# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Alves, M Jose' 'Azoia, Nuno G.' 'Bickley, Jamie F.' 'Fortes, A Gil' 'Gilchrist, T.' 'Mendonca, Ricardo' _publ_contact_author_name 'Dr T Gilchrist' _publ_contact_author_address ; Department of Chemistry University of Liverpool Liverpool L69 7ZD ; _publ_contact_author_email 'TLG57@LIV.AC.UK' _publ_section_title ; Diels-Alder Rections of Alkyl 2H-Azirine-3-carboylates with Furans ; data_na21f9 _database_code_CSD 168566 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 Cl2 N O4' _chemical_formula_weight 344.18 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 'C c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 10.120(2) _cell_length_b 11.740(2) _cell_length_c 25.984(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.78(3) _cell_angle_gamma 90.00 _cell_volume 3085.9(11) _cell_formula_units_Z 8 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Needle' _exptl_crystal_colour ? _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.437 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'Stoe IPDS' _diffrn_measurement_method 'Image plate' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9233 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 24.23 _reflns_number_total 4636 _reflns_number_gt 3643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (STOE, 1997)' _computing_cell_refinement ? _computing_data_reduction 'X-RED (STOE, 1996)' _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^)+(0.0698P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(7) _refine_ls_number_reflns 4636 _refine_ls_number_parameters 405 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _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 0.6265(4) 1.0678(4) 0.39225(16) 0.0275(10) Uani 1 1 d . . . C2 C 0.7309(5) 1.0942(5) 0.36140(19) 0.0358(12) Uani 1 1 d . . . H2 H 0.7933 1.1496 0.3718 0.043 Uiso 1 1 calc R . . C3 C 0.7425(5) 1.0385(4) 0.3153(2) 0.0365(12) Uani 1 1 d . . . H3 H 0.8132 1.0557 0.2941 0.044 Uiso 1 1 calc R . . C4 C 0.6507(5) 0.9571(4) 0.29994(17) 0.0329(11) Uani 1 1 d . . . H4 H 0.6578 0.9196 0.2682 0.039 Uiso 1 1 calc R . . C5 C 0.5487(5) 0.9320(4) 0.33193(19) 0.0312(12) Uani 1 1 d . . . C6 C 0.5338(4) 0.9833(4) 0.37939(17) 0.0259(10) Uani 1 1 d . . . C7 C 0.4188(4) 0.9587(4) 0.41325(16) 0.0242(10) Uani 1 1 d . . . H7 H 0.3392 1.0049 0.4049 0.029 Uiso 1 1 calc R . . C8 C 0.4285(4) 0.9196(4) 0.46754(16) 0.0250(10) Uani 1 1 d . . . C9 C 0.5559(5) 0.8966(4) 0.4979(2) 0.0345(12) Uani 1 1 d . . . C10 C 0.7603(5) 0.8034(6) 0.5010(2) 0.0539(15) Uani 1 1 d . . . H10A H 0.8194 0.7620 0.4791 0.081 Uiso 1 1 calc R . . H10B H 0.7342 0.7546 0.5291 0.081 Uiso 1 1 calc R . . H10C H 0.8053 0.8701 0.5149 0.081 Uiso 1 1 calc R . . C11 C 0.3230(5) 0.9621(4) 0.50401(17) 0.0297(10) Uani 1 1 d . . . H11 H 0.3541 1.0319 0.5220 0.036 Uiso 1 1 calc R . . C12 C 0.2797(5) 0.8752(4) 0.54244(17) 0.0342(12) Uani 1 1 d . . . H12 H 0.3363 0.8377 0.5663 0.041 Uiso 1 1 calc R . . C13 C 0.1522(5) 0.8593(5) 0.53791(17) 0.0375(13) Uani 1 1 d . . . H13 H 0.1048 0.8065 0.5573 0.045 Uiso 1 1 calc R . . C14 C 0.0915(5) 0.9366(5) 0.4977(2) 0.0358(12) Uani 1 1 d . . . H14 H 0.0374 0.8926 0.4723 0.043 Uiso 1 1 calc R . . C15 C -0.0492(6) 1.0927(5) 0.4860(3) 0.0598(17) Uani 1 1 d . . . H15A H -0.0998 1.1482 0.5048 0.090 Uiso 1 1 calc R . . H15B H -0.1081 1.0495 0.4632 0.090 Uiso 1 1 calc R . . H15C H 0.0160 1.1318 0.4658 0.090 Uiso 1 1 calc R . . Cl1 Cl 0.43161(11) 0.83308(12) 0.30972(5) 0.0419(3) Uani 1 1 d . . . Cl2 Cl 0.60841(11) 1.14570(10) 0.44883(5) 0.0391(3) Uani 1 1 d . . . N1 N 0.3904(4) 0.8408(3) 0.42633(15) 0.0300(9) Uani 1 1 d . . . H1 H 0.314(5) 0.834(4) 0.4300(19) 0.034(15) Uiso 1 1 d . . . O1 O 0.6433(3) 0.8387(3) 0.47104(14) 0.0434(9) Uani 1 1 d . . . O2 O 0.5735(4) 0.9268(4) 0.54104(14) 0.0556(11) Uani 1 1 d . . . O3 O 0.2046(3) 0.9858(3) 0.47394(12) 0.0344(8) Uani 1 1 d . . . O4 O 0.0159(3) 1.0177(3) 0.52129(13) 0.0412(8) Uani 1 1 