data_a loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 8 _journal_issue 4 _journal_year 2017 _journal_page_first 422 _journal_page_last 429 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H9 Cl N2 O4' _chemical_formula_sum 'C16 H9 Cl N2 O4' _chemical_formula_weight 328.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.4835(6) _cell_length_b 16.3002(15) _cell_length_c 13.5332(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.264(2) _cell_angle_gamma 90.00 _cell_volume 1424.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1298 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 22.07 _exptl_crystal_description 'BLOCK' _exptl_crystal_colour 'COLORLES' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9118 _exptl_absorpt_correction_T_max 0.9637 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 SMART APEX CCD area-detector diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8330 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2647 _reflns_number_gt 1722 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009) ; _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^)+(0.0623P)^2^+1.0421P] 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 2647 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.840 _refine_ls_restrained_S_all 0.840 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.20755(16) 0.56195(7) 0.98360(6) 0.0909(4) Uani 1 1 d . . . O3 O 0.1101(3) 0.62762(12) 0.61024(11) 0.0497(5) Uani 1 1 d . . . C4 C -0.0261(4) 0.59844(15) 0.34022(16) 0.0383(6) Uani 1 1 d . . . O4 O 0.3542(3) 0.71765(12) 0.57226(12) 0.0542(5) Uani 1 1 d . . . C9 C 0.0062(4) 0.63508(16) 0.51583(17) 0.0417(6) Uani 1 1 d . . . C8 C 0.0849(4) 0.59435(15) 0.43550(17) 0.0383(6) Uani 1 1 d . . . N1 N -0.3525(3) 0.64604(16) 0.24081(17) 0.0545(6) Uani 1 1 d . . . C11 C 0.3747(4) 0.65931(15) 0.73423(17) 0.0389(6) Uani 1 1 d . . . C3 C -0.2181(4) 0.64149(16) 0.33485(17) 0.0419(6) Uani 1 1 d . . . C10 C 0.2860(4) 0.67295(16) 0.63044(17) 0.0410(6) Uani 1 1 d . . . N2 N 0.2675(3) 0.55286(14) 0.45358(16) 0.0481(6) Uani 1 1 d . . . O2 O -0.4813(3) 0.70059(14) 0.23139(16) 0.0754(7) Uani 1 1 d . . . C12 C 0.2651(4) 0.61820(16) 0.80168(17) 0.0462(6) Uani 1 1 d . . . H12A H 0.1354 0.5962 0.7821 0.055 Uiso 1 1 calc R . . C5 C 0.0688(4) 0.56138(17) 0.26137(18) 0.0489(7) Uani 1 1 d . . . H5A H 0.0066 0.5644 0.1968 0.059 Uiso 1 1 calc R . . C7 C 0.3435(4) 0.51735(18) 0.3781(2) 0.0555(7) Uani 1 1 d . . . H7A H 0.4659 0.4877 0.3899 0.067 Uiso 1 1 calc R . . C1 C -0.1749(4) 0.67631(18) 0.50629(18) 0.0514(7) Uani 1 1 d . . . H1A H -0.2230 0.7025 0.5607 0.062 Uiso 1 1 calc R . . C16 C 0.5675(4) 0.69167(17) 0.76436(19) 0.0502(7) Uani 1 1 d . . . H16A H 