# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Ji-Young Shin.' ;Department of Chemistry, UBC 2036 Main Mall, Vancouver, BC V6T1Z1, Canada ; D.Dolphin ;Department of Chemistry, UBC 2036 Main Mall, Vancouver, BC V6T1Z1, Canada ; _publ_contact_author_address ;Department of Chemistry, UBC 2036 Main Mall, Vancouver, BC V6T1Z1, Canada ; _publ_contact_author_email jiyoung@chem.ubc.ca _publ_contact_author_fax 604-822-9678 _publ_contact_author_phone 604-822-3200 _publ_contact_author_name 'Ji-Young Shin' data_dd314 _database_code_depnum_ccdc_archive 'CCDC 750127' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H17 Cl4 N3 O3' _chemical_formula_weight 549.22 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5524(4) _cell_length_b 12.9084(7) _cell_length_c 13.1120(7) _cell_angle_alpha 102.326(2) _cell_angle_beta 94.333(2) _cell_angle_gamma 98.378(2) _cell_volume 1227.94(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9956 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 27.89 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.516 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.674 _exptl_absorpt_correction_T_max 0.814 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38153 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _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 2.54 _diffrn_reflns_theta_max 28.08 _reflns_number_total 5806 _reflns_number_gt 4685 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0492P)^2^+1.1165P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5806 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 C1 C 0.5489(3) 0.11082(17) 0.75959(16) 0.0304(4) Uani 1 1 d . . . C2 C 0.5013(3) -0.00649(17) 0.73961(17) 0.0304(4) Uani 1 1 d . . . C3 C 0.3916(3) -0.04158(15) 0.64958(16) 0.0274(4) Uani 1 1 d . . . C4 C 0.3668(3) 0.05018(15) 0.60672(15) 0.0253(4) Uani 1 1 d . . . C5 C 0.2768(2) 0.06036(15) 0.51632(15) 0.0244(4) Uani 1 1 d . . . C6 C 0.2693(3) 0.16006(15) 0.48478(15) 0.0243(4) Uani 1 1 d . . . C7 C 0.3467(3) 0.26602(16) 0.53288(16) 0.0295(4) Uani 1 1 d . . . H7 H 0.4184 0.2897 0.5988 0.035 Uiso 1 1 calc R . . C8 C 0.2988(3) 0.33053(16) 0.46580(17) 0.0311(4) Uani 1 1 d . . . H8 H 0.3330 0.4063 0.4777 0.037 Uiso 1 1 calc R . . C9 C 0.1923(3) 0.26437(15) 0.37864(16) 0.0270(4) Uani 1 1 d . . . C10 C 0.1037(3) 0.29268(15) 0.28973(16) 0.0275(4) Uani 1 1 d . . . C11 C -0.0034(3) 0.22111(15) 0.21024(15) 0.0266(4) Uani 1 1 d . . . C12 C -0.1057(3) 0.24480(17) 0.12108(16) 0.0318(4) Uani 1 1 d . . . H12 H -0.1094 0.3138 0.1073 0.038 Uiso 1 1 calc R . . C13 C -0.1929(3) 0.15061(18) 0.06274(17) 0.0343(5) Uani 1 1 d . . . H13 H -0.2716 0.1388 -0.0001 0.041 Uiso 1 1 calc R . . C14 C -0.1406(3) 0.06993(16) 0.11668(16) 0.0292(4) Uani 1 1 d . . . C15 C 0.1811(3) -0.03411(15) 0.44300(16) 0.0279(4) Uani 1 1 d . . . C16 C 0.1330(3) 0.40959(15) 0.28972(16) 0.0293(4) Uani 1 1 d . . . C17 C 0.0182(3) 0.47736(16) 0.33355(17) 0.0333(5) Uani 1 1 d . . . C18 C 0.0465(3) 0.58694(17) 0.33659(19) 0.0405(5) Uani 1 1 d . . . H18 H -0.0337 0.6314 0.3678 0.049 Uiso 1 1 calc R . . C19 C 0.1921(4) 0.62968(18) 0.2937(2) 0.0452(6) Uani 1 1 d . . . H19 H 0.2121 0.7043 