# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2018 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_p21c _database_code_depnum_ccdc_archive 'CCDC 1589617' _audit_update_record ; 2017-12-06 deposited with the CCDC. 2018-01-22 downloaded from the CCDC. ; _audit_creation_date 2016-02-26T09:53:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ethyl 2-(5-(4-nitrophenyl)isoxazol-4-yl)-2-oxoacetate ; _chemical_name_common 'ethyl 2-(5-(4-nitrophenyl)isoxazol-4-yl)-2-ox' _chemical_formula_moiety 'C13 H10 N2 O6' _chemical_formula_sum 'C13 H10 N2 O6' _chemical_formula_weight 290.23 _chemical_melting_point none #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P2ybc 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 12.6326(13) _cell_length_b 14.5578(13) _cell_length_c 7.3585(7) _cell_angle_alpha 90 _cell_angle_beta 106.635(3) _cell_angle_gamma 90 _cell_volume 1296.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 9900 _cell_measurement_theta_min 2.918 _cell_measurement_theta_max 24.84 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_special_details ; none ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.12 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical absorption correction based on the indexed faces of the crystal. ; _exptl_absorpt_correction_T_min 0.9666 _exptl_absorpt_correction_T_max 0.9887 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'micro-focus tube' _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'Montel type 2-dim beam shaping X ray optics' _diffrn_detector_area_resol_mean 10.4167 _diffrn_measurement_device_type 'Bruker D8 Quest Photon 100 diffractometer' _diffrn_measurement_method '2\% \f & \w scans' _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_unetI/netI 0.0159 _diffrn_reflns_number 87599 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 30.58 _diffrn_reflns_theta_full 30.58 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 3988 _reflns_number_gt 2971 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker Instrument Service v4.2.7' _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_structure_solution 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond (version 3.2i; Crystal Impact G' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0964P)^2^+0.4367P] 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 none _refine_ls_number_reflns 3988 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1774 _refine_ls_wR_factor_gt 0.1607 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.343 _refine_diff_density_min -0.27 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O1 O 0.34502(10) 0.51702(9) 0.25844(16) 0.0510(3) Uani 1 1 d . . . O43 O 0.69463(10) 0.78833(9) 0.5020(2) 0.0586(4) Uani 1 1 d . . . O41 O 0.50967(11) 0.74539(9) 0.5829(2) 0.0589(4) Uani 1 1 d . . . O42 O 0.71555(11) 0.63897(9) 0.4504(2) 0.0597(4) Uani 1 1 d . . . N2 N 0.42424(13) 0.50657(11) 0.1570(2) 0.0534(4) Uani 1 1 d . . . C4 C 0.47912(12) 0.61585(9) 0.38300(19) 0.0356(3) Uani 1 1 d . . . C41 C 0.54340(12) 0.69231(10) 0.4862(2) 0.0380(3) Uani 1 1 d . . . C42 C 0.66189(12) 0.70282(11) 0.4735(2) 0.0404(3) Uani 1 1 d . . . C5 C 0.37914(12) 0.58282(10) 0.39092(19) 0.0380(3) Uani 1 1 d . . . O541 O 0.11513(17) 0.67235(16) 0.9859(3) 0.0972(6) Uani 1 1 d . . . C3 C 0.50124(14) 0.56463(10) 0.2325(2) 0.0424(3) Uani 1 1 d . . . H3 H 0.5644 0.5723 0.1932 0.051 Uiso 1 1 calc R . . C51 C 0.30289(12) 0.60068(10) 0.5044(2) 0.0392(3) Uani 1 1 d . . . C53 C 0.26787(14) 0.64804(12) 0.7951(2) 0.0472(4) Uani 1 1 d . . . H53 H 0.2925 0.6704 0.9185 0.057 Uiso 1 1 calc R . . C52 C 0.34092(13) 0.63346(11) 0.6892(2) 0.0435(3) Uani 1 1 d . . . H52 H 0.4157 0.6456 0.7419 