d . . . C20 C 0.3730(5) 0.8351(4) 0.77147(17) 0.0326(11) Uani 1 1 d . . . C21 C 0.2671(5) 0.8607(5) 0.8021(2) 0.0393(13) Uani 1 1 d . . . H21 H 0.2050 0.9166 0.7919 0.047 Uiso 1 1 calc R . . C22 C 0.2550(5) 0.8028(5) 0.8473(2) 0.0447(14) Uani 1 1 d . . . H22 H 0.1830 0.8185 0.8682 0.054 Uiso 1 1 calc R . . C23 C 0.3463(5) 0.7219(5) 0.8630(2) 0.0414(13) Uani 1 1 d . . . H23 H 0.3382 0.6836 0.8945 0.050 Uiso 1 1 calc R . . C24 C 0.4521(5) 0.6981(4) 0.83065(18) 0.0314(11) Uani 1 1 d . . . C25 C 0.4662(4) 0.7511(4) 0.78370(17) 0.0262(10) Uani 1 1 d . . . C26 C 0.5790(4) 0.7271(4) 0.74924(17) 0.0309(11) Uani 1 1 d . . . H26 H 0.6554 0.7789 0.7545 0.037 Uiso 1 1 calc R . . C27 C 0.5655(5) 0.6798(4) 0.69652(17) 0.0280(10) Uani 1 1 d . . . C28 C 0.4296(7) 0.6410(6) 0.6779(3) 0.0550(18) Uani 1 1 d . A . C29 C 0.2689(9) 0.5857(10) 0.6222(7) 0.208(8) Uani 1 1 d . A 1 H29A H 0.2378 0.5881 0.5865 0.312 Uiso 1 1 calc R A 1 H29B H 0.2038 0.6208 0.6438 0.312 Uiso 1 1 calc R A 1 H29C H 0.2821 0.5071 0.6326 0.312 Uiso 1 1 calc R A 1 C30 C 0.6622(5) 0.7203(5) 0.65656(19) 0.0411(13) Uani 1 1 d . . . H30 H 0.6229 0.7836 0.6361 0.049 Uiso 1 1 calc R . . C31 C 0.7098(6) 0.6287(5) 0.62156(18) 0.0400(13) Uani 1 1 d . . . H31 H 0.6556 0.5851 0.5991 0.048 Uiso 1 1 calc R . . C32 C 0.8387(6) 0.6183(5) 0.6270(2) 0.0466(14) Uani 1 1 d . . . H32 H 0.8886 0.5646 0.6091 0.056 Uiso 1 1 calc R . . C33 C 0.8984(7) 0.7026(5) 0.6655(2) 0.0548(15) Uani 1 1 d . . . H33 H 0.9486 0.6639 0.6937 0.066 Uiso 1 1 calc R . . C34 C 1.0476(7) 0.8487(6) 0.6759(3) 0.078(2) Uani 1 1 d . . . H34A H 1.1013 0.9026 0.6575 0.117 Uiso 1 1 calc R . . H34B H 1.1042 0.8018 0.6980 0.117 Uiso 1 1 calc R . . H34C H 0.9855 0.8898 0.6967 0.117 Uiso 1 1 calc R . . Cl3 Cl 0.38949(13) 0.91010(12) 0.71382(5) 0.0463(3) Uani 1 1 d . . . Cl4 Cl 0.56751(12) 0.60005(12) 0.85411(5) 0.0461(4) Uani 1 1 d . . . N2 N 0.6152(5) 0.6091(4) 0.73905(16) 0.0380(10) Uani 1 1 d . . . H20 H 0.710(8) 0.615(6) 0.741(3) 0.09(2) Uiso 1 1 d . . . O5 O 0.3513(4) 0.5943(4) 0.7050(2) 0.0776(15) Uani 1 1 d . . . O6 O 0.4108(4) 0.6558(5) 0.62845(17) 0.0838(17) Uani 1 1 d . . . O7 O 0.7813(4) 0.7584(3) 0.68365(16) 0.0598(12) Uani 1 1 d . . . O8 O 0.9758(4) 0.7771(4) 0.63938(16) 0.0602(11) 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 C1 0.026(2) 0.023(2) 0.033(2) 0.006(2) 0.003(2) -0.002(2) C2 0.027(3) 0.035(3) 0.046(3) 0.004(2) 0.006(2) -0.002(2) C3 0.025(3) 0.035(3) 0.050(3) 0.013(3) 0.013(2) 0.003(2) C4 0.034(3) 0.038(3) 0.027(2) 0.000(2) 0.011(2) 0.001(2) C5 0.030(3) 0.025(3) 0.039(3) 0.004(2) 0.002(2) -0.005(2) C6 0.024(2) 0.024(3) 0.030(2) 0.0096(19) 0.0025(19) 0.003(2) C7 0.020(2) 0.024(2) 0.028(2) -0.0037(19) -0.0031(18) -0.001(2) C8 0.023(2) 0.026(2) 0.026(2) 0.0011(19) 0.0009(19) -0.001(2) C9 0.026(3) 0.036(3) 0.042(3) 0.008(2) 0.003(2) -0.003(2) C10 0.034(3) 0.078(4) 0.049(3) 0.023(3) 0.006(2) 0.017(3) C11 0.029(2) 0.032(3) 0.029(2) 0.003(2) 0.0014(19) 0.001(2) C12 0.040(3) 0.040(3) 0.023(2) -0.002(2) -0.007(2) 0.003(3) C13 0.050(4) 0.040(3) 0.024(2) 0.001(2) 0.017(2) -0.005(3) C14 0.029(3) 0.039(3) 0.040(3) -0.005(2) 0.016(2) -0.007(3) C15 0.051(4) 0.049(4) 0.080(4) 0.005(3) -0.001(3) 0.015(3) Cl1 0.0433(8) 0.0485(8) 0.0341(6) -0.0062(6) 0.0023(6) -0.0129(7) Cl2 0.0406(7) 0.0332(7) 0.0436(6) -0.0081(6) 0.0042(5) -0.0074(6) N1 0.027(2) 0.029(2) 0.035(2) 0.0016(16) 0.0034(19) -0.0060(19) O1 0.0276(18) 0.047(2) 0.056(2) 0.0105(17) 0.0044(16) 0.0081(17) O2 0.043(2) 0.084(3) 0.039(2) -0.0031(19) -0.0166(17) -0.003(2) O3 0.0248(17) 0.042(2) 0.0370(17) 0.0095(15) 0.0024(14) 0.0048(15) O4 0.0327(18) 0.042(2) 0.049(2) -0.0074(17) 0.0078(16) 0.0076(17) C20 0.033(3) 0.026(3) 0.038(3) -0.003(2) -0.004(2) -0.002(2) C21 0.029(3) 0.031(3) 0.058(3) -0.018(3) 0.001(2) 0.005(2) C22 0.039(3) 0.040(4) 0.056(3) -0.020(3) 0.012(3) -0.003(3) C23 0.044(3) 0.041(3) 0.040(3) -0.016(2) 0.010(2) -0.007(3) C24 0.030(3) 0.033(3) 0.031(3) -0.010(2) -0.002(2) -0.001(2) C25 0.023(2) 