0.2950 0.054 Uiso 1 1 calc R . . C20 C 0.3100(3) 0.56603(19) 0.24884(19) 0.0427(6) Uani 1 1 d . . . H20 H 0.4100 0.5962 0.2188 0.051 Uiso 1 1 calc R . . C21 C 0.2805(3) 0.45697(17) 0.24814(17) 0.0346(5) Uani 1 1 d . . . C22 C -0.1298(3) -0.10802(16) 0.13210(17) 0.0321(4) Uani 1 1 d . . . H22A H -0.1586 -0.0938 0.2057 0.039 Uiso 1 1 calc R . . H22B H 0.0027 -0.0992 0.1325 0.039 Uiso 1 1 calc R . . C23 C -0.2156(3) -0.22047(17) 0.07467(18) 0.0357(5) Uani 1 1 d . . . H23A H -0.1880 -0.2332 0.0008 0.043 Uiso 1 1 calc R . . H23B H -0.3480 -0.2281 0.0745 0.043 Uiso 1 1 calc R . . C24 C -0.1462(4) -0.3036(2) 0.1270(2) 0.0529(7) Uani 1 1 d . . . H24A H -0.0131 -0.2925 0.1306 0.063 Uiso 1 1 calc R . . H24B H -0.1786 -0.2920 0.1998 0.063 Uiso 1 1 calc R . . C25 C -0.2205(5) -0.4184(2) 0.0699(3) 0.0686(9) Uani 1 1 d . . . H25A H -0.3524 -0.4288 0.0617 0.103 Uiso 1 1 calc R . . H25B H -0.1800 -0.4678 0.1105 0.103 Uiso 1 1 calc R . . H25C H -0.1773 -0.4331 0.0005 0.103 Uiso 1 1 calc R . . N1 N 0.1767(2) 0.16137(13) 0.39137(13) 0.0250(3) Uani 1 1 d . . . N2 N -0.0325(2) 0.10900(13) 0.20274(13) 0.0264(3) Uani 1 1 d . . . N3 N 0.1015(3) -0.10256(15) 0.37861(16) 0.0402(4) Uani 1 1 d . . . O1 O 0.6395(2) 0.17554(13) 0.82907(12) 0.0405(4) Uani 1 1 d . . . O2 O 0.46140(19) 0.14077(11) 0.67510(11) 0.0286(3) Uani 1 1 d . . . O3 O -0.2018(2) -0.03424(11) 0.07712(12) 0.0347(3) Uani 1 1 d . . . Cl1 Cl 0.58016(8) -0.07686(5) 0.82271(5) 0.04187(15) Uani 1 1 d . . . Cl2 Cl 0.29782(7) -0.17052(4) 0.59489(5) 0.03731(14) Uani 1 1 d . . . Cl3 Cl -0.16814(8) 0.42395(4) 0.38710(6) 0.04569(16) Uani 1 1 d . . . Cl4 Cl 0.43195(9) 0.37760(5) 0.19478(5) 0.04801(16) Uani 1 1 d . . . H1N H 0.114(3) 0.1077(19) 0.3433(19) 0.026(6) Uiso 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 C1 0.0292(10) 0.0374(11) 0.0300(11) 0.0184(9) 0.0027(8) 0.0076(8) C2 0.0302(10) 0.0324(10) 0.0381(11) 0.0223(9) 0.0093(8) 0.0119(8) C3 0.0269(9) 0.0239(9) 0.0373(11) 0.0152(8) 0.0110(8) 0.0076(7) C4 0.0259(9) 0.0237(9) 0.0297(10) 0.0117(8) 0.0050(7) 0.0062(7) C5 0.0254(9) 0.0219(9) 0.0281(10) 0.0084(7) 0.0050(7) 0.0060(7) C6 0.0266(9) 0.0224(9) 0.0258(10) 0.0087(7) 0.0013(7) 0.0063(7) C7 0.0359(11) 0.0245(9) 0.0273(10) 0.0059(8) -0.0045(8) 0.0065(8) C8 0.0387(11) 0.0203(9) 0.0335(11) 0.0082(8) -0.0063(8) 0.0050(8) C9 0.0325(10) 0.0202(8) 0.0299(10) 0.0099(7) -0.0004(8) 0.0053(7) C10 0.0327(10) 0.0226(9) 0.0293(10) 0.0117(8) 0.0007(8) 0.0048(7) C11 0.0314(10) 0.0230(9) 0.0276(10) 0.0111(8) 0.0013(7) 0.0050(7) C12 0.0382(11) 0.0309(10) 0.0290(11) 0.0151(8) -0.0018(8) 0.0049(8) C13 0.0403(12) 0.0357(11) 0.0277(11) 0.0123(9) -0.0042(8) 0.0051(9) C14 0.0332(10) 0.0258(9) 0.0288(10) 0.0066(8) 0.0024(8) 0.0052(8) C15 0.0295(10) 0.0232(9) 0.0352(11) 0.0124(8) 0.0067(8) 0.0083(8) C16 0.0367(11) 0.0219(9) 0.0284(10) 0.0113(8) -0.0082(8) -0.0002(8) C17 0.0388(11) 0.0245(9) 0.0373(12) 0.0142(8) -0.0050(9) 0.0016(8) C18 0.0517(14) 0.0241(10) 0.0470(14) 0.0139(9) -0.0062(10) 0.0077(9) C19 0.0620(16) 0.0246(10) 0.0482(14) 0.0175(10) -0.0085(12) -0.0013(10) C20 0.0513(14) 0.0335(12) 0.0401(13) 0.0178(10) -0.0066(10) -0.0115(10) C21 0.0402(12) 0.0314(10) 0.0312(11) 