#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206813.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_2206813 _space_group_IT_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _[local]_cod_cif_authors_sg_H-M 'P 21' loop_ _publ_author_name 'Jia, Hong-Hua' 'Ni, Fang' 'Wang, Jun' 'Wei, Ping' 'Ouyang, Ping-Kai' _publ_section_title ; 5-(4-Fluorobenzylidene)imidazolidine-2,4-dione ; _journal_coeditor_code WW6390 _journal_issue 9 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o2784 _journal_page_last o2786 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C10 H7 F N2 O2' _chemical_formula_moiety 'C10 H7 F N2 O2' _chemical_formula_sum 'C10 H7 F N2 O2' _chemical_formula_weight 206.18 _chemical_name_common para-fluorobenzalhydantoin _chemical_name_systematic ; 5-(4-Fluorobenzylidene)imidazolidine-2,4-dione ; _symmetry_cell_setting monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 95.25(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 3.8250(8) _cell_length_b 6.2410(12) _cell_length_c 18.988(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12 _cell_measurement_theta_min 9 _cell_volume 451.38(16) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1989)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _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 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 1155 _diffrn_reflns_theta_full 25.96 _diffrn_reflns_theta_max 25.96 _diffrn_reflns_theta_min 1.08 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type none _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_description sheet _exptl_crystal_F_000 212 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.180 _refine_diff_density_min -0.164 _refine_ls_extinction_coef 0.026(9) _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 1.064 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 985 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0397 _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^)+(0.064P)^2^+0.038P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1020 _refine_ls_wR_factor_ref 0.1140 _reflns_number_gt 806 _reflns_number_total 985 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ww6390.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 F 1.3552(7) -0.3128(6) 0.44119(13) 0.0854(12) Uani d . 1 F O2 0.4354(9) 0.6359(5) 0.16225(15) 0.0572(9) Uani d . 1 O O1 0.1868(8) 0.0370(5) 0.02950(14) 0.0617(9) Uani d . 1 O C10 0.5661(8) 0.2600(6) 0.18368(17) 0.0315(7) Uani d . 1 C N1 0.4905(9) 0.0875(5) 0.13867(16) 0.0379(7) Uani d . 1 N N2 0.2659(8) 0.3724(6) 0.08143(16) 0.0412(8) Uani d . 1 N C1 1.1995(10) -0.1685(8) 0.3937(2) 0.0514(12) Uani d . 1 C C2 1.1545(9) -0.2264(8) 0.3244(2) 0.0485(9) Uani d . 1 C H2B 1.2300 -0.3594 0.3097 0.058 Uiso calc R 1 H C3 0.9949(9) -0.0836(6) 0.27647(18) 0.0376(8) Uani d . 1 C H3A 0.9610 -0.1211 0.2289 0.045 Uiso calc R 1 H C4 0.8826(8) 0.1173(6) 0.29826(17) 0.0348(8) Uani d . 1 C C5 0.9381(10) 0.1679(7) 0.36921(18) 0.0462(10) Uani d . 