0.029(2) 0.027(2) -0.0083(19) -0.0001(18) 0.002(2) C26 0.025(2) 0.032(3) 0.036(3) -0.006(2) 0.001(2) 0.001(2) C27 0.028(2) 0.023(2) 0.033(2) -0.0045(19) 0.003(2) -0.001(2) C28 0.048(4) 0.046(4) 0.070(4) -0.039(3) -0.017(3) 0.019(3) C29 0.074(6) 0.119(9) 0.42(2) -0.130(12) -0.143(10) 0.016(6) C30 0.058(3) 0.034(3) 0.031(3) -0.003(2) 0.006(2) -0.002(3) C31 0.053(4) 0.042(3) 0.025(2) -0.010(2) 0.010(2) -0.005(3) C32 0.049(4) 0.046(4) 0.045(3) -0.022(3) 0.015(3) -0.004(3) C33 0.066(4) 0.045(4) 0.055(3) 0.000(3) 0.039(3) 0.001(3) C34 0.067(4) 0.064(5) 0.104(5) -0.032(4) 0.007(4) -0.027(4) Cl3 0.0522(8) 0.0375(8) 0.0490(7) 0.0035(6) -0.0002(6) 0.0114(7) Cl4 0.0502(9) 0.0505(9) 0.0373(7) 0.0038(6) -0.0023(6) 0.0131(7) N2 0.040(3) 0.038(3) 0.036(2) -0.0026(18) 0.006(2) 0.016(2) O5 0.035(2) 0.060(3) 0.138(5) -0.014(3) 0.004(3) -0.021(2) O6 0.049(3) 0.147(5) 0.055(3) -0.047(3) -0.017(2) 0.025(3) O7 0.049(2) 0.062(3) 0.070(3) -0.035(2) 0.033(2) -0.027(2) O8 0.062(2) 0.058(3) 0.061(2) -0.003(2) 0.020(2) -0.016(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 C2 1.382(6) . ? C1 C6 1.398(7) . ? C1 Cl2 1.746(5) . ? C2 C3 1.373(7) . ? C3 C4 1.383(7) . ? C4 C5 1.377(7) . ? C5 C6 1.385(7) . ? C5 Cl1 1.744(5) . ? C6 C7 1.508(6) . ? C7 N1 1.456(6) . ? C7 C8 1.484(6) . ? C8 N1 1.458(6) . ? C8 C9 1.515(7) . ? C8 C11 1.533(6) . ? C9 O2 1.183(6) . ? C9 O1 1.332(6) . ? C10 O1 1.457(6) . ? C11 O3 1.437(5) . ? C11 C12 1.502(7) . ? C12 C13 1.306(7) . ? C13 C14 1.500(8) . ? C14 O4 1.376(6) . ? C14 O3 1.439(6) . ? C15 O4 1.419(7) . ? C20 C21 1.387(7) . ? C20 C25 1.395(7) . ? C20 Cl3 1.750(5) . ? C21 C22 1.367(8) . ? C22 C23 1.377(8) . ? C23 C24 1.411(7) . ? C24 C25 1.381(7) . ? C24 Cl4 1.736(5) . ? C25 C26 1.499(6) . ? C26 N2 1.460(6) . ? C26 C27 1.481(6) . ? C27 N2 1.459(6) . ? C27 C28 1.514(8) . ? C27 C30 1.525(7) . ? C28 O5 1.208(8) . ? C28 O6 1.304(8) . ? C29 O6 1.659(10) . ? C30 O7 1.447(7) . ? C30 C31 1.498(7) . ? C31 C32 1.313(8) . ? C32 C33 1.518(8) . ? C33 O8 1.367(7) . ? C33 O7 1.446(7) . ? C34 O8 1.446(8) . ? 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 C2 C1 C6 122.7(4) . . ? C2 C1 Cl2 118.2(4) . . ? C6 C1 Cl2 119.1(3) . . ? C3 C2 C1 119.1(5) . . ? C2 C3 C4 120.5(5) . . ? C5 C4 C3 118.9(5) . . ? C4 C5 C6 123.3(5) . . ? C4 C5 Cl1 117.2(4) . . ? C6 C5 Cl1 119.5(4) . . ? C5 C6 C1 115.5(4) . . ? C5 C6 C7 122.9(4) . . ? C1 C6 C7 121.3(4) . . ? N1 C7 C8 59.4(3) . . ? N1 C7 C6 118.7(4) . . ? C8 C7 C6 125.8(4) . . ? N1 C8 C7 59.3(3) . . ? N1 C8 C9 118.1(4) . . ? C7 C8 C9 125.5(4) . . ? N1 C8 C11 119.2(4) . . ? C7 C8 C11 117.4(4) . . ? C9 C8 C11 109.5(4) . . ? O2 C9 O1 124.5(5) . . ? O2 C9 C8 122.7(5) . . ? O1 C9 C8 112.7(4) . . ? O3 C11 C12 103.8(4) . . ? O3 C11 C8 108.2(3) . . ? C12 C11 C8 114.4(4) . . ? C13 C12 C11 110.2(4) . . ? C12 C13 C14 111.0(5) . . ? O4 C14 O3 112.0(4) . . ? O4 C14 C13 109.3(4) . . ? O3 C14 C13 103.1(4) . . ? C7 N1 C8 61.2(3) . . ? C9 O1 C10 114.0(4) . . ? C11 O3 C14 110.4(3) . . ? C14 O4 C15 113.3(4) . . ? C21 C20 C25 123.5(5) . . ? C21 C20 Cl3 118.5(4) . . ? C25 C20 Cl3 117.9(4) . . ? C22 C21 C20 118.5(5) . . ? C21 C22 C23 121.4(5) . . ? C22 C23 C24 118.4(5) . . ? C25 C24 C23 122.6(5) . . ? C25 C24 Cl4 121.5(4) . . ? C23 C24 Cl4 115.9(4) . . ? C24 C25 C20 115.6(4) . . ? C24 C25 C26 123.0(4) . . ? C20 C25 C26 121.3(4) . . ? N2 C26 C27 59.5(3) . . ? N2 C26 C25 119.1(4) . . ? C27 C26 C25 125.0(4) . . ? N2 C27 C26 59.5(3) . . ? N2 C27 C28 111.1(5) . . ? C26 C27 C28 117.8(4) . . ? N2 C27 C30 118.6(4) . . ? C26 C27 C30 118.1(4) . . ? C28 C27 C30 118.1(5) . . ? O5 C28 O6 123.8(6) . . ? O5 C28 C27 123.7(6) . . ? O6 C28 C27 112.2(6) . . ? O7 C30 C31 103.8(4) . . ? O7 C30 C27 107.9(4) . . ? C31 C30 C27 114.5(4) . . ? C32 C31 C30 109.8(5) . . ? C31 C32 C33 112.6(5) . . ? O8 C33 O7 111.2(5) . . ? O8 C33 C32 108.2(5) . . ? O7 C33 C32 101.3(5) . . ? C27 N2 C26 61.0(3) . . ? C28 O6 C29 97.5(8) . . ? C33 O7 C30 112.3(4) . . ? C33 O8 C34 109.3(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 