0.0121(9) -0.0050(9) 0.0000(9) C22 0.0370(11) 0.0263(10) 0.0327(11) 0.0072(8) -0.0017(8) 0.0062(8) C23 0.0390(12) 0.0277(10) 0.0373(12) 0.0041(9) -0.0005(9) 0.0031(9) C24 0.0701(18) 0.0307(12) 0.0541(16) 0.0106(11) -0.0118(13) 0.0042(12) C25 0.101(3) 0.0289(13) 0.071(2) 0.0127(13) -0.0090(18) 0.0020(14) N1 0.0301(8) 0.0189(7) 0.0261(8) 0.0076(6) -0.0009(6) 0.0033(6) N2 0.0307(8) 0.0218(8) 0.0266(8) 0.0069(6) -0.0002(6) 0.0039(6) N3 0.0467(11) 0.0277(9) 0.0435(11) 0.0063(8) 0.0003(9) 0.0026(8) O1 0.0462(9) 0.0412(9) 0.0338(9) 0.0170(7) -0.0082(7) 0.0001(7) O2 0.0335(7) 0.0246(7) 0.0296(7) 0.0134(6) -0.0031(6) 0.0037(5) O3 0.0428(8) 0.0254(7) 0.0324(8) 0.0041(6) -0.0093(6) 0.0046(6) Cl1 0.0435(3) 0.0456(3) 0.0492(3) 0.0328(3) 0.0057(2) 0.0160(2) Cl2 0.0412(3) 0.0225(2) 0.0523(3) 0.0155(2) 0.0091(2) 0.0062(2) Cl3 0.0463(3) 0.0264(3) 0.0674(4) 0.0144(3) 0.0113(3) 0.0080(2) Cl4 0.0460(3) 0.0445(3) 0.0545(4) 0.0151(3) 0.0099(3) 0.0023(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 C1 O1 1.188(3) . ? C1 O2 1.400(2) . ? C1 C2 1.466(3) . ? C2 C3 1.341(3) . ? C2 Cl1 1.6880(19) . ? C3 C4 1.445(2) . ? C3 Cl2 1.690(2) . ? C4 C5 1.362(3) . ? C4 O2 1.376(2) . ? C5 C15 1.439(3) . ? C5 C6 1.441(2) . ? C6 N1 1.368(2) . ? C6 C7 1.398(3) . ? C7 C8 1.397(3) . ? C7 H7 0.9500 . ? C8 C9 1.388(3) . ? C8 H8 0.9500 . ? C9 N1 1.364(2) . ? C9 C10 1.440(3) . ? C10 C11 1.356(3) . ? C10 C16 1.493(3) . ? C11 N2 1.413(2) . ? C11 C12 1.463(3) . ? C12 C13 1.338(3) . ? C12 H12 0.9500 . ? C13 C14 1.460(3) . ? C13 H13 0.9500 . ? C14 N2 1.301(3) . ? C14 O3 1.333(2) . ? C15 N3 1.142(3) . ? C16 C17 1.389(3) . ? C16 C21 1.396(3) . ? C17 C18 1.391(3) . ? C17 Cl3 1.739(2) . ? C18 C19 1.370(4) . ? C18 H18 0.9500 . ? C19 C20 1.378(4) . ? C19 H19 0.9500 . ? C20 C21 1.391(3) . ? C20 H20 0.9500 . ? C21 Cl4 1.733(2) . ? C22 O3 1.452(2) . ? C22 C23 1.510(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.523(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.515(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? N1 H1N 0.88(2) . ? 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 C1 O2 121.61(19) . . ? O1 C1 C2 132.47(19) . . ? O2 C1 C2 105.92(17) . . ? C3 C2 C1 108.72(17) . . ? C3 C2 Cl1 129.52(17) . . ? C1 C2 Cl1 121.76(16) . . ? C2 C3 C4 108.19(18) . . ? C2 C3 Cl2 126.32(15) . . ? C4 C3 Cl2 125.49(16) . . ? C5 C4 O2 119.11(16) . . ? C5 C4 C3 132.92(19) . . ? O2 C4 C3 107.94(16) . . ? C4 C5 C15 119.58(17) . . ? C4 C5 C6 125.43(18) . . ? C15 C5 C6 114.98(17) . . ? N1 C6 C7 107.58(16) . . ? N1 C6 C5 120.83(17) . . ? C7 C6 C5 131.58(18) . . ? C8 C7 C6 107.12(17) . . ? C8 C7 H7 126.4 . . ? C6 C7 H7 126.4 . . ? C9 C8 C7 107.90(17) . . ? C9 C8 H8 126.0 . . ? C7 C8 H8 126.0 . . ? N1 C9 C8 107.67(17) . . ? N1 C9 C10 123.02(18) . . ? C8 C9 C10 129.28(18) . . ? C11 C10 C9 124.25(17) . . ? C11 C10 C16 120.00(17) . . ? C9 C10 C16 115.75(17) . . ? C10 C11 N2 123.33(17) . . ? C10 C11 C12 127.15(18) . . ? N2 C11 C12 109.52(17) . . ? C13 C12 C11 106.84(18) . . ? C13 C12 H12 126.6 . . ? C11 C12 H12 126.6 . . ? C12 C13 C14 105.03(18) . . ? C12 C13 H13 127.5 . . ? C14 C13 H13 127.5 . . ? N2 C14 O3 125.06(18) . . ? N2 C14 C13 114.48(18) . . ? O3 