#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206797.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_2206797 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Wang, Xin' 'Zhang, Shu-Ping' 'Shao, Si-Chang' _publ_section_title ; 3,5-Dichloro-N-(4-fluorobenzylidene)aniline ; _journal_coeditor_code SU6226 _journal_issue 9 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3071 _journal_page_last o3072 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C13 H8 Cl2 F N' _chemical_formula_moiety 'C13 H8 Cl2 F N' _chemical_formula_sum 'C13 H8 Cl2 F N' _chemical_formula_weight 268.10 _chemical_name_systematic ; 3,5-Dichloro-N-(4-fluorobenzylidene)aniline ; _symmetry_cell_setting monoclinic _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 94.7520(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.1311(7) _cell_length_b 3.8481(2) _cell_length_c 22.0365(11) _cell_measurement_reflns_used 1023 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 28.6 _cell_measurement_theta_min 4.4 _cell_volume 1194.18(10) _computing_cell_refinement SMART _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART CCD 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 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0121 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 13224 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 2.26 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.530 _exptl_absorpt_correction_T_max 0.8200 _exptl_absorpt_correction_T_min 0.7417 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.39 _refine_diff_density_max 0.376 _refine_diff_density_min -0.505 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 157 _refine_ls_number_reflns 2863 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0368 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0573P)^2^+0.3432P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1039 _refine_ls_wR_factor_ref 0.1064 _reflns_number_gt 2506 _reflns_number_total 2863 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file su6226.cif 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' F F 0.0171 0.0103 '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' 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 Cl1 0.32754(4) -0.35584(17) 0.999714(18) 0.07205(18) Uani d . 1 Cl Cl2 0.58696(3) -0.00790(14) 0.84603(2) 0.06158(16) Uani d . 1 Cl F1 -0.05438(8) 0.3787(4) 0.55361(5) 0.0776(4) Uani d . 1 F N1 0.22726(9) 0.1260(4) 0.78919(5) 0.0457(3) Uani d . 1 N C1 0.15786(9) 0.1598(4) 0.68603(6) 0.0380(3) Uani d . 1 C C2 0.07465(10) 0.3226(4) 0.70090(6) 0.0408(3) Uani d . 1 C H2 0.0674 0.3824 0.7411 0.049 Uiso calc R 1 H C3 0.00291(10) 0.3957(5) 0.65631(7) 0.0468(3) Uani d . 1 C H3 -0.0530 0.5016 0.6660 0.056 Uiso calc R 1 H C4 0.01643(11) 0.3078(5) 0.59714(7) 0.0504(4) Uani d . 1 C C5 0.09772(12) 0.1545(5) 0.58017(7) 0.0533(4) Uani d . 1 C H5 0.1050 0.1028 0.5396 0.064 Uiso calc R 1 H C6 0.16859(11) 0.0790(4) 0.62542(7) 0.0462(3) Uani d . 1 C H6 0.2242 -0.0272 0.6152 0.055 Uiso calc R 1 H C7 0.23260(10) 0.0630(4) 0.73301(6) 0.0402(3) Uani d . 