0.6410 0.7201 0.7194 0.060 Uiso 1 1 calc R . . C2 C -0.2890(4) 0.67915(18) 0.41401(19) 0.0510(7) Uani 1 1 d . . . H2B H -0.4145 0.7071 0.4068 0.061 Uiso 1 1 calc R . . C13 C 0.3503(5) 0.61013(18) 0.89848(18) 0.0539(7) Uani 1 1 d . . . C6 C 0.2508(4) 0.52151(19) 0.2809(2) 0.0568(8) Uani 1 1 d . . . H6A H 0.3143 0.4969 0.2296 0.068 Uiso 1 1 calc R . . C15 C 0.6508(4) 0.68178(19) 0.8610(2) 0.0599(8) Uani 1 1 d . . . H15A H 0.7815 0.7028 0.8805 0.072 Uiso 1 1 calc R . . O1 O -0.3348(4) 0.59360(17) 0.17803(16) 0.0843(8) Uani 1 1 d . . . C14 C 0.5435(5) 0.64139(19) 0.9287(2) 0.0588(8) Uani 1 1 d . . . H14A H 0.6000 0.6351 0.9940 0.071 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 0.1097(8) 0.1181(9) 0.0447(4) 0.0213(5) 0.0057(4) -0.0323(6) O3 0.0513(11) 0.0652(13) 0.0310(9) 0.0047(8) -0.0044(8) -0.0145(9) C4 0.0380(14) 0.0404(15) 0.0356(12) 0.0025(11) -0.0012(10) -0.0075(11) O4 0.0542(12) 0.0650(14) 0.0431(10) 0.0109(9) 0.0025(9) -0.0110(9) C9 0.0406(14) 0.0520(17) 0.0317(12) 0.0017(11) -0.0017(10) -0.0078(12) C8 0.0365(13) 0.0400(14) 0.0375(13) 0.0044(11) -0.0009(10) -0.0050(10) N1 0.0454(14) 0.0678(18) 0.0477(14) 0.0098(13) -0.0100(11) -0.0055(12) C11 0.0432(14) 0.0401(14) 0.0329(12) -0.0036(10) 0.0012(10) 0.0011(11) C3 0.0371(14) 0.0485(16) 0.0385(13) 0.0072(11) -0.0044(10) -0.0060(11) C10 0.0375(14) 0.0473(16) 0.0382(13) -0.0014(12) 0.0039(11) 0.0005(11) N2 0.0427(12) 0.0476(14) 0.0517(13) 0.0008(11) -0.0077(10) 0.0033(10) O2 0.0556(13) 0.0812(17) 0.0838(15) 0.0158(12) -0.0237(11) 0.0102(12) C12 0.0500(15) 0.0498(17) 0.0378(13) -0.0023(12) -0.0018(11) -0.0059(12) C5 0.0549(17) 0.0543(17) 0.0371(13) -0.0043(12) 0.0020(12) -0.0069(13) C7 0.0471(16) 0.0492(18) 0.070(2) -0.0065(15) 0.0042(14) 0.0064(13) C1 0.0478(16) 0.066(2) 0.0412(14) -0.0056(13) 0.0087(12) 0.0029(13) C16 0.0488(16) 0.0585(18) 0.0432(14) -0.0061(13) 0.0029(12) -0.0083(13) C2 0.0368(14) 0.0637(19) 0.0523(16) 0.0018(14) 0.0026(12) 0.0063(12) C13 0.0689(19) 0.0543(19) 0.0380(14) 0.0035(12) 0.0019(13) -0.0041(14) C6 0.0548(18) 0.059(2) 0.0575(18) -0.0135(14) 0.0120(14) 0.0009(14) C15 0.0496(17) 0.078(2) 0.0495(16) -0.0118(15) -0.0081(13) -0.0079(15) O1 0.0800(16) 0.115(2) 0.0528(13) -0.0157(14) -0.0230(11) 0.0111(14) C14 0.069(2) 0.067(2) 0.0375(14) -0.0060(14) -0.0133(13) 0.0020(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 C13 1.731(3) . ? O3 C10 1.365(3) . ? O3 C9 1.394(3) . ? C4 C5 1.415(3) . ? C4 C8 1.420(3) . ? C4 C3 1.425(3) . ? O4 C10 1.188(3) . ? C9 C1 1.348(4) . ? C9 C8 1.409(3) . ? C8 N2 1.366(3) . ? N1 O2 1.219(3) . ? N1 O1 1.218(3) . ? N1 C3 1.477(3) . ? C11 C12 1.381(3) . ? C11 C16 1.383(3) . ? C11 C10 1.485(3) . ? C3 C2 1.351(4) . ? N2 C7 1.309(3) . ? C12 