# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 188/182 data_sag1 _audit_creation_method SHELXL-97 #------------------------------------------------------------------------------ _publ_requested_journal ' J. Chem. Soc. Perkin Transactions 2' _publ_contact_author ; Prof S.A.Glover Division of Chemistry, School of Physical Sciences and Engineering, University of New England, Armidale, 2351 ; _publ_contact_author_phone ' 61 02 67732361 ' _publ_contact_author_fax ' 61 02 37733268 ' _publ_contact_author_email ' sglover@metz.une.edu.au ' loop_ _publ_author_name _publ_author_address ' Stephen A Glover ' ; FIRST AUTHORS ADDRESS Division of Chemistry, School of Physical Sciences and Engineering, University of New England, Armidale, 2351 ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Sheldrick, G. M. SHELXL97: Program for Structure Refinement; University of Gottingen, Germany, 1997. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1993). J. Appl. Cryst., 26, 343. ; _chemical_name_systematic ; N,N'-di-(p-chlorobenzoyl)-N,N'-diethoxyhydrazine ; _chemical_name_common ? _chemical_melting_point '100-101 C ex Methanol' _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Cl2 N2 O4' _chemical_formula_weight 397.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 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' 'Cl' 'Cl' 0.3639 0.7018 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 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 8.1227(5) _cell_length_b 10.1880(10) _cell_length_c 22.116(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.450(6) _cell_angle_gamma 90.00 _cell_volume 1829.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 193.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 19.64 _cell_measurement_theta_max 28.95 _exptl_crystal_description 'cut prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.375 _exptl_crystal_size_mid 0.325 _exptl_crystal_size_min 0.225 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 3.426 _exptl_absorpt_correction_type 'psi scan' _exptl_absorpt_correction_T_min 0.61 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_special_details ; The scan width was (1.47+0.35tan\q)\% with an \w scan speed of 16\% per minute (up to 11 scans to achieve I/\s(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; _diffrn_ambient_temperature 193.2 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.77 _diffrn_reflns_number 3029 _diffrn_reflns_av_R_equivalents 0.0913 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.00 _diffrn_reflns_theta_max 65.08 _reflns_number_total 2644 _reflns_number_gt 2470 _reflns_threshold_expression >2sigma(I) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'teXsan (MSC, 1995)' #------------------------------------------------------------------------------ _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^)+(0.1213P)^2^+0.8254P] 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 refined _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0022(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2644 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1540 _refine_ls_wR_factor_gt 0.1513 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.53159(7) -0.15020(7) 0.54231(3) 0.0324(3) Uani 1 1 d . . . Cl2 Cl -0.13427(9) 0.68776(7) 0.47575(3) 0.0395(3) Uani 1 1 d . . . O1 O -0.1897(2) 0.09989(19) 0.61816(8) 0.0300(5) Uani 1 1 d . . . O2 O 0.0718(2) 0.20966(16) 0.73267(7) 0.0220(4) Uani 1 1 d . . . O3 O -0.2603(2) 0.15924(17) 0.74842(8) 0.0247(5) Uani 1 1 d . . . O4 O -0.4610(2) 0.29608(19) 0.67941(9) 0.0319(5) Uani 1 1 d . . . N1 N -0.0489(2) 0.2214(2) 0.68651(9) 0.0201(5) Uani 1 1 d . . . N2 N -0.1971(2) 0.2590(2) 0.71129(9) 0.0210(5) Uani 1 1 d . . . C1 C -0.0568(3) 0.1210(2) 0.64249(11) 0.0212(6) Uani 1 1 d . . . C2 C 0.0973(3) 0.0571(2) 0.62175(11) 0.0214(5) Uani 1 1 d . . . C3 C 0.0734(3) -0.0421(3) 0.57896(11) 0.0245(6) Uani 1 1 d . . . C4 C 0.2066(3) -0.1063(3) 0.55424(13) 0.0285(6) Uani 1 1 d . . . C5 C 0.3635(3) -0.0694(3) 0.57225(11) 0.0254(6) Uani 1 1 d . . . C6 C 0.3913(3) 0.0297(3) 0.61383(12) 0.0253(6) Uani 1 1 d . . . C7 C 0.2576(3) 0.0928(3) 0.63847(12) 0.0257(6) Uani 1 1 d . . . C8 C -0.3164(3) 0.3135(2) 0.67125(12) 0.0229(6) Uani 1 1 d . . . C9 C -0.2560(3) 0.4030(2) 0.62318(11) 0.0224(6) Uani 1 1 d . . . C10 C -0.3314(3) 0.3925(3) 0.56668(13) 0.0294(6) Uani 1 1 d . . . C11 C -0.2909(3) 0.4776(3) 0.52065(13) 0.0327(7) Uani 1 1 d . . . C12 C -0.1777(3) 0.5751(3) 0.53219(12) 0.0274(6) Uani 1 1 d . . . C13 C -0.1012(3) 0.5884(3) 0.58828(13) 0.0307(7) Uani 1 1 d . . . C14 C -0.1405(3) 0.5008(3) 0.63378(13) 0.0287(6) Uani 1 1 d . . . C15 C 0.1462(3) 0.3372(3) 0.74376(14) 0.0277(6) Uani 1 1 d . . . C16 C 0.2712(4) 0.3201(3) 0.79390(15) 0.0381(8) Uani 1 1 d . . . C17 C -0.2828(3) 0.2123(3) 0.80784(12) 0.0285(6) Uani 1 1 d . . . C18 C -0.3577(5) 0.1066(3) 0.84553(16) 0.0412(8) Uani 1 1 d . . . H3 H -0.034(4) -0.059(3) 0.5657(13) 0.033(8) Uiso 1 1 d . . . H4 H 0.187(4) -0.168(4) 0.5248(15) 0.040(9) Uiso 1 1 d . . . H6 H 0.499(3) 0.058(3) 0.6249(12) 0.025(7) Uiso 1 1 d . . . H7 H 0.282(4) 0.159(3) 0.6663(13) 0.024(7) Uiso 1 1 d . . . H10 H -0.403(4) 0.324(3) 0.5609(13) 0.027(7) Uiso 1 1 d . . . H11 H -0.333(4) 0.467(3) 0.4808(16) 0.047(9) Uiso 1 1 d . . . H13 H -0.031(4) 0.658(3) 0.5949(13) 0.030(8) Uiso 1 1 d . . . H14 H -0.092(4) 0.510(3) 0.6703(14) 0.031(8) Uiso 1 1 d . . . H15A H 0.064(4) 0.398(3) 0.7550(13) 0.028(7) Uiso 1 1 d . . . H15B H 0.190(5) 0.365(4) 0.7050(18) 0.055(11) Uiso 1 1 d . . . H16A H 0.223(4) 0.290(4) 0.8298(18) 0.048(10) Uiso 1 1 d . . . H16B H 0.324(4) 0.413(4) 0.7998(15) 0.046(9) Uiso 1 1 d . . . H16C H 0.358(5) 0.252(4) 0.7838(19) 0.063(12) Uiso 1 1 d . . . H17A H -0.349(4) 0.290(4) 0.8001(16) 0.044(9) Uiso 1 1 d . . . H17B H -0.177(4) 0.242(3) 0.8267(16) 0.037(8) Uiso 1 1 d . . . H18A H -0.450(4) 0.075(3) 0.8265(15) 0.039(9) Uiso 1 1 d . . . H18B H -0.392(5) 0.144(4) 0.883(2) 0.063(12) Uiso 1 1 d . . . H18C H -0.273(5) 0.042(4) 0.8538(17) 0.059(11) 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 Cl1 0.0314(4) 0.0291(5) 0.0369(5) -0.0044(3) 0.0059(3) 0.0063(2) Cl2 0.0492(5) 0.0362(5) 0.0333(5) 0.0134(3) 0.0047(3) 0.0076(3) O1 0.0239(9) 0.0324(11) 