data_rj1105 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_absolute_configuration ad # syn absolute configuration from synthetic procedure # ad absolute configuration from anomalous dispersion effects # rm absolute configuration from reference to a chiral # reference molecule of known abs. conf. _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H7 Cl2 N O4' _chemical_formula_weight 312.10 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 Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.2660(5) _cell_length_b 14.4142(16) _cell_length_c 20.684(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1271.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1742 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.522 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.826 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2899 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1311 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2899 _reflns_number_gt 1713 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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. The Flack x parameter for the inverted structure refined to 1.00(11). ; _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^)+(0.0233P)^2^+0.5332P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(11) _refine_ls_number_reflns 2899 _refine_ls_number_parameters 182 _refine_ls_number_restraints 120 _refine_ls_R_factor_all 0.1610 _refine_ls_R_factor_gt 0.0702 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.119 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.003 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 0.9636(3) 0.66102(7) 0.52756(5) 0.0467(4) Uani 1 1 d U . . Cl2 Cl 0.5964(3) 0.53835(8) 0.62803(5) 0.0475(4) Uani 1 1 d U . . O1 O 0.7530(7) 0.4346(2) 0.30514(13) 0.0431(9) Uani 1 1 d U . . O2 O 0.1513(8) 0.2652(2) 0.44609(12) 0.0422(8) Uani 1 1 d U . . O3 O 0.6363(7) 0.20175(17) 0.31434(12) 0.0379(8) Uani 1 1 d U . . O4 O 0.6669(9) 0.1344(2) 0.15090(14) 0.0559(10) Uani 1 1 d U . . N1 N 0.4404(9) 0.3325(2) 0.36345(13) 0.0312(8) Uani 1 1 d U . . C2 C 0.6283(11) 0.4109(3) 0.35544(18) 0.0313(11) Uani 1 1 d U . . C3 C 0.6446(11) 0.4553(3) 0.41999(17) 0.0299(10) Uani 1 1 d U . . C4 C 0.7988(10) 0.5355(3) 0.43851(19) 0.0337(11) Uani 1 1 d U . . H4 H 0.9139 0.5717 0.4083 0.040 Uiso 1 1 calc R . . C5 C 0.7780(10) 0.5606(3) 0.50304(19) 0.0321(11) Uani 1 1 d U . . C6 C 0.6053(11) 0.5072(3) 0.54697(17) 0.0328(10) Uani 1 1 d U . . C7 C 0.4472(11) 0.4283(3) 0.52770(18) 0.0316(10) Uani 1 1 d U . . H7 H 0.3286 0.3924 0.5575 0.038 Uiso 1 1 calc R . . C8 C 0.4691(11) 0.4037(2) 0.46294(17) 0.0279(10) Uani 1 1 d U . . C9 C 0.3282(11) 