C14 C13 120.45(18) . . ? N3 C15 C5 173.3(2) . . ? C17 C16 C21 116.53(18) . . ? C17 C16 C10 121.92(19) . . ? C21 C16 C10 121.5(2) . . ? C16 C17 C18 122.5(2) . . ? C16 C17 Cl3 119.08(15) . . ? C18 C17 Cl3 118.40(19) . . ? C19 C18 C17 118.9(2) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C18 C19 C20 121.0(2) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C19 C20 C21 119.1(2) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C20 C21 C16 121.9(2) . . ? C20 C21 Cl4 119.09(19) . . ? C16 C21 Cl4 118.97(16) . . ? O3 C22 C23 107.22(17) . . ? O3 C22 H22A 110.3 . . ? C23 C22 H22A 110.3 . . ? O3 C22 H22B 110.3 . . ? C23 C22 H22B 110.3 . . ? H22A C22 H22B 108.5 . . ? C22 C23 C24 110.72(19) . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C25 C24 C23 113.3(2) . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24B 108.9 . . ? C23 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C9 N1 C6 109.73(16) . . ? C9 N1 H1N 120.8(15) . . ? C6 N1 H1N 129.5(15) . . ? C14 N2 C11 104.11(16) . . ? C4 O2 C1 109.21(15) . . ? C14 O3 C22 115.93(16) . . ? 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 O1 C1 C2 C3 179.1(2) . . . . ? O2 C1 C2 C3 -0.6(2) . . . . ? O1 C1 C2 Cl1 -0.7(4) . . . . ? O2 C1 C2 Cl1 179.57(14) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? Cl1 C2 C3 C4 -178.97(16) . . . . ? C1 C2 C3 Cl2 -178.82(15) . . . . ? Cl1 C2 C3 Cl2 1.0(3) . . . . ? C2 C3 C4 C5 176.8(2) . . . . ? Cl2 C3 C4 C5 -3.2(3) . . . . ? C2 C3 C4 O2 -1.4(2) . . . . ? Cl2 C3 C4 O2 178.62(14) . . . . ? O2 C4 C5 C15 178.47(17) . . . . ? C3 C4 C5 C15 0.5(3) . . . . ? O2 C4 C5 C6 -0.7(3) . . . . ? C3 C4 C5 C6 -178.7(2) . . . . ? C4 C5 C6 N1 179.13(19) . . . . ? C15 C5 C6 N1 -0.1(3) . . . . ? C4 C5 C6 C7 0.7(3) . . . . ? C15 C5 C6 C7 -178.5(2) . . . . ? N1 C6 C7 C8 -0.2(2) . . . . ? C5 C6 C7 C8 178.3(2) . . . . ? C6 C7 C8 C9 0.5(2) . . . . ? C7 C8 C9 N1 -0.6(2) . . . . ? C7 C8 C9 C10 177.2(2) . . . . ? N1 C9 C10 C11 0.1(3) . . . . ? C8 C9 C10 C11 -177.4(2) . . . . ? N1 C9 C10 C16 178.86(19) . . . . ? C8 C9 C10 C16 1.3(3) . . . . ? C9 C10 C11 N2 -3.6(3) . . . . ? C16 C10 C11 N2 177.67(19) . . . . ? C9 C10 C11 C12 176.1(2) . . . . ? C16 C10 C11 C12 -2.6(3) . . . . ? C10 C11 C12 C13 -179.6(2) . . . . ? N2 C11 C12 C13 0.2(2) . . . . ? C11 C12 C13 C14 -0.7(2) . . . . ? C12 C13 C14 N2 1.1(3) . . . . ? C12 C13 C14 O3 -178.5(2) . . . . ? C4 C5 C15 N3 -176.7(18) . . . . ? C6 C5 C15 N3 3(2) . . . . ? C11 C10 C16 C17 87.8(3) . . . . ? C9 C10 C16 C17 -91.0(2) . . . . ? C11 C10 C16 C21 -94.0(2) . . . . ? C9 C10 C16 C21 87.1(2) . . . . ? C21 C16 C17 C18 0.0(3) . . . . ? C10 C16 C17 C18 178.2(2) . . . . ? C21 C16 C17 Cl3 -179.87(15) . . . . ? C10 C16 C17 Cl3 -1.6(3) . . . . ? C16 C17 C18 C19 0.7(3) . . . . ? Cl3 C17 C18 C19 -179.40(18) . . . . ? C17 C18 C19 C20 -0.5(4) . . . . ? C18 C19 C20 C21 -0.5(4) . . . . ? C19 C20 C21 C16 1.3(3) . . . . ? C19 C20 C21 Cl4 -178.33(18) . . . . ? C17 C16 C21 C20 -1.0(3) . . . . ? C10 C16 C21 C20 -179.26(19) . . . . ? C17 C16 C21 Cl4 178.60(15) . . . . ? C10 C16 C21 Cl4 0.4(3) . . . . ? O3 C22 C23 C24 179.6(2) . . . . ? C22 C23 C24 C25 -177.2(3) . . . . ? C8 C9 N1 C6 0.5(2) . . . . ? C10 C9 