0.052 Uiso 1 1 calc R . . C54 C 0.15785(14) 0.62862(12) 0.7131(3) 0.0488(4) Uani 1 1 d . . . C56 C 0.19126(14) 0.58108(14) 0.4267(3) 0.0544(4) Uani 1 1 d . . . H56 H 0.1659 0.5582 0.3039 0.065 Uiso 1 1 calc R . . C55 C 0.11804(15) 0.59566(15) 0.5318(3) 0.0597(5) Uani 1 1 d . . . H55 H 0.0432 0.5833 0.4806 0.072 Uiso 1 1 calc R . . C44 C 0.80710(16) 0.80893(17) 0.4988(4) 0.0715(6) Uani 1 1 d . . . H44A H 0.8093 0.8165 0.369 0.086 Uiso 1 1 calc R . . H44B H 0.856 0.7588 0.5555 0.086 Uiso 1 1 calc R . . C45 C 0.84309(17) 0.89357(17) 0.6056(3) 0.0702(6) Uani 1 1 d . . . H45A H 0.9172 0.9078 0.6051 0.105 Uiso 1 1 calc R . . H45B H 0.8408 0.8855 0.7339 0.105 Uiso 1 1 calc R . . H45C H 0.7948 0.943 0.5478 0.105 Uiso 1 1 calc R . . N451 N 0.08027(15) 0.64200(14) 0.8255(3) 0.0691(5) Uani 1 1 d . . . O542 O -0.01560(15) 0.6192(2) 0.7544(3) 0.1268(10) 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 O1 0.0585(7) 0.0525(7) 0.0445(6) -0.0155(5) 0.0188(5) -0.0139(5) O43 0.0429(6) 0.0490(7) 0.0884(10) -0.0130(6) 0.0262(6) -0.0101(5) O41 0.0592(7) 0.0524(7) 0.0769(9) -0.0295(6) 0.0385(7) -0.0145(6) O42 0.0524(7) 0.0543(7) 0.0788(9) -0.0043(6) 0.0292(7) 0.0082(6) N2 0.0674(9) 0.0544(8) 0.0432(7) -0.0153(6) 0.0234(7) -0.0076(7) C4 0.0440(7) 0.0333(6) 0.0316(6) 0.0004(5) 0.0144(5) 0.0008(5) C41 0.0418(7) 0.0361(7) 0.0386(7) -0.0023(5) 0.0156(6) -0.0008(5) C42 0.0409(7) 0.0436(8) 0.0380(7) -0.0007(6) 0.0133(6) -0.0004(6) C5 0.0449(7) 0.0381(7) 0.0305(6) -0.0022(5) 0.0097(5) -0.0030(5) O541 0.1023(13) 0.1234(16) 0.0885(13) -0.0226(12) 0.0634(11) -0.0091(12) C3 0.0550(8) 0.0408(7) 0.0348(7) -0.0032(6) 0.0182(6) 0.0011(6) C51 0.0415(7) 0.0400(7) 0.0370(7) 0.0017(5) 0.0129(6) -0.0022(6) C53 0.0528(9) 0.0506(9) 0.0417(8) -0.0017(7) 0.0191(7) 0.0003(7) C52 0.0416(7) 0.0498(8) 0.0401(7) -0.0022(6) 0.0132(6) -0.0043(6) C54 0.0478(8) 0.0524(9) 0.0526(9) 0.0098(7) 0.0247(7) 0.0074(7) C56 0.0454(8) 0.0743(12) 0.0414(8) -0.0032(8) 0.0091(7) -0.0084(8) C55 0.0385(8) 0.0839(13) 0.0557(10) 0.0048(9) 0.0118(7) -0.0023(8) C44 0.0508(10) 0.0809(14) 0.0933(16) -0.0235(12) 0.0375(11) -0.0225(10) C45 0.0523(10) 0.0870(15) 0.0711(13) -0.0065(11) 0.0171(9) -0.0253(10) N451 0.0604(10) 0.0848(13) 0.0736(12) 0.0110(10) 0.0374(9) 0.0138(9) O542 0.0539(10) 0.228(3) 0.1113(16) -0.0132(17) 0.0445(11) 0.0031(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 C5 1.3466(18) . ? O1 N2 1.4177(19) . ? O43 C42 1.310(2) . ? O43 C44 1.459(2) . ? O41 C41 1.2078(18) . ? O42 C42 1.1908(19) . ? N2 C3 1.288(2) . ? C4 C5 1.368(2) . ? C4 C3 1.428(2) . ? C4 C41 1.457(2) . ? C41 C42 1.534(2) . ? C5 C51 1.467(2) . ? O541 N451 1.218(3) . ? C51 C56 1.391(2) . ? C51 C52 1.391(2) . ? C53 C54 1.377(2) . ? C53 C52 1.384(2) . ? C54 C55 1.370(3) . ? C54 N451 1.465(2) . ? C56 C55 1.382(3) . ? C44 C45 1.462(3) . ? N451 O542 1.220(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 C5 O1 N2 109.25(12) . . ? C42 O43 C44 117.20(15) . . ? C3 N2 O1 105.20(12) . . ? C5 C4 C3 103.75(13) . . ? C5 C4 C41 129.04(13) . . ? C3 C4 C41 126.86(13) . . ? O41 C41 C4 123.92(14) . . ? O41 C41 C42 119.15(13) . . ? C4 C41 C42 116.90(12) . . ? O42 C42 O43 126.75(15) . . ? O42 C42 C41 122.42(14) . . ? O43 C42 C41 110.73(13) . . ? O1 C5 C4 109.10(13) . . ? O1 C5 C51 114.32(13) . . ? C4 C5 C51 136.58(13) . . ? N2 C3 C4 112.69(15) . . ? C56 C51 C52 119.89(14) . . ? C56 C51 C5 118.87(14) . . ? C52 C51 C5 121.20(13) . . ? C54 C53 C52 118.29(15) . . ? C53 C52 C51 120.25(15) . . ? C55 C54 C53 122.81(16) . . ? C55 C54 N451 118.54(17) . . ? C53 C54 N451 118.65(17) . . ? C55 C56 C51 120.03(16) . . ? C54 C55 C56 118.74(16) . . ? O43 C44 C45 108.60(17) . . ? O542 N451 O541 123.6(2) . . ? O542 N451 C54 117.6(2) . . ? O541 N451 C54 118.72(19) . . ? ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_p-1 _database_code_depnum_ccdc_archive 'CCDC 1589620' _audit_update_record ; 2017-12-06 deposited with the CCDC. 2018-01-22 downloaded from the CCDC. ; _audit_creation_date 2016-03-16T17:29:23-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ethyl 4-formyl-5-(4-nitrophenyl)isozaxole-3-carboxylate ; _chemical_name_common 'ethyl 4-formyl-5-(4-nitrophenyl)isozaxole-3-carboxylate' _chemical_formula_moiety 'C13 H10 N2 O6' _chemical_formula_sum 'C13 H10 N2 O6' _chemical_formula_weight 290.23 _chemical_melting_point none #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8104(5) _cell_length_b 8.2881(8) _cell_length_c 13.1190(12) _cell_angle_alpha 89.312(3) _cell_angle_beta 82.695(3) _cell_angle_gamma 85.322(3) _cell_volume 624.56(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7233 _cell_measurement_theta_min 2.464 _cell_measurement_theta_max 30.346 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_special_details ; none ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical absorption correction based on the indexed faces of the crystal. ; _exptl_absorpt_correction_T_min 0.9348 _exptl_absorpt_correction_T_max 0.9691 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'micro-focus tube' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'Montel type 2-dim beam shaping X ray optics' _diffrn_detector_area_resol_mean 10.4167 _diffrn_measurement_device_type 'Bruker D8 Venture Photon 100 diffractometer' _diffrn_measurement_method '2\% \f & \w scans' _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_unetI/netI 0.1047 _diffrn_reflns_number 6648 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 29.98 _diffrn_reflns_theta_full 29.98 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 3625 _reflns_number_gt 2149 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker Instrument Service v4.2.7' _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_structure_solution 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond (version 3.2i; Crystal Impact G' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0564P)^2^+0.0840P] 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 none _refine_ls_number_reflns 3625 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1191 _refine_ls_R_factor_gt 0.056 _refine_ls_wR_factor_ref 0.1556 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.287 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.069 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O1 O 0.8431(2) 0.65307(16) 0.44238(10) 0.0233(3) Uani 1 1 d . . . O32 O 1.1222(2) 0.80434(17) 0.16572(11) 0.0282(4) Uani 1 1 d . . . O42 O 0.2463(2) 0.99076(16) 0.39248(11) 0.0282(4) Uani 1 1 d . . . O31 O 0.7960(3) 0.96750(19) 0.16051(12) 0.0360(4) Uani 1 1 d . . . O542 O 0.1631(3) 0.4726(2) 0.88019(12) 0.0382(4) Uani 1 1 d . . . O541 O -0.1005(3) 0.6623(2) 0.85223(13) 0.0457(5) Uani 1 1 d . . . N2 N 0.9688(3) 0.6922(2) 0.34828(13) 0.0239(4) Uani 1 1 d . . . N541 N 0.0872(3) 0.5855(2) 0.82968(13) 0.0295(4) Uani 1 1 d . . . C51 C 0.4891(3) 0.7034(2) 0.55103(15) 0.0188(4) Uani 1 1 d . . . C53 C 0.1322(3) 0.7360(2) 0.66725(16) 0.0234(4) Uani 1 1 d . . . H53 H -0.022 0.7837 0.6845 0.028 Uiso 1 1 calc R . . C5 C 0.6322(3) 0.7390(2) 0.45429(15) 0.0194(4) Uani 1 1 d . . . C56 C 0.5861(3) 0.5972(2) 0.62112(15) 0.0207(4) Uani 1 1 d . . . H56 H 0.7414 0.5508 0.6053 0.025 Uiso 1 1 calc R . . C4 C 0.6137(3) 0.8349(2) 0.36860(15) 0.0198(4) Uani 1 1 d . . . C3 C 0.8323(3) 0.7987(2) 0.30629(15) 0.0213(4) Uani 1 1 d . . . C52 C 0.2616(3) 0.7726(2) 0.57482(15) 0.0214(4) Uani 1 1 d . . . H52 H 0.1954 0.8448 0.5277 0.026 