#------------------------------------------------------------------------------ #$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2014399.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2014399 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2006 _journal_volume 62 _journal_page_first o118 _journal_page_last o121 _publ_section_title ; 2,4-Difluorobenzaldehyde benzoylhydrazone and 2,4-dichlorobenzaldehyde benzoylhydrazone are isostructural at 120 K with Z' = 2: complex sheets built from N---H...O, C---H...O and C---H...\p(arene) hydrogen bonds ; loop_ _publ_author_name 'Wardell, Solange M. S. V.' 'de Lima Ferreira, Marcelle' 'de Souza, Marcus V. N.' 'Wardell, James L.' 'Low, John N.' 'Glidewell, Christopher' _chemical_formula_moiety 'C14 H10 F2 N2 O' _chemical_formula_sum 'C14 H10 F2 N2 O' _chemical_formula_iupac 'C14 H10 F2 N2 O' _chemical_formula_weight 260.24 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 10.1310(3) _cell_length_b 17.2172(6) _cell_length_c 14.4288(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.957(2) _cell_angle_gamma 90.00 _cell_volume 2442.48(14) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _exptl_crystal_density_diffrn 1.415 _diffrn_ambient_temperature 120(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_disorder_assembly _atom_site_disorder_group C C11 0.99764(19) 0.27524(11) 0.42068(15) 0.0239(4) Uani d . 1 . . C C12 1.0390(2) 0.25610(12) 0.33871(15) 0.0265(5) Uani d . 1 . . F F12 0.94624(12) 0.25951(8) 0.25303(9) 0.0423(4) Uani d . 1 . . C C13 1.1691(2) 0.23343(12) 0.33807(15) 0.0294(5) Uani d . 1 . . C C14 1.26080(19) 0.23045(12) 0.42535(16) 0.0279(5) Uani d . 1 . . F F14 1.39040(12) 0.20814(8) 0.42768(10) 0.0419(4) Uani d . 1 . . C C15 1.2284(2) 0.24928(11) 0.50982(16) 0.0277(5) Uani d . 1 . . C C16 1.09665(19) 0.27149(12) 0.50665(15) 0.0259(5) Uani d . 1 . . C C17 0.85690(19) 0.29890(11) 0.41486(15) 0.0253(5) Uani d . 1 . . N N11 0.81731(15) 0.31313(9) 0.49087(12) 0.0236(4) Uani d . 1 . . N N21 0.68381(15) 0.33782(9) 0.47659(12) 0.0246(4) Uani d . 1 . . C C27 0.63571(19) 0.35462(11) 0.55360(15) 0.0224(4) Uani d . 1 . . O O27 0.70367(13) 0.34086(8) 0.63547(10) 0.0281(3) Uani d . 1 . . C C21 0.49811(18) 0.39067(11) 0.53653(15) 0.0231(4) Uani d . 1 . . C C22 0.4473(2) 0.40510(12) 0.61610(16) 0.0295(5) Uani d . 1 . . C C23 0.3216(2) 0.44082(13) 0.60593(18) 0.0374(6) Uani d . 1 . . C C24 0.2462(2) 0.46161(13) 0.51643(18) 0.0372(6) Uani d . 1 . . C C25 0.2953(2) 0.44722(12) 0.43656(17) 0.0329(5) Uani d . 1 . . C C26 0.42156(19) 0.41249(11) 0.44662(16) 0.0268(5) Uani d . 1 . . C C31 0.61992(18) 0.07412(11) 0.28898(15) 0.0235(4) Uani d . 1 . . C C32 0.61079(19) -0.00380(12) 0.26511(16) 0.0278(5) Uani d . 1 . . F F32 0.51203(13) -0.02688(7) 0.18904(11) 0.0494(4) Uani d . 1 . . C C33 0.6983(2) -0.05991(12) 0.31253(17) 0.0314(5) Uani d . 1 . . C C34 0.8001(2) -0.03505(12) 0.38748(16) 0.0318(5) Uani d . 