0.0333(11) -0.0096(8) -0.0042(7) -0.0018(7) O2 0.0268(8) 0.0182(10) 0.0207(10) 0.0020(7) -0.0047(7) -0.0010(7) O3 0.0341(9) 0.0185(10) 0.0218(10) 0.0008(7) 0.0050(7) -0.0033(7) O4 0.0232(9) 0.0321(11) 0.0403(12) 0.0022(8) -0.0003(8) -0.0023(7) N1 0.0204(9) 0.0210(11) 0.0189(11) -0.0006(8) -0.0003(8) 0.0006(8) N2 0.0252(10) 0.0162(11) 0.0217(11) 0.0011(8) 0.0032(8) -0.0004(8) C1 0.0244(11) 0.0172(13) 0.0219(14) 0.0028(10) 0.0002(10) -0.0023(9) C2 0.0263(12) 0.0156(12) 0.0223(13) 0.0038(10) -0.0008(9) -0.0002(10) C3 0.0258(12) 0.0222(14) 0.0254(14) 0.0002(10) -0.0026(10) -0.0014(10) C4 0.0334(13) 0.0259(15) 0.0261(15) -0.0064(11) -0.0016(11) 0.0000(11) C5 0.0286(12) 0.0219(14) 0.0258(15) 0.0025(11) 0.0038(10) 0.0050(10) C6 0.0243(12) 0.0227(14) 0.0290(14) 0.0007(11) 0.0005(10) 0.0000(10) C7 0.0286(12) 0.0210(14) 0.0273(15) -0.0042(11) -0.0009(11) -0.0022(10) C8 0.0264(12) 0.0174(13) 0.0247(14) -0.0062(10) -0.0025(10) 0.0014(10) C9 0.0249(11) 0.0173(13) 0.0250(14) -0.0027(10) -0.0014(10) 0.0039(9) C10 0.0304(12) 0.0278(15) 0.0296(15) -0.0028(12) -0.0050(11) -0.0040(11) C11 0.0374(14) 0.0369(17) 0.0236(15) -0.0022(12) -0.0075(11) 0.0045(12) C12 0.0323(12) 0.0232(15) 0.0267(15) 0.0041(11) 0.0033(11) 0.0108(11) C13 0.0355(13) 0.0225(15) 0.0337(16) 0.0022(12) -0.0063(12) -0.0043(11) C14 0.0351(13) 0.0235(14) 0.0268(15) -0.0012(11) -0.0111(11) -0.0009(11) C15 0.0325(13) 0.0201(14) 0.0303(16) -0.0042(11) -0.0054(12) -0.0036(11) C16 0.0411(16) 0.0343(18) 0.038(2) -0.0048(14) -0.0132(14) -0.0030(14) C17 0.0370(14) 0.0259(15) 0.0228(15) -0.0029(11) 0.0015(11) 0.0006(12) C18 0.0592(19) 0.0326(18) 0.0325(18) 0.0023(14) 0.0124(16) 0.0024(16) _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 C5 1.739(2) . ? Cl2 C12 1.738(3) . ? O1 C1 1.213(3) . ? O2 N1 1.403(2) . ? O2 C15 1.451(3) . ? O3 N2 1.411(3) . ? O3 C17 1.437(3) . ? O4 C8 1.207(3) . ? N1 N2 1.389(3) . ? N1 C1 1.412(3) . ? N2 C8 1.410(3) . ? C1 C2 1.494(3) . ? C2 C7 1.393(3) . ? C2 C3 1.395(3) . ? C3 C4 1.388(4) . ? C3 H3 0.93(3) . ? C4 C5 1.378(4) . ? C4 H4 0.91(4) . ? C5 C6 1.381(4) . ? C6 C7 1.385(4) . ? C6 H6 0.95(3) . ? C7 H7 0.93(3) . ? C8 C9 1.493(4) . ? C9 C10 1.382(4) . ? C9 C14 1.384(4) . ? C10 C11 1.383(4) . ? C10 H10 0.92(3) . ? C11 C12 1.374(4) . ? C11 H11 0.94(3) . ? C12 C13 1.380(4) . ? C13 C14 1.388(4) . ? C13 H13 0.92(3) . ? C14 H14 0.89(3) . ? C15 C16 1.495(4) . ? C15 H15A 0.95(3) . ? C15 H15B 0.98(4) . ? C16 H16A 0.95(4) . ? C16 H16B 1.05(4) . ? C16 H16C 1.02(5) . ? C17 C18 1.500(4) . ? C17 H17A 0.97(4) . ? C17 H17B 0.99(3) . ? C18 H18A 0.90(3) . ? C18 H18B 0.95(5) . ? C18 H18C 0.97(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 O2 C15 109.11(17) . . ? N2 O3 C17 108.52(18) . . ? N2 N1 O2 109.47(17) . . ? N2 N1 C1 116.57(18) . . ? O2 N1 C1 117.32(18) . . ? N1 N2 C8 116.71(19) . . ? N1 N2 O3 111.23(17) . . ? C8 N2 O3 113.25(19) . . ? O1 C1 N1 117.3(2) . . ? O1 C1 C2 122.0(2) . . ? N1 C1 C2 120.25(19) . . ? C7 C2 C3 118.8(2) . . ? C7 C2 C1 126.1(2) . . ? C3 C2 C1 114.9(2) . . ? C4 C3 C2 120.8(2) . . ? C4 C3 H3 121.6(19) . . ? C2 C3 H3 117.4(19) . . ? C5 C4 C3 118.8(3) . . ? C5 C4 H4 122(2) . . ? C3 C4 H4 