C6 C1 C2 C3 2.3(7) . . . . ? Cl2 C1 C2 C3 -176.3(4) . . . . ? C1 C2 C3 C4 0.1(7) . . . . ? C2 C3 C4 C5 -0.9(7) . . . . ? C3 C4 C5 C6 -0.7(8) . . . . ? C3 C4 C5 Cl1 177.4(4) . . . . ? C4 C5 C6 C1 2.9(7) . . . . ? Cl1 C5 C6 C1 -175.2(3) . . . . ? C4 C5 C6 C7 177.5(4) . . . . ? Cl1 C5 C6 C7 -0.6(6) . . . . ? C2 C1 C6 C5 -3.7(7) . . . . ? Cl2 C1 C6 C5 174.9(3) . . . . ? C2 C1 C6 C7 -178.4(4) . . . . ? Cl2 C1 C6 C7 0.2(6) . . . . ? C5 C6 C7 N1 53.4(6) . . . . ? C1 C6 C7 N1 -132.3(4) . . . . ? C5 C6 C7 C8 124.7(5) . . . . ? C1 C6 C7 C8 -61.0(6) . . . . ? C6 C7 C8 N1 -105.1(5) . . . . ? N1 C7 C8 C9 104.5(5) . . . . ? C6 C7 C8 C9 -0.6(7) . . . . ? N1 C7 C8 C11 -109.3(5) . . . . ? C6 C7 C8 C11 145.5(4) . . . . ? N1 C8 C9 O2 -152.7(5) . . . . ? C7 C8 C9 O2 136.5(5) . . . . ? C11 C8 C9 O2 -11.9(7) . . . . ? N1 C8 C9 O1 26.7(6) . . . . ? C7 C8 C9 O1 -44.1(6) . . . . ? C11 C8 C9 O1 167.5(4) . . . . ? N1 C8 C11 O3 -41.1(5) . . . . ? C7 C8 C11 O3 27.3(5) . . . . ? C9 C8 C11 O3 178.5(4) . . . . ? N1 C8 C11 C12 74.0(5) . . . . ? C7 C8 C11 C12 142.4(4) . . . . ? C9 C8 C11 C12 -66.4(5) . . . . ? O3 C11 C12 C13 -5.0(5) . . . . ? C8 C11 C12 C13 -122.6(5) . . . . ? C11 C12 C13 C14 -2.6(6) . . . . ? C12 C13 C14 O4 -110.2(5) . . . . ? C12 C13 C14 O3 9.1(6) . . . . ? C6 C7 N1 C8 116.8(4) . . . . ? C9 C8 N1 C7 -116.6(4) . . . . ? C11 C8 N1 C7 106.4(4) . . . . ? O2 C9 O1 C10 6.4(7) . . . . ? C8 C9 O1 C10 -173.0(4) . . . . ? C12 C11 O3 C14 10.9(5) . . . . ? C8 C11 O3 C14 132.8(4) . . . . ? O4 C14 O3 C11 105.1(5) . . . . ? C13 C14 O3 C11 -12.2(5) . . . . ? O3 C14 O4 C15 68.3(6) . . . . ? C13 C14 O4 C15 -178.1(5) . . . . ? C25 C20 C21 C22 1.8(7) . . . . ? Cl3 C20 C21 C22 -179.4(4) . . . . ? C20 C21 C22 C23 0.9(8) . . . . ? C21 C22 C23 C24 -1.2(8) . . . . ? C22 C23 C24 C25 -1.1(7) . . . . ? C22 C23 C24 Cl4 177.2(4) . . . . ? C23 C24 C25 C20 3.6(7) . . . . ? Cl4 C24 C25 C20 -174.6(3) . . . . ? C23 C24 C25 C26 179.4(4) . . . . ? Cl4 C24 C25 C26 1.2(6) . . . . ? C21 C20 C25 C24 -3.9(7) . . . . ? Cl3 C20 C25 C24 177.2(3) . . . . ? C21 C20 C25 C26 -179.9(4) . . . . ? Cl3 C20 C25 C26 1.3(6) . . . . ? C24 C25 C26 N2 47.0(6) . . . . ? C20 C25 C26 N2 -137.3(5) . . . . ? C24 C25 C26 C27 118.4(5) . . . . ? C20 C25 C26 C27 -65.9(6) . . . . ? C25 C26 C27 N2 -106.1(5) . . . . ? N2 C26 C27 C28 99.3(5) . . . . ? C25 C26 C27 C28 -6.8(7) . . . . ? N2 C26 C27 C30 -108.5(5) . . . . ? C25 C26 C27 C30 145.4(5) . . . . ? N2 C27 C28 O5 28.4(7) . . . . ? C26 C27 C28 O5 -37.3(8) . . . . ? C30 C27 C28 O5 170.5(5) . . . . ? N2 C27 C28 O6 -146.7(5) . . . . ? C26 C27 C28 O6 147.5(5) . . . . ? C30 C27 C28 O6 -4.7(7) . . . . ? N2 C27 C30 O7 -43.8(6) . . . . ? C26 C27 C30 O7 24.8(6) . . . . ? C28 C27 C30 O7 177.0(4) . . . . ? N2 C27 C30 C31 71.2(6) . . . . ? C26 C27 C30 C31 139.9(5) . . . . ? C28 C27 C30 C31 -68.0(6) . . . . ? O7 C30 C31 C32 -1.5(6) . . . . ? C27 C30 C31 C32 -118.9(5) . . . . ? C30 C31 C32 C33 -1.3(7) . . . . ? C31 C32 C33 O8 -113.5(6) . . . . ? C31 C32 C33 O7 3.5(7) . . . . ? C28 C27 N2 C26 -110.7(4) . . . . ? C30 C27 N2 C26 107.5(5) . . . . ? C25 C26 N2 C27 115.7(5) . . . . ? O5 C28 O6 C29 -4.1(8) . . . . ? C27 C28 O6 C29 171.0(5) . . . . ? O8 C33 O7 C30 110.4(5) . . . . ? C32 C33 O7 C30 -4.4(6) . . . . ? C31 C30 O7 C33 3.9(6) . . . . ? C27 C30 O7 C33 125.8(5) . . . . ? O7 C33 O8 C34 77.1(7) . . . . ? C32 C33 O8 C34 -172.5(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H20 Cl1 0.96(8) 2.88(8) 3.704(5) 144(6) 4_565 N1 H1 O3 0.78(5) 2.41(5) 2.847(5) 117(4) . _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 24.23 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.464 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.057 data_nao4f3 _database_code_CSD 168567 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 Cl2 N O4' _chemical_formula_weight 330.15 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 9.0873(18) _cell_length_b 9.1031(18) _cell_length_c 9.6666(19) _cell_angle_alpha 84.86(3) _cell_angle_beta 82.88(3) _cell_angle_gamma 69.28(3) _cell_volume 741.