1 C H5A 0.8675 0.3012 0.3847 0.055 Uiso calc R 1 H C6 1.0964(11) 0.0248(10) 0.41768(19) 0.0592(12) Uani d . 1 C H6A 1.1314 0.0597 0.4654 0.071 Uiso calc R 1 H C7 0.7229(8) 0.2774(6) 0.24941(17) 0.0353(7) Uani d . 1 C H7A 0.7315 0.4165 0.2671 0.042 Uiso calc R 1 H C8 0.3013(10) 0.1501(6) 0.07797(18) 0.0395(9) Uani d . 1 C C9 0.4189(10) 0.4490(6) 0.1435(2) 0.0378(8) Uani d . 1 C H2 0.141(10) 0.437(8) 0.0468(18) 0.046(12) Uiso d . 1 H H1 0.507(10) -0.041(7) 0.1497(19) 0.034(10) Uiso d . 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 F 0.081(2) 0.089(3) 0.0805(19) 0.0062(17) -0.0233(15) 0.0459(19) O2 0.083(2) 0.0242(14) 0.0613(18) 0.0020(15) -0.0125(16) -0.0016(14) O1 0.083(2) 0.0479(18) 0.0492(14) -0.0019(18) -0.0219(15) -0.0116(15) C10 0.0336(16) 0.0228(15) 0.0378(16) 0.0009(16) 0.0013(13) 0.0002(15) N1 0.0511(18) 0.0222(16) 0.0383(14) 0.0009(14) -0.0080(13) 0.0008(13) N2 0.0497(19) 0.0322(17) 0.0401(18) 0.0021(16) -0.0050(15) 0.0084(15) C1 0.0369(18) 0.063(3) 0.051(2) -0.0042(19) -0.0115(17) 0.023(2) C2 0.0404(19) 0.043(2) 0.060(2) 0.000(2) -0.0032(17) 0.005(2) C3 0.0338(17) 0.037(2) 0.0402(18) -0.0022(16) -0.0062(14) 0.0028(16) C4 0.0294(15) 0.0373(19) 0.0366(15) -0.0072(16) -0.0032(13) 0.0019(17) C5 0.0447(19) 0.052(2) 0.0406(18) 0.0015(19) -0.0060(17) -0.0027(18) C6 0.056(2) 0.085(3) 0.0345(19) -0.004(3) -0.0057(18) 0.008(2) C7 0.0365(17) 0.0289(16) 0.0392(17) -0.0014(17) -0.0026(14) -0.0068(17) C8 0.043(2) 0.035(2) 0.039(2) 0.0015(17) -0.0078(16) -0.0017(17) C9 0.044(2) 0.0242(17) 0.0445(19) -0.0002(16) 0.0005(16) 0.0047(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag F C1 1.371(5) yes O2 C9 1.220(5) yes O1 C8 1.209(4) yes C10 C7 1.339(4) yes C10 N1 1.388(5) yes C10 C9 1.487(5) yes N1 C8 1.361(5) yes N1 H1 0.83(4) ? N2 C9 1.354(5) yes N2 C8 1.396(5) yes N2 H2 0.88(4) ? C1 C2 1.361(6) yes C1 C6 1.360(8) ? C2 C3 1.376(5) yes C2 H2B 0.9300 ? C3 C4 1.400(5) yes C3 H3A 0.9300 ? C4 C5 1.381(5) ? C4 C7 1.459(5) yes C5 C6 1.382(6) ? C5 H5A 0.9300 ? C6 H6A 0.9300 ? C7 H7A 0.9300 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C7 C10 N1 133.4(3) yes C7 C10 C9 122.0(3) yes N1 C10 C9 104.5(3) yes C8 N1 C10 111.3(3) yes C8 N1 H1 121(3) ? C10 N1 H1 126(3) ? C9 N2 C8 111.0(3) yes C9 N2 H2 131(3) ? C8 N2 H2 118(3) ? C2 C1 C6 123.0(4) ? C2 C1 F 118.0(5) yes C6 C1 F 119.0(4) yes C1 C2 C3 118.5(4) ? C1 C2 H2B 120.8 ? C3 C2 H2B 120.8 ? C2 C3 C4 120.9(3) ? C2 C3 H3A 119.5 ? C4 C3 H3A 119.5 ? C5 C4 C3 118.0(4) ? C5 C4 C7 118.8(4) yes C3 C4 C7 123.2(3) yes C4 C5 C6 121.4(4) ? C4 C5 H5A 119.3 ? C6 C5 H5A 119.3 ? C1 C6 C5 118.2(4) ? C1 C6 H6A 120.9 ? C5 C6 H6A 120.9 ? C10 C7 C4 131.5(4) yes C10 C7 H7A 114.2 ? C4 C7 H7A 114.2 ? O1 C8 N1 127.2(4) yes O1 C8 N2 125.9(4) yes N1 C8 N2 107.0(3) yes O2 C9 N2 126.8(4) yes O2 C9 C10 127.0(4) yes N2 C9 C10 106.2(3) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O2 1_545 0.83(4) 2.05(4) 2.865(4) 166(4) yes N2 H2 O1 2_555 0.88(4) 1.93(4) 2.797(4) 170(5) yes _cod_database_code 2206813