Uiso 1 1 calc R . . C55 C 0.4568(3) 0.5594(2) 0.71350(15) 0.0225(4) Uani 1 1 d . . . H55 H 0.5213 0.4877 0.7614 0.027 Uiso 1 1 calc R . . C54 C 0.2315(3) 0.6291(2) 0.73371(15) 0.0221(4) Uani 1 1 d . . . C31 C 0.9127(3) 0.8680(2) 0.20270(15) 0.0238(4) Uani 1 1 d . . . C41 C 0.4261(3) 0.9494(2) 0.33969(16) 0.0251(5) Uani 1 1 d . . . H41 H 0.4488 0.9953 0.2728 0.03 Uiso 1 1 calc R . . C33 C 1.2008(4) 0.8516(3) 0.05982(16) 0.0328(5) Uani 1 1 d . . . H33A H 1.2362 0.9665 0.0573 0.039 Uiso 1 1 calc R . . H33B H 1.0778 0.8381 0.0156 0.039 Uiso 1 1 calc R . . C34 C 1.4132(4) 0.7458(3) 0.02328(18) 0.0396(6) Uani 1 1 d . . . H34A H 1.4699 0.7748 -0.0476 0.059 Uiso 1 1 calc R . . H34B H 1.3761 0.6325 0.0259 0.059 Uiso 1 1 calc R . . H34C H 1.5339 0.7604 0.0674 0.059 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 O1 0.0206(7) 0.0227(7) 0.0255(8) 0.0060(6) -0.0030(5) 0.0042(5) O32 0.0260(7) 0.0330(8) 0.0235(8) 0.0054(6) 0.0003(6) 0.0035(6) O42 0.0235(7) 0.0233(8) 0.0370(9) 0.0047(6) -0.0055(6) 0.0046(6) O31 0.0368(9) 0.0358(9) 0.0318(9) 0.0133(7) 0.0001(7) 0.0096(7) O542 0.0372(9) 0.0488(11) 0.0287(9) 0.0131(8) -0.0072(7) -0.0007(7) O541 0.0305(9) 0.0625(12) 0.0384(10) 0.0073(9) 0.0083(7) 0.0102(8) N2 0.0224(8) 0.0257(9) 0.0228(9) 0.0052(7) -0.0018(7) 0.0002(7) N541 0.0272(9) 0.0402(11) 0.0215(9) 0.0002(8) -0.0043(7) -0.0037(8) C51 0.0198(9) 0.0147(9) 0.0227(10) 0.0000(7) -0.0061(7) -0.0014(7) C53 0.0200(9) 0.0211(10) 0.0293(11) -0.0013(8) -0.0042(8) -0.0003(7) C5 0.0187(9) 0.0153(9) 0.0248(10) -0.0002(8) -0.0069(7) 0.0013(7) C56 0.0179(9) 0.0178(9) 0.0269(11) 0.0001(8) -0.0060(8) 0.0009(7) C4 0.0201(9) 0.0176(9) 0.0228(10) -0.0016(8) -0.0070(7) -0.0014(7) C3 0.0238(9) 0.0153(9) 0.0253(10) 0.0010(8) -0.0058(8) -0.0011(7) C52 0.0235(9) 0.0162(10) 0.0255(10) 0.0022(8) -0.0084(8) -0.0002(7) C55 0.0255(10) 0.0208(10) 0.0228(10) 0.0028(8) -0.0097(8) -0.0012(8) C54 0.0221(9) 0.0234(10) 0.0209(10) 0.0008(8) -0.0035(8) -0.0023(8) C31 0.0260(10) 0.0207(10) 0.0246(11) 0.0012(8) -0.0044(8) 0.0009(8) C41 0.0266(10) 0.0238(11) 0.0257(11) 0.0058(8) -0.0076(8) -0.0007(8) C33 0.0341(12) 0.0375(13) 0.0242(11) 0.0054(10) 0.0021(9) 0.0026(10) C34 0.0309(12) 0.0498(15) 0.0349(13) 0.0011(11) 0.0025(10) 0.0055(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 C5 1.358(2) . ? O1 N2 1.4009(19) . ? O32 C31 1.322(2) . ? O32 C33 1.465(2) . ? O42 C41 1.205(2) . ? O31 C31 1.200(2) . ? O542 N541 1.225(2) . ? O541 N541 1.221(2) . ? N2 C3 1.303(3) . ? N541 C54 1.479(2) . ? C51 C52 1.396(3) . ? C51 C56 1.404(3) . ? C51 C5 1.467(3) . ? C53 C54 1.380(3) . ? C53 C52 1.387(3) . ? C5 C4 1.380(3) . ? C56 C55 1.389(3) . ? C4 C3 1.432(3) . ? C4 C41 1.469(3) . ? C3 C31 1.503(3) . ? C55 C54 1.382(3) . ? C33 C34 1.485(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 C5 O1 N2 109.98(14) . . ? C31 O32 C33 114.59(16) . . ? C3 N2 O1 105.15(15) . . ? O541 N541 O542 124.55(17) . . ? O541 N541 C54 117.97(18) . . ? O542 N541 C54 117.47(17) . . ? C52 C51 C56 119.70(17) . . ? C52 C51 C5 121.85(18) . . ? C56 C51 C5 118.46(17) . . ? C54 C53 C52 118.79(18) . . ? O1 C5 C4 108.73(15) . . ? O1 C5 C51 113.20(16) . . ? C4 C5 C51 138.06(18) . . ? C55 C56 C51 120.49(17) . . ? C5 C4 C3 103.30(17) . . ? C5 C4 C41 132.28(17) . . ? C3 C4 C41 124.42(18) . . ? N2 C3 C4 112.84(17) . . ? N2 C3 C31 119.62(17) . . ? C4 C3 C31 127.53(18) . . ? C53 C52 C51 120.05(19) . . ? C54 C55 C56 118.05(18) . . ? C53 C54 C55 122.91(17) . . ? C53 C54 N541 118.06(17) . . ? C55 C54 N541 119.02(18) . . ? O31 C31 O32 125.72(18) . . ? O31 C31 C3 122.77(18) . . ? O32 C31 C3 111.51(18) . . ? O42 C41 C4 126.39(19) . . ? O32 C33 C34 107.65(18) . . ? ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_p-1_CCDC1 _database_code_depnum_ccdc_archive 'CCDC 1589618' _audit_update_record ; 2017-12-06 deposited with the CCDC. 2018-01-22 downloaded from the CCDC. ; _audit_creation_date 2015-11-24T09:56:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ethyl 4-(4-nitrobenzoyl)isoxazol-5-carboxylate ; _chemical_name_common 'ethyl 4-(4-nitrobenzoyl)isoxazol-5-carboxylate' _chemical_formula_moiety 'C13 H10 N2 O6' _chemical_formula_sum 'C13 H10 N2 O6' _chemical_formula_weight 290.23 _chemical_melting_point none #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6907(15) _cell_length_b 8.7715(16) _cell_length_c 12.002(4) _cell_angle_alpha 97.212(18) _cell_angle_beta 93.54(2) _cell_angle_gamma 107.759(18) _cell_volume 661.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9520 _cell_measurement_theta_min 3.731 _cell_measurement_theta_max 72.237 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_special_details ; none ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.011 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical absorption correction based on the indexed faces of the crystal. ; _exptl_absorpt_correction_T_min 0.659 _exptl_absorpt_correction_T_max 0.8234 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'micro-focus tube' _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator 'Montel type 2-dim beam shaping X ray optics' _diffrn_detector_area_resol_mean 10.4167 _diffrn_measurement_device_type 'Bruker D8 Quest Photon 100 diffractometer' _diffrn_measurement_method '2\% \f & \w scans' _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_unetI/netI 0.0308 _diffrn_reflns_number 20722 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 72.58 _diffrn_reflns_theta_full 72.58 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2633 _reflns_number_gt 1815 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker Instrument Service v4.2.7' _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_structure_solution 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond (version 3.2i; Crystal Impact G' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0871P)^2^+0.2087P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.035(6) _refine_ls_number_reflns 2633 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.06 _refine_ls_wR_factor_ref 0.1853 _refine_ls_wR_factor_gt 0.1637 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.313 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.04 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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 O1 O 0.3366(3) 0.6470(2) 1.03853(14) 0.0764(6) Uani 1 1 d . . . O41 O 0.0730(3) 0.6050(2) 0.68629(16) 0.0860(6) Uani 1 1 d . . . O52 O 0.1010(4) 0.2812(2) 0.85824(16) 0.0902(7) Uani 1 1 d . . . O51 O 0.1828(4) 0.3247(3) 1.04585(18) 0.0963(7) Uani 1 1 d . . . O451 O 0.7366(4) 0.1351(3) 0.4990(2) 0.1049(8) Uani 1 1 d . . . O452 O 0.5144(4) 0.1279(3) 0.3578(2) 0.1155(9) Uani 1 1 d . . . N2 N 0.4072(4) 0.8034(3) 1.0109(2) 0.0833(7) Uani 1 1 d . . . N451 N 0.5874(5) 0.1686(3) 0.4571(2) 0.0851(7) Uani 1 1 d . . . C47 C 0.4931(4) 0.4296(3) 0.70467(19) 0.0618(6) Uani 1 1 d . . . H47 H 0.5559 0.4779 0.7771 0.074 Uiso 1 1 calc R . . C42 C 0.3090(4) 0.4539(3) 0.66366(18) 0.0554(6) Uani 1 1 d . . . C41 C 0.2092(4) 0.5606(3) 0.7301(2) 0.0593(6) Uani 1 1 d . . . C5 C 0.2643(4) 0.5410(3) 0.9416(2) 0.0608(6) Uani 1 1 d . . . C43 C 0.2158(4) 0.3816(3) 0.5555(2) 0.0665(7) Uani 1 1 d . . . H43 H 0.0914 0.397 0.5281 0.08 Uiso 1 1 calc R . . C51 C 0.1784(4) 0.3703(3) 0.9562(2) 0.0690(7) Uani 1 1 d . . . C4 C 0.2825(4) 0.6210(3) 0.85203(19) 0.0582(6) Uani 1 1 d . . . C44 C 0.3051(5) 0.2882(3) 0.4890(2) 0.0737(7) Uani 