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Needle' _exptl_crystal_colour ? _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.452 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'Stoe IPDS' _diffrn_measurement_method 'Image plate' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4739 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 24.15 _reflns_number_total 2202 _reflns_number_gt 1778 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (STOE, 1997)' _computing_cell_refinement ? _computing_data_reduction 'X-RED (STOE, 1996)' _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^)+(0.0472P)^2^+0.1796P] 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 SHELXL _refine_ls_extinction_coef 0.062(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2202 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.3702(3) 0.1029(3) 0.2876(2) 0.0350(5) Uani 1 1 d . . . C2 C 0.5210(3) 0.0195(3) 0.2291(3) 0.0462(6) Uani 1 1 d . . . H2 H 0.5789 -0.0796 0.2677 0.055 Uiso 1 1 calc R . . C3 C 0.5847(3) 0.0847(3) 0.1129(3) 0.0516(7) Uani 1 1 d . . . H3 H 0.6848 0.0274 0.0695 0.062 Uiso 1 1 calc R . . C4 C 0.5030(3) 0.2317(3) 0.0608(2) 0.0468(6) Uani 1 1 d . . . H4 H 0.5480 0.2772 -0.0163 0.056 Uiso 1 1 calc R . . C5 C 0.3539(3) 0.3133(3) 0.1222(2) 0.0366(5) Uani 1 1 d . . . C6 C 0.2798(2) 0.2489(2) 0.2337(2) 0.0294(5) Uani 1 1 d . . . C7 C 0.1141(2) 0.3336(2) 0.2930(2) 0.0303(5) Uani 1 1 d . . . H7 H 0.1049 0.3944 0.3756 0.036 Uiso 1 1 calc R . . C8 C -0.0164(2) 0.2685(2) 0.2901(2) 0.0296(5) Uani 1 1 d . . . C9 C 0.0236(2) 0.1187(2) 0.2171(2) 0.0323(5) Uani 1 1 d . . . C10 C 0.0156(3) -0.1382(3) 0.2378(3) 0.0522(7) Uani 1 1 d . . . H10A H -0.0147 -0.1252 0.1435 0.078 Uiso 1 1 calc R . . H10B H -0.0389 -0.1998 0.2952 0.078 Uiso 1 1 calc R . . H10C H 0.1289 -0.1921 0.2363 0.078 Uiso 1 1 calc R . . C11 C -0.1542(2) 0.3036(2) 0.4057(2) 0.0332(5) Uani 1 1 d . . . H11 H -0.1363 0.2147 0.4760 0.040 Uiso 1 1 calc R . . C12 C -0.3067(3) 0.3362(3) 0.3453(2) 0.0392(5) Uani 1 1 d . . . H12 H -0.3381 0.2607 0.3091 0.047 Uiso 1 1 calc R . . C13 C -0.3900(3) 0.4868(3) 0.3507(3) 0.0475(6) Uani 1 1 d . . . H13 H -0.4908 0.5348 0.3192 0.057 Uiso 1 1 calc R . . C14 C -0.3028(3) 0.5706(3) 0.4135(3) 0.0498(7) Uani 1 1 d . . . H14 H -0.3721 0.6340 0.4900 0.060 Uiso 1 1 calc R . . Cl1 Cl 0.29272(8) 0.01925(8) 0.43450(7) 0.0557(2) Uani 1 1 d . . . Cl2 Cl 0.25926(8) 0.50445(8) 0.05757(8) 0.0601(3) Uani 1 1 d . . . N1 N -0.0111(2) 0.4052(2) 0.1991(2) 0.0344(4) Uani 1 1 d . . . H21 H 0.020(3) 0.376(3) 0.115(3) 0.043(7) Uiso 1 1 d . . . O1 O 0.0923(2) 0.09737(19) 0.10200(16) 0.0456(4) Uani 1 1 d . . . O2 O -0.02684(19) 0.01494(17) 0.29516(16) 0.0402(4) Uani 1 1 d . . . O3 O -0.17503(18) 0.44594(18) 0.47049(17) 0.0430(4) Uani 1 1 d . . . O4 O -0.2465(2) 0.6673(2) 0.3178(2) 0.0658(6) Uani 1 1 d . . . H24 H -0.1907 0.6147 0.2524 0.099 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 C1 0.0330(12) 0.0329(12) 0.0396(12) -0.0058(9) -0.0053(10) -0.0106(9) C2 0.0341(13) 0.0363(13) 0.0651(16) -0.0150(11) -0.0100(12) -0.0038(10) C3 0.0306(12) 0.0654(18) 0.0580(15) -0.0325(13) 0.0048(12) -0.0119(12) C4 0.0365(13) 0.0715(18) 0.0391(13) -0.0120(12) 0.0044(11) -0.0274(13) C5 0.0369(12) 0.0412(13) 0.0369(12) -0.0026(9) -0.0049(10) -0.0192(10) C6 0.0282(11) 0.0298(11) 0.0315(10) -0.0078(8) -0.0034(9) -0.0102(9) C7 0.0291(11) 0.0274(11) 0.0333(11) -0.0058(8) -0.0031(9) -0.0074(9) C8 0.0296(11) 0.0305(11) 0.0287(10) -0.0041(8) -0.0021(9) -0.0099(9) C9 0.0278(11) 0.0382(12) 0.0322(11) -0.0062(9) -0.0037(10) -0.0115(9) C10 0.0678(18) 0.0349(13) 0.0576(15) -0.0135(11) -0.0079(14) -0.0193(12) C11 0.0343(12) 0.0334(12) 0.0326(11) -0.0117(9) 0.0040(10) -0.0125(9) C12 0.0340(12) 0.0495(14) 0.0389(12) -0.0124(10) 0.0040(10) -0.0204(11) C13 0.0277(12) 0.0564(16) 0.0553(15) -0.0100(12) 0.0025(11) -0.0111(11) C14 0.0306(13) 0.0430(14) 