C13 1.381(3) . ? C5 C6 1.352(4) . ? C7 C6 1.397(4) . ? C1 C2 1.393(4) . ? C16 C15 1.378(4) . ? C13 C14 1.379(4) . ? C15 C14 1.369(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 C10 O3 C9 117.45(19) . . ? C5 C4 C8 116.4(2) . . ? C5 C4 C3 127.6(2) . . ? C8 C4 C3 115.9(2) . . ? C1 C9 O3 118.3(2) . . ? C1 C9 C8 122.3(2) . . ? O3 C9 C8 119.2(2) . . ? N2 C8 C9 117.7(2) . . ? N2 C8 C4 123.0(2) . . ? C9 C8 C4 119.3(2) . . ? O2 N1 O1 123.1(2) . . ? O2 N1 C3 118.1(3) . . ? O1 N1 C3 118.7(2) . . ? C12 C11 C16 119.8(2) . . ? C12 C11 C10 121.3(2) . . ? C16 C11 C10 118.9(2) . . ? C2 C3 C4 122.8(2) . . ? C2 C3 N1 116.4(2) . . ? C4 C3 N1 120.8(2) . . ? O4 C10 O3 123.7(2) . . ? O4 C10 C11 125.7(2) . . ? O3 C10 C11 110.6(2) . . ? C7 N2 C8 117.5(2) . . ? C11 C12 C13 119.2(2) . . ? C6 C5 C4 119.3(2) . . ? N2 C7 C6 123.6(3) . . ? C9 C1 C2 119.2(2) . . ? C15 C16 C11 120.0(3) . . ? C3 C2 C1 120.3(2) . . ? C14 C13 C12 121.3(3) . . ? C14 C13 Cl1 119.8(2) . . ? C12 C13 Cl1 118.9(2) . . ? C5 C6 C7 120.0(3) . . ? C14 C15 C16 120.9(3) . . ? C15 C14 C13 118.9(2) . . ? 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 C10 O3 C9 C1 -107.5(3) . . . . ? C10 O3 C9 C8 77.3(3) . . . . ? C1 C9 C8 N2 -178.6(2) . . . . ? O3 C9 C8 N2 -3.6(3) . . . . ? C1 C9 C8 C4 1.8(4) . . . . ? O3 C9 C8 C4 176.9(2) . . . . ? C5 C4 C8 N2 -4.1(4) . . . . ? C3 C4 C8 N2 177.6(2) . . . . ? C5 C4 C8 C9 175.5(2) . . . . ? C3 C4 C8 C9 -2.9(3) . . . . ? C5 C4 C3 C2 -175.7(3) . . . . ? C8 C4 C3 C2 2.4(4) . . . . ? C5 C4 C3 N1 5.1(4) . . . . ? C8 C4 C3 N1 -176.8(2) . . . . ? O2 N1 C3 C2 21.1(4) . . . . ? O1 N1 C3 C2 -156.2(3) . . . . ? O2 N1 C3 C4 -159.7(2) . . . . ? O1 N1 C3 C4 23.0(4) . . . . ? C9 O3 C10 O4 -0.2(4) . . . . ? C9 O3 C10 C11 178.8(2) . . . . ? C12 C11 C10 O4 167.9(3) . . . . ? C16 C11 C10 O4 -9.3(4) . . . . ? C12 C11 C10 O3 -11.1(3) . . . . ? C16 C11 C10 O3 171.7(2) . . . . ? C9 C8 N2 C7 -177.8(2) . . . . ? C4 C8 N2 C7 1.7(4) . . . . ? C16 C11 C12 C13 0.0(4) . . . . ? C10 C11 C12 C13 -177.2(2) . . . . ? C8 C4 C5 C6 3.1(4) . . . . ? C3 C4 C5 C6 -178.7(3) . . . . ? C8 N2 C7 C6 1.6(4) . . . . ? O3 C9 C1 C2 -175.1(2) . . . . ? C8 C9 C1 C2 -0.1(4) . . . . ? C12 C11 C16 C15 0.9(4) . . . . ? C10 C11 C16 C15 178.2(3) . . . . ? C4 C3 C2 C1 -0.8(4) . . . . ? N1 C3 C2 C1 178.4(2) . . . . ? C9 C1 C2 C3 -0.5(4) . . . . ? C11 C12 C13 C14 -0.8(4) . . . . ? C11 C12 C13 Cl1 177.6(2) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? N2 C7 C6 C5 -2.5(5) . . . . ? C11 C16 C15 C14 -1.1(4) . . . . ? C16 C15 C14 C13 0.4(5) . . . . ? C12 C13 C14 C15 0.6(5) . . . . ? Cl1 C13 C14 C15 -177.7(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.299 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.038