119(2) . . ? C4 C5 C6 121.8(2) . . ? C4 C5 Cl1 119.4(2) . . ? C6 C5 Cl1 118.88(19) . . ? C5 C6 C7 119.0(2) . . ? C5 C6 H6 122.0(17) . . ? C7 C6 H6 118.9(17) . . ? C6 C7 C2 120.8(2) . . ? C6 C7 H7 116.2(18) . . ? C2 C7 H7 123.0(18) . . ? O4 C8 N2 120.3(2) . . ? O4 C8 C9 122.3(2) . . ? N2 C8 C9 117.1(2) . . ? C10 C9 C14 119.5(2) . . ? C10 C9 C8 116.8(2) . . ? C14 C9 C8 123.5(2) . . ? C9 C10 C11 120.6(2) . . ? C9 C10 H10 116.9(19) . . ? C11 C10 H10 122.4(19) . . ? C12 C11 C10 119.2(2) . . ? C12 C11 H11 119(2) . . ? C10 C11 H11 122(2) . . ? C11 C12 C13 121.5(2) . . ? C11 C12 Cl2 119.4(2) . . ? C13 C12 Cl2 119.1(2) . . ? C12 C13 C14 118.8(2) . . ? C12 C13 H13 118.8(19) . . ? C14 C13 H13 122.3(19) . . ? C9 C14 C13 120.5(2) . . ? C9 C14 H14 121(2) . . ? C13 C14 H14 119(2) . . ? O2 C15 C16 107.0(2) . . ? O2 C15 H15A 109.6(18) . . ? C16 C15 H15A 110.6(17) . . ? O2 C15 H15B 106(2) . . ? C16 C15 H15B 115(2) . . ? H15A C15 H15B 109(3) . . ? C15 C16 H16A 112(2) . . ? C15 C16 H16B 104.9(18) . . ? H16A C16 H16B 112(3) . . ? C15 C16 H16C 112(2) . . ? H16A C16 H16C 105(3) . . ? H16B C16 H16C 111(3) . . ? O3 C17 C18 107.5(2) . . ? O3 C17 H17A 103(2) . . ? C18 C17 H17A 117(2) . . ? O3 C17 H17B 112(2) . . ? C18 C17 H17B 110(2) . . ? H17A C17 H17B 107(3) . . ? C17 C18 H18A 110(2) . . ? C17 C18 H18B 109(3) . . ? H18A C18 H18B 107(3) . . ? C17 C18 H18C 107(2) . . ? H18A C18 H18C 115(3) . . ? H18B C18 H18C 109(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 O2 N1 N2 -86.0(2) . . . . ? C15 O2 N1 C1 138.2(2) . . . . ? O2 N1 N2 C8 161.25(19) . . . . ? C1 N1 N2 C8 -62.6(3) . . . . ? O2 N1 N2 O3 -66.7(2) . . . . ? C1 N1 N2 O3 69.4(2) . . . . ? C17 O3 N2 N1 123.0(2) . . . . ? C17 O3 N2 C8 -103.3(2) . . . . ? N2 N1 C1 O1 19.0(3) . . . . ? O2 N1 C1 O1 151.7(2) . . . . ? N2 N1 C1 C2 -168.7(2) . . . . ? O2 N1 C1 C2 -36.0(3) . . . . ? O1 C1 C2 C7 166.9(3) . . . . ? N1 C1 C2 C7 -5.0(4) . . . . ? O1 C1 C2 C3 -9.2(4) . . . . ? N1 C1 C2 C3 178.9(2) . . . . ? C7 C2 C3 C4 1.3(4) . . . . ? C1 C2 C3 C4 177.6(2) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C3 C4 C5 Cl1 179.3(2) . . . . ? C4 C5 C6 C7 0.6(4) . . . . ? Cl1 C5 C6 C7 -179.0(2) . . . . ? C5 C6 C7 C2 0.0(4) . . . . ? C3 C2 C7 C6 -1.0(4) . . . . ? C1 C2 C7 C6 -176.9(2) . . . . ? N1 N2 C8 O4 147.2(2) . . . . ? O3 N2 C8 O4 16.1(3) . . . . ? N1 N2 C8 C9 -38.8(3) . . . . ? O3 N2 C8 C9 -169.88(19) . . . . ? O4 C8 C9 C10 -45.5(4) . . . . ? N2 C8 C9 C10 140.6(2) . . . . ? O4 C8 C9 C14 129.0(3) . . . . ? N2 C8 C9 C14 -44.8(3) . . . . ? C14 C9 C10 C11 0.8(4) . . . . ? C8 C9 C10 C11 175.6(2) . . . . ? C9 C10 C11 C12 -1.7(4) . . . . ? C10 C11 C12 C13 1.3(4) . . . . ? C10 C11 C12 Cl2 -176.6(2) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? Cl2 C12 C13 C14 177.9(2) . . . . ? C10 C9 C14 C13 0.5(4) . . . . ? C8 C9 C14 C13 -174.0(2) . . . . ? C12 C13 C14 C9 -0.9(4) . . . . ? N1 O2 C15 C16 178.9(2) . . . . ? N2 O3 C17 C18 177.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.849 _diffrn_reflns_theta_full 65.08 _diffrn_measured_fraction_theta_full 0.849 _refine_diff_density_max 0.543 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.090