N1 C6 -177.50(19) . . . . ? C7 C6 N1 C9 -0.1(2) . . . . ? C5 C6 N1 C9 -178.91(17) . . . . ? O3 C14 N2 C11 178.6(2) . . . . ? C13 C14 N2 C11 -1.0(2) . . . . ? C10 C11 N2 C14 -179.7(2) . . . . ? C12 C11 N2 C14 0.5(2) . . . . ? C5 C4 O2 C1 -177.42(17) . . . . ? C3 C4 O2 C1 1.0(2) . . . . ? O1 C1 O2 C4 180.0(2) . . . . ? C2 C1 O2 C4 -0.3(2) . . . . ? N2 C14 O3 C22 -4.5(3) . . . . ? C13 C14 O3 C22 175.02(19) . . . . ? C23 C22 O3 C14 -179.83(18) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.08 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.514 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.063 #===End data_dd315 _database_code_depnum_ccdc_archive 'CCDC 750128' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H8 Cl2 F5 N3 O3' _chemical_formula_weight 528.21 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' F F 0.0171 0.0103 '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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0689(13) _cell_length_b 9.6348(19) _cell_length_c 16.074(3) _cell_angle_alpha 94.959(7) _cell_angle_beta 95.467(7) _cell_angle_gamma 106.429(7) _cell_volume 1037.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9860 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 27.87 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.391 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.890 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20249 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.99 _reflns_number_total 4938 _reflns_number_gt 4046 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0547P)^2^+0.5607P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4938 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 C1 C 0.9420(2) 0.72487(18) 0.49315(11) 0.0286(4) Uani 1 1 d . . . C2 C 0.9766(2) 0.74151(19) 0.58501(11) 0.0284(4) Uani 1 1 d . . . C3 C 0.8760(2) 0.61764(19) 0.61277(11) 0.0270(3) Uani 1 1 d . . . C4 C 0.7706(2) 0.51568(18) 0.54013(10) 0.0241(3) Uani 1 1 d . . . C5 C 0.6478(2) 0.37712(18) 0.53280(10) 0.0235(3) Uani 1 1 d . . . C6 C 0.5496(2) 0.28341(17) 0.45682(10) 0.0218(3) Uani 1 1 d . . . C7 C 0.4245(2) 0.14109(17) 0.45228(10) 0.0243(3) Uani 1 1 d . . . H7 H 0.3855 0.0898 0.4987 0.029 Uiso 1 1 calc R . . C8 C 0.3673(2) 0.08797(17) 0.36752(10) 0.0233(3) Uani 1 1 d . . . H8 H 0.2824 -0.0062 0.3458 0.028 Uiso 1 1 calc R . . C9 C 0.4564(2) 0.19732(16) 0.32022(10) 0.0211(3) Uani 1 1 d . . . C10 C 0.4474(2) 0.19344(16) 0.23034(10) 0.0226(3) Uani 1 1 d . . . C11 C 0.5353(2) 0.30790(17) 0.18906(10) 0.0241(3) Uani 1 1 d . . . C12 C 0.5331(3) 0.30855(19) 0.09821(11) 0.0315(4) Uani 1 1 d . . . H12 H 0.4681 0.2296 0.0561 0.038 Uiso 1 1 calc R . . C13 C 0.6408(3) 0.4421(2) 0.08585(11) 0.0346(4) Uani 1 1 d . . . H13 H 0.6684 0.4777 0.0337 0.042 Uiso 1 1 calc R . . C14 C 0.7066(2) 0.52127(18) 0.17037(11) 0.0275(3) Uani 1 1 d . . . C15 C 0.6094(3) 0.30898(19) 0.60877(11) 0.0280(3) Uani 1 1 d . . . C16 C 0.3351(2) 0.05187(17) 0.17903(10) 0.0242(3) Uani 1 1 d . . . C17 C 0.4198(2) -0.06083(18) 0.16773(10) 0.0276(3) Uani 1 1 d . . . C18 C 0.3204(3) -0.19099(19) 0.11857(12) 0.0329(4) Uani 1 1 d . . . C19 C 0.1332(3) -0.20936(19) 