1 . . F F34 0.88836(13) -0.08888(7) 0.43573(10) 0.0469(4) Uani d . 1 . . C C35 0.8163(2) 0.04103(13) 0.41593(17) 0.0387(6) Uani d . 1 . . C C36 0.7253(2) 0.09501(12) 0.36670(16) 0.0321(5) Uani d . 1 . . C C37 0.52320(19) 0.13100(12) 0.23681(15) 0.0257(5) Uani d . 1 . . N N31 0.54556(15) 0.20317(10) 0.25460(12) 0.0247(4) Uani d . 1 . . N N41 0.44667(15) 0.25306(9) 0.20581(12) 0.0246(4) Uani d . 1 . . C C47 0.46447(19) 0.33006(12) 0.22207(14) 0.0243(4) Uani d . 1 . . O O47 0.56955(13) 0.35678(8) 0.27418(10) 0.0277(3) Uani d . 1 . . C C41 0.34917(19) 0.38236(11) 0.17673(14) 0.0243(4) Uani d . 1 . . C C42 0.3717(2) 0.46184(12) 0.18762(16) 0.0335(5) Uani d . 1 . . C C43 0.2679(2) 0.51418(13) 0.15371(17) 0.0405(6) Uani d . 1 . . C C44 0.1399(2) 0.48801(13) 0.10782(17) 0.0360(6) Uani d . 1 . . C C45 0.1168(2) 0.40922(13) 0.09610(17) 0.0352(6) Uani d . 1 . . C C46 0.2200(2) 0.35639(12) 0.12975(15) 0.0301(5) Uani d . 1 . . H H13 1.1941 0.2206 0.2806 0.035 Uiso calc R 1 . . H H15 1.2950 0.2470 0.5687 0.033 Uiso calc R 1 . . H H16 1.0726 0.2846 0.5644 0.031 Uiso calc R 1 . . H H17 0.7947 0.3037 0.3543 0.030 Uiso calc R 1 . . H H21 0.6404 0.3456 0.4167 0.030 Uiso d R 1 . . H H22 0.4988 0.3905 0.6777 0.035 Uiso calc R 1 . . H H23 0.2876 0.4509 0.6606 0.045 Uiso calc R 1 . . H H24 0.1602 0.4859 0.5096 0.045 Uiso calc R 1 . . H H25 0.2427 0.4611 0.3750 0.039 Uiso calc R 1 . . H H26 0.4560 0.4035 0.3919 0.032 Uiso calc R 1 . . H H33 0.6886 -0.1130 0.2943 0.038 Uiso calc R 1 . . H H35 0.8882 0.0562 0.4682 0.046 Uiso calc R 1 . . H H36 0.7346 0.1478 0.3862 0.039 Uiso calc R 1 . . H H37 0.4448 0.1146 0.1903 0.031 Uiso calc R 1 . . H H41 0.3719 0.2359 0.1665 0.030 Uiso d R 1 . . H H42 0.4595 0.4804 0.2188 0.040 Uiso calc R 1 . . H H43 0.2846 0.5683 0.1620 0.049 Uiso calc R 1 . . H H44 0.0684 0.5239 0.0845 0.043 Uiso calc R 1 . . H H45 0.0289 0.3911 0.0645 0.042 Uiso calc R 1 . . H H46 0.2029 0.3023 0.1208 0.036 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 C11 0.0253(10) 0.0206(10) 0.0251(12) 0.0019(8) 0.0043(9) 0.0016(9) C12 0.0297(10) 0.0279(11) 0.0199(11) 0.0048(9) 0.0020(9) -0.0008(9) F12 0.0417(7) 0.0572(9) 0.0245(7) 0.0154(6) 0.0013(6) -0.0036(6) C13 0.0352(11) 0.0310(11) 0.0251(12) 0.0070(9) 0.0137(10) 0.0013(9) C14 0.0232(10) 0.0262(11) 0.0358(13) 0.0049(8) 0.0103(9) 0.0025(10) F14 0.0285(6) 0.0514(8) 0.0481(9) 0.0108(6) 0.0138(6) 0.0014(7) C15 0.0256(10) 0.0291(11) 0.0271(12) -0.0001(9) 0.0038(9) 0.0025(9) C16 0.0258(10) 0.0278(11) 0.0245(12) 0.0002(9) 0.0069(9) -0.0002(9) C17 0.0257(10) 0.0261(11) 0.0223(12) 0.0014(8) 0.0026(9) 0.0001(9) N11 0.0187(8) 0.0264(9) 0.0246(10) 0.0022(7) 0.0029(7) 0.0008(7) N21 0.0195(8) 0.0303(9) 0.0220(10) 0.0046(7) 0.0012(7) 0.0013(7) C27 0.0230(9) 0.0191(10) 0.0240(12) -0.0017(8) 0.0037(9) -0.0011(8) O27 0.0271(7) 0.0347(8) 0.0217(8) 0.0035(6) 0.0040(6) 0.0044(6) C21 0.0197(9) 0.0203(10) 0.0287(12) -0.0014(8) 0.0050(9) -0.0010(9) C22 0.0282(10) 