.0049(9) C9 0.0541(12) 0.0500(13) 0.0772(13) 0.0011(12) 0.0105(10) 0.0065(11) C10 0.0876(17) 0.0553(14) 0.0761(14) -0.0144(14) 0.0086(12) 0.0119(14) C11 0.0956(19) 0.0771(19) 0.0559(13) -0.0036(12) 0.0192(12) 0.0255(16) C12 0.0745(15) 0.0615(15) 0.0590(12) 0.0089(11) 0.0241(11) 0.0157(12) C13 0.0652(13) 0.0392(11) 0.0563(11) 0.0036(9) 0.0259(10) 0.0068(10) C14 0.0574(12) 0.0433(11) 0.0516(10) 0.0018(9) 0.0246(9) -0.0020(9) C15 0.0532(12) 0.0564(15) 0.0874(15) 0.0191(12) 0.0289(11) -0.0034(11) C16 0.0583(13) 0.0534(14) 0.0909(15) 0.0130(13) 0.0228(11) 0.0035(12) C17 0.0525(12) 0.0777(18) 0.0586(12) 0.0001(11) 0.0245(10) -0.0009(11) C18 0.0621(16) 0.105(2) 0.1012(19) 0.0297(18) 0.0359(14) -0.0182(15) C19 0.0751(17) 0.0653(17) 0.0954(17) 0.0308(14) 0.0325(14) -0.0055(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 Cl1 C17 1.746(2) . ? O1 N1 1.219(2) . ? O2 N1 1.220(3) . ? O3 C9 1.215(3) . ? N1 C3 1.450(3) . ? C1 C2 1.371(3) . ? C1 C6 1.394(3) . ? C1 H1A 0.9300 . ? C2 C3 1.378(3) . ? C2 H2A 0.9300 . ? C3 C4 1.376(3) . ? C4 C5 1.370(4) . ? C4 H4A 0.9300 . ? C5 C6 1.393(3) . ? C5 H5A 0.9300 . ? C6 C7 1.465(3) . ? C7 C8 1.332(3) . ? C7 H7A 0.9300 . ? C8 C9 1.499(3) . ? C8 C13 1.515(3) . ? C9 C10 1.491(3) . ? C10 C11 1.516(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.503(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.535(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.523(3) . ? C13 H13A 0.9800 . ? C14 C15 1.373(3) . ? C14 C19 1.378(3) . ? C15 C16 1.384(3) . ? C15 H15A 0.9300 . ? C16 C17 1.349(3) . ? C16 H16A 0.9300 . ? C17 C18 1.360(4) . ? C18 C19 1.385(4) . ? C18 H18A 0.9300 . ? C19 H19A 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 O1 N1 O2 122.9(2) . . ? O1 N1 C3 118.4(2) . . ? O2 N1 C3 118.67(19) . . ? C2 C1 C6 121.29(19) . . ? C2 C1 H1A 119.4 . . ? C6 C1 H1A 119.4 . . ? C1 C2 C3 118.73(19) . . ? C1 C2 H2A 120.6 . . ? C3 C2 H2A 120.6 . . ? C4 C3 C2 121.7(2) . . ? C4 C3 N1 119.50(19) . . ? C2 C3 N1 118.8(2) . . ? C5 C4 C3 118.83(19) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C4 C5 C6 121.3(2) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C5 C6 C1 117.9(2) . . ? C5 C6 C7 119.3(2) . . ? C1 C6 C7 122.78(19) . . ? C8 C7 C6 128.3(2) . . ? C8 C7 H7A 115.9 . . ? C6 C7 H7A 115.9 . . ? C7 C8 C9 117.4(2) . . ? C7 C8 C13 125.3(2) . . ? C9 C8 C13 117.26(19) . . ? O3 C9 C10 121.2(2) . . ? O3 C9 C8 120.7(2) . . ? C10 C9 C8 118.1(2) . . ? C9 C10 C11 115.3(2) . . ? C9 C10 H10A 108.5 . . ? C11 C10 H10A 108.5 . . ? C9 C10 H10B 108.5 . . ? C11 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C12 C11 C10 111.0(2) . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C13 111.47(19) . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C8 C13 C14 112.31(17) . . ? C8 C13 C12 109.53(18) . . ? C14 C13 C12 111.12(17) . . ? C8 C13 H13A 107.9 . . ? C14 C13 H13A 107.9 . . ? C12 C13 H13A 107.9 . . ? C15 C14 C19 116.9(2) . . ? C15 C14 C13 123.61(18) . . ? C19 C14 C13 119.5(2) . . ? C14 C15 C16 122.1(2) . . ? C14 C15 H15A 119.0 . . ? C16 C15 H15A 119.0 . . ? C17 C16 C15 119.4(2) . . ? C17 C16 H16A 120.3 . . ? C15 C16 H16A 120.3 . . ? C16 C17 C18 120.4(2) . . ? C16 C17 Cl1 120.1(2) . . ? C18 C17 Cl1 119.51(19) . . ? C17 C18 C19 119.9(2) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C14 C19 C18 121.2(2) . . ? C14 C19 H19A 119.4 . . ? C18 C19 H19A 119.4 . . ? 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 C6 C1 C2 C3 0.9(3) . . . . ? C1 C2 C3 C4 2.3(3) . . . . ? C1 C2 C3 N1 -177.83(19) . . . . ? O1 N1 C3 C4 1.5(3) . . . . ? O2 N1 C3 C4 -178.9(2) . . . . ? O1 N1 C3 C2 -178.3(2) . . . . ? O2 N1 C3 C2 1.3(3) . . . . ? C2 C3 C4 C5 -2.1(3) . . . . ? N1 C3 C4 C5 178.1(2) . . . . ? C3 C4 C5 C6 -1.4(3) . . . . ? C4 C5 C6 C1 4.4(3) . . . . ? C4 C5 C6 C7 -176.3(2) . . . . ? C2 C1 C6 C5 -4.2(3) . . . . ? C2 C1 C6 C7 176.61(19) . . . . ? C5 C6 C7 C8 141.9(2) . . . . ? C1 C6 C7 C8 -39.0(3) . . . . ? C6 C7 C8 C9 -177.04(19) . . . . ? C6 C7 C8 C13 0.0(3) . . . . ? C7 C8 C9 O3 -30.6(3) . . . . ? C13 C8 C9 O3 152.1(2) . . . . ? C7 C8 C9 C10 147.2(2) . . . . ? C13 C8 C9 C10 -30.1(3) . . . . ? O3 C9 C10 C11 -151.3(3) . . . . ? C8 C9 C10 C11 31.0(3) . . . . ? C9 C10 C11 C12 -45.9(3) . . . . ? C10 C11 C12 C13 60.6(3) . . . . ? C7 C8 C13 C14 101.4(2) . . . . ? C9 C8 C13 C14 -81.6(2) . . . . ? C7 C8 C13 C12 -134.6(2) . . . . ? C9 C8 C13 C12 42.4(2) . . . . ? C11 C12 C13 C8 -58.2(3) . . . . ? C11 C12 C13 C14 66.5(3) . . . . ? C8 C13 C14 C15 6.2(3) . . . . ? C12 C13 C14 C15 -116.9(2) . . . . ? C8 C13 C14 C19 -172.4(2) . . . . ? C12 C13 C14 C19 64.5(3) . . . . ? C19 C14 C15 C16 -2.9(3) . . . . ? C13 C14 C15 C16 178.4(2) . . . . ? C14 C15 C16 C17 -0.1(4) . . . . ? C15 C16 C17 C18 3.1(4) . . . . ? C15 C16 C17 Cl1 -179.22(18) . . . . ? C16 C17 C18 C19 -3.0(4) . . . . ? Cl1 C17 C18 C19 179.3(2) . . . . ? C15 C14 C19 C18 3.0(4) . . . . ? C13 C14 C19 C18 -178.3(2) . . . . ? C17 C18 C19 C14 -0.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.179 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.024