0.0711(17) -0.0208(12) 0.0082(13) -0.0069(11) Cl1 0.0520(4) 0.0547(4) 0.0581(4) 0.0224(3) -0.0138(3) -0.0191(3) Cl2 0.0555(4) 0.0569(4) 0.0727(5) 0.0265(3) -0.0147(3) -0.0296(3) N1 0.0297(10) 0.0335(10) 0.0374(10) 0.0007(8) -0.0029(8) -0.0086(8) O1 0.0477(10) 0.0569(11) 0.0361(9) -0.0199(7) 0.0099(8) -0.0234(8) O2 0.0502(10) 0.0348(9) 0.0388(8) -0.0099(6) 0.0023(7) -0.0191(7) O3 0.0348(9) 0.0453(10) 0.0498(9) -0.0255(7) 0.0016(7) -0.0112(7) O4 0.0465(11) 0.0331(10) 0.1084(17) -0.0101(9) 0.0137(11) -0.0077(8) _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 C6 1.386(3) . ? C1 C2 1.386(3) . ? C1 Cl1 1.741(2) . ? C2 C3 1.382(4) . ? C3 C4 1.366(4) . ? C4 C5 1.381(3) . ? C5 C6 1.395(3) . ? C5 Cl2 1.743(2) . ? C6 C7 1.495(3) . ? C7 N1 1.473(3) . ? C7 C8 1.506(3) . ? C8 N1 1.470(3) . ? C8 C9 1.498(3) . ? C8 C11 1.534(3) . ? C9 O1 1.203(2) . ? C9 O2 1.329(2) . ? C10 O2 1.451(3) . ? C11 O3 1.431(3) . ? C11 C12 1.492(3) . ? C12 C13 1.313(3) . ? C13 C14 1.487(4) . ? C14 O4 1.396(3) . ? C14 O3 1.433(3) . ? 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 C6 C1 C2 122.7(2) . . ? C6 C1 Cl1 119.21(16) . . ? C2 C1 Cl1 118.13(18) . . ? C3 C2 C1 118.9(2) . . ? C4 C3 C2 120.3(2) . . ? C3 C4 C5 119.6(2) . . ? C4 C5 C6 122.3(2) . . ? C4 C5 Cl2 117.71(17) . . ? C6 C5 Cl2 119.94(17) . . ? C1 C6 C5 115.91(19) . . ? C1 C6 C7 122.14(18) . . ? C5 C6 C7 121.94(19) . . ? N1 C7 C6 119.90(18) . . ? N1 C7 C8 59.11(13) . . ? C6 C7 C8 121.99(17) . . ? N1 C8 C9 115.19(17) . . ? N1 C8 C7 59.31(13) . . ? C9 C8 C7 117.33(17) . . ? N1 C8 C11 114.86(17) . . ? C9 C8 C11 116.67(17) . . ? C7 C8 C11 120.47(17) . . ? O1 C9 O2 125.0(2) . . ? O1 C9 C8 123.48(19) . . ? O2 C9 C8 111.53(17) . . ? O3 C11 C12 104.05(18) . . ? O3 C11 C8 110.83(16) . . ? C12 C11 C8 110.48(17) . . ? C13 C12 C11 109.4(2) . . ? C12 C13 C14 110.5(2) . . ? O4 C14 O3 111.05(18) . . ? O4 C14 C13 113.7(2) . . ? O3 C14 C13 103.61(19) . . ? C8 N1 C7 61.57(13) . . ? C9 O2 C10 115.82(17) . . ? C11 O3 C14 108.76(18) . . ? 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 0.5(4) . . . . ? Cl1 C1 C2 C3 -179.62(18) . . . . ? C1 C2 C3 C4 2.9(4) . . . . ? C2 C3 C4 C5 -2.1(4) . . . . ? C3 C4 C5 C6 -2.2(4) . . . . ? C3 C4 C5 Cl2 176.6(2) . . . . ? C2 C1 C6 C5 -4.5(3) . . . . ? Cl1 C1 C6 C5 175.62(16) . . . . ? C2 C1 C6 C7 176.6(2) . . . . ? Cl1 C1 C6 C7 -3.3(3) . . . . ? C4 C5 C6 C1 5.4(3) . . . . ? Cl2 C5 C6 C1 -173.45(17) . . . . ? C4 C5 C6 C7 -175.7(2) . . . . ? Cl2 C5 C6 C7 5.5(3) . . . . ? C1 C6 C7 N1 -133.7(2) . . . . ? C5 C6 C7 N1 47.4(3) . . . . ? C1 C6 C7 C8 -63.5(3) . . . . ? C5 C6 C7 C8 117.6(2) . . . . ? C6 C7 C8 N1 -108.1(2) . . . . ? N1 C7 C8 C9 104.5(2) . . . . ? C6 C7 C8 C9 -3.6(3) . . . . ? N1 C7 C8 C11 -102.6(2) . . . . ? C6 C7 C8 C11 149.3(2) . . . . ? N1 C8 C9 O1 17.9(3) . . . . ? C7 C8 C9 O1 -49.0(3) . . . . ? C11 C8 C9 O1 157.0(2) . . . . ? N1 C8 C9 O2 -161.77(17) . . . . ? C7 C8 C9 O2 131.30(19) . . . . ? C11 C8 C9 O2 -22.6(3) . . . . ? N1 C8 C11 O3 -43.3(2) . . . . ? C9 C8 C11 O3 177.42(18) . . . . ? C7 C8 C11 O3 24.3(3) . . . . ? N1 C8 C11 C12 71.5(2) . . . . ? C9 C8 C11 C12 -67.8(2) . . . . ? C7 C8 C11 C12 139.15(19) . . . . ? O3 C11 C12 C13 11.2(2) . . . . ? C8 C11 C12 C13 -107.8(2) . . . . ? C11 C12 C13 C14 0.4(3) . . . . ? C12 C13 C14 O4 108.8(2) . . . . ? C12 C13 C14 O3 -11.9(3) . . . . ? C9 C8 N1 C7 -108.1(2) . . . . ? C11 C8 N1 C7 112.0(2) . . . . ? C6 C7 N1 C8 111.6(2) . . . . ? O1 C9 O2 C10 4.4(3) . . . . ? C8 C9 O2 C10 -175.9(2) . . . . ? C12 C11 O3 C14 -18.7(2) . . . . ? C8 C11 O3 C14 100.0(2) . . . . ? O4 C14 O3 C11 -103.5(2) . . . . ? C13 C14 O3 C11 18.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H21 O1 0.86(3) 2.39(2) 2.829(3) 112.0(19) . O4 H24 N1 0.83 2.08 2.803(3) 145.1 . _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 24.15 _diffrn_measured_fraction_theta_full 0.926 _refine_diff_density_max 0.446 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.042 data_amf01 _database_code_CSD 168568 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 Cl2 N O3' _chemical_formula_weight 312.