0.3240(3) 0.42776(18) 0.0313(11) Uani 1 1 d U . . C10 C 0.3738(12) 0.2626(3) 0.31524(17) 0.0322(11) Uani 1 1 d U . . H10 H 0.1863 0.2265 0.3297 0.039 Uiso 1 1 calc R . . C11 C 0.3057(11) 0.3021(3) 0.25041(19) 0.0395(12) Uani 1 1 d U . . H11 H 0.1905 0.3584 0.2475 0.047 Uiso 1 1 calc R . . C12 C 0.4007(12) 0.2614(3) 0.19664(19) 0.0429(12) Uani 1 1 d U . . H12 H 0.3584 0.2897 0.1561 0.051 Uiso 1 1 calc R . . C13 C 0.5690(11) 0.1738(3) 0.1987(2) 0.0399(11) Uani 1 1 d U . . C14 C 0.6091(13) 0.1323(3) 0.26491(19) 0.0444(12) Uani 1 1 d U . . H14A H 0.4269 0.0921 0.2746 0.053 Uiso 1 1 calc R . . H14B H 0.7993 0.0929 0.2653 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0627(9) 0.0320(5) 0.0454(6) -0.0027(5) -0.0081(6) -0.0035(6) Cl2 0.0693(10) 0.0458(6) 0.0275(5) -0.0040(5) -0.0005(6) 0.0015(7) O1 0.044(2) 0.052(2) 0.0329(16) 0.0007(16) 0.0121(15) -0.0061(17) O2 0.047(2) 0.0435(17) 0.0358(16) 0.0010(14) 0.0033(16) -0.0138(18) O3 0.038(2) 0.0384(16) 0.0378(16) -0.0065(14) -0.0089(16) 0.0042(16) O4 0.054(2) 0.065(2) 0.0486(19) -0.0211(17) 0.0146(18) 0.0012(19) N1 0.031(2) 0.0368(18) 0.0258(17) -0.0039(16) 0.0007(17) -0.0064(19) C2 0.028(3) 0.035(2) 0.031(2) -0.0007(19) -0.002(2) 0.006(2) C3 0.030(3) 0.032(2) 0.028(2) 0.0014(19) 0.001(2) 0.007(2) C4 0.031(3) 0.035(2) 0.035(2) 0.005(2) -0.001(2) 0.003(2) C5 0.031(3) 0.027(2) 0.038(2) 0.004(2) -0.003(2) 0.007(2) C6 0.037(3) 0.036(2) 0.026(2) -0.0014(18) -0.003(2) 0.013(2) C7 0.034(3) 0.033(2) 0.028(2) 0.0031(19) 0.000(2) 0.006(2) C8 0.028(3) 0.026(2) 0.030(2) 0.0025(18) 0.001(2) 0.0047(19) C9 0.028(3) 0.038(2) 0.028(2) 0.005(2) -0.002(2) 0.005(2) C10 0.030(3) 0.034(2) 0.032(2) -0.0020(19) -0.002(2) 0.002(2) C11 0.044(3) 0.040(2) 0.035(2) -0.001(2) 0.000(2) 0.009(2) C12 0.051(3) 0.048(3) 0.029(2) -0.001(2) -0.004(3) 0.001(3) C13 0.032(3) 0.047(3) 0.041(2) -0.013(2) -0.002(2) -0.007(3) C14 0.042(3) 0.040(2) 0.051(3) -0.010(2) -0.005(3) 0.005(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 Cl1 C5 1.726(4) . ? Cl2 C6 1.736(4) . ? O1 C2 1.218(5) . ? O2 C9 1.197(5) . ? O3 C10 1.422(5) . ? O3 C14 1.436(4) . ? O4 C13 1.214(5) . ? N1 C2 1.396(5) . ? N1 C9 1.419(5) . ? N1 C10 1.446(5) . ? C2 C3 1.482(5) . ? C3 C8 1.380(5) . ? C3 C4 1.384(5) . ? C4 C5 1.386(5) . ? C4 H4 0.9500 . ? C5 C6 1.400(5) . ? C6 C7 1.382(5) . ? C7 C8 1.389(5) . ? C7 H7 0.9500 . ? C8 C9 1.486(5) . ? C10 C11 1.486(5) . ? C10 H10 1.0000 . ? C11 C12 1.322(5) . ? C11 H11 0.9500 . ? C12 C13 1.453(6) . ? C12 H12 0.9500 . ? C13 C14 1.505(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 C10 O3 C14 112.0(3) . . ? C2 N1 C9 112.0(3) . . ? C2 N1 C10 126.5(3) . . ? C9 N1 C10 121.4(3) . . ? O1 C2 N1 125.4(3) . . ? O1 C2 C3 