#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/44/2214435.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_2214435 loop_ _publ_author_name 'Ming-Hua Yang' 'Guo-Bing Yan' 'Yun-Fa Zheng' _publ_section_title ; 2-Fluoro-N-(3-nitrobenzylidene)-5-(trifluoromethyl)aniline ; _journal_coeditor_code WN2153 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3202 _journal_page_last o3202 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C14 H8 F4 N2 O2' _chemical_formula_moiety 'C14 H8 F4 N2 O2' _chemical_formula_sum 'C14 H8 F4 N2 O2' _chemical_formula_weight 312.22 _chemical_name_systematic ; 2-Fluoro-N-(3-Nitrobenzylidene)-5-(trifluoromethyl)aniline ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.100(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.863(3) _cell_length_b 12.549(2) _cell_length_c 8.3211(16) _cell_measurement_reflns_used 2406 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.29 _cell_measurement_theta_min 2.27 _cell_volume 1343.2(5) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker,1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'Bruker APEX area-detector' _diffrn_measurement_method '\f and \w' _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 0.0865 _diffrn_reflns_av_sigmaI/netI 0.0637 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 8038 _diffrn_reflns_theta_full 25.29 _diffrn_reflns_theta_max 25.29 _diffrn_reflns_theta_min 2.27 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_correction_T_min 0.9481 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.305 _refine_diff_density_min -0.337 _refine_ls_extinction_coef 0.006(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 2406 _refine_ls_number_restraints 96 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0488 _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^)+(0.089P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1465 _refine_ls_wR_factor_ref 0.1547 _reflns_number_gt 1526 _reflns_number_total 2406 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file wn2153.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 1343.1(4) _cod_database_code 2214435 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' 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_type_symbol _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_disorder_assembly _atom_site_disorder_group F F1 0.19004(12) 0.98237(12) -0.08870(18) 0.0833(5) Uani d . 1 . . F F2 0.59865(15) 0.96853(16) 0.3082(3) 0.1065(8) Uani d PDU 0.888(4) A 1 F F3 0.50517(18) 0.8671(3) 0.4495(2) 0.1311(11) Uani d PDU 0.888(4) A 1 F F4 0.5854(2) 0.8061(2) 0.2409(4) 0.1325(11) Uani d PDU 0.888(4) A 1 N N2 0.24083(14) 0.77557(14) -0.0569(2) 0.0564(5) Uani d . 1 . . N N1 0.1229(2) 0.30915(18) -0.0163(3) 0.0858(7) Uani d . 1 . . O O2 0.0583(2) 0.24421(15) -0.0567(3) 0.1127(8) Uani d . 1 . . O O1 0.1894(2) 0.28961(18) 0.0814(4) 0.1400(11) Uani d . 1 . . C C8 0.22886(17) 0.68459(18) 0.0073(3) 0.0560(6) Uani d . 1 . . H H8 0.2590 0.6716 0.1069 0.067 Uiso calc R 1 . . C C6 0.29922(16) 0.85362(17) 0.0263(2) 0.0520(6) Uani d . 