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.731(13) _cell_length_b 8.372(4) _cell_length_c 19.99(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.72(14) _cell_angle_gamma 90.00 _cell_volume 2774(5) _cell_formula_units_Z 8 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Plate' _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.473 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'Stoe IPDS' _diffrn_measurement_method 'Image Plate' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7830 _diffrn_reflns_av_R_equivalents 0.0952 _diffrn_reflns_av_sigmaI/netI 0.0989 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 24.05 _reflns_number_total 2145 _reflns_number_gt 890 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (STOE, 1997)' _computing_cell_refinement ? _computing_data_reduction 'X-RED (STOE, 1996)' _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^)+(0.0475P)^2^+0.0000P] 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 2145 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1102 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 0.762 _refine_ls_restrained_S_all 0.762 _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 C1 C 0.0338(3) 0.2707(6) 0.5252(2) 0.0657(12) Uani 1 1 d . . . C2 C -0.0347(3) 0.1898(6) 0.5137(3) 0.0799(15) Uani 1 1 d . . . H2 H -0.0632 0.1270 0.4703 0.096 Uiso 1 1 calc R . . C3 C -0.0609(3) 0.2037(7) 0.5686(3) 0.0859(17) Uani 1 1 d . . . H3 H -0.1067 0.1467 0.5626 0.103 Uiso 1 1 calc R . . C4 C -0.0206(3) 0.2996(7) 0.6315(3) 0.0821(16) Uani 1 1 d . . . H4 H -0.0394 0.3087 0.6676 0.099 Uiso 1 1 calc R . . C5 C 0.0468(3) 0.3812(6) 0.6408(2) 0.0699(13) Uani 1 1 d . . . C6 C 0.0794(2) 0.3647(6) 0.5899(2) 0.0606(12) Uani 1 1 d . . . C7 C 0.1561(3) 0.4386(6) 0.6025(2) 0.0648(12) Uani 1 1 d . . . H7 H 0.1515 0.5419 0.5766 0.078 Uiso 1 1 calc R . . C8 C 0.2293(2) 0.3382(6) 0.6171(2) 0.0541(11) Uani 1 1 d . . . C9 C 0.2977(3) 0.4237(6) 0.6098(2) 0.0664(13) Uani 1 1 d . . . H9 H 0.3009 0.4040 0.5624 0.080 Uiso 1 1 calc R . . C10 C 0.3731(3) 0.3823(6) 0.6831(3) 0.0714(13) Uani 1 1 d . . . H10 H 0.4154 0.3138 0.6889 0.086 Uiso 1 1 calc R . . C11 C 0.3662(3) 0.4641(6) 0.7373(3) 0.0761(14) Uani 1 1 d . . . H11 H 0.404(3) 0.472(6) 0.790(3) 0.091 Uiso 1 1 d . . . C12 C 0.2873(3) 0.5500(6) 0.6974(2) 0.0730(14) Uani 1 1 d . . . H12 H 0.2822 0.6448 0.7245 0.088 Uiso 1 1 calc R . . C13 C 0.2252(3) 0.1632(6) 0.6171(2) 0.0611(12) Uani 1 1 d . . . C14 C 0.2747(3) -0.0708(6) 0.5870(3) 0.0835(15) Uani 1 1 d . . . H14A H 0.3096 -0.1050 0.5660 0.100 Uiso 1 1 calc R . . H14B H 0.2206 -0.1112 0.5558 0.100 Uiso 1 1 calc R . . H14C H 0.2950 -0.1120 0.6379 0.100 Uiso 1 1 calc R . . Cl1 Cl 0.06606(7) 0.25254(18) 0.45593(6) 0.0837(4) Uani 1 1 d . . . Cl2 Cl 0.09044(8) 0.5162(2) 0.71586(7) 0.0954(5) Uani 1 1 d . . . N1 N 0.2238(2) 0.4251(4) 0.68011(18) 0.0635(10) Uani 1 1 d . . . O1 O 0.28384(18) 0.5850(4) 0.62348(16) 0.0737(9) Uani 1 1 d . . . O2 O 0.18554(18) 0.0809(4) 0.63741(17) 0.0734(9) Uani 1 1 d . . . O3 O 0.27278(17) 0.1008(4) 0.58860(16) 0.0690(8) 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 C1 0.070(3) 0.070(4) 0.067(3) 0.001(3) 0.040(2) 0.009(3) C2 0.072(3) 0.090(4) 0.081(3) -0.015(3) 0.037(3) 0.000(3) C3 0.062(3) 0.097(5) 0.103(4) -0.010(3) 0.042(3) -0.011(3) C4 0.068(3) 0.109(5) 0.084(3) 0.001(3) 0.048(3) 0.000(3) C5 0.066(3) 0.086(4) 0.060(3) -0.011(2) 0.032(2) 0.003(3) C6 0.062(3) 0.067(3) 0.060(3) 0.002(2) 0.034(2) 0.008(2) C7 0.075(3) 0.068(4) 0.061(3) -0.001(2) 0.039(2) 0.003(3) C8 0.065(3) 0.051(3) 0.057(3) -0.003(2) 0.037(2) -0.001(2) C9 0.082(3) 0.066(4) 0.069(3) 0.000(2) 0.049(3) -0.003(3) C10 0.065(3) 0.081(4) 0.079(3) 0.001(3) 0.043(3) -0.003(3) C11 0.077(3) 0.082(4) 0.075(3) -0.005(3) 0.040(3) -0.007(3) C12 0.095(4) 0.071(4) 0.069(3) -0.011(3) 0.052(3) -0.012(3) C13 0.067(3) 0.062(4) 0.052(3) -0.001(2) 0.026(2) 