#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/39/2013969.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_2013969 loop_ _publ_author_name 'Dale, Sophie H.' 'Elsegood, Mark R.J.' _publ_section_title ; Hydrogen-bonding adducts of benzenepolycarboxylic acids with N,N-dimethylformamide: benzene-1,4-dicarboxylic acid N,N-dimethylformamide disolvate, benzene-1,2,4,5-tetracarboxylic acid N,N-dimethylformamide tetrasolvate and benzene-1,2,3-tricarboxylic acid N,N-dimethylformamide disolvate monohydrate ; _journal_name_full 'Acta Crystallographica, Section C' _journal_page_first o444 _journal_page_last o448 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C9 H6 O6, 2C3 H7 N O, H2 O' _chemical_formula_moiety 'C9 H6 O6, 2C3 H7 N O, H2 O' _chemical_formula_sum 'C15 H22 N2 O9' _chemical_formula_weight 374.35 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.8441(15) _cell_length_b 19.745(2) _cell_length_c 6.6606(7) _cell_measurement_temperature 150(2) _cell_volume 1820.7(3) _diffrn_ambient_temperature 150(2) _exptl_crystal_density_diffrn 1.366 _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'Y' changed to 'y' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (15 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 2013969 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 _atom_site_type_symbol C1 0.70722(16) 0.22164(11) 0.4858(4) 0.0215(5) Uani d . 1 . . C C2 0.76594(14) 0.16416(10) 0.5032(4) 0.0174(4) Uani d . 1 . . C C3 0.72210(16) 0.09996(11) 0.5152(4) 0.0204(4) Uani d . 1 . . C C4 0.62119(17) 0.09517(12) 0.5166(4) 0.0246(5) Uani d . 1 . . C H4A 0.5917 0.0519 0.5265 0.030 Uiso calc R 1 . . H C5 0.56364(16) 0.15232(12) 0.5038(4) 0.0262(5) Uani d . 1 . . C H5A 0.4953 0.1483 0.5077 0.031 Uiso calc R 1 . . H C6 0.60639(16) 0.21563(12) 0.4852(4) 0.0243(5) Uani d . 1 . . C H6 0.5672 0.2549 0.4721 0.029 Uiso calc R 1 . . H C7 0.75213(17) 0.29089(11) 0.4701(4) 0.0237(5) Uani d . 1 . . C O1 0.69869(14) 0.33449(9) 0.3663(4) 0.0355(5) Uani d . 1 . . O H1 0.728(3) 0.378(2) 0.359(7) 0.053 Uiso d . 1 . . H O2 0.82946(13) 0.30466(9) 0.5413(3) 0.0334(5) Uani d . 1 . . O C8 0.87487(15) 0.17298(10) 0.4967(4) 0.0197(4) Uani d . 1 . . C O3 0.91671(12) 0.18029(9) 0.3363(3) 0.0246(4) Uani d . 1 . . O O4 0.92184(12) 0.17362(9) 0.6663(3) 0.0238(4) Uani d . 1 . . O H4 0.888(3) 0.1673(17) 0.774(6) 0.036 Uiso d . 1 . . H C9 0.77795(18) 0.03485(11) 0.5189(4) 0.0239(5) Uani d . 1 . . C O5 0.87118(12) 0.04261(8) 0.5093(4) 0.0347(5) Uani d . 1 . . O H5 0.900(3) -0.003(2) 0.505(7) 0.052 Uiso d . 1 . . H O6 0.73742(15) -0.01970(8) 0.5300(4) 0.0363(5) Uani d . 1 . . O C10 0.93429(19) -0.11833(12) 0.5068(4) 0.0286(5) Uani d . 1 . . C H10 0.8658 -0.1204 0.5147 0.034 Uiso calc R 1 . . H O7 0.97352(14) -0.06117(9) 0.5093(4) 0.0354(5) Uani d . 1 . . O N1 0.98230(15) -0.17588(10) 0.4940(3) 0.0258(4) Uani d . 1 . . N C11 1.08763(19) -0.17693(13) 0.4816(5) 0.0341(6) Uani d . 1 . . C H11A 1.1118 -0.1305 0.4680 0.051 Uiso calc R 1 . . H H11B 1.1075 -0.2036 0.3646 0.051 Uiso calc R 1 . . H H11C 1.1142 -0.1974 0.6038 0.051 Uiso calc R 1 . . H C12 0.9320(2) -0.24081(12) 0.4907(5) 0.0319(5) Uani d . 1 . . C H12A 0.8621 -0.2330 0.4894 0.048 Uiso calc R 1 . . H H12B 0.9495 -0.2670 0.6104 0.048 Uiso calc R 1 . . H H12C 0.9507 -0.2661 0.3701 0.048 Uiso calc R 1 . . H C13 0.83670(19) 0.47076(13) 0.4570(5) 0.0332(6) Uani d . 1 . . C H13 0.8410 0.4455 0.5780 0.040 Uiso calc R 1 . . H O8 0.78043(15) 0.44991(10) 0.3228(4) 0.0391(5) Uani d . 