#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/44/2014400.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_2014400 _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 ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _[local]_cod_cif_authors_sg_H-M 'P 21/n' 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 Cl2 N2 O' _chemical_formula_sum 'C14 H10 Cl2 N2 O' _chemical_formula_iupac 'C14 H10 Cl2 N2 O' _chemical_formula_weight 293.14 _symmetry_cell_setting monoclinic 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 10.5093(5) _cell_length_b 17.6499(9) _cell_length_c 14.7982(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.732(2) _cell_angle_gamma 90.00 _cell_volume 2654.7(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _exptl_crystal_density_diffrn 1.467 _diffrn_ambient_temperature 120(2) 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 C C11 0.9744(3) 0.2791(2) 0.4130(2) 0.0297(8) Uani d . 1 . . C C12 1.0069(4) 0.2530(2) 0.3333(2) 0.0366(9) Uani d . 1 . . Cl Cl12 0.88367(11) 0.24508(8) 0.22962(7) 0.0652(4) Uani d . 1 . . C C13 1.1341(4) 0.2319(2) 0.3322(2) 0.0373(9) Uani d . 1 . . C C14 1.2304(3) 0.2401(2) 0.4129(2) 0.0316(8) Uani d . 1 . . Cl Cl14 1.38988(9) 0.21204(6) 0.41435(7) 0.0436(3) Uani d . 1 . . C C15 1.2047(3) 0.2684(2) 0.4935(2) 0.0378(9) Uani d . 1 . . C C16 1.0782(3) 0.2879(2) 0.4932(2) 0.0345(8) Uani d . 1 . . C C17 0.8401(3) 0.30026(19) 0.4129(2) 0.0299(8) Uani d . 1 . . N N11 0.8088(2) 0.31225(16) 0.48924(18) 0.0276(6) Uani d . 1 . . N N21 0.6809(2) 0.33750(15) 0.47809(18) 0.0269(6) Uani d . 1 . . C C27 0.6388(3) 0.35245(19) 0.5553(2) 0.0272(7) Uani d . 1 . . O O27 0.7063(2) 0.33619(14) 0.63429(15) 0.0317(5) Uani d . 1 . . C C21 0.5089(3) 0.39111(19) 0.5402(2) 0.0273(7) Uani d . 1 . . C C22 0.4681(3) 0.4105(2) 0.6196(2) 0.0342(8) Uani d . 1 . . C C23 0.3509(3) 0.4491(2) 0.6110(3) 0.0405(9) Uani d . 1 . . C C24 0.2736(3) 0.4686(2) 0.5233(3) 0.0380(9) Uani d . 1 . . C C25 0.3138(3) 0.4495(2) 0.4452(3) 0.0374(9) Uani d . 1 . . C C26 0.4316(3) 0.4117(2) 0.4533(2) 0.0307(8) Uani d . 1 . . C C31 0.6153(3) 0.08524(19) 0.2827(2) 0.0282(7) Uani d . 1 . . C C32 0.6209(3) 0.0106(2) 0.2537(2) 0.0319(8) Uani d . 1 . . Cl Cl32 0.52231(9) -0.01937(6) 0.14709(7) 0.0473(3) Uani d . 1 . . C C33 0.7043(3) -0.0421(2) 0.3072(3) 0.0365(8) Uani d . 1 . . C C34 0.7821(4) -0.0205(2) 0.3925(3) 0.0386(9) Uani d . 1 . . Cl Cl34 0.88383(11) -0.08745(6) 0.46080(8) 0.0576(3) Uani d . 1 . . C C35 0.7790(4) 0.0525(2) 0.4258(3) 0.0393(9) Uani d . 1 . . C C36 0.6955(3) 0.1049(2) 0.3702(2) 0.0349(8) Uani d . 1 . . C C37 0.5242(3) 0.1414(2) 0.2283(2) 0.0298(8) Uani d . 1 . . N N31 0.5423(3) 0.21111(16) 0.24940(18) 0.0282(6) Uani d . 1 . . N N41 0.4467(3) 0.25948(16) 0.20021(18) 0.0292(6) Uani d . 