0.003(3) C14 0.089(4) 0.070(4) 0.094(4) -0.010(3) 0.044(3) 0.010(3) Cl1 0.0925(9) 0.1010(10) 0.0680(7) -0.0080(7) 0.0461(6) 0.0062(8) Cl2 0.0843(8) 0.1315(14) 0.0771(8) -0.0283(8) 0.0432(7) 0.0041(9) N1 0.073(2) 0.062(3) 0.066(2) -0.0048(19) 0.041(2) -0.002(2) O1 0.097(2) 0.060(3) 0.078(2) 0.0013(16) 0.0534(18) -0.0073(18) O2 0.083(2) 0.064(2) 0.086(2) 0.0076(17) 0.0497(18) -0.0075(17) O3 0.081(2) 0.060(3) 0.078(2) -0.0027(16) 0.0475(17) 0.0055(17) _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 C2 1.373(6) . ? C1 C6 1.412(6) . ? C1 Cl1 1.757(4) . ? C2 C3 1.398(6) . ? C3 C4 1.383(7) . ? C4 C5 1.371(6) . ? C5 C6 1.416(5) . ? C5 Cl2 1.747(5) . ? C6 C7 1.475(6) . ? C7 N1 1.483(6) . ? C7 C8 1.515(6) . ? C8 C13 1.467(6) . ? C8 N1 1.498(5) . ? C8 C9 1.534(6) . ? C9 O1 1.425(5) . ? C9 C10 1.529(7) . ? C10 C11 1.337(6) . ? C11 C12 1.497(7) . ? C12 O1 1.478(5) . ? C12 N1 1.499(5) . ? C13 O2 1.213(5) . ? C13 O3 1.365(5) . ? C14 O3 1.438(5) . ? 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 C2 C1 C6 123.3(4) . . ? C2 C1 Cl1 117.6(4) . . ? C6 C1 Cl1 119.1(3) . . ? C1 C2 C3 118.0(5) . . ? C4 C3 C2 121.3(4) . . ? C5 C4 C3 119.4(4) . . ? C4 C5 C6 122.1(4) . . ? C4 C5 Cl2 118.2(3) . . ? C6 C5 Cl2 119.6(4) . . ? C1 C6 C5 115.7(4) . . ? C1 C6 C7 121.1(4) . . ? C5 C6 C7 123.3(4) . . ? C6 C7 N1 115.9(4) . . ? C6 C7 C8 121.5(4) . . ? N1 C7 C8 59.9(3) . . ? C13 C8 N1 117.5(4) . . ? C13 C8 C7 120.8(4) . . ? N1 C8 C7 58.9(3) . . ? C13 C8 C9 120.8(4) . . ? N1 C8 C9 103.9(4) . . ? C7 C8 C9 116.3(4) . . ? O1 C9 C10 101.5(4) . . ? O1 C9 C8 100.9(3) . . ? C10 C9 C8 104.0(4) . . ? C11 C10 C9 105.5(4) . . ? C10 C11 C12 105.0(5) . . ? O1 C12 C11 101.6(4) . . ? O1 C12 N1 104.3(3) . . ? C11 C12 N1 105.6(4) . . ? O2 C13 O3 122.8(5) . . ? O2 C13 C8 127.4(4) . . ? O3 C13 C8 109.8(4) . . ? C7 N1 C8 61.1(3) . . ? C7 N1 C12 112.9(3) . . ? C8 N1 C12 100.1(3) . . ? C9 O1 C12 94.4(3) . . ? C13 O3 C14 114.8(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 1.0(8) . . . . ? Cl1 C1 C2 C3 -180.0(4) . . . . ? C1 C2 C3 C4 1.9(8) . . . . ? C2 C3 C4 C5 -0.8(8) . . . . ? C3 C4 C5 C6 -3.2(7) . . . . ? C3 C4 C5 Cl2 173.8(4) . . . . ? C2 C1 C6 C5 -4.6(7) . . . . ? Cl1 C1 C6 C5 176.3(3) . . . . ? C2 C1 C6 C7 175.0(5) . . . . ? Cl1 C1 C6 C7 -4.1(6) . . . . ? C4 C5 C6 C1 5.7(7) . . . . ? Cl2 C5 C6 C1 -171.3(3) . . . . ? C4 C5 C6 C7 -173.9(5) . . . . ? Cl2 C5 C6 C7 9.1(6) . . . . ? C1 C6 C7 N1 -135.5(4) . . . . ? C5 C6 C7 N1 44.1(6) . . . . ? C1 C6 C7 C8 -66.3(6) . . . . ? C5 C6 C7 C8 113.3(5) . . . . ? C6 C7 C8 C13 1.8(6) . . . . ? N1 C7 C8 C13 105.6(4) . . . . ? C6 C7 C8 N1 -103.8(4) . . . . ? C6 C7 C8 C9 165.3(4) . . . . ? N1 C7 C8 C9 -90.9(4) . . . . ? C13 C8 C9 O1 -172.0(3) . . . . ? N1 C8 C9 O1 -37.4(4) . . . . ? C7 C8 C9 O1 24.5(4) . . . . ? C13 C8 C9 C10 -67.0(5) . . . . ? N1 C8 C9 C10 67.5(4) . . . . ? C7 C8 C9 C10 129.5(4) . . . . ? O1 C9 C10 C11 33.3(4) . . . . ? C8 C9 C10 C11 -71.1(5) . . . . ? C9 C10 C11 C12 1.2(5) . . . . ? C10 C11 C12 O1 -34.1(5) . . . . ? C10 C11 C12 N1 74.5(4) . . . . ? N1 C8 C13 O2 35.0(6) . . . . ? C7 C8 C13 O2 -33.4(6) . . . . ? C9 C8 C13 O2 163.8(4) . . . . ? N1 C8 C13 O3 -146.1(3) . . . . ? C7 C8 C13 O3 145.4(3) . . . . ? C9 C8 C13 O3 -17.4(5) . . . . ? C6 C7 N1 C8 112.9(4) . . . . ? C6 C7 N1 C12 -158.0(4) . . . . ? C8 C7 N1 C12 89.1(4) . . . . ? C13 C8 N1 C7 -111.1(4) . . . . ? C9 C8 N1 C7 112.6(4) . . . . ? C13 C8 N1 C12 138.2(4) . . . . ? C7 C8 N1 C12 -110.7(4) . . . . ? C9 C8 N1 C12 1.9(4) . . . . ? O1 C12 N1 C7 -29.6(4) . . . . ? C11 C12 N1 C7 -136.2(3) . . . . ? O1 C12 N1 C8 33.2(4) . . . . ? C11 C12 N1 C8 -73.5(4) . . . . ? C10 C9 O1 C12 -51.3(4) . . . . ? C8 C9 O1 C12 55.6(4) . . . . ? C11 C12 O1 C9 52.7(4) . . . . ? N1 C12 O1 C9 -56.9(4) . . . . ? O2 C13 O3 C14 -2.1(6) . . . . ? C8 C13 O3 C14 179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 24.05 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.200 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.051