128.9(4) . . ? N1 C2 C3 105.7(3) . . ? C8 C3 C4 122.0(3) . . ? C8 C3 C2 108.7(4) . . ? C4 C3 C2 129.2(4) . . ? C3 C4 C5 117.0(4) . . ? C3 C4 H4 121.5 . . ? C5 C4 H4 121.5 . . ? C4 C5 C6 121.0(4) . . ? C4 C5 Cl1 118.2(3) . . ? C6 C5 Cl1 120.8(3) . . ? C7 C6 C5 121.5(3) . . ? C7 C6 Cl2 118.7(3) . . ? C5 C6 Cl2 119.8(3) . . ? C6 C7 C8 117.1(4) . . ? C6 C7 H7 121.4 . . ? C8 C7 H7 121.4 . . ? C3 C8 C7 121.3(4) . . ? C3 C8 C9 108.7(3) . . ? C7 C8 C9 130.0(4) . . ? O2 C9 N1 124.8(4) . . ? O2 C9 C8 130.3(4) . . ? N1 C9 C8 104.9(4) . . ? O3 C10 N1 106.5(3) . . ? O3 C10 C11 112.3(4) . . ? N1 C10 C11 113.2(3) . . ? O3 C10 H10 108.3 . . ? N1 C10 H10 108.3 . . ? C11 C10 H10 108.3 . . ? C12 C11 C10 121.9(4) . . ? C12 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? C11 C12 C13 120.9(4) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? O4 C13 C12 123.6(4) . . ? O4 C13 C14 121.1(4) . . ? C12 C13 C14 115.4(4) . . ? O3 C14 C13 112.3(3) . . ? O3 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? O3 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? 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 C9 N1 C2 O1 -179.7(4) . . . . ? C10 N1 C2 O1 3.8(7) . . . . ? C9 N1 C2 C3 1.4(4) . . . . ? C10 N1 C2 C3 -175.1(4) . . . . ? O1 C2 C3 C8 -179.3(5) . . . . ? N1 C2 C3 C8 -0.4(5) . . . . ? O1 C2 C3 C4 1.7(8) . . . . ? N1 C2 C3 C4 -179.5(4) . . . . ? C8 C3 C4 C5 1.9(6) . . . . ? C2 C3 C4 C5 -179.1(4) . . . . ? C3 C4 C5 C6 -0.6(6) . . . . ? C3 C4 C5 Cl1 -179.2(3) . . . . ? C4 C5 C6 C7 -0.6(6) . . . . ? Cl1 C5 C6 C7 177.9(3) . . . . ? C4 C5 C6 Cl2 177.6(3) . . . . ? Cl1 C5 C6 Cl2 -3.8(5) . . . . ? C5 C6 C7 C8 0.5(6) . . . . ? Cl2 C6 C7 C8 -177.7(3) . . . . ? C4 C3 C8 C7 -2.1(7) . . . . ? C2 C3 C8 C7 178.7(4) . . . . ? C4 C3 C8 C9 178.5(4) . . . . ? C2 C3 C8 C9 -0.7(5) . . . . ? C6 C7 C8 C3 0.8(6) . . . . ? C6 C7 C8 C9 -179.9(4) . . . . ? C2 N1 C9 O2 176.4(4) . . . . ? C10 N1 C9 O2 -6.9(6) . . . . ? C2 N1 C9 C8 -1.8(4) . . . . ? C10 N1 C9 C8 174.9(4) . . . . ? C3 C8 C9 O2 -176.5(4) . . . . ? C7 C8 C9 O2 4.1(8) . . . . ? C3 C8 C9 N1 1.5(5) . . . . ? C7 C8 C9 N1 -177.9(4) . . . . ? C14 O3 C10 N1 -176.0(3) . . . . ? C14 O3 C10 C11 -51.6(4) . . . . ? C2 N1 C10 O3 80.8(4) . . . . ? C9 N1 C10 O3 -95.4(4) . . . . ? C2 N1 C10 C11 -43.0(6) . . . . ? C9 N1 C10 C11 140.8(4) . . . . ? O3 C10 C11 C12 22.3(6) . . . . ? N1 C10 C11 C12 142.9(5) . . . . ? C10 C11 C12 C13 1.9(7) . . . . ? C11 C12 C13 O4 -178.4(5) . . . . ? C11 C12 C13 C14 3.1(6) . . . . ? C10 O3 C14 C13 57.1(5) . . . . ? O4 C13 C14 O3 149.4(4) . . . . ? C12 C13 C14 O3 -32.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.309 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.075