1 1 d . . . H44 H 0.2433 0.2404 0.4163 0.088 Uiso 1 1 calc R . . C3 C 0.3727(4) 0.7852(3) 0.9020(2) 0.0730(7) Uani 1 1 d . . . H3 H 0.4037 0.871 0.8609 0.088 Uiso 1 1 calc R . . C46 C 0.5840(4) 0.3335(3) 0.6381(2) 0.0676(7) Uani 1 1 d . . . H46 H 0.7066 0.3152 0.6652 0.081 Uiso 1 1 calc R . . C45 C 0.4882(4) 0.2660(3) 0.5311(2) 0.0661(7) Uani 1 1 d . . . C53 C 0.0232(8) 0.1064(4) 0.8580(4) 0.1330(16) Uani 1 1 d . . . H53A H 0.0974 0.0788 0.9205 0.16 Uiso 1 1 calc R . . H53B H -0.1258 0.0738 0.8682 0.16 Uiso 1 1 calc R . . C54 C 0.0527(9) 0.0234(4) 0.7573(4) 0.1364(16) Uani 1 1 d . . . H54A H 0.0046 -0.0909 0.7598 0.205 Uiso 1 1 calc R . . H54B H 0.1999 0.0569 0.7466 0.205 Uiso 1 1 calc R . . H54C H -0.026 0.0468 0.6957 0.205 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 O1 0.0907(13) 0.0830(13) 0.0575(10) -0.0054(8) 0.0034(9) 0.0374(10) O41 0.0894(13) 0.0897(14) 0.0825(13) 0.0010(10) -0.0199(10) 0.0442(11) O52 0.1249(17) 0.0575(11) 0.0791(13) 0.0045(9) 0.0342(11) 0.0131(10) O51 0.1154(17) 0.0998(16) 0.0823(14) 0.0327(12) 0.0274(12) 0.0359(13) O451 0.0999(17) 0.0916(16) 0.125(2) 0.0036(13) 0.0399(15) 0.0326(13) O452 0.1279(19) 0.1130(19) 0.0828(16) -0.0210(13) 0.0354(14) 0.0143(15) N2 0.0979(17) 0.0687(15) 0.0781(16) -0.0114(11) -0.0042(13) 0.0299(13) N451 0.0918(18) 0.0649(14) 0.0862(18) 0.0029(12) 0.0346(15) 0.0052(13) C47 0.0653(14) 0.0668(15) 0.0503(12) 0.0076(10) 0.0022(10) 0.0177(11) C42 0.0610(13) 0.0491(12) 0.0500(12) 0.0081(9) -0.0009(10) 0.0097(10) C41 0.0592(13) 0.0528(13) 0.0605(14) 0.0086(10) -0.0051(10) 0.0121(10) C5 0.0616(13) 0.0652(15) 0.0583(13) -0.0010(11) 0.0037(10) 0.0286(11) C43 0.0697(15) 0.0619(15) 0.0597(14) 0.0050(11) -0.0059(12) 0.0128(12) C51 0.0759(16) 0.0726(17) 0.0661(16) 0.0098(13) 0.0221(13) 0.0320(13) C4 0.0589(13) 0.0547(13) 0.0601(14) 0.0004(10) -0.0008(10) 0.0213(10) C44 0.0826(18) 0.0641(15) 0.0570(14) -0.0025(11) 0.0017(13) 0.0034(13) C3 0.0808(17) 0.0606(15) 0.0728(17) -0.0026(12) -0.0038(13) 0.0227(13) C46 0.0681(15) 0.0674(15) 0.0687(15) 0.0139(12) 0.0125(12) 0.0211(12) C45 0.0753(16) 0.0536(14) 0.0617(14) 0.0049(11) 0.0210(12) 0.0078(11) C53 0.182(4) 0.0563(18) 0.145(3) 0.0052(19) 0.083(3) 0.007(2) C54 0.201(5) 0.072(2) 0.126(3) -0.011(2) 0.004(3) 0.041(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 C5 1.355(3) . ? O1 N2 1.397(3) . ? O41 C41 1.211(3) . ? O52 C51 1.307(3) . ? O52 C53 1.461(4) . ? O51 C51 1.196(3) . ? O451 N451 1.221(3) . ? O452 N451 1.225(3) . ? N2 C3 1.294(3) . ? N451 C45 1.479(4) . ? C47 C42 1.384(3) . ? C47 C46 1.387(4) . ? C42 C43 1.389(3) . ? C42 C41 1.489(3) . ? C41 C4 1.491(3) . ? C5 C4 1.348(3) . ? C5 C51 1.468(4) . ? C43 C44 1.364(4) . ? C4 C3 1.417(3) . ? C44 C45 1.374(4) . ? C46 C45 1.373(3) . ? C53 C54 1.388(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 C5 O1 N2 108.34(19) . . ? C51 O52 C53 116.1(3) . . ? C3 N2 O1 105.3(2) . . ? O451 N451 O452 124.6(3) . . ? O451 N451 C45 117.8(3) . . ? O452 N451 C45 117.6(3) . . ? C42 C47 C46 120.2(2) . . ? C47 C42 C43 119.7(2) . . ? C47 C42 C41 122.3(2) . . ? C43 C42 C41 118.0(2) . . ? O41 C41 C42 121.4(2) . . ? O41 C41 C4 118.4(2) . . ? C42 C41 C4 120.11(19) . . ? C4 C5 O1 110.2(2) . . ? C4 C5 C51 134.5(2) . . ? O1 C5 C51 115.2(2) . . ? C44 C43 C42 120.6(2) . . ? O51 C51 O52 127.0(3) . . ? O51 C51 C5 123.2(3) . . ? O52 C51 C5 109.7(2) . . ? C5 C4 C3 103.1(2) . . ? C5 C4 C41 130.4(2) . . ? C3 C4 C41 126.2(2) . . ? C43 C44 C45 118.8(2) . . ? N2 C3 C4 113.0(2) . . ? C45 C46 C47 118.2(2) . . ? C46 C45 C44 122.5(2) . . ? C46 C45 N451 119.1(3) . . ? C44 C45 N451 118.4(2) . . ? C54 C53 O52 110.9(3) . . ? ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_p21c_CCDC1 _database_code_depnum_ccdc_archive 'CCDC 1589619' _audit_update_record ; 2017-12-06 deposited with the CCDC. 2018-01-22 downloaded from the CCDC. ; _audit_creation_date 2016-03-14T10:36:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ethyl4-(4-nitrobenzoyl)isoxazole-3-carboxylate ; _chemical_name_common ethyl4-(4-nitrobenzoyl)isoxazole-3-carboxylate _chemical_formula_moiety 'C13 H10 N2 O6' _chemical_formula_sum 'C13 H10 N2 O6' _chemical_formula_weight 290.23 _chemical_melting_point none #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P2ybc 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 7.3487(2) _cell_length_b 17.1804(4) _cell_length_c 10.4508(3) _cell_angle_alpha 90 _cell_angle_beta 98.1670(10) _cell_angle_gamma 90 _cell_volume 1306.07(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9842 _cell_measurement_theta_min 4.274 _cell_measurement_theta_max 72.186 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_special_details ; none ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.025 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical absorption correction based on the indexed faces of the crystal. ; _exptl_absorpt_correction_T_min 0.6907 _exptl_absorpt_correction_T_max 0.7624 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'micro-focus tube' _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator 'Montel type 2-dim beam shaping X ray optics' _diffrn_detector_area_resol_mean 10.4167 _diffrn_measurement_device_type 'Bruker D8 Quest Photon 100 diffractometer' _diffrn_measurement_method '2\% \f & \w scans' _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_unetI/netI 0.0155 _diffrn_reflns_number 22262 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.99 _diffrn_reflns_theta_max 72.24 _diffrn_reflns_theta_full 72.24 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2565 _reflns_number_gt 2260 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker Instrument Service v4.2.7' _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_structure_solution 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond (version 3.2i; Crystal Impact G' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0533P)^2^+0.3949P] 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 none _refine_ls_number_reflns 2565 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1095 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_restrained_S_all 1.05 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.194 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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 O1 O 0.84444(15) 0.43890(7) 1.03870(10) 0.0507(3) Uani 1 1 d . . . O31 O 0.49635(17) 0.59672(7) 0.76124(10) 0.0538(3) Uani 1 1 d . . . O32 O 0.57181(16) 0.64059(6) 0.96413(10) 0.0523(3) Uani 1 1 d . . . O41 O 0.71333(19) 0.39164(7) 0.64253(11) 0.0634(4) Uani 1 1 d . . . N2 N 0.74125(17) 0.50775(8) 1.03408(11) 0.0451(3) Uani 1 1 d . . . O452 O 0.8929(2) 0.69188(9) 0.24553(12) 0.0788(4) Uani 1 1 d . . . N451 N 0.91860(19) 0.70310(8) 0.36231(13) 0.0514(3) Uani 1 1 d . . . O451 O 0.9781(2) 0.76394(8) 0.41128(14) 0.0795(4) Uani 1 1 d . . . C42 C 0.79180(18) 0.52184(8) 0.60566(12) 0.0351(3) Uani 1 1 d . . . C3 C 0.69621(19) 0.52285(8) 0.91083(13) 0.0373(3) Uani 1 1 d . . . C4 C 0.76382(19) 0.46551(8) 0.83108(13) 0.0379(3) Uani 1 1 d . . . C31 C 0.57667(19) 0.59093(8) 0.86876(13) 0.0391(3) Uani 1 1 d . . . C47 C 0.7367(2) 0.51691(9) 0.47260(13) 0.0409(3) Uani 1 1 d . . . H47 H 0.6717 0.4735 0.438 0.049 Uiso 1 1 calc R . . C45 C 0.87498(19) 0.63932(8) 0.44670(14) 0.0395(3) Uani 1 1 d . . . C44 C 0.9335(2) 0.64562(8) 0.57759(14) 0.0432(3) Uani 1 1 d . . . H44 H 1 0.6888 0.6114 0.052 Uiso 1 