1 . . C C47 0.4585(3) 0.3342(2) 0.2229(2) 0.0286(7) Uani d . 1 . . O O47 0.5583(2) 0.36061(14) 0.27595(15) 0.0336(6) Uani d . 1 . . C C41 0.3420(3) 0.3832(2) 0.1820(2) 0.0300(8) Uani d . 1 . . C C42 0.3613(4) 0.4617(2) 0.1883(2) 0.0383(9) Uani d . 1 . . C C43 0.2562(4) 0.5106(2) 0.1570(3) 0.0461(10) Uani d . 1 . . C C44 0.1312(4) 0.4825(2) 0.1200(3) 0.0433(10) Uani d . 1 . . C C45 0.1109(4) 0.4053(2) 0.1131(3) 0.0439(10) Uani d . 1 . . C C46 0.2154(3) 0.3552(2) 0.1441(2) 0.0356(8) Uani d . 1 . . H H13 1.1531 0.2124 0.2772 0.045 Uiso calc R 1 . . H H15 1.2738 0.2742 0.5486 0.045 Uiso calc R 1 . . H H16 1.0607 0.3078 0.5484 0.041 Uiso calc R 1 . . H H17 0.7754 0.3051 0.3552 0.036 Uiso calc R 1 . . H H21 0.6384 0.3498 0.4207 0.032 Uiso d R 1 . . H H22 0.5206 0.3971 0.6797 0.041 Uiso calc R 1 . . H H23 0.3234 0.4623 0.6653 0.049 Uiso calc R 1 . . H H24 0.1932 0.4950 0.5176 0.046 Uiso calc R 1 . . H H25 0.2605 0.4622 0.3851 0.045 Uiso calc R 1 . . H H26 0.4596 0.3999 0.3987 0.037 Uiso calc R 1 . . H H33 0.7078 -0.0925 0.2853 0.044 Uiso calc R 1 . . H H35 0.8326 0.0666 0.4853 0.047 Uiso calc R 1 . . H H36 0.6929 0.1552 0.3923 0.042 Uiso calc R 1 . . H H37 0.4530 0.1260 0.1781 0.036 Uiso calc R 1 . . H H41 0.3745 0.2418 0.1621 0.035 Uiso d R 1 . . H H42 0.4469 0.4814 0.2142 0.046 Uiso calc R 1 . . H H43 0.2703 0.5638 0.1610 0.055 Uiso calc R 1 . . H H44 0.0592 0.5162 0.0994 0.052 Uiso calc R 1 . . H H45 0.0250 0.3861 0.0870 0.053 Uiso calc R 1 . . H H46 0.2006 0.3021 0.1395 0.043 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 0.0274(17) 0.035(2) 0.0250(16) 0.0012(15) 0.0034(13) -0.0004(14) C12 0.037(2) 0.042(2) 0.0278(18) 0.0082(17) 0.0027(15) -0.0017(16) Cl12 0.0516(6) 0.0989(10) 0.0353(5) 0.0291(6) -0.0069(4) -0.0224(6) C13 0.044(2) 0.042(2) 0.0285(18) 0.0037(17) 0.0144(16) -0.0002(15) C14 0.0282(17) 0.0290(19) 0.040(2) -0.0011(15) 0.0136(15) -0.0014(15) Cl14 0.0308(5) 0.0503(6) 0.0515(6) -0.0003(4) 0.0140(4) -0.0079(4) C15 0.0288(19) 0.051(2) 0.0312(18) -0.0039(17) 0.0031(15) -0.0051(16) C16 0.0344(19) 0.041(2) 0.0276(17) -0.0023(16) 0.0069(15) -0.0041(15) C17 0.0277(17) 0.0313(19) 0.0269(17) 0.0037(15) 0.0000(14) -0.0016(14) N11 0.0212(13) 0.0323(16) 0.0274(14) 0.0037(12) 0.0028(11) 0.0031(12) N21 0.0213(13) 0.0320(16) 0.0250(14) 0.0067(12) 0.0015(11) 0.0008(12) C27 0.0238(16) 0.0250(18) 0.0316(18) -0.0047(14) 0.0051(14) 0.0002(14) O27 0.0241(12) 0.0443(15) 0.0252(12) 0.0040(11) 0.0033(9) 0.0036(10) C21 0.0206(16) 0.0271(18) 0.0330(17) -0.0018(13) 0.0047(13) -0.0004(14) C22 0.0272(18) 0.040(2) 0.0345(19) -0.0001(16) 0.0068(15) -0.0025(16) C23 0.0311(19) 0.044(2) 0.049(2) 0.0006(17) 0.0131(17) -0.0094(18) C24 0.0252(18) 0.037(2) 0.051(2) 0.0029(16) 0.0086(16) -0.0020(17) C25 