1 . . O N2 0.89063(18) 0.52613(12) 0.4398(4) 0.0348(6) Uani d . 1 . . N C14 0.8855(3) 0.56746(18) 0.2587(7) 0.0565(10) Uani d . 1 . . C H14A 0.8639 0.5394 0.1458 0.085 Uiso calc R 1 . . H H14B 0.9495 0.5862 0.2290 0.085 Uiso calc R 1 . . H H14C 0.8396 0.6046 0.2795 0.085 Uiso calc R 1 . . H C15 0.9484(2) 0.55029(17) 0.6057(6) 0.0428(8) Uani d . 1 . . C H15A 0.9494 0.5160 0.7121 0.064 Uiso calc R 1 . . H H15B 0.9204 0.5923 0.6580 0.064 Uiso calc R 1 . . H H15C 1.0145 0.5589 0.5595 0.064 Uiso calc R 1 . . H O9 0.82103(14) 0.15198(10) -0.0129(3) 0.0300(4) Uani d . 1 . . O H9B 0.848(3) 0.160(2) 0.088(7) 0.045 Uiso d . 1 . . H H9A 0.808(3) 0.110(2) 0.019(6) 0.045 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 C1 0.0205(9) 0.0206(10) 0.0233(11) -0.0003(8) 0.0000(10) -0.0011(10) C2 0.0173(9) 0.0178(9) 0.0171(10) -0.0021(7) -0.0007(9) -0.0009(9) C3 0.0221(9) 0.0173(9) 0.0219(11) -0.0023(8) 0.0008(10) -0.0001(9) C4 0.0231(10) 0.0252(10) 0.0255(12) -0.0082(8) 0.0008(10) -0.0015(11) C5 0.0177(9) 0.0326(11) 0.0284(12) -0.0032(9) 0.0036(11) -0.0007(12) C6 0.0190(9) 0.0269(11) 0.0270(12) 0.0032(8) -0.0001(10) -0.0022(11) C7 0.0235(10) 0.0191(10) 0.0285(12) 0.0008(8) -0.0006(10) -0.0020(10) O1 0.0325(10) 0.0200(8) 0.0539(13) -0.0006(8) -0.0123(10) 0.0061(9) O2 0.0266(8) 0.0230(8) 0.0506(13) -0.0042(7) -0.0115(9) 0.0017(9) C8 0.0176(9) 0.0142(8) 0.0273(11) -0.0010(7) -0.0003(10) 0.0008(10) O3 0.0217(8) 0.0268(9) 0.0252(9) -0.0029(7) 0.0041(7) 0.0005(7) O4 0.0198(8) 0.0255(8) 0.0261(9) -0.0038(7) -0.0035(7) 0.0031(7) C9 0.0275(10) 0.0185(9) 0.0257(12) -0.0014(8) -0.0006(10) -0.0012(10) O5 0.0250(8) 0.0171(7) 0.0621(14) 0.0021(6) -0.0013(10) -0.0003(10) O6 0.0391(10) 0.0180(8) 0.0518(13) -0.0065(7) 0.0025(10) 0.0013(9) C10 0.0308(11) 0.0254(10) 0.0296(13) 0.0082(9) -0.0038(13) -0.0003(11) O7 0.0358(9) 0.0224(8) 0.0479(12) 0.0067(7) -0.0021(11) -0.0037(9) N1 0.0322(10) 0.0225(9) 0.0228(10) 0.0062(8) 0.0014(10) -0.0008(10) C11 0.0326(12) 0.0300(12) 0.0397(15) 0.0094(10) -0.0015(13) -0.0015(13) C12 0.0385(13) 0.0230(11) 0.0343(14) 0.0031(10) 0.0018(15) 0.0006(11) C13 0.0294(12) 0.0230(11) 0.0472(17) 0.0008(9) -0.0022(12) 0.0039(12) O8 0.0406(10) 0.0257(9) 0.0508(13) -0.0079(8) -0.0102(10) 0.0046(10) N2 0.0299(11) 0.0256(10) 0.0490(16) -0.0032(9) -0.0023(11) -0.0007(11) C14 0.064(2) 0.0409(17) 0.064(2) -0.0229(17) -0.005(2) 0.0161(18) C15 0.0322(14) 0.0375(14) 0.059(2) 0.0001(12) -0.0034(14) -0.0132(15) O9 0.0340(9) 0.0241(8) 0.0320(10) -0.0073(7) -0.0023(10) 0.0013(9) 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 C1 C2 . 1.401(3) y C1 C6 . 1.401(3) y C1 C7 . 1.506(3) y C2 C3 . 1.408(3) y C2 C8 . 1.519(3) y C3 C4 . 1.400(3) y C3 C9 . 1.500(3) y C4 C5 . 1.384(3) y C4 H4A . 0.9500 ? C5 C6 . 1.389(3) y C5 H5A . 0.9500 ? C6 H6 . 0.9500 ? C7 O2 . 1.202(3) y C7 O1 . 1.329(3) y O1 H1 . 0.95(4) ? C8 O3 . 1.224(3) y C8 O4 . 1.303(3) y O4 H4 . 0.86(4) ? C9 O6 . 1.217(3) y C9 O5 . 1.301(3) y O5 H5 . 0.99(4) ? C10 O7 . 1.253(3) ? C10 N1 . 1.319(3) ? C10 H10 . 0.9500 ? N1 C12 . 1.459(3) ? N1 C11 . 1.461(3) ? C11 H11A . 0.9800 ? C11 H11B . 0.9800 ? C11 H11C . 0.9800 ? C12 H12A . 0.9800 ? C12 H12B . 0.9800 ? C12 H12C . 0.9800 ? C13 O8 . 1.255(4) ? C13 N2 . 1.329(3) ? C13 H13 . 0.9500 ? N2 C15 . 1.445(4) ? N2 C14 . 1.458(5) ? C14 H14A . 0.9800 ? C14 H14B . 0.9800 ? C14 H14C . 0.9800 ? C15 H15A . 0.9800 ? C15 H15B . 0.9800 ? C15 H15C . 0.9800 ? O9 H9B . 0.78(4) ? O9 H9A . 0.87(4) ?