0.07779(11) 0.0326(4) Uani 1 1 d . . . C20 C 0.0449(3) -0.10020(19) 0.08756(11) 0.0313(4) Uani 1 1 d . . . C21 C 0.1449(2) 0.02844(18) 0.13780(11) 0.0277(3) Uani 1 1 d . . . C22 C 0.8795(3) 0.72639(19) 0.26544(11) 0.0319(4) Uani 1 1 d . . . H22A H 0.7612 0.7239 0.2932 0.048 Uiso 1 1 calc R . . H22B H 0.9594 0.8278 0.2657 0.048 Uiso 1 1 calc R . . H22C H 0.9586 0.6735 0.2957 0.048 Uiso 1 1 calc R . . N1 N 0.56576(19) 0.31617(14) 0.37559(8) 0.0210(3) Uani 1 1 d . . . N2 N 0.64657(19) 0.44540(14) 0.23102(8) 0.0240(3) Uani 1 1 d . . . N3 N 0.5750(3) 0.24841(19) 0.66591(10) 0.0415(4) Uani 1 1 d . . . O1 O 1.0023(2) 0.80485(14) 0.44303(9) 0.0377(3) Uani 1 1 d . . . O2 O 0.81293(16) 0.58260(12) 0.46869(7) 0.0259(2) Uani 1 1 d . . . O3 O 0.81942(19) 0.65846(13) 0.17960(8) 0.0339(3) Uani 1 1 d . . . F1 F 0.60499(15) -0.04389(12) 0.20325(7) 0.0369(3) Uani 1 1 d . . . F2 F 0.40653(19) -0.29783(12) 0.11006(8) 0.0482(3) Uani 1 1 d . . . F3 F 0.03732(18) -0.33390(12) 0.02934(7) 0.0463(3) Uani 1 1 d . . . F4 F -0.13774(16) -0.11794(13) 0.04828(7) 0.0437(3) Uani 1 1 d . . . F5 F 0.05501(16) 0.13304(12) 0.14489(8) 0.0404(3) Uani 1 1 d . . . Cl1 Cl 1.12321(6) 0.89762(5) 0.64061(3) 0.03749(13) Uani 1 1 d . . . Cl2 Cl 0.87251(7) 0.58722(5) 0.71475(3) 0.03762(13) Uani 1 1 d . . . H1N H 0.629(3) 0.395(3) 0.3599(14) 0.040(6) Uiso 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 C1 0.0235(7) 0.0244(8) 0.0343(9) -0.0074(7) -0.0009(7) 0.0060(6) C2 0.0222(7) 0.0284(8) 0.0320(9) -0.0101(7) -0.0043(6) 0.0100(6) C3 0.0248(7) 0.0307(9) 0.0262(8) -0.0069(7) -0.0040(6) 0.0147(7) C4 0.0225(7) 0.0275(8) 0.0232(8) -0.0031(6) -0.0010(6) 0.0118(6) C5 0.0238(7) 0.0269(8) 0.0219(8) -0.0005(6) 0.0006(6) 0.0125(6) C6 0.0210(7) 0.0213(7) 0.0236(8) 0.0002(6) 0.0015(6) 0.0084(6) C7 0.0248(7) 0.0238(8) 0.0253(8) 0.0036(6) 0.0043(6) 0.0079(6) C8 0.0214(7) 0.0196(7) 0.0270(8) 0.0000(6) 0.0016(6) 0.0044(6) C9 0.0191(7) 0.0177(7) 0.0243(8) -0.0023(6) -0.0007(6) 0.0044(5) C10 0.0201(7) 0.0197(7) 0.0249(8) -0.0027(6) -0.0011(6) 0.0035(6) C11 0.0227(7) 0.0218(7) 0.0233(8) -0.0021(6) 0.0002(6) 0.0019(6) C12 0.0335(9) 0.0303(9) 0.0222(8) -0.0020(7) 0.0000(7) -0.0015(7) C13 0.0384(9) 0.0338(9) 0.0230(8) 0.0018(7) 0.0022(7) -0.0021(7) C14 0.0262(8) 0.0237(8) 0.0272(8) 0.0007(6) 0.0020(6) -0.0004(6) C15 0.0309(8) 0.0288(8) 0.0258(8) -0.0017(7) 0.0017(6) 0.0131(7) C16 0.0274(8) 0.0204(7) 0.0194(7) -0.0008(6) 0.0011(6) -0.0002(6) C17 0.0286(8) 0.0265(8) 0.0229(8) -0.0021(6) 0.0004(6) 0.0029(6) C18 0.0421(10) 0.0224(8) 0.0304(9) -0.0044(7) 0.0068(7) 0.0050(7) C19 0.0379(9) 0.0248(8) 0.0231(8) -0.0064(7) 0.0029(7) -0.0068(7) C20 0.0278(8) 0.0317(9) 0.0241(8) 0.0009(7) -0.0024(6) -0.0052(7) C21 0.0282(8) 0.0233(8) 0.0269(8) 0.0020(6) 0.0009(6) 0.0010(6) C22 0.0352(9) 0.0226(8) 0.0301(9) -0.0041(7) 0.0027(7) -0.0014(7) N1 0.0213(6) 0.0173(6) 0.0219(7) -0.0010(5) 0.0006(5) 0.0032(5) N2 0.0241(6) 0.0199(6) 0.0233(7) -0.0010(5) 0.0010(5) 0.0007(5) N3 0.0554(10) 0.0421(9) 0.0299(9) 0.0047(7) 0.0076(7) 0.0180(8) O1 0.0397(7) 0.0275(7) 0.0377(7) -0.0018(6) 0.0039(6) -0.0011(5) O2 0.0261(5) 0.0225(6) 0.0250(6) -0.0043(4) 0.0003(4) 0.0035(4) O3 0.0400(7) 0.0240(6) 