1 calc R . . C43 C 0.8908(2) 0.58623(8) 0.65720(13) 0.0407(3) Uani 1 1 d . . . H43 H 0.9284 0.5893 0.7459 0.049 Uiso 1 1 calc R . . C41 C 0.74953(19) 0.45551(8) 0.68833(14) 0.0395(3) Uani 1 1 d . . . C46 C 0.7778(2) 0.57588(9) 0.39194(13) 0.0439(3) Uani 1 1 d . . . H46 H 0.7411 0.573 0.3032 0.053 Uiso 1 1 calc R . . C5 C 0.8533(2) 0.41555(9) 0.91764(14) 0.0456(4) Uani 1 1 d . . . H5 H 0.9132 0.3708 0.896 0.055 Uiso 1 1 calc R . . C33 C 0.4598(2) 0.71040(9) 0.93570(15) 0.0515(4) Uani 1 1 d . . . H33A H 0.3361 0.6965 0.8973 0.062 Uiso 1 1 calc R . . H33B H 0.513 0.7438 0.876 0.062 Uiso 1 1 calc R . . C34 C 0.4567(3) 0.75105(10) 1.06206(17) 0.0619(5) Uani 1 1 d . . . H34A H 0.3843 0.7976 1.0482 0.093 Uiso 1 1 calc R . . H34B H 0.58 0.7644 1.0989 0.093 Uiso 1 1 calc R . . H34C H 0.404 0.7173 1.1201 0.093 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 O1 0.0566(7) 0.0529(6) 0.0411(6) 0.0106(4) 0.0025(5) 0.0034(5) O31 0.0664(7) 0.0579(7) 0.0351(5) 0.0002(5) 0.0002(5) 0.0118(5) O32 0.0632(7) 0.0482(6) 0.0423(6) -0.0085(4) -0.0034(5) 0.0099(5) O41 0.0966(10) 0.0405(6) 0.0519(7) -0.0075(5) 0.0065(6) -0.0168(6) N2 0.0475(7) 0.0506(7) 0.0373(6) 0.0048(5) 0.0062(5) -0.0008(6) O452 0.1142(12) 0.0771(9) 0.0463(7) 0.0181(6) 0.0152(7) -0.0060(8) N451 0.0577(8) 0.0487(8) 0.0500(8) 0.0096(6) 0.0148(6) 0.0036(6) O451 0.1172(13) 0.0495(7) 0.0745(9) 0.0053(6) 0.0224(8) -0.0215(8) C42 0.0356(7) 0.0377(7) 0.0325(6) -0.0039(5) 0.0067(5) -0.0005(5) C3 0.0364(7) 0.0413(7) 0.0344(7) 0.0022(5) 0.0061(5) -0.0064(6) C4 0.0392(7) 0.0368(7) 0.0380(7) 0.0028(5) 0.0062(5) -0.0060(5) C31 0.0399(7) 0.0426(7) 0.0358(7) 0.0003(5) 0.0083(6) -0.0031(6) C47 0.0419(7) 0.0440(8) 0.0363(7) -0.0075(6) 0.0038(6) -0.0055(6) C45 0.0422(7) 0.0391(7) 0.0390(7) 0.0026(6) 0.0124(6) 0.0033(6) C44 0.0518(8) 0.0388(7) 0.0403(7) -0.0071(6) 0.0110(6) -0.0076(6) C43 0.0483(8) 0.0434(7) 0.0305(6) -0.0053(5) 0.0061(6) -0.0060(6) C41 0.0406(7) 0.0373(7) 0.0402(7) -0.0026(6) 0.0036(6) -0.0030(6) C46 0.0457(8) 0.0542(8) 0.0311(7) -0.0025(6) 0.0035(6) -0.0005(6) C5 0.0489(8) 0.0418(8) 0.0461(8) 0.0044(6) 0.0067(6) -0.0007(6) C33 0.0617(10) 0.0426(8) 0.0499(9) 0.0016(7) 0.0062(7) 0.0071(7) C34 0.0783(12) 0.0480(9) 0.0590(10) -0.0103(8) 0.0078(9) 0.0053(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 C5 1.3376(18) . ? O1 N2 1.4021(17) . ? O31 C31 1.1968(17) . ? O32 C31 1.3164(17) . ? O32 C33 1.4611(18) . ? O41 C41 1.2115(17) . ? N2 C3 1.3096(18) . ? O452 N451 1.2234(18) . ? N451 O451 1.2174(19) . ? N451 C45 1.4703(18) . ? C42 C43 1.3898(19) . ? C42 C47 1.3946(18) . ? C42 C41 1.4892(19) . ? C3 C4 1.4246(19) . ? C3 C31 1.491(2) . ? C4 C5 1.348(2) . ? C4 C41 1.4906(19) . ? C47 C46 1.379(2) . ? C45 C44 1.379(2) . ? C45 C46 1.382(2) . ? C44 C43 1.381(2) . ? C33 C34 1.497(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 C5 O1 N2 108.61(11) . . ? C31 O32 C33 116.95(11) . . ? C3 N2 O1 105.12(11) . . ? O451 N451 O452 123.35(14) . . ? O451 N451 C45 118.93(13) . . ? O452 N451 C45 117.72(14) . . ? C43 C42 C47 119.78(13) . . ? C43 C42 C41 121.67(12) . . ? C47 C42 C41 118.49(12) . . ? N2 C3 C4 112.21(13) . . ? N2 C3 C31 120.10(13) . . ? C4 C3 C31 127.57(12) . . ? C5 C4 C3 103.01(12) . . ? C5 C4 C41 123.80(13) . . ? C3 C4 C41 133.19(12) . . ? O31 C31 O32 126.45(14) . . ? O31 C31 C3 122.23(13) . . ? O32 C31 C3 111.31(11) . . ? C46 C47 C42 120.48(13) . . ? C44 C45 C46 122.88(13) . . ? C44 C45 N451 118.21(13) . . ? C46 C45 N451 118.91(13) . . ? C45 C44 C43 118.31(13) . . ? C44 C43 C42 120.39(13) . . ? O41 C41 C42 121.07(13) . . ? O41 C41 C4 118.69(13) . . ? C42 C41 C4 120.10(11) . . ? C47 C46 C45 118.15(13) . . ? O1 C5 C4 111.04(14) . . ? O32 C33 C34 106.39(13) . . ?