0.0304(11) 0.0309(13) 0.0012(9) 0.0087(9) 0.0004(10) C23 0.0318(11) 0.0405(13) 0.0448(15) 0.0035(10) 0.0188(11) -0.0039(11) C24 0.0229(10) 0.0325(12) 0.0565(17) 0.0045(9) 0.0100(11) 0.0014(11) C25 0.0250(10) 0.0323(12) 0.0393(14) 0.0066(9) 0.0039(10) 0.0035(10) C26 0.0257(10) 0.0257(10) 0.0287(12) 0.0014(8) 0.0062(9) 0.0000(9) C31 0.0214(9) 0.0255(10) 0.0239(12) -0.0012(8) 0.0059(8) 0.0001(9) C32 0.0193(9) 0.0322(11) 0.0298(12) -0.0031(9) 0.0016(9) -0.0054(10) F32 0.0393(7) 0.0364(8) 0.0587(10) 0.0018(6) -0.0154(7) -0.0141(7) C33 0.0299(11) 0.0242(10) 0.0406(14) -0.0003(9) 0.0093(10) -0.0008(10) C34 0.0287(11) 0.0285(11) 0.0356(14) 0.0042(9) 0.0028(10) 0.0062(10) F34 0.0449(8) 0.0322(7) 0.0542(9) 0.0083(6) -0.0066(7) 0.0099(6) C35 0.0392(12) 0.0315(12) 0.0370(14) -0.0003(10) -0.0070(11) 0.0032(10) C36 0.0370(12) 0.0239(11) 0.0319(13) -0.0011(9) 0.0013(10) -0.0023(9) C37 0.0224(10) 0.0279(11) 0.0257(12) -0.0003(8) 0.0037(9) -0.0010(9) N31 0.0221(8) 0.0285(9) 0.0228(10) 0.0040(7) 0.0037(7) 0.0024(7) N41 0.0201(8) 0.0251(9) 0.0248(10) 0.0027(7) -0.0022(7) -0.0002(7) C47 0.0242(10) 0.0294(11) 0.0190(11) 0.0003(8) 0.0049(9) 0.0001(9) O47 0.0248(7) 0.0293(8) 0.0246(8) -0.0028(6) -0.0027(6) -0.0019(6) C41 0.0275(10) 0.0252(10) 0.0190(11) 0.0020(8) 0.0032(8) 0.0016(9) C42 0.0323(11) 0.0278(11) 0.0357(14) 0.0003(9) -0.0008(10) -0.0014(10) C43 0.0490(14) 0.0259(11) 0.0410(15) 0.0045(10) -0.0003(12) -0.0017(11) C44 0.0374(12) 0.0347(13) 0.0333(14) 0.0121(10) 0.0033(10) 0.0042(10) C45 0.0264(11) 0.0399(13) 0.0354(14) 0.0029(10) -0.0002(10) 0.0053(11) C46 0.0281(10) 0.0296(11) 0.0301(13) 0.0015(9) 0.0019(9) 0.0034(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C11 C12 . 1.386(3) no C11 C16 . 1.396(3) no C11 C17 . 1.466(3) no C12 F12 . 1.362(2) no C12 C13 . 1.378(3) no C13 C14 . 1.374(3) no C13 H13 . 0.95 no C14 F14 . 1.361(2) no C14 C15 . 1.375(3) no C15 C16 . 1.379(3) no C15 H15 . 0.95 no C16 H16 . 0.95 no C17 N11 . 1.279(3) no C17 H17 . 0.95 no N11 N21 . 1.385(2) no N21 C27 . 1.348(3) no N21 H21 . 0.88 no C27 O27 . 1.238(2) no C27 C21 . 1.491(3) no C21 C22 . 1.389(3) no C21 C26 . 1.393(3) no C22 C23 . 1.390(3) no C22 H22 . 0.95 no C23 C24 . 1.380(3) no C23 H23 . 0.95 no C24 C25 . 1.383(3) no C24 H24 . 0.95 no C25 C26 . 1.388(3) no C25 H25 . 0.95 no C26 H26 . 0.95 no C31 C32 . 1.383(3) no C31 C36 . 1.396(3) no C31 C37 . 1.459(3) no C32 F32 . 1.354(2) no C32 C33 . 1.376(3) no C33 C34 . 1.371(3) no C33 H33 . 0.95 no C34 F34 . 1.358(2) no C34 C35 . 1.371(3) no C35 C36 . 1.379(3) no C35 H35 . 0.95 no C36 H36 . 0.95 no C37 N31 . 1.278(3) no C37 H37 . 0.95 no N31 N41 . 1.377(2) no N41 C47 . 1.351(3) no N41 H41 . 0.88 no C47 O47 . 1.235(2) no C47 C41 . 1.495(3) no C41 C42 . 1.390(3) no C41 C46 . 1.394(3) no C42 C43 . 1.381(3) no C42 H42 . 0.95 no C43 C44 . 1.382(3) no C43 H43 . 0.95 no C44 C45 . 1.380(3) no C44 H44 . 0.95 no C45 C46 . 1.383(3) no C45 H45 . 0.95 no C46 H46 . 0.95 no