0.0293(19) 0.037(2) 0.042(2) 0.0051(16) 0.0036(16) 0.0031(17) C26 0.0266(17) 0.031(2) 0.0330(18) 0.0016(15) 0.0054(14) 0.0009(15) C31 0.0218(16) 0.0309(19) 0.0323(18) -0.0019(14) 0.0079(13) 0.0016(14) C32 0.0254(17) 0.034(2) 0.0379(19) -0.0045(15) 0.0118(15) -0.0026(15) Cl32 0.0376(5) 0.0474(6) 0.0522(6) -0.0016(4) 0.0026(4) -0.0182(5) C33 0.0326(19) 0.030(2) 0.051(2) -0.0012(16) 0.0180(17) 0.0008(17) C34 0.036(2) 0.036(2) 0.045(2) 0.0055(17) 0.0138(17) 0.0137(17) Cl34 0.0626(7) 0.0435(6) 0.0636(7) 0.0166(5) 0.0102(5) 0.0225(5) C35 0.039(2) 0.040(2) 0.0336(19) 0.0021(17) -0.0001(16) 0.0049(16) C36 0.0356(19) 0.032(2) 0.0345(19) 0.0024(16) 0.0040(16) 0.0035(15) C37 0.0237(17) 0.039(2) 0.0267(17) -0.0008(15) 0.0065(13) 0.0000(15) N31 0.0239(14) 0.0315(17) 0.0281(14) 0.0044(12) 0.0043(11) 0.0026(12) N41 0.0226(14) 0.0341(17) 0.0256(14) 0.0022(12) -0.0037(11) -0.0008(12) C47 0.0283(18) 0.037(2) 0.0202(15) 0.0035(15) 0.0050(13) 0.0023(14) O47 0.0279(12) 0.0373(14) 0.0287(12) 0.0006(11) -0.0056(10) -0.0025(10) C41 0.0301(18) 0.034(2) 0.0236(16) 0.0050(15) 0.0033(14) -0.0011(14) C42 0.037(2) 0.036(2) 0.036(2) 0.0019(16) -0.0017(16) -0.0049(16) C43 0.052(2) 0.034(2) 0.046(2) 0.0134(19) 0.0010(19) -0.0039(18) C44 0.040(2) 0.046(3) 0.040(2) 0.0192(19) 0.0042(17) 0.0006(18) C45 0.0302(19) 0.054(3) 0.044(2) 0.0072(18) 0.0039(17) -0.0017(19) C46 0.0302(18) 0.037(2) 0.0361(19) 0.0039(16) 0.0021(15) 0.0016(16) 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 . 1.387(5) no C11 C16 . 1.401(4) no C11 C17 . 1.459(5) no C12 C13 . 1.392(5) no C12 Cl12 . 1.744(3) no C13 C14 . 1.362(5) no C13 H13 . 0.95 no C14 C15 . 1.382(5) no C14 Cl14 . 1.743(3) no C15 C16 . 1.372(5) no C15 H15 . 0.95 no C16 H16 . 0.95 no C17 N11 . 1.273(4) no C17 H17 . 0.95 no N11 N21 . 1.386(4) no N21 C27 . 1.352(4) no N21 H21 . 0.88 no C27 O27 . 1.236(4) no C27 C21 . 1.492(4) no C21 C26 . 1.384(4) no C21 C22 . 1.392(5) no C22 C23 . 1.385(5) no C22 H22 . 0.95 no C23 C24 . 1.387(5) no C23 H23 . 0.95 no C24 C25 . 1.371(5) no C24 H24 . 0.95 no C25 C26 . 1.384(5) no C25 H25 . 0.95 no C26 H26 . 0.95 no C31 C32 . 1.391(5) no C31 C36 . 1.397(5) no C31 C37 . 1.468(5) no C32 C33 . 1.382(5) no C32 Cl32 . 1.735(3) no C33 C34 . 1.372(5) no C33 H33 . 0.95 no C34 C35 . 1.383(5) no C34 Cl34 . 1.735(4) no C35 C36 . 1.391(5) no C35 H35 . 0.95 no C36 H36 . 0.95 no C37 N31 . 1.271(4) no C37 H37 . 0.95 no N31 N41 . 1.377(4) no N41 C47 . 1.360(4) no N41 H41 . 0.88 no C47 O47 . 1.230(4) no C47 C41 . 1.496(4) no C41 C46 . 1.396(5) no C41 C42 . 1.398(5) no C42 C43 . 1.386(5) no C42 H42 . 0.95 no C43 C44 . 1.381(6) no C43 H43 . 0.95 no C44 C45 . 1.377(6) no C44 H44 . 0.95 no C45 C46 . 1.394(5) no C45 H45 . 0.95 no C46 H46 . 0.95 no _cod_database_code 2014400