1 C H7 0.2847(13) -0.053(5) 0.7189(8) 0.048 Uiso d . 1 H C8 0.30393(10) 0.0247(4) 0.83091(6) 0.0417(3) Uani d . 1 C C9 0.39851(10) 0.0545(4) 0.81808(6) 0.0415(3) Uani d . 1 C H9 0.4141 0.1402 0.7807 0.050 Uiso calc R 1 H C10 0.46860(10) -0.0459(4) 0.86194(7) 0.0418(3) Uani d . 1 C C11 0.44932(11) -0.1733(4) 0.91805(6) 0.0453(3) Uani d . 1 C H11 0.4977 -0.2401 0.9469 0.054 Uiso calc R 1 H C12 0.35492(11) -0.1972(4) 0.92943(6) 0.0470(3) Uani d . 1 C C13 0.28228(11) -0.0973(5) 0.88757(6) 0.0489(4) Uani d . 1 C H13 0.2195 -0.1112 0.8970 0.059 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 Cl1 0.0739(3) 0.1035(4) 0.0390(2) -0.0008(3) 0.00640(19) 0.0221(2) Cl2 0.0396(2) 0.0847(3) 0.0603(3) -0.00487(19) 0.00354(17) -0.0023(2) F1 0.0566(6) 0.1277(11) 0.0454(5) 0.0139(7) -0.0145(4) 0.0047(6) N1 0.0408(6) 0.0591(8) 0.0367(6) 0.0074(6) 0.0005(5) 0.0040(5) C1 0.0377(6) 0.0424(7) 0.0336(6) -0.0014(5) 0.0016(5) 0.0020(5) C2 0.0409(7) 0.0484(8) 0.0335(6) 0.0012(6) 0.0042(5) 0.0007(6) C3 0.0386(7) 0.0581(9) 0.0433(7) 0.0047(6) 0.0022(6) 0.0018(6) C4 0.0427(7) 0.0685(10) 0.0384(7) -0.0007(7) -0.0063(6) 0.0047(7) C5 0.0535(8) 0.0744(11) 0.0320(6) 0.0023(8) 0.0025(6) -0.0040(7) C6 0.0428(7) 0.0585(9) 0.0380(7) 0.0041(7) 0.0063(6) -0.0021(6) C7 0.0373(6) 0.0447(7) 0.0385(7) 0.0028(6) 0.0026(5) 0.0023(6) C8 0.0418(7) 0.0486(8) 0.0341(6) 0.0055(6) 0.0000(5) 0.0016(6) C9 0.0441(7) 0.0457(8) 0.0345(6) 0.0001(6) 0.0022(5) 0.0022(6) C10 0.0386(6) 0.0445(7) 0.0420(7) -0.0005(6) 0.0011(5) -0.0032(6) C11 0.0459(7) 0.0505(8) 0.0381(7) 0.0038(6) -0.0057(6) 0.0017(6) C12 0.0524(8) 0.0560(9) 0.0326(6) 0.0012(7) 0.0034(6) 0.0061(6) C13 0.0413(7) 0.0681(10) 0.0373(7) 0.0022(7) 0.0042(6) 0.0047(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C12 1.7379(15) Cl2 C10 1.7432(15) F1 C4 1.3552(17) N1 C7 1.2699(18) N1 C8 1.4164(17) C1 C6 1.3918(19) C1 C2 1.3952(19) C1 C7 1.4644(19) C2 C3 1.3809(19) C2 H2 0.9300 C3 C4 1.376(2) C3 H3 0.9300 C4 C5 1.371(2) C5 C6 1.384(2) C5 H5 0.9300 C6 H6 0.9300 C7 H7 0.936(18) C8 C13 1.392(2) C8 C9 1.393(2) C9 C10 1.380(2) C9 H9 0.9300 C10 C11 1.378(2) C11 C12 1.381(2) C11 H11 0.9300 C12 C13 1.377(2) C13 H13 0.9300 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C7 N1 C8 118.44(12) C6 C1 C2 119.12(13) C6 C1 C7 119.48(13) C2 C1 C7 121.38(12) C3 C2 C1 120.51(13) C3 C2 H2 119.7 C1 C2 H2 119.7 C4 C3 C2 118.22(14) C4 C3 H3 120.9 C2 C3 H3 120.9 F1 C4 C5 118.69(14) F1 C4 C3 117.96(14) C5 C4 C3 123.35(13) C4 C5 C6 117.81(13) C4 C5 H5 121.1 C6 C5 H5 121.1 C5 C6 C1 120.97(14) C5 C6 H6 119.5 C1 C6 H6 119.5 N1 C7 C1 122.89(13) N1 C7 H7 121.8(10) C1 C7 H7 115.3(10) C13 C8 C9 119.72(13) C13 C8 N1 117.52(13) C9 C8 N1 122.72(13) C10 C9 C8 118.65(13) C10 C9 H9 120.7 C8 C9 H9 120.7 C11 C10 C9 122.96(14) C11 C10 Cl2 118.33(11) C9 C10 Cl2 118.71(11) C10 C11 C12 116.90(13) C10 C11 H11 121.6 C12 C11 H11 121.6 C13 C12 C11 122.53(13) C13 C12 Cl1 119.11(12) C11 C12 Cl1 118.36(11) C12 C13 C8 119.22(14) C12 C13 H13 120.4 C8 C13 H13 120.4 _cod_database_code 2206797