1 . . C C14 0.17518(18) 0.49656(18) -0.0107(3) 0.0579(6) Uani d . 1 . . H H14 0.2178 0.4809 0.0764 0.069 Uiso calc R 1 . . C C7 0.38544(17) 0.83251(18) 0.1211(3) 0.0557(6) Uani d . 1 . . H H7 0.4077 0.7625 0.1341 0.067 Uiso calc R 1 . . C C5 0.27186(19) 0.95961(18) 0.0080(3) 0.0598(6) Uani d . 1 . . C C13 0.11706(18) 0.41783(17) -0.0826(3) 0.0595(6) Uani d . 1 . . C C2 0.43918(18) 0.91442(19) 0.1972(3) 0.0606(6) Uani d . 1 A . C C9 0.16923(16) 0.59942(17) -0.0702(2) 0.0510(6) Uani d . 1 . . C C11 0.04589(19) 0.53895(19) -0.2696(3) 0.0639(6) Uani d . 1 . . H H11 0.0028 0.5537 -0.3565 0.077 Uiso calc R 1 . . C C12 0.05175(19) 0.43717(19) -0.2105(3) 0.0641(6) Uani d . 1 . . H H12 0.0126 0.3825 -0.2557 0.077 Uiso calc R 1 . . C C3 0.4067(2) 1.0184(2) 0.1792(3) 0.0710(7) Uani d . 1 . . H H3 0.4421 1.0730 0.2312 0.085 Uiso calc R 1 . . C C1 0.53030(17) 0.88854(16) 0.2968(2) 0.0805(8) Uani d DU 1 . . F F2' 0.5717(13) 0.9541(12) 0.4066(16) 0.1065(8) Uani d PDU 0.112(4) A 2 F F3' 0.5223(16) 0.7972(9) 0.379(2) 0.1311(11) Uani d PDU 0.112(4) A 2 F F4' 0.6153(9) 0.8669(16) 0.210(2) 0.1325(11) Uani d PDU 0.112(4) A 2 C C10 0.10359(16) 0.61967(18) -0.2007(2) 0.0571(6) Uani d . 1 . . H H10 0.0988 0.6885 -0.2417 0.069 Uiso calc R 1 . . C C4 0.3218(2) 1.04161(19) 0.0841(3) 0.0727(7) Uani d . 1 . . H H4 0.2990 1.1115 0.0719 0.087 Uiso calc R 1 . . 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 F1 0.0829(11) 0.0742(10) 0.0930(10) 0.0090(7) -0.0250(8) 0.0103(7) F2 0.0812(14) 0.1240(17) 0.1144(18) -0.0439(11) -0.0324(12) 0.0193(13) F3 0.1160(16) 0.198(3) 0.0790(14) -0.0485(18) -0.0326(12) 0.0497(15) F4 0.1058(17) 0.113(2) 0.178(2) 0.0311(15) -0.0713(16) -0.0253(18) N2 0.0582(12) 0.0519(11) 0.0590(11) -0.0046(9) -0.0073(9) -0.0036(9) N1 0.0954(18) 0.0547(14) 0.1074(18) 0.0008(13) -0.0218(15) -0.0023(12) O2 0.146(2) 0.0564(12) 0.1361(19) -0.0302(13) -0.0375(16) 0.0007(11) O1 0.149(2) 0.0699(14) 0.201(3) -0.0046(14) -0.087(2) 0.0301(15) C8 0.0571(13) 0.0566(14) 0.0544(13) -0.0035(11) -0.0078(10) -0.0025(10) C6 0.0537(13) 0.0506(13) 0.0518(12) -0.0084(10) -0.0010(10) -0.0002(10) C14 0.0574(14) 0.0555(14) 0.0607(13) 0.0021(11) -0.0121(11) -0.0035(11) C7 0.0568(14) 0.0504(13) 0.0598(13) -0.0035(10) -0.0040(11) -0.0001(10) C5 0.0587(14) 0.0585(15) 0.0623(13) 0.0015(11) -0.0075(11) 0.0033(11) C13 0.0611(14) 0.0440(13) 0.0733(15) -0.0002(11) -0.0051(12) -0.0033(11) C2 0.0615(14) 0.0598(15) 0.0605(13) -0.0123(12) -0.0051(11) -0.0012(11) C9 0.0493(12) 0.0505(13) 0.0532(12) -0.0028(10) -0.0030(9) -0.0047(10) C11 0.0617(15) 0.0664(16) 0.0634(14) -0.0064(12) -0.0172(11) -0.0024(12) C12 0.0639(15) 0.0569(14) 0.0715(15) -0.0093(12) -0.0088(12) -0.0113(12) C3 0.0803(18) 0.0568(15) 0.0758(16) -0.0196(13) -0.0098(14) -0.0060(12) C1 0.0770(18) 0.0820(19) 0.0824(19) -0.0195(16) -0.0213(14) 0.0061(15) F2' 0.0812(14) 0.1240(17) 0.1144(18) -0.0439(11) -0.0324(12) 0.0193(13) F3' 0.1160(16) 0.198(3) 0.0790(14) -0.0485(18) -0.0326(12) 0.0497(15) F4' 0.1058(17) 0.113(2) 0.178(2) 0.0311(15) -0.0713(16) -0.0253(18) C10 