0.0278(6) 0.0013(5) 0.0044(5) -0.0060(5) F1 0.0325(5) 0.0349(6) 0.0399(6) -0.0078(5) -0.0055(4) 0.0111(4) F2 0.0584(7) 0.0309(6) 0.0525(7) -0.0145(5) 0.0007(6) 0.0162(5) F3 0.0491(7) 0.0327(6) 0.0388(6) -0.0174(5) 0.0024(5) -0.0101(5) F4 0.0311(5) 0.0452(7) 0.0403(6) -0.0017(5) -0.0120(5) -0.0047(5) F5 0.0329(5) 0.0339(6) 0.0497(7) -0.0035(5) -0.0084(5) 0.0090(4) Cl1 0.0289(2) 0.0318(2) 0.0442(3) -0.01707(19) -0.00828(18) 0.00730(17) Cl2 0.0478(3) 0.0409(3) 0.0241(2) -0.00556(18) -0.00674(18) 0.0194(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 C1 O1 1.188(2) . ? C1 O2 1.4132(19) . ? C1 C2 1.461(3) . ? C2 C3 1.342(3) . ? C2 Cl1 1.6865(17) . ? C3 C4 1.451(2) . ? C3 Cl2 1.6913(18) . ? C4 C5 1.359(2) . ? C4 O2 1.381(2) . ? C5 C6 1.443(2) . ? C5 C15 1.448(2) . ? C6 N1 1.377(2) . ? C6 C7 1.397(2) . ? C7 C8 1.393(2) . ? C7 H7 0.9500 . ? C8 C9 1.393(2) . ? C8 H8 0.9500 . ? C9 N1 1.3758(19) . ? C9 C10 1.437(2) . ? C10 C11 1.364(2) . ? C10 C16 1.496(2) . ? C11 N2 1.4083(19) . ? C11 C12 1.460(2) . ? C12 C13 1.340(3) . ? C12 H12 0.9500 . ? C13 C14 1.464(2) . ? C13 H13 0.9500 . ? C14 N2 1.300(2) . ? C14 O3 1.324(2) . ? C15 N3 1.139(2) . ? C16 C17 1.387(2) . ? C16 C21 1.390(2) . ? C17 F1 1.337(2) . ? C17 C18 1.384(2) . ? C18 F2 1.340(2) . ? C18 C19 1.377(3) . ? C19 F3 1.3354(18) . ? C19 C20 1.372(3) . ? C20 F4 1.340(2) . ? C20 C21 1.382(2) . ? C21 F5 1.337(2) . ? C22 O3 1.445(2) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N1 H1N 0.84(2) . ? 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 C1 O2 121.92(16) . . ? O1 C1 C2 132.07(16) . . ? O2 C1 C2 106.01(14) . . ? C3 C2 C1 109.18(15) . . ? C3 C2 Cl1 129.19(14) . . ? C1 C2 Cl1 121.63(14) . . ? C2 C3 C4 108.02(15) . . ? C2 C3 Cl2 125.68(13) . . ? C4 C3 Cl2 126.30(14) . . ? C5 C4 O2 119.75(14) . . ? C5 C4 C3 132.16(16) . . ? O2 C4 C3 108.09(14) . . ? C4 C5 C6 128.07(15) . . ? C4 C5 C15 118.43(15) . . ? C6 C5 C15 113.49(14) . . ? N1 C6 C7 107.47(13) . . ? N1 C6 C5 126.41(14) . . ? C7 C6 C5 126.10(15) . . ? C8 C7 C6 107.70(14) . . ? C8 C7 H7 126.2 . . ? C6 C7 H7 126.2 . . ? C7 C8 C9 107.92(14) . . ? C7 C8 H8 126.0 . . ? C9 C8 H8 126.0 . . ? N1 C9 C8 107.59(14) . . ? N1 C9 C10 123.52(14) . . ? C8 C9 C10 128.87(14) . . ? C11 C10 C9 124.90(14) . . ? C11 C10 C16 118.19(14) . . ? C9 C10 C16 116.90(13) . . ? C10 C11 N2 122.98(14) . . ? C10 C11 C12 126.90(14) . . ? N2 C11 C12 110.12(14) . . ? C13 C12 C11 106.61(15) . . ? C13 C12 H12 126.7 . . ? C11 C12 H12 126.7 . . ? C12 C13 C14 104.90(15) . . ? C12 C13 H13 127.6 . . ? C14 C13 H13 127.6 . . ? N2 C14 O3 125.78(15) . . ? N2 C14 C13 114.54(15) . . ? O3 C14 C13 119.68(15) . . ? N3 C15 C5 176.33(19) . . ? C17 C16 C21 116.67(14) . . ? C17 C16 C10 121.27(14) . . ? C21 C16 C10 122.02(15) . . ? F1 C17 C18 118.00(16) . . ? F1 C17 C16 119.86(14) . . ? C18 C17 C16 122.12(16) . . ? F2 C18 C19 120.23(15) . . ? F2 C18 C17 120.28(17) . . ? C19 C18 C17 119.50(17) . . ? F3 C19 C20 120.18(17) . . ? F3 C19 C18 119.88(17) . . ? C20 C19 C18 119.93(15) . . ? F4 C20 C19 120.11(15) . . ? F4 C20 C21 120.00(17) . . ? C19 C20 C21 119.89(16) . . ? F5 C21 C20 118.14(15) . . ? F5 C21 C16 119.97(14) . . ? C20 C21 C16 121.88(17) . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C9 N1 C6 109.32(13) . . ? C9 N1 H1N 122.9(16) . . ? C6 N1 H1N 127.8(16) . . ? C14 N2 C11 103.83(13) . . ? C4 O2 C1 108.70(12) . . ? C14 O3 C22 115.56(13) . . ? 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 O1 C1 C2 C3 -178.94(19) . . . . ? O2 C1 C2 C3 0.31(18) . . . . ? O1 C1 C2 Cl1 1.1(3) . . . . ? O2 C1 C2 Cl1 -179.63(11) . . . . ? C1 C2 C3 C4 -0.44(18) . . . . ? Cl1 C2 C3 C4 179.49(13) . . . . ? C1 C2 C3 Cl2 179.95(12) . . . . ? Cl1 C2 C3 Cl2 -0.1(2) . . . . ? C2 C3 C4 C5 -179.60(17) . . . . ? Cl2 C3 C4 C5 0.0(3) . . . . ? C2 C3 C4 O2 0.42(18) . . . . ? Cl2 C3 C4 O2 -179.98(11) . . . . ? O2 C4 C5 C6 0.2(2) . . . . ? C3 C4 C5 C6 -179.74(16) . . . . ? O2 C4 C5 C15 178.82(13) . . . . ? C3 C4 C5 C15 -1.2(3) . . . . ? C4 C5 C6 N1 1.7(3) . . . . ? C15 C5 C6 N1 -176.92(14) . . . . ? C4 C5 C6 C7 179.89(16) . . . . ? C15 C5 C6 C7 1.3(2) . . . . ? N1 C6 C7 C8 0.62(18) . . . . ? C5 C6 C7 C8 -177.83(15) . . . . ? C6 C7 C8 C9 -0.14(18) . . . . ? C7 C8 C9 N1 -0.39(17) . . . . ? C7 C8 C9 C10 177.98(15) . . . . ? N1 C9 C10 C11 -3.9(2) . . . . ? C8 C9 C10 C11 177.98(16) . . . . ? N1 C9 C10 C16 175.17(14) . . . . ? C8 C9 C10 C16 -3.0(2) . . . . ? C9 C10 C11 N2 -0.2(3) . . . . ? C16 C10 C11 N2 -179.19(14) . . . . ? C9 C10 C11 C12 178.89(16) . . . . ? C16 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C13 -178.80(17) . . . . ? N2 C11 C12 C13 0.3(2) . . . . ? C11 C12 C13 C14 -0.2(2) . . . . ? C12 C13 C14 N2 0.0(2) . . . . ? C12 C13 C14 O3 179.41(17) . . . . ? C4 C5 C15 N3 -166(3) . . . . ? C6 C5 C15 N3 13(3) . . . . ? C11 C10 C16 C17 99.42(19) . . . . ? C9 C10 C16 C17 -79.7(2) . . . . ? C11 C10 C16 C21 -78.0(2) . . . . ? C9 C10 C16 C21 102.83(18) . . . . ? C21 C16 C17 F1 177.75(15) . . . . ? C10 C16 C17 F1 0.2(2) . . . . ? C21 C16 C17 C18 -0.5(2) . . . . ? C10 C16 C17 C18 -178.13(16) . . . . ? F1 C17 C18 F2 2.5(3) . . . . ? C16 C17 C18 F2 -179.20(16) . . . . ? F1 C17 C18 C19 -176.89(16) . . . . ? C16 C17 C18 C19 1.4(3) . . . . ? F2 C18 C19 F3 -0.3(3) . . . . ? C17 C18 C19 F3 179.12(16) . . . . ? F2 C18 C19 C20 179.22(16) . . . . ? C17 C18 C19 C20 -1.4(3) . . . . ? F3 C19 C20 F4 -0.2(3) . . . . ? C18 C19 C20 F4 -179.70(16) . . . . ? F3 C19 C20 C21 -179.99(15) . . . . ? C18 C19 C20 C21 0.5(3) . . . . ? F4 C20 C21 F5 -0.6(2) . . . . ? C19 C20 C21 F5 179.13(15) . . . . ? F4 C20 C21 C16 -179.40(15) . . . . ? C19 C20 C21 C16 0.4(3) . . . . ? C17 C16 C21 F5 -179.11(15) . . . . ? C10 C16 C21 F5 -1.5(2) . . . . ? C17 C16 C21 C20 -0.4(2) . . . . ? C10 C16 C21 C20 177.21(15) . . . . ? C8 C9 N1 C6 0.79(17) . . . . ? C10 C9 N1 C6 -177.69(14) . . . . ? C7 C6 N1 C9 -0.88(17) . . . . ? C5 C6 N1 C9 177.57(14) . . . . ? O3 C14 N2 C11 -179.16(17) . . . . ? C13 C14 N2 C11 0.2(2) . . . . ? C10 C11 N2 C14 178.84(16) . . . . ? C12 C11 N2 C14 -0.34(18) . . . . ? C5 C4 O2 C1 179.80(14) . . . . ? C3 C4 O2 C1 -0.22(16) . . . . ? O1 C1 O2 C4 179.30(16) . . . . ? C2 C1 O2 C4 -0.04(16) . . . . ? N2 C14 O3 C22 0.4(3) . . . . ? C13 C14 O3 C22 -178.98(16) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.406 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.052 #===End