#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2202439.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2202439 loop_ _publ_author_name 'Moreno-Fuquen, Rodolfo' 'Valencia, Hoover' 'Abonia, Rodrigo' 'Kennedy, Alan R.' 'Graham, Duncan' _publ_section_title ; p-Nitrophenylmaleimide ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1717 _journal_page_last o1718 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C10 H6 N2 O4' _chemical_formula_moiety 'C10 H6 N2 O4' _chemical_formula_sum 'C10 H6 N2 O4' _chemical_formula_weight 218.17 _chemical_melting_point 436.0(10) _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 109.69(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.535(2) _cell_length_b 11.624(3) _cell_length_c 8.148(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16 _cell_measurement_theta_min 8 _cell_volume 939.5(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CAD-4 SDP (Frenz, 1978)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 0.99 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0106 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 870 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_min 2.70 _diffrn_standards_decay_% 1.2 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.137 _refine_diff_density_min -0.201 _refine_ls_extinction_coef 0.0169(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 76 _refine_ls_number_reflns 824 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0302 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.4529P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0815 _refine_ls_wR_factor_ref 0.0845 _reflns_number_gt 738 _reflns_number_total 824 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cf6281.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_database_code 2202439 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol N1 0.5000 0.21145(13) 0.2500 0.0394(4) Uani d S 1 N N2 0.5000 -0.27159(14) 0.2500 0.0426(4) Uani d S 1 N C4 0.5000 0.08902(15) 0.2500 0.0345(4) Uani d S 1 C C1 0.5000 -0.14578(15) 0.2500 0.0359(4) Uani d S 1 C C3 0.39783(13) 0.03000(11) 0.12627(18) 0.0407(4) Uani d . 1 C H3 0.3294 0.0703 0.0438 0.049 Uiso calc R 1 H O2 0.43544(12) -0.32156(9) 0.11594(15) 0.0611(4) Uani d . 1 O C2 0.39760(13) -0.08862(12) 0.12539(17) 0.0405(4) Uani d . 1 C H2 0.3297 -0.1292 0.0424 0.049 Uiso calc R 1 H O1 0.27411(10) 0.24654(10) 0.20227(15) 0.0572(4) Uani d . 1 O C5 0.38614(15) 0.28100(12) 0.22655(18) 0.0441(4) Uani d . 1 C C6 0.43556(17) 0.40155(13) 0.2380(2) 0.0566(4) Uani d . 1 C H6 0.3828 0.4669 0.2293 0.068 Uiso calc R 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0392(8) 0.0297(8) 0.0479(9) 0.000 0.0128(7) 0.000 N2 0.0480(9) 0.0326(9) 0.0474(10) 0.000 0.0164(8) 0.000 C4 0.0349(9) 0.0311(9) 0.0402(9) 0.000 0.0161(8) 0.000 C1 0.0399(10) 0.0299(9) 0.0408(10) 0.000 0.0175(8) 0.000 C3 0.0364(7) 0.0370(8) 0.0431(8) 0.0024(5) 0.0062(6) 0.0039(6) O2 0.0801(8) 0.0380(6) 0.0563(7) -0.0050(5) 0.0113(6) -0.0102(5) C2 0.0374(7) 0.0370(7) 0.0428(7) -0.0048(6) 0.0078(6) -0.0020(6) O1 0.0444(6) 0.0538(7) 0.0729(8) 0.0088(5) 0.0189(5) -0.0050(5) C5 0.0481(8) 0.0384(8) 0.0430(8) 0.0079(6) 0.0115(6) -0.0009(6) C6 0.0698(9) 0.0341(8) 0.0570(9) 0.0086(7) 0.0098(8) -0.0023(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' 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' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 -7 -5 4 -2 -4 0 -2 1 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C5 N1 C5 2_655 . 109.75(16) C5 N1 C4 2_655 . 125.12(8) C5 N1 C4 . . 125.12(8) O2 N2 O2 . 2_655 123.22(17) O2 N2 C1 . . 118.39(8) O2 N2 C1 2_655 . 118.39(8) C3 C4 C3 . 2_655 120.56(17) C3 C4 N1 . . 119.72(9) C3 C4 N1 2_655 . 119.72(9) C2 C1 C2 2_655 . 122.33(17) C2 C1 N2 2_655 . 118.83(9) C2 C1 N2 . . 118.83(9) C2 C3 C4 . . 119.94(13) C2 C3 H3 . . 120.0 C4 C3 H3 . . 120.0 C1 C2 C3 . . 118.61(12) C1 C2 H2 . . 120.7 C3 C2 H2 . . 120.7 O1 C5 N1 . . 125.34(13) O1 C5 C6 . . 129.06(14) N1 C5 C6 . . 105.59(13) C6 C6 C5 2_655 . 109.52(9) C6 C6 H6 2_655 . 125.2 C5 C6 H6 . . 125.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance N1 C5 2_655 1.4052(17) N1 C5 . 1.4052(17) N1 C4 . 1.423(2) N2 O2 . 1.2217(13) N2 O2 2_655 1.2217(13) N2 C1 . 1.462(2) C4 C3 . 1.3835(16) C4 C3 2_655 1.3835(16) C1 C2 2_655 1.3777(16) C1 C2 . 1.3777(16) C3 C2 . 1.379(2) C3 H3 . 0.930 C2 H2 . 0.930 O1 C5 . 1.1979(18) C5 C6 . 1.487(2) C6 C6 2_655 1.305(3) C6 H6 . 0.930 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion C5 N1 C4 C3 2_655 . -136.82(10) C5 N1 C4 C3 . . 43.18(10) C5 N1 C4 C3 2_655 2_655 43.18(10) C5 N1 C4 C3 . 2_655 -136.82(10) O2 N2 C1 C2 . 2_655 -159.26(10) O2 N2 C1 C2 2_655 2_655 20.74(10) O2 N2 C1 C2 . . 20.74(10) O2 N2 C1 C2 2_655 . -159.26(10) C3 C4 C3 C2 2_655 . -0.20(9) N1 C4 C3 C2 . . 179.80(9) C2 C1 C2 C3 2_655 . -0.20(9) N2 C1 C2 C3 . . 179.80(9) C4 C3 C2 C1 . . 0.39(18) C5 N1 C5 O1 2_655 . 179.43(17) C4 N1 C5 O1 . . -0.57(17) C5 N1 C5 C6 2_655 . -0.39(7) C4 N1 C5 C6 . . 179.61(7) O1 C5 C6 C6 . 2_655 -178.66(18) N1 C5 C6 C6 . 2_655 1.2(2)