0.0580(14) 0.0556(14) 0.0579(13) -0.0042(11) -0.0051(11) 0.0017(10) C4 0.0902(19) 0.0472(14) 0.0806(17) -0.0046(13) -0.0061(15) 0.0025(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C5 1.355(3) F2 C1 1.3377(10) F3 C1 1.3381(10) F4 C1 1.3380(10) N2 C8 1.270(3) N2 C6 1.415(3) N1 O1 1.205(3) N1 O2 1.212(3) N1 C13 1.473(3) C8 C9 1.465(3) C8 H8 0.9300 C6 C5 1.384(3) C6 C7 1.387(3) C14 C13 1.376(3) C14 C9 1.385(3) C14 H14 0.9300 C7 C2 1.391(3) C7 H7 0.9300 C5 C4 1.368(3) C13 C12 1.378(3) C2 C3 1.378(4) C2 C1 1.472(3) C9 C10 1.399(3) C11 C12 1.371(3) C11 C10 1.380(3) C11 H11 0.9300 C12 H12 0.9300 C3 C4 1.380(4) C3 H3 0.9300 C1 F2' 1.3395(11) C1 F4' 1.3398(11) C1 F3' 1.3399(11) C10 H10 0.9300 C4 H4 0.9300 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C8 N2 C6 118.75(19) O1 N1 O2 122.5(3) O1 N1 C13 118.5(2) O2 N1 C13 118.9(2) N2 C8 C9 122.3(2) N2 C8 H8 118.8 C9 C8 H8 118.8 C5 C6 C7 116.7(2) C5 C6 N2 118.4(2) C7 C6 N2 124.8(2) C13 C14 C9 119.0(2) C13 C14 H14 120.5 C9 C14 H14 120.5 C6 C7 C2 121.0(2) C6 C7 H7 119.5 C2 C7 H7 119.5 F1 C5 C4 118.7(2) F1 C5 C6 117.7(2) C4 C5 C6 123.5(2) C14 C13 C12 122.7(2) C14 C13 N1 118.3(2) C12 C13 N1 118.9(2) C3 C2 C7 120.0(2) C3 C2 C1 120.8(2) C7 C2 C1 119.3(2) C14 C9 C10 118.70(19) C14 C9 C8 119.6(2) C10 C9 C8 121.7(2) C12 C11 C10 120.4(2) C12 C11 H11 119.8 C10 C11 H11 119.8 C11 C12 C13 118.3(2) C11 C12 H12 120.8 C13 C12 H12 120.8 C2 C3 C4 120.2(2) C2 C3 H3 119.9 C4 C3 H3 119.9 F2 C1 F4 104.9(2) F2 C1 F3 104.06(17) F4 C1 F3 107.6(2) F2 C1 F2' 39.6(7) F4 C1 F2' 120.1(9) F3 C1 F2' 64.7(7) F2 C1 F4' 69.8(8) F4 C1 F4' 39.0(8) F3 C1 F4' 132.1(10) F2' C1 F4' 99.8(8) F2 C1 F3' 131.1(8) F4 C1 F3' 63.7(9) F3 C1 F3' 47.4(8) F2' C1 F3' 102.0(8) F4' C1 F3' 99.6(8) F2 C1 C2 113.42(19) F4 C1 C2 113.36(18) F3 C1 C2 112.74(19) F2' C1 C2 124.4(9) F4' C1 C2 112.9(9) F3' C1 C2 114.6(9) C11 C10 C9 120.9(2) C11 C10 H10 119.6 C9 C10 H10 119.6 C5 C4 C3 118.6(2) C5 C4 H4 120.7 C3 C4 H4 120.7 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 C6 N2 C8 C9 179.72(18) C8 N2 C6 C5 -147.5(2) C8 N2 C6 C7 35.2(3) C5 C6 C7 C2 1.8(3) N2 C6 C7 C2 179.17(19) C7 C6 C5 F1 177.73(19) N2 C6 C5 F1 0.2(3) C7 C6 C5 C4 -3.4(3) N2 C6 C5 C4 179.1(2) C9 C14 C13 C12 -0.9(4) C9 C14 C13 N1 -179.0(2) O1 N1 C13 C14 -11.1(4) O2 N1 C13 C14 165.8(2) O1 N1 C13 C12 170.7(3) O2 N1 C13 C12 -12.4(4) C6 C7 C2 C3 0.2(3) C6 C7 C2 C1 179.99(18) C13 C14 C9 C10 0.5(3) C13 C14 C9 C8 178.6(2) N2 C8 C9 C14 167.7(2) N2 C8 C9 C10 -14.2(3) C10 C11 C12 C13 -0.6(3) C14 C13 C12 C11 1.0(4) N1 C13 C12 C11 179.1(2) C7 C2 C3 C4 -0.9(4) C1 C2 C3 C4 179.3(2) C3 C2 C1 F2 -26.3(3) C7 C2 C1 F2 153.9(2) C3 C2 C1 F4 -145.8(3) C7 C2 C1 F4 34.4(3) C3 C2 C1 F3 91.7(3) C7 C2 C1 F3 -88.2(3) C3 C2 C1 F2' 17.6(10) C7 C2 C1 F2' -162.2(10) C3 C2 C1 F4' -103.2(10) C7 C2 C1 F4' 77.0(10) C3 C2 C1 F3' 143.7(10) C7 C2 C1 F3' -36.1(11) C12 C11 C10 C9 0.2(3) C14 C9 C10 C11 -0.1(3) C8 C9 C10 C11 -178.3(2) F1 C5 C4 C3 -178.4(2) C6 C5 C4 C3 2.7(4) C2 C3 C4 C5 -0.5(4) _cod_database_